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19 Awesome Road Trips from Chicago (with Timings)

Keeping your introduction to road trips from Chicago short and simple, let’s take a look at the summer, winter and weekend favourites!

The city of Chicago is awesome and all, but it’s also a great starting point for some great Chicago road trips. The city’s prime location acts as a portal to the Midwest – from historical cities to sprawling state parks and urban-stress-relieving beer. 

chicago road trip

Best Chicago Road Trips in Summer

If you’re looking for one of the longest Chicago road trips, how about driving from Chicago to New Orleans ? If you’re thinking a little shorter, then read on…

Distance: as far as you can go

No American road trip is complete without covering some part of classic Road 66 – of which, lucky for us, kicks off in Chicago!

road trips from Chicago

Snap a selfie at the official sign between East Adams and South Michigan Avenue then check-off stops such as the Gemini Giant, the Pontiac murals, Lincoln Presidential Library and more. If you can spare a month, make it all the way down to the Pacific Ocean.

best road trips USA

2. Illinois’ Great River Road

Distance: 3.5-hour drive

In a seemingly never-ending chain of historical sites and activities, the drive along Mississippi River to East Dubuque is one of the best road trips from Chicago.

Chicago road trips

Moline and Rock Island are two cool detours but you can head straight for East Dubuque for its Chicago Great Western Railway Depot Museum. John Deere Pavilion lets you hop from car to farm machines, while the city Nauvoo shows off many historic homes. 

3. Lake Michigan to South Haven

Distance: 2.5-hour drive

Escape the heat by packing your car with beach gear and setting off for a nice drive around Lake Michigan and towards South Haven.

Road adventures Lake Michigan

There are plenty of berry farms along the way so you can stain your hands with blueberries; or maybe you prefer to climb up a lighthouse?

To take your road trip even further, bring a bike! Cruise along the water front; take a dip or two. 

Do you have a favourite road trip quote? Click for the best long drive quotes to inspir e your next adventure!

4. Shawnee National Forest

Distance: 6-hour drive

One of the longest Chicago road trips on the list, it’s more than worth it to visit Shawnee National Forest. In fact, plan to camp amidst the spectacular range of landscapes for one of the best driving trips from Chicago!

Chicago days out

Local favourites include the Garden of the Gods – you’ll find super special rock formations like Anvil Rock. Little Grand Canyon and Bell Smith Springs feature moderate hikes; Inspiration Point offers panoramic views over the prairie, Mississippi River and the forest.

Not convinced? Shawnee Hills Wine Trail is a brilliant drive that links up vineyards and wineries in the area – a great stop on a road trip from Chicago.

How about driving from Chicago to Atlanta? Here’s my guide to the best stops on a Chicago to Atlanta road trip , just for you.

Best Chicago road trips in Winter

If you want the best road trips from Chicago when it’s colder and darker, then these are the best ones for you.

5. Grand Rapids

Distance: 3-hour drive

After just long enough of a drive, pull into Grand Rapids for a nice sweep of activities. The Beer City Ale Trail will keep you road-tripping on foot (or car, if you have a Designated Driver); or wander through Downtown Market for food adventures instead.

Chicago road trips

Warmed by booze, drop by the 158-acre Frederik Meijer Gardens & Sculpture Park where their installations are bright pops of colour against an all-white backdrop. 

6. Muskegon

Speaking of unusual winter activities, I’ve heard so much about Muskegon Winter Sports Complex. Just an hour from Grand Rapids, it’s a great next stop on your Chicago road trip.

Chicago road trip adventures

Their Olympian-designed ice-luge course is perfect for beginners, spanning 850 feet of forested speed racing. Muskegon is also home to USS Silversides Submarine Museum if you’re into marine vehicles, and there’s a great pier and lighthouse too.

7. Indianapolis

When temperatures are cold, cold, cold – you might opt for staying indoors. The city of Indianapolis is one of the best road trips from Chicago during winter because of its incredible indoor entertainment: museums.

Chicago road trip

From the Indianapolis Museum of Art to the Indianapolis Children’s Museum to quirky Indiana Medical History Museum, you can escape the cold all day!

Of course, drop by famous City Market for great eats and then maybe go on a catacombs tour underground too. This makes for one of the best road trips from Chicago.

8. Boyne Mountain Resort

Distance: 5-hour drive

Michigan winters are best captured with the ski resort of Boyne. Drive past snowy landscapes to reach 850 acres of skiing, snowmobiling, dogsledding and photography escapades.

Boyne Mountain Chicago

While the forested grounds offer romantic snow-covered views, don’t miss out on the epic zip lines that take you through the trees and slopes. 

If you like your road trips from Chicago with a bit of snow and ski thrown in, then this is a great option for you.

Your ESTA for the USA

Before you go to the USA make sure you have your ESTA organised. You can find help with this on this link: . It doesn’t take long and organising it beforehand will make things go that bit smoother at the airport.

9. Apostle Islands

Distance: 7-hour drive

Does driving over ice count as going off-road?

chicago road trip

It’s an unforgettable journey to Apostle Islands National Lakeshore as winter ice freezes thickly to transform water into road, ending with stunning ice caves!

Make sure to visit the only inhabited Madeline Island as well for a cool wind sled experience and hot tub stay. 

Day Road Trips from Chicago

10. lake geneva.

Distance: 1.5-hour drive

Chicago’s number one when it comes to day trips, Lake Geneva is one of the best lake town’s in the US.

Road trips from Chicago

Downtown boasts all the food and drinks you need for the inevitable food baby; you might even land a booze cruise.

Hot air balloon rides, Lake Shore Path, ziplines and even ski slopes make it a year-round place to visit. It’s a multi-visit destination for sure!

11. Harbor Country

Distance: 1-hour drive

Wind between the towns of Michiana, Grand Beach, Three Oaks, New Buffalo, Lakeside, Union Pier, Harbert and Sawyer. This Chicago road trip will have you hopping between wineries and breweries, not to mention the beach.

Road trips through chicago

It’s so close to the city, but the sand dunes and soft grasses make it a wholly different world. 

12. Starved Rock State Park

Distance: 2-hour drive

Families and romantics will love Starved Rock State Park for reasons that include: 13 miles of hiking, 18 canyons, free entry and nature-surround lodge.

It’s a great location to unplug for a day as you hunt down natural rock pools, waterfalls and incredible moss-strewn glades. You can even visit in the winter for cross-country skiing and cuddles in front of expansive mountain views. 

13. Saugatuck 

Making up Lake Michigan’s “art coast of Michigan”, Saugatuck and its neighbours (Fennville and Douglas) are house dozens of art galleries!

best road trips starting in chicago

Unique and LGBTQ+-friendly shops feature alongside artsy hubs to make it a super welcoming town. Of course, famous Oval Beach appeals with soft dunes and paddleboat rides too. From craft booze tours to fruit picking and corn mazes, it’s one of Chicago’s best road trips.

14. Elkhart Lake

I won’t spoil it for you but this 292-acre lake and nearby Kettle Moraine State Forest is truly a place to unwind from the crowds.

Road trip in Chicago

You can hike the epic Ice Age National Scenic Trail or bike down Old Plank Road Trail. Pumpkin patches, race-tracking and fishing are all inclusive!

Want a charming hideaway? This is it.

Road Trips 4 hours from Chicago

Want your road trips from Chicago for a special weekend? Then these Chicago road trips are only 4 hours away.

15. Ann Arbor

If you’re looking for an all-season destination, Ann Arbor is the perfect road trip from Chicago.

driving from chicago

Huron River entertains with kayaking, paddle-boarding, tubing and swimming; Matthaei Botanical Gardens and Nichols Arboretum displaying beautiful foliage. Definitely spare some time for Kerrytown Market and Shops for all their indie offerings! 

16. Door Country

Also called ‘Cape Cod of the Midwest’, Door Country is a 70-miles-long basket of fun!

You’ll never get tired of exploring its orchards, coves, lighthouses and wineries. Away from the light pollution, Newport State Park offers stunning starlit skies while Ephraim is all the small-town charm you need. Just imagine – 300 miles of coastline.

You can reach Galena under 4 hours but I recommend taking your time. Pull up through scenic rolling hills to go back in time because the Galena Historic District is made up of cobblestone streets and over 1,000 buildings from the 19 th century.

Day trips from Chicago

For those non-history buffs, Chestnut Mountain opens as a ski resort in the winter; Stagecoach Trail and Apple River Canyon State Park are open year-round. 

18. Richland County

To really escape from people, Richland County is a rural road trip destination where you can bunk for the night. But away from the isolated and lush property of Candlewood Cabins are fields and hills that keep you outdoors all day.

The Ridge Road and Pine River Recreation Trail fulfils all your adventurous needs – where else would you find wildlife while biking over abandoned railroads?

You also have three rivers and five state parks within an hour’s distance, and the lovely 100-mile Lower Wisconsin River Scenic Byway for more driving way. 

19. Huron-Manistee National Forest

Michigan really surprises us again and again!

Huron-Manistee National Forest

Along the peninsula is the expansive Huron-Manistee National Forest, one of the best road trips from Chicago if you are a nature enthusiast. A single paved road takes you through dense forest (beautiful in the fall) to parking areas so you can hike your way through the serene space or canoe on the rivers. 

Road trips from Chicago

Of course there are loads of great things to do in Chicago but visiting Chicago really opens up a world of opportunities when it comes to road trips.

VickyFlipFlop up the Skydeck

Whether you’re taking the car out for an hour-long spin or you’re willing to buckle down for a few hours, you won’t be disappointed by the scenery along your journey or the fantastic destinations ahead. 

Related Posts:

  • 7 Ways to Make the Most of Your Road Trip Budget
  • Planning a Road Trip in the USA: 13 Best Routes!
  • 57 Coolest Things to Do in Chicago for 2023
  • Christmas Things to Do in Chicago in Winter: 21+…
  • 14 Awesome Stops on a Chicago to New Orleans Road Trip
  • 11 Unique Stops on the Drive from Chicago to Atlanta

Hi, I'm Vicky! I wrote this. You can find me on all the social media @VickyFlipFlop. I love a bit of adventure, will try anything once, and have a strong passion for the local food and drink, whatever it may be. I'm here to help inspire you to travel to places a little out of your comfort zone, or at least to explore the usual destinations in a different way. Stay, have a look around, and if you have any questions – let me know below.

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The 17 best road trips from Chicago

Need a change of scenery? Load up the car and embark on one of the best road trips from Chicago.

No coast? No problem. Chicago can sometimes feel like a Midwest oasis, but there's plenty to see just a scenic road trip away. With summer quickly approaching, you can spend a few weekends sipping bourbon in Louisville, hiking  in Eau Claire or sunbathing in Door County. So if you're not sure where to start, check out our list of unique nearby destinations , load up the car, turn up "Life is a Highway" and hit the road—one of these routes from Chicago could quickly become your preferred weekend getaway . 

RECOMMENDED: The best day trips from Chicago

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Best road trips from Chicago

St Louis, MO

1.  St Louis, MO

Driving time from Chicago:  Four and a half hours

While beer, blues and BBQ are likely on the top of your St Louis bucket list (and rightfuly so), there's a lot more to discover in the Gateway to the West—like custard from Ted Drewes and a walk around Forest Park. There's also a ton to see on the five-hour drive from Chicago: Stop off in Springfield to see attractions like the Illinois State Capitol, or in Atlanta, IL to take a photo with Paul Bunyon holding a massive hotdog. 

Eau Claire, WI

2.  Eau Claire, WI

Driving time from Chicago:  Five hours

Folks head to the Chippewa Valley in northern Wisconsin for its rolling hills and colorful foliage (plus plenty of beer and cheese to smuggle back to Chicago), but there are some worthy sights along the road as well. Snap a selfie with Pinkie the Elephant in DeForest, WI and sample cranberry-flavored everything at the Wisconsin Cranberry Discovery Center   in Warrens, WI. Once you're in Eau Claire, trade in the car for a kayak:  Riverside Bike & Skate   in downtown Eau Claire rents canoes and kayaks and has shuttles that will drive you upstream so you can hit the Chippewa River. 

Traverse City, MI

3.  Traverse City, MI

The charming resort town of Traverse City, located at Michigan’s northern tip, offers plenty to do for nature enthusiasts. Clinch Park and Bryant Park have gorgeous, popular beaches while the more remote Haserot and North Bar Lake beaches offer the chance for a secluded getaway. You’re also within a stones throw of the coastal M-22, one of the most scenic drives in America, as well photo-ops at the Grand Traverse and Little Sable lighthouses. 

Detroit, MI

4.  Detroit, MI

Driving time from Chicago:  Four and a half hours

Despite what Blackhawks fans may chant, there is plenty about Detroit that doesn’t suck. You could easily spend a day or two on art alone, thanks to world-class museums like the Detroit Institute of Arts and the Museum of Contemporary Art Detroit ; powerful, immersive public art like the Heidelberg Project and colorful, whimsical folk art like Hamtramck Disneyland . Enjoy a leisurely morning browsing at Eastern Market showcasing dozens of artisan food producers, makers and crafters, and then check out the tempting restaurant and bar options nearby. On the way home, stop in neighboring Dearborn, home to the largest and most diverse Arab community in the U.S., for delicious food at spots like Al-Ameer , Sheeba and Shatila Bakery .

5.  Galena, IL

Driving time from Chicago : Three hours

At the top of many Chicagoans city escape must-visit list is Galena, Illinois. This charming town just under three hours from the city is known for its history, 19th-century architecture and resorts. There are hundreds of unique and antique shops in the city center to add some vintage pizzazz to your living room. History buffs can head over to the  Ulysses S. Grant Home  to tour the city’s proudest attraction. Once you’ve worked up an appetite, stop into  Log Cabin Steakhouse , which has been in operation since 1937. During the third weekend of June, tourists and locals alike gather for the annual  Great Galena Balloon Race .

Door County, WI

6.  Door County, WI

The road trip doesn't end when you reach Door County; There's plenty to navigate by car as you wander the series of small towns located on a beautiful 75-mile peninsula surrounded by Lake Michigan and Green Bay. There are also 53 public beaches, five state parks, and 300 miles of shoreline so get ready to put some miles on your car. Need a pit stop? Milwaukee is a little less than half way. 

Louisville, KY

7.  Louisville, KY

Kentucky’s largest city, located just across the Ohio River from southern Indiana, is steeped in bourbon and long on charm. The home of the old fashioned and mint julep embraces its role as the gateway to Bourbon Country. The city now has over 10 tourable distilleries, including   Evan Williams,   Angel’s Envy   and  Old Forester . If bourbon and honkytonk aren't for you, downtown Louisville has an incredible art scene and is booming with independent businesses and charming shops. 

Discover the best things to do in Louisville

Madison, WI

8.  Madison, WI

Driving time from Chicago: Three hours

Sure the Midwest loves its college towns, but Madison's proximity to five surrounding lakes make it one of the more of the scenic ones. The abundance of waterways make kayaking, rafting and canoeing especially popular—you can book them directly through Madison Boats . For those averse to using their sea legs, there's the 16-acre Olbrich Botanical Gardens for all ages or the National Mustard Museum (yes, you read that correctly). It wouldn't be a trip to Wisconsin without trying blocks and blocks of cheese, so make sure to stop by the "Capital of Cheese" known as Fromagination in downtown Madison. 

Cincinnati, OH

9.  Cincinnati, OH

If Skyline Chili is not your bag, don’t worry—there’s a whole lot more to the Queen City than its most famous tourist foodstuff. Cincy has been undergoing a major glow-up over the past decade or so, from the ever-evolving Smale Riverfront Park, which offers lots to do and gorgeous views of the skyline and the Ohio River to the revitalization of the historic Over-the-Rhine neighborhood. There, you'll find a number of must-visit spots, including the popular Rhinegeist Brewery, the vibrant Findlay Market , the stunning Music Hall and Washington Park , which sports a sweet playground and community events throughout the year. Plus, the Cincinnati Zoo is one of the best in the country, and the only place you can see Internet icon Fiona the Hippo in person. That in itself is worth the trip.

Shawnee Hills Wine Trail, IL

10.  Shawnee Hills Wine Trail, IL

Driving time from Chicago:  Six hours

Not going to make it to Napa this year? Opt for the just-as-beautiful Shawnee Hills Wine Trail instead. The 3 5-mile scenic drive meanders through Shawnee National Forest in southern Illinois and features over 10  award-winning wineries in cute towns like Cobden, Alto Pass, and Pomona. If you need more than wine to prompt a trip, there's plenty of nature in the vicinity and the nearby town of Murphysboro is home to some of the finest BBQ in the Midwest at 17th Street Barbecue . 

Bloomington, IN

11.  Bloomington, IN

Driving time from Chicago:  Four hours

This cozy college town offers some big-city amenities, but it's the surrounding hills, forests and lakes that make it special. A short itinerary could look like: Hike the Deam Wilderness trails ; s ee the Morgan-Monroe State Forest wildflowers; admire the Cedar Bluffs Nature Preserve limestone bluffs; g o fishing at the reservoir lakes. Just don't forget to leave room for a meal at  Feast Market & Cellar , a family-owned kitchen with a lovely corner porch where everything is made from scratch daily. 

Saugatuck, MI

12.  Saugatuck, MI

Driving time from Chicago:  Two and a half hours

This dreamy lakeside town (and next-door neighbor Douglas) has long been a favorite of Chicagoans looking to spend time on the water, whether it’s a boat on the Kalamazoo River or a relaxing day on one of the area’s six clean, inviting beaches. From hiking the Saugatuck Dunes to window shopping on Butler Street to enjoying dinner and drinks alfresco, there are many ways to get some much-needed fresh air here. It’s also one of the Midwest’s best queer-friendly vacation destinations, home to more than 100 LGBTQ-owned and friendly businesses. 

Ann Arbor, MI

13.  Ann Arbor, MI

Driving time from Chicago:  Four hours

If you'd rather stick to less-crowded cities, skip Detroit and opt for Ann Arbor instead. Foodies and beer nerds will love this low-key vacation spot for its plethora of good restaurants and breweries. Home to the renowned University of Michigan, this city’s quaint downtown is full of unique shops, spots to eat and so much more (make sure Blank Slate Creamery is on your list). 

Toledo, OH

14.  Toledo, OH

The road from Chicago to Ohio is filled with worthwhile attractions, including Indiana Dunes State Park and the Hall of Heroes Super Hero Museum in Elkhart, Indiana. Once you arrive in Toledo, you'll be greeted with picturesque churches, wild urban parks, a trendy jazz culture and plenty of microbreweries to keep you busy. Just outside the city you'll also find fall-harvest overload in the way of apple and pumpkin farms where you can pick your own fruits and veggies and gorge on baked treats.

Shipshewana, IN

15.  Shipshewana, IN

Driving time from Chicago:  Two hours

OK, just hear us out. The heart of Indiana Amish country is a great option for a convenient road trip perfect for families, history buffs and, most of all, antiquers. The Shipshewana Trading Place Flea Market is a bargain-hunter’s dream—the largest flea market in the Midwest, with lively auctions Wednesday mornings. After a morning of browsing and bargaining, you’ll work up an appetite for some Amish home cooking, which you can even sample in a  literal Amish home . For outdoorsy types, nearby Mongo offers canoe and kayak rentals for a relaxing day on the water. 

Des Moines, IA

16.  Des Moines, IA

Driving time from Chicago: Five hours

There's a surprising amount to explore over a weekend in Des Moines, from more than 20 breweries in the metro area to the six-mile Art Route , which showcases 87 public art pieces from sculptures to murals. But what really makes Des Moines worth visiting are its summer events, like the eclectic 80/35 music festival, and, of course, the festive juggernaut that is the Iowa State Fair , where you can get 69 different food-on-a-stick creations (nice). When you're heading back on I-80, don't miss the World's Largest Truck Stop in Walcott, truly a site to behold.

Columbus, IN

17.  Columbus, IN

Driving time from Chicago : Three and a half hours

In the heart of Southern Indiana, Columbus is an unexpected center for boundary-pushing architecture—in fact, the American Institute of Architects ranked the city sixth in the nation for architectural innovation. Roughly 70 different constructions sprinkled around the city and county make this city an architectural wonder. Take an  Architectural Highlights Tour  of more than 30 of Columbus' structures and learn how this city became the state's award-winning arts and design destination. Make another pit stop of striking constructions with a stroll through Mill Race Park , an 85-acre riverfront park near the city's center. Once you’ve worked up an appetite, stop by  Columbus Bar , the oldest bar and restaurant in town.

Need more travel inspiration?

The best weekend getaways from Chicago for families

The best weekend getaways from Chicago for families

Take a break from the city and find family-friendly activities throughout the Midwest on these weekend getaways.

The best places to go camping near Chicago

The best places to go camping near Chicago

  • Things to do

Make a quick escape and spend a few nights amidst nature. 

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30 Delightful Road Trips from Chicago

If you’re looking to get away from the city, here are the best destinations for day trips and weekend road trips from Chicago.

Sunrise in Sheboygan Wisconsin from my balcony at Blue Harbor Resort

Chicago’s location makes it an ideal place to get in the car and go, whether you live in the city or you make it your home base for some Midwestern exploration.

I’ve lived in Chicago and its suburbs for twenty years, and in the Midwest my entire life (except for a brief four years in my early twenties).

Let’s just say I’ve been to a LOT of towns, villages, cities, parks, etc., that are within easy driving distance from the Windy City.

And while I love Chicago (I even wrote a book about it ) and The Local Tourist began as a guide to the city’s River North neighborhood, sometimes even I just need to get away.

I’ve hand-picked some of my favorite Midwest road trips from Chicago. If you’re looking for delightful towns with delicious food and drink, boutiques and artisan shops, intriguing history, outdoor adventures, natural beauty, and so much more, you’re sure to find your perfect road trip from Chicago.

Road trips are the equivalent of human wings. Ask me to go on one, anywhere. We’ll stop in every small town and learn the history and stories, feel the ground and capture the spirit. Then we’ll turn it into our own story that will live inside our history. Victoria Erickson

Love travel quotes? Here you go!

Sign marking the beginning of Route 66, which is one the best road trips from Chicago you can possibly take

There may be affiliate links in this post, which means we may get a small commission if you make a purchase. It’s at no extra cost to you and helps keep TLT free. Everybody wins!

Road Trips from Chicago

How to choose the best road trips from chicago.

Old rusty car that says LA to Chicago on back. Sitting in a field with grass growing around it

How far will you drive for a weekend trip?

I asked that question of members of The Local Tourist Facebook group and their answers surprised me. The winning time was five hours, and second place was four hours.

Several of these road trippers would even drive eight hours for a weekend vacation!

Based on their input, and my own obsession with road trips, I’ve included some destinations that require a few hours behind the wheel.

I’ve also included places that are much closer. In fact, there are a few towns and cities that are technically suburbs of Chicago. Depending on your starting point, these destinations may provide more of a staycation than a vacation.

But hey – that’s what being a Local Tourist is all about, right?

I’m only including destinations that I’ve personally visited and enjoyed. Clearly, I need to spend more time in Ohio and Michigan.

For each road trip destination, I’ve included driving time. This assumes you’ll be driving interstates and won’t be avoiding toll roads. It also assumes no traffic.

Depending on when you leave for your weekend road trips from Chicago, traffic could increase times by at least an hour, so check Google maps or Waze before you go.

I’ve also included suggestions for places to stay, as well as links to each destination’s official Convention and Visitors Bureau, or CVB. These local resources are my travel planning not-so-secret weapon .

Ready to plan your road trips from Chicago? Let’s go!

Related: before you go, check out all my tips for planning a road trip .

10 Day Trips from Chicago

If you’re looking for a quick getaway or even a day trip, these locations are short road trips from Chicago and all within two hours of the Windy City.

Elgin, Illinois

Driving time: 1 hour

Elgin History Museum is one of the many reasons Elgin is a good road trip from Chicago

Known as the City in the Suburbs, Elgin, Illinois, is a relatively quick drive or an easy train ride from downtown Chicago. Its proximity makes it perfect for a day trip, but there’s enough to do that you’ll want to make a weekend of it.

A good place to start is downtown Elgin. Located right on the Fox River, it’s filled with public art and historic buildings.

Get the history of the area at the Elgin History Museum (pictured above).

Historic home in Elgin Historic District

You can also take a free self-guided walking tour of the Elgin Historic District.

Since that walking will make you hungry, grab a sandwich at Blue Box Café or head up to West Dundee for a burger and a pint at Emmett’s Brewing Co., an award-winning brewery.

Outside of Emmett’s Brewing Co in West Dundee Illinois

Another one of the great things to do in Elgin is visit Lords Park and Zoo. On its grounds is the Elgin Public Museum, the only natural history museum in the Fox Valley.

Where to stay in Elgin, Illinois: Most of the hotels in Elgin are along the I-90 corridor. The Holiday Inn & Suites is one of the most highly rated accommodations near Elgin.

CVB: Explore Elgin Area,

Indiana Dunes National Park, Indiana

best road trips starting in chicago

One of our newest national parks is a short drive or train ride from Chicago. Established in 2019 , Indiana Dunes National Park is 15,000 acres along the southern shores of Lake Michigan.

There are over fifty miles of trails, making hiking Indiana Dunes National Park one of its top attractions. Hikers can traverse dunes, wetlands, prairies, rivers, and forests, all in one park.

There’s a fee to access the park: $15 per person (up to $25 per family group) and $25 per carload.

You could spend the entire weekend at the park. However, if you want a break, drive a little further east to Michigan City.

While the town is known for Lighthouse Place Premium Outlets, it’s also home to several museums, including the Old Lighthouse Museum.

Where to stay near Indiana Dunes State Park: Camping is available within the park itself, and there are several hotel chains in Michigan City .

CVA: South Shore Indiana,

Harbor Country, Michigan

Driving time: 1 hour 15 minutes

Round Barn Winery in Southwest Michigan, one of many wineries in Harbor Country

Just across the border from Michigan City, Indiana, is Harbor Country.

The Red Arrow Highway takes you through eight small towns, each unique, each charming in its own away. Think boutique instead of big box, locally owned versus chain.

Outdoor enthusiasts will find everything from kayaking and paddle boating to fishing, surfing, and golf. Of course, you can also spend the day at the beach.

Sculpture with lighthouse in the background at Silver Beach in Saint Joseph, Michigan in Harbor Country

One of the biggest attractions is the number of Southwest Michigan wineries and breweries. The climate is very similar to Napa Valley, and the area’s known for its award-winning wines.

Where to stay in Harbor Country: You can find inexpensive hotels as well as private homes in New Buffalo, Michigan .

CVB: Harbor Country Chamber of Commerce,

Kenosha, Wisconsin

Driving time: 1 hour 20 minutes

Kenosha Wisconsin frame and lighthouse with Lake Michigan on the horizon. Kenosha is one of many great road trips from Chicago.

Kenosha is the fourth largest metro area in Wisconsin, as well as the fourth-largest city on the shores of Lake Michigan, and there are TONS of things to do.

It’s the home of the oldest operating velodrome in the country, a free dinosaur museum, historic restaurants, not one but two lighthouses, and you can still ride an electric trolley.

Carthage Institute of Paleontology and the Dinosaur Discovery Museum in Kenosha Wisconsin

Start your visit at the Kenosha History Center for an overview of the area’s past. Then don’t miss the Dinosaur Discovery Museum or Kenosha Public Museum, both of which are free.

The Civil War Museum is an impressive look at Wisconsin’s role in the war.

A must-visit restaurant is House of Gerhard, featuring traditional German specialties. Another favorite is Franks Diner. Guy Fieri featured it on  Diners, Drive-ins, and Dives and it serves up tasty American cuisine with a side of sass.

Check out more reasons you should visit Kenosha, Wisconsin .

Where to stay in Kenosha: you can stay in Kenosha hotels that are conveniently located off I-94, or you can choose an historic inn like The Stella Hotel and Ballroom. For a great view, check out Wyndham Garden Kenosha, right on the harbor.

CVB: Visit Kenosha Wisconsin,

McHenry County, Illinois

Driving time: 1 hour 30 minutes

Gorgeous pond with lily pads and picturesque bridge at Fel-Pro RRR

I lived in McHenry County, whose northern border is shared with Wisconsin, for five years and still found new things to do.

One of the most surprising aspects of the area is the sheer number of parks. The McHenry County Conservation District manages more than thirty conservation areas, and most of them have hiking trails.

There are also city and village parks, as well as two state parks within the county.

Another great thing about the area is the food. Oh, the food! There’s farm-to-table at 1776 Restaurant and Duke’s Alehouse and Kitchen, incredible Italian at 750° Cucina Rustica, rich encased meats at Richmond Brathaus, and the best custard anywhere at Julie Ann’s Frozen Custard.

Sundae at Julie Ann's Frozen Custard with their signature ice cream truck in the background

All are local; all are family-owned; all are delicious.

McHenry County’s county seat is Woodstock, which you might recognize. It’s where Groundhog Day was filmed, and the town celebrates with their very own groundhog, Woodstock Willie.

Cherry Tree Inn Bed and Breakfast in McHenry County Illinois, where Bill Murray's character stayed in Groundhog Day

You can even stay in the same bed and breakfast where Bill Murray’s character woke up again, and again, and again.

With the mouthwatering breakfasts served each morning at Cherry Tree Inn Bed and Breakfast, though, you won’t mind if the same thing happens to you.

Read more about why I love being a Local Tourist in McHenry County , and you will, too!

Where to stay in McHenry County: Cherry Tree Inn Bed and Breakfast , of course! Since there are only four rooms, if they’re full, you can find hotels in Crystal Lake , the largest town in the county.

CVB: Visit McHenry County,

Starved Rock State Park

Waterfall in Starved Rock State Park

Head to Starved Rock State Park for a day of fresh air, physical fun, and outdoor adventure.

Located just 94 miles southwest of Chicago, the landscape is an unexpected tableau of bluffs, steep trails, and waterfalls. Since it’s on the Illinois River, there’s also fishing and boating.

You can bring a lunch to enjoy at the waterfront picnic area, or grab a bite to eat at the historic lodge.

Nearby Ottawa is a charming town with lots of creative chefs, so you can have the best of both worlds.

Where to stay in Starved Rock State Park: There’s a lodge at the park itself, but I personally prefer camping. Starved Rock has one of the best campgrounds in the Midwest .

Janesville, Wisconsin

Driving time: 1 hour 45 minutes

Exterior of Lincoln-Tallman House in Janesville Wisconsin, a must-see when you take a road trip from Chicago

Located right off I-90, Janesville is an ideal weekend road trip from Chicago, especially if you like the great outdoors, art, and history.

The town’s tagline is “Wisconsin’s Great Outside,” and there are thirty miles of trails in Janesville, including a portion of Wisconsin’s Ice Age Trail. One of the most scenic treks is the mile and a half hike to Devil’s Staircase.

Devil's Staircase on Wisconsin's Ice Age Trail in Janesville

The Rotary Botanical Gardens is a non-profit garden covering twenty acres. You won’t want to miss their Holiday Light Show.

From Thanksgiving weekend through December, the gardens become a magical winter wonderland strewn with hundreds of thousands of lights.

Holiday Light Show at Rotary Botanical Gardens in Janesville Wisconsin

History buffs will get a kick out of exploring Janesville’s thirteen historic districts. One of the highlights of any visit to Janesville would be the Lincoln-Tallman House.

Built in 1857, it’s been a museum since 1951. Eighty-five percent of the furnishings in the house are original, including the bed that Lincoln slept in when he was a guest.

Janesville’s dining scene is relatively new, but with restaurants like Genisa Wine Bar and the Sandwich Bar, it’s gaining steam and there are enough unique spots to keep your palate happy.

I definitely recommend bellying up to the 1933 Art Deco bar at O’Riley and Conway’s Irish Pub for some Scotch eggs.

Combine history and beer at Gray Brewing Co. They’ve been brewing beer since 1856, except during that pesky Prohibition when they turned to sodas. It’s one of the oldest family-owned breweries, not just in Wisconsin, but in the United States.

best road trips starting in chicago

When you visit Janesville, make sure you’ve got your walking shoes and plenty of room on your SD card, because the town is filled with vibrant and colorful murals.

Where to stay in Janesville, Wisconsin: Renovated in 2019, the Hampton Inn provides comfortable rooms with modern décor. Breakfast is included, and it’s one of the better spreads I’ve seen.

When I stayed, the hot items were frequently replenished and there were several options including both waffles and mini-waffles.

CVB: Janesville Area Convention and Visitors Bureau,

Lake Geneva, Wisconsin

Yerkes Observatory in Lake Geneva Wisconsin

Located just 75 miles northwest of Chicago on the other side of the Wisconsin border, Lake Geneva provides a year-round escape from hectic city life and is a short day trip from Chicago or great weekend destination.

One attraction with a direct tie to Chicago is the Yerkes Observatory (pictured above).

Yerkes is considered the birthplace of modern astrophysics and was funded by Charles Yerkes, who had a huge role in developing Chicago’s public transportation.

Lake Geneva has long been a playground for Chicagoans. In the late 1800s and early 1900s, it seemed that every wealthy Chicagoan built a mansion on the shores of the lake. Today, many of those mansions still stand.

The best way to see them is to take a boat tour, especially if you can ride along when they’re delivering the mail. Lake Geneva is one of the few places left in the country where mail is delivered by boat.

Mansions on Geneva Lake seen from the mailboat tour

Another way to see the mansions is to walk the path that surrounds the lake. Like Chicago’s lakefront with its public beaches, Geneva Lake is surrounded by a trail that’s open to everyone.

The lakefront path is one of the most popular things to do in Lake Geneva .

One place you can only visit from a boat, unless you have physical limitations and can’t climb the many stairs from the dock, is Black Point Estate. This historic mansion has many ties to Chicago, including Jane Addams .

Black Point Estate on Geneva Lake, an historic mansion with many ties to Chicago.

For something completely different, feed an ostrich. Safari Lake Geneva is a drive-through experience that allows you to feed giraffes, alpacas, elands, and emus.

An experience that’s both fun and tasty is taking a class at Lake Geneva Cooking School. Chef John teaches you how to make dishes you might never attempt on your own, and he pairs them with stellar wines.

Like many, during lockdowns he pivoted and fulfilled his dream of publishing a cookbook . I’ve made several recipes from it, and highly recommend it.

Golf is one of Lake Geneva’s biggest draws. During the winter months, you can ski, snowboard, snowshoe, and ice fish.

Where to stay in Lake Geneva: Technically located in Fontana on the west side of Geneva Lake, The Abbey Resort is a sprawling complex with beautiful rooms overlooking a marina.

They also have multiple pools and there’s often live music, either in the bar or outside during the summer.

CVB: Visit Lake Geneva,

Milwaukee, Wisconsin

Harley Davidson Museum entrance - one of the many things to do in Milwaukee, an easy road trip from Chicago.

Milwaukee, Wisconsin, is an urban getaway filled with culture and outdoor fun.

The instantly recognizable Milwaukee Art Museum is definitely worth visiting, and after you’ve browsed its collections you can take a walk along the lakefront.

For more art, book a room at Saint Kate The Arts Hotel . This astounding hotel is like staying in a work of art – because you are. It’s right downtown, providing easy access to the river walk.

Beer lovers will have a blast exploring Milwaukee’s breweries. Lakefront Brewery is known for its fun tours. Milwaukee Brewing Company and Mobcraft are also great places to visit.

There’s no beer at the Pabst Mansion, but you’ll still want to see Captain Frederick Pabst’s house, built in 1892. It’s a gorgeous Flemish Renaissance Revival mansion that’s on the National Register of Historic Places.

Fun fact: Captain Pabst earned his stripes with the Goodrich Line of steamships, which was based out of Chicago.

Another nautical stop is North Point Lighthouse. Built in 1888 high on a bluff, Frederick Law Olmsted himself designed the grounds. Chicagoans will recognize the famous landscaper’s name from the 1893 World’s Columbian Exposition and the University of Chicago, among others.

Olmsted also landscaped Lake Geneva’s Yerkes Observatory, which was part of the University until recently.

The Harley-Davidson Museum is another must-stop and be sure to dine at Motor, the on-site restaurant.

During the summer there are festivals just about every weekend, so check Visit Milwaukee’s events calendar to find out what’s happening.

And of course, make sure you have some cheese curds, brats, and beer.

Where to stay in Milwaukee: Saint Kate The Arts Hotel for a modern art experience, The Pfister Hotel for a dose of history, and Iron Horse for more industrial décor and easy access to the Harley-Davidson Museum.

CVB: Visit Milwaukee,

Lafayette, Indiana

Driving time: 2 hours

Haan Mansion Museum of Indiana Art

My grandparents lived in West Lafayette, Indiana, so I grew up visiting. However, it wasn’t until a few years ago that I actually explored the town. Boy, had I been missing out on a lot.

Known as the home of Purdue University, West Lafayette, and its sister city Lafayette, have history, art, culture, delicious food and drink, and a vital sense of community.

There are several places that make this a great place for a road trip from Chicago. One is the Haan Mansion Museum of American Art.

The mansion was originally built for the 1904 World’s Fair in Saint Louis. Now it’s in West Lafayette and is filled with impressionist paintings and historic furniture.

SAMARA in West Lafayette, Indiana

Another is SAMARA. Designed inside and out by Frank Lloyd Wright for Dr. John and Catherine Christian, it’s a nearly perfectly preserved example of Wright’s Usonian architecture.

Another fascinating spot is Prophetstown State Park, combining a landscape that’s distinctly Indiana with the history of the Native Americans who fought the settlers’ encroachment, and the farmers who eventually tilled the land. While there, visit the nearby Tippecanoe Battlefield.

I’ve got even more places to visit in Lafayette. These include not only places I’ve been, but also spots recommended by students at Purdue University. I’ve partnered with a 400-level travel-writing class since 2018, and many of their submissions are local to the college town.

See why you should visit Lafayette and West Lafayette Indiana

Where to stay in Lafayette, Indiana: Mr. TLT and I loved the cozy intimacy of Black Blanket Farms Bed and Breakfast . If they’re booked, Lafayette has a gazillion hotel options since it’s a college town.

CVB: Visit Lafayette-West Lafayette,

9 Weekend Road Trips from Chicago between 2 and 3 hours

Shipshewana, indiana.

Driving time: 2 hours 15 minutes

Blue Gate Restaurant in Shipshewana, Indiana, with man-made pond and bushes in foreground and people outside.

If you’re looking for a slower pace, yet still want plenty to do, add Shipshewana to your weekend adventures.

Shipshewana is in LaGrange County, also known as Indiana Amish Country. You’ll know when you get close because you’ll start seeing horse-drawn buggies and bicyclists everywhere.

With the third largest Amish population in the world, this area is a definite departure from the hustle and bustle of city life. Instead, it’s antiques and hand-crafted furniture, delicious food, and fun entertainment.

One of Shipshewana’s most well-known attractions is the Shipshewana Flea Market . Begun in 1922 with a livestock auction, this family-owned business is the largest flea market in the Midwest.

Learn what it’s like to attend the Shipshewana Misc & Antique Auction .

You also don’t want to miss the Davis Mercantile . Another family affair, it’s a destination for dining, shopping, and riding the carousel.

If you plan your trip in advance, you might be able to dine in an Amish home, which is a real treat (and the best mashed potatoes ever). If it’s a last-minute getaway, The Blue Gate Restaurant is always a favorite. After dinner, head upstairs for a show at the theater.

Other fun things to do in Shipshewana include touring Cook’s Bison Ranch, exploring one of the many county parks, having dinner in an Amish home , canoeing or kayaking on the Pigeon River, and taking a driving tour on a hunt for barn quilts.

Where to stay in Shipshewana: The Blue Gate Garden Inn is a comfortable hotel that’s filled with amenities, including outdoor fire pits and an ice cream shop.

CVB: Visit Shipshewana,

Sheboygan, Wisconsin

Driving time: 2 hours 30 minutes

When people ask me the destination that surprised me the most, Sheboygan, Wisconsin, tops the list.

I visited in August 2021, and it was my first press trip post-cancer. It was exactly the experience I needed: waves, beaches, amazing food, brilliant art, and a community that preserves its past.

Your first stop should be the Sheboygan Visitor Center. It is absolutely the coolest visitor center I’ve ever seen – and I’ve been to a lot.

Sheboygan’s known as the Malibu of the Midwest, so of course I had to get out on the water. One of my favorite things to do was take a first sailing lesson in Lake Michigan. That’s right – you can learn how to sail on a weekend trip to Sheboygan.

Learning how to sail in Sheboygan Wisconsin

The Kohler name is prominent in the area. In addition to the manufacturing company and a nearby resort, there’s also the Kohler Arts Center and the Kohler Art Preserve, which opened in 2021.

Kohler also manages the James Tellen Woodland Sculpture Garden, one of several artist-built environments throughout the state.

A squirrel sits on top of a sculpture of a gnome playing a cello, part of the James Tellen Woodland Sculpture Garden near Sheboygan, Wisconsin

History geeks will want to stop at Sheboygan Indian Mound Park and the Sheboygan County Historical Society and Museum.

For dining, don’t miss Black Pig, Il Ritrovo, and BoMallies. Breakfast should absolutely begin at Paradigm Coffee and Music. Best. bagel. sandwich. ever.

Check out my piece about this surprising place, and I’ve even included the perfect 3-day Sheboygan itinerary .

Where to stay in Sheboygan: Blue Harbor Resort offers gorgeous rooms and an even better view. They’ve also got a whole water park, on-site dining, and easy access to the beach.

CVB: Visit Sheboygan,

Elkhart Lake, Wisconsin

Dock extending into Elkhart Lake at sunset

About twenty minutes from Sheboygan is another delightful road trip from Chicago.

Elkhart Lake has all the feelings of a resort town. There are historic accommodations, unique boutiques, and delicious dining.

The eponymous lake is gorgeous, with crystal clear water. You can take a pontoon boat ride, or go kayaking or paddle boarding.

The village is also right by the Ice Age Scenic Trail and Kettle Moraine State Forest – Northern Unit, providing lots of opportunity for outdoor activities.

Racing fans won’t want to miss Road America. This four-mile road course is considered the best in the United States and one of the top in the world.

Not only can you watch racing, you can also take a spin around the track yourself. They offer both motorcycle and automobile driving schools.

Where to stay in Elkhart Lake, Wisconsin: Osthoff Resort is an historic inn that offers a variety of room options, including suites and villas, and features amenities such as an indoor and outdoor pool, spa, and fitness center.

The resort also has several dining options on-site, including a fine-dining restaurant and a casual bistro.

CVB: Elkhart Lake, visit website

Galena, Illinois

Driving time: 3 hours

Historic downtown Galena, Illinois

Galena, Illinois, is located near the Mississippi River on the opposite side of the state from Chicago. Surrounded by the rolling hills and bluffs of the Driftless Region, it’s an area dotted with wineries and golf courses.

There are many reasons nearly a million people visit the former mining mecca each year. From shopping along its historic main street to the many wineries in the area, it’s a great spot for a romantic weekend or a girls getaway.

A stroll down Main Street feels like a step back in time. Be sure to stop into Galena Canning Company for a taste of salsas and jams, and Galena Brewing Company offers a lineup of tasty beers.

Thrill-seekers will love a visit to Long Hollow Canopy Tours , a zipline adventure through the woods.

Long Hollow Canopy Tours in Galena Illinois near Eagle Ridge Resort

Nature lovers can explore trails along the nearby Mississippi River, and golfers will love a few rounds at Eagle Ridge Resort & Spa.

There are also several historic buildings, and the Ulysses S. Grant Home is one of the most popular places to visit for a look into the past.

Where to stay in Galena, Illinois: While there are hotels that are closer to Galena’s historic Main Street, two of my favorites are a short drive from downtown. Goldmoor Inn Bed and Breakfast is an elegant getaway overlooking the Mississippi River.

Eagle Ridge Resort and Spa is my home away from home when I’m in Galena. I’ve stayed there at least five times. I love the variety of accommodations, activities, and the delicious food.

CVB: Visit Galena,

Hendricks County, Indiana

Pond at Natural Valley Ranch in Hendricks County Indiana, an easy road trip from Chicago

My first visit to Hendricks County, Indiana, was in 2017, and since then I’ve returned four? five? times. You might say I like it. I even taught the first writing workshop for Midwest Travel Network (I’ve now taught three) at Natural Valley Ranch, a cabin with that private pond out its back door.

There are also horses, that you can ride. Squeee!

It’s a large county comprised of several towns. Some are large, like Plainfield and Avon, and others are small, like the tiny Lizton, which is home to the best barbecue – and pecan pie – in Indiana (and possibly the Midwest).

Race fans not only have easy access to the Indianapolis Motor Speedway, they can also see the NHRA Finals at the Lucas Oil Raceway within Hendricks County.

The only Doctor Who Museum and Store is in Hendricks County, as is the Tie-Dye Lab, where you can make your own tie-dye apparel. Beasley’s Orchard has the best apple cider. Oasis Diner is the only diner on the National Road and it’s got one of the best pork tenderloin sandwiches anywhere.

Basically, go to Hendricks County . There’s so much to do I bet you’ll want to go back again and again, just like I do.

Where to stay in Hendricks County: Natural Valley Ranch is great if there’s a big group of you exploring the area. If not, then I’m a fan of Staybridge Suites . Each room includes a kitchenette, plus they offer free breakfast and weekday happy hours.

CVB: Visit Hendricks County,

More Road Trips from Chicago between 2 and 3 hours

  • Madison, Wisconsin; 2 hours 45 minutes
  • New Glarus, Wisconsin; 2 hours 45 minutes
  • Indianapolis, Indiana; 3 hours
  • Quad Cities, Illinois/Iowa; 3 hours

11 Weekend Road Trips from Chicago between 3 and 5 hours

Fort wayne, indiana.

Driving time: 3 hours 10 minutes

Columbia Street at The Landing in Fort Wayne

When you go to Fort Wayne, go hungry. And thirsty. This northeastern Indiana town has a thriving food and beer scene that will have you coming back for more.

This All-American City is located at the confluence of three rivers, and that riparian location has fed its personality since it was founded when General “Mad” Anthony Wayne built a fort there in 1794. That fort didn’t last long, and by 1815 the town was on its third fort, built by Major John Whistler.

Chicagoans might recognize that name: he built Fort Dearborn when he was a Captain. You can visit a replica of Whistler’s fort, and they often have events.

Reenactors at Old Historic Fort Wayne

One of the best things to do in Fort Wayne is visit the YLNI Farmers Market. This bustling marketplace features everything from handmade chocolates to hot sauces that’ll blow your top off to candles that smell like Fort Wayne (and Montana, Chicago, and everywhere else Simple Nature‘s creative creator has been). 

But what about that food, you ask? A few favorites include Club Soda, for white tablecloth dining with a side of live music, Birdie’s for shared plates in an airy rooftop, and Hall’s Prime Rib for down-home diner cooking.

Burrata at Birdie's in Fort Wayne Indiana

Beer fans will want to belly up at Junk Ditch, The Hoppy Gnome, and Hop River Brewing Company.

Where to stay in Fort Wayne, Indiana: Courtyard Fort Wayne Downtown at Grand Wayne Convention Center is in a great location; across from the convention center and in between Parkview Field and Embassy Theatre.

CVB: Visit Fort Wayne,

Green Bay, Wisconsin

Driving time: 3 hours 15 minutes

Captain's Walk Winery in Green Bay Wisconsin

While it may seem blasphemous to some to suggest driving to the home of the Packers from the home of the Bears, I guarantee there’s a lot more going on than gridiron battles.

Auto enthusiasts will love The Automobile Gallery. Opened in 2016, this collection of pristine vehicles span over a century of automotive history.

best road trips starting in chicago

From the iconic 1908 Cadillac Model T to the sleek 1960 Chevrolet Corvette, every car enthusiast will find something to admire.

The museum also features a rotating selection of vehicles, ensuring that there is always something new and exciting to discover.

For transportation of another kind, visit the National Railroad Museum. The museum began in 1956 and now covers a sprawling 33-acre campus.

Not only can you see locomotives like the iconic “Big Boy” No. 4017, you can step inside a Pullman sleeper car and learn about the porters who worked America’s rail lines.

Ready for a drink? From Captain’s Walk Winery to Zambaldi Beer, you’ll find something to whet your whistle.

And if you’re hungry, Green Bay will keep you fat and happy. (Speaking from experience here.) Don’t miss the authentic kringles at Uncle Mike’s Bake Shoppe or a cup of Booyah, a hearty Belgium chicken stew.

Where to stay in Green Bay, Wisconsin: Stay in the heart of Green Bay at the historic Hotel Northland . The hotel’s especially great for a romantic getaway.

CVB: Discover Green Bay, website

Dubuque, Iowa

Driving time: 3 hours 20 minutes

View of downtown Dubuque Iowa from the top of the Fenelon Place Elevator

You’ll be glad Dubuque Iowa is one of these easy road trips from Chicago, because there’s so much to do you’ll want to return again and again.

Dubuque’s location on the Mississippi means it’s filled with river lore. Begin your visit at the Mines of Spain, a National Historic Landmark and Iowa State Recreation Area. It’s named for the mines that Julien Dubuque, the town’s founder, worked with permission from first the Mesquakie and then the Spanish. The Julien Dubuque Monument resembles a rook and overlooks the Mississippi; Dubuque is buried on the site.

Julien Dubuque Monument at the Mines of Spain State Recreation Area in Dubuque Iowa

Get an in-depth introduction to the river and the region at the National Mississippi River Museum and Aquarium, then go on the river itself. You can take a steamboat tour or an American Lady River Cruise aboard a yacht.

Like Janesville, Dubuque’s downtown is also covered with murals, and it’s a fun afternoon to walk the streets and find your favorite.

Dubuque’s most unusual attraction is the Fenelon Place Elevator. It’s the shortest, steepest railroad and a ride to the top provides some of the best views in the city.

The world's shortest steepest railroad is the Fenelon Place Elevator in Dubuque Iowa

Another spot for great views is Eagle Point Park. You’ll get a birds eye view of Lock and Dam #11 and can see into both Wisconsin and Illinois.

One of the most famous attractions is in nearby Dyer. The Field of Dreams Movie Site is surprisingly moving, especially now that you can tour the house. Inside you’ll discover stories behind the filming of this beloved classic.

I think the food scene in Dubuque will surprise you. It certainly surprised me to discover several innovative chefs serving quality cuisine. Make reservations for both Brazen Open Kitchen and Pepper Sprout and you’ll be one happy diner.

Lobby of Hotel Julien Dubuque

Where to stay in Dubuque, Iowa: since it’s right downtown, you can’t get much more convenient than Hotel Julien Dubuque . Plus, it’s a gorgeous hotel with oodles of history, including stories about Mr. and Mrs. Lincoln and a certain gangster from Chicago.

CVB: Travel Dubuque,

Brown County, Indiana

Driving time: 4 hours

Brown County Playhouse

Brown County, Indiana, is known for its beauty when the leaves change colors, but that doesn’t mean you can only visit in the fall. The rolling hills are beautiful year round.

While the area is easy to get to now, that wasn’t always the case. Its relative isolation fostered a vibrant artists community, which thrives to this day.

Visit Brown County and you can see the home and studio of one of the founding artists T.C. Steele. He was one of the five members of the acclaimed Hoosier Group. In the late 1800s, that group put Indiana’s art scene on the map, and Brown County in particular.

Browse the galleries of Nashville, Indiana, and you’ll see works of art from those early painters as well as artists of today.

Get a two-for-one cultural experience at Country Heritage Winery. Not only can you taste wines, when you take a weekend road trip from Chicago, you can do so while listening to live music.

Another favorite is Hard Truth Hills. Inspired by Sierra Nevada’s set-up in Asheville, North Carolina, this is a multi-purpose destination with a brewery, a distillery, a restaurant, and an outdoor stage. Pro tip: get the to-die-for pulled pork nachos.

Brown County is one of those places where you can choose to go-go-go, or you can kick back and relax. Either way, it’s definitely worth the drive.

Learn more about Brown County and how it became the tourist destination it is today.

Where to stay in Brown County: Abe Martin Lodge is located within Brown County State Park. Bring the kids and your swimsuits; they’ve got an indoors water park. Want something more secluded? There are cabins, too.

CVB: Brown County,

Sandusky, Ohio

Driving time: 4 hours 45 minutes

Taking a tour with Sandusky Segwave is a great way to explore Sandusky, Ohio. In this photo, the tour director is pointing out something of interest in a city park.

Sandusky is most famous for being the home of Cedar Point amusement park, but this city on the shores of Lake Erie is much more than roller coasters and funnel cakes.

A fun way to get an overview is to take a Segway tour. Sandusky Segwave offers guided tours through the historic downtown. Perched atop your personal transporter, you’ll glide past historic sites, through city parks, along the lakefront, and past the Merry-Go-Round Museum. You’ll learn about the town’s very beginnings, as well as its role in the Underground Railroad.

Another reason to visit Sandusky is Kelleys Island. Take a high-speed ferry to the largest American island in Lake Erie for a day of art, shopping, and wine.

While you’re on the island, don’t miss Glacial Grooves State Memorial. This National Natural Landmark protects the largest easily accessible grooves in the world. To see them is to witness the power of the glaciers that shaped North America.

Glacial Grooves State Memorial. This National Natural Landmark protects the largest easily accessible grooves in the world. To see them is to witness the power of the glaciers that shaped North America.

Before you go back to Sandusky, get a scoop of Lake Erie Cookie Island Monster. It’s the official ice cream of Ohio’s Lake Erie Shores and Islands , Sandusky’s visitors bureau.

Warning: it will turn your tongue blue!

Check out my guide to see many more things to do on Kelleys Island .

Lake Erie Cookie Island Monster at Dipper Dan's on Kelleys Island,

Where to stay in Sandusky, Ohio: Hotel Kilbourne . This place puts the boutique in boutique hotel. In addition to being the only Sandusky hotel that’s on the water, it’s also got a rooftop bar and an on-site restaurant.

CVB: Ohio’s Lake Erie Shores and Islands,

Driving time: 5 hours, or as long as you’d like!

Illinois Route 66 sign with the L tracks in the background

Route 66 epitomizes the freedom of the open road, and it begins in Chicago. The route became official in 1926, providing many small towns access to significant national roadways for the first time. Although it was decertified in 1985, the Mother Road lives on.

This scenic byway changed course over the years, and these alignments are well marked in Illinois. If you’re short on time, I-55 will take you from one attraction to the next, but the fun of driving one of the country’s most historic byways is in following its original path.

Some of the most popular roadside attractions include Buckingham Fountain (not technically on Route 66, but you’re so close!), the Gemini Giant, Bunyon’s Statue, and Carlinville’s Million Dollar Courthouse.

Route 66 in Illinois is only 301 miles, but it’s nearly a century of Illinois history, so take your time.

More road trips from Chicago between 3 and 5 hours:

  • Iowa City, Iowa; 3 hours 45 minutes
  • Door County, Wisconsin ; 3 hours 50 minutes
  • Bloomington, Indiana ; 4 hours
  • Spencer, Indiana : 4 hours
  • Collinsville, Illinois and Cahokia Mounds State Historic Site : 4 hours 45 minutes
  • Traverse City, Michigan; 4 hours 55 minutes

Want an epic trip from Chicago but don’t feel like driving? Consider a train to Seattle – here’s what it’s really like to ride the Amtrak Empire Builder !

Map of Road Trips from Chicago

I hope these delightful road trips from Chicago will help you find someplace wonderful to visit for your weekend getaways. Each place is special and offers unique experiences. When you go, I’d love it if you’d share your photos in our Facebook group .

Oh, and be sure to bookmark this page, because I’ve got more destinations to add!

Hit the road with dozens of road trips from Chicago. Photo is of a Segway tour in Sandusky, Ohio on the bottom and downtown Galena, Illinois, on the top.

Dang Travelers


The Best Road Trips from Chicago with Itineraries

Looking to get out and explore? There are so many unique places to visit that are just a car ride away! From quaint small towns to interesting cities to exciting outdoor adventure and everything in between, here are the best road trips from Chicago.

Afterward, you may also be interested in reading suggestions for

Fun Spring Break Trips from Chicago .

The Best Road Trips from Chicago

Starting with quick weekend getaways, this list is ordered by distance and ends with long road trips from Chicago.

best road trips starting in chicago


This 90-mile scenic route will take you through northern Indiana's off-the-beaten-path towns where time slows down. The loop rambles through the communities of Goshen, Elkhart, Middlebury, Nappanee, Bristol, Wakarusa, and Shipshewana.

You'll discover winding country roads, talented artists, old-fashioned entertainment, recreational areas, blossoming gardens, and delicious treats.

From mid-May to mid-September, the trail coincides with the colorful Quilt Gardens project. 16 gigantic gardens and 23 painted murals embellish the trail with dazzling flowers in unique designs.

Drive Time: 2 hours to Elkhart Visitor Center

On the Way: University of Notre Dame, The Oliver Mansion, and Bonnie Doon Drive-In.

What to Do: Quilt Gardens, Wellfield Botanical Gardens, RV/MH Hall of Fame & Museum, Pumpkinvine Bike Trail, Ruthmere Mansion, Old Bag Factory, Linton's Enchanted Gardens, Bonneyville Mill County Park, and Menno-Hof.

Where to Eat & Drink: Rise N' Roll, Blue Gate Restaurant & Bakery, Iechyd Da Brewing, Das Dutchman Essenhaus, and Dutch Country Market.

Where to Stay: Excellent Hotel with a Great Location and Free Buffet Breakfast

best road trips starting in chicago


If you're looking for a relaxing destination with beach access, good restaurants, and a bike trail, South Haven is it. With its close proximity, southwest Michigan is amongst the top one day road trips from Chicago.

The walkable idyllic small town is right down the street from the Lake Michigan waterfront where you can see some of the best sunsets in the Midwest. There's plenty of opportunities to get out on the water: charter a fishing boat, take a sailing excursion or rent a jet ski.

If you'd like to do more than hit the beach then check out the Kal-Haven Trail, a former railroad route, that runs 33.5 miles from South Haven to Kalamazoo. It's a quiet and easy ride through blueberry fields, tree tunnels, and across a few bridges.

Drive Time: 2 hours, 15 minutes

On the Way: Four Winds Casino

What to Do: Kal-Haven Trail, DeGrandchamp Farms, Michigan Maritime Museum, Friends Good Will Tall Ship, and the Farmers Market.

Where to Eat & Drink: Golden Brown Bakery, Harbor Light Brewery, Chomp Gourmet Hot Dogs, Captain Nemo's, Phoenix Street Cafe, Idler Riverboat, Clementine's, and 12 Corners Vineyards.

Where to Stay: Historic Hotel in the Heart of Town walking distance to the Beach

best road trips starting in chicago


Galena is a must-experience destination in the Midwest especially if you live in Illinois. It is one of the unforgettable places to visit near Chicago with rolling hills, historic landmarks, and a super charming Main Street that will make you feel like you stepped into a Hallmark movie.

Start your visit at the historic Old Market House built in 1845 and now serves as Galena's Welcome Center. You'll learn about the fascinating history of the area and find information for your visit.

From springtime through fall, bike the River Trail, hike at Casper Bluff Preserve, or paddle the Galena River. The Alpine Slide, a 2,050-foot outdoor track, is a unique 2-minute adventure on the banks of the Mississippi River.

When the snow starts to fall, hit the slopes at Chestnut Mountain, one of the most popular ski destinations in the Midwest, or ice skate, sled or snowshoe at The Nordic Center at Eagle Ridge Resort.

While in town, hop on a trolley for a tour, visit wineries, and browse all the specialty and boutique shops.

Galena is on the Great River Road in Illinois along with some other special stops that make the scenic byway a unique Midwest road trip. Click on the link to read all about it!

Drive Time: 2 hours, 45 minutes

On the Way: Rafters Restaurant, Apple River Fort State Historic Site, Highway 20 Brewing Company, Horseshoe Mound Preserve, and Long Hollow Scenic Overlook.

What to Do: Galena Cellars Vineyard, Ulysses S. Grant Home, Galena Trolley Tour, and Grant Park

Where to Eat & Drink: Frank O'Dowd's Irish Pub & Grill, Durty Gurt's, The Log Cabin Steakhouse, Fried Green Tomatoes, Otto's Place, and Gobby's Sports Pub & Eatery.

Where to Stay: Cozy Hotel with an Indoor Pool & Spa and Cool Bar

best road trips starting in chicago


Indiana has 98 historic covered bridges and Parke County is home to 31 of them. The central west area is also home to Indiana's largest festival, The Parke County Covered Bridge Festival, held every October in honor of the famous crossings.

Here, you'll also find quaint towns among rolling hills and two state parks to hike with deep gorges, wooden ladders, rocky hollows, and natural arches making the area one of the best fall road trips from Chicago.

Drive Time: 3 hours

On the Way: Kankakee Sands Bison Viewing

What to Do: Bridgeton Mill, Turkey Run State Park, Mansfield Roller Mill and Covered Bridge, Narrows Covered Bridge, Rockville Lake Park, Roseville Covered Bridge and downtown Rockville.

Where to Eat & Drink: Wheel House Donuts, Cross at Walk Winery, Thirty-Six Saloon, Big Berry, and Drunk Tank Winery.

Where to Stay: Cabin or Hotel Stay with an Indoor Pool

best road trips starting in chicago


Under 200 miles away from Chicago and just 23 miles north of Indianapolis, Hamilton County is a fantastic option for a weekend getaway.

With lively communities bursting with arts and entertainment districts, outdoor activities, historic squares, boutique shopping, and diverse restaurants, Hamilton County deserves its own place on the list.

If you like to eat and drink, you can dedicate an entire weekend chasing giant pork tenderloins, local donut shops, and/or craft breweries. Make sure to spread your time evenly within the cities of Westfield, Carmel, Noblesville, and Fishers.

On the Way: Fair Oaks Farm, Cairo Skywatch Tower, Wildcreek Winery, and Jerry E. Botanic Gardens.

What to Do: Monon Bike Trail, Carmel Arts and Design District, Strawtown Koteewi Park, Hamilton County Courthouse & Old Sheriff's Residence and County Jail, Center of the Performing Arts,

Where to Eat & Drink: Urban Vines Winery and Brewery, Wolfies Grill, Rosie's Place, Cafe Patachou, Books & Brews, and Divvy Restaurant.

Where to Stay: Upscale Boutique Hotel in a Great Location

best road trips starting in chicago


Home to the state capitol, the world's oldest continuously operated racecourse, and the world's largest children's museum, Indianapolis has endless vacation potential.

Kick off your visit at Monument Circle, an impressive centerpiece circling the 284- foot tall Soldiers' and Sailors' Monument. The spectacular views from the observation deck will get you pumped to explore the city.

Once back on the ground, don't miss The Indianapolis Motor Speedway Museum, home of the Indy 500, for a chance to learn all about the history of racing, fast cars, and to see the track up close and personal.

For those looking for outdoor adventure, the Central Canal and White River State Park offer quiet respites from the bustling urban atmosphere with biking, pedal boat rentals, kayaking and segway tours.

If traveling with kids, spend an entire day at the gigantic Children's Museum of Indianapolis. Each exhibit will entertain the whole family.

What to Do: Indianapolis Motor Speedway, The Children's Museum, Monument Circle, Connor Prairie Interactive History Park, Canal Walk, Indiana State House, White River State Park, and Indianapolis Zoo.

Where to Eat & Drink: St. Joseph Brewery, Cafe Patachou, BRU Burger Bar, The Rathskeller, St. Elmo Steak House, and Slippery Noodle Inn.

Where to Stay: Hotel with Ideal Downtown Location & Indoor Swimming Pool

best road trips starting in chicago


It's time to ditch Lake Michigan and discover another one of the Great Lakes. You can pick up the Lake Erie Ohio Coastal Trail in Toledo and follow the shoreline to Conneaut.

Along the 293-mile route, you'll discover the second-oldest operating amusement park in the United States (which happens to also be the best in the Midwest), old-time lighthouses, water parks an underrated cool city, swimming beaches, coastal towns, and beautiful state parks.

Being along the lake, there are numerous outdoor activities to choose from, plus historical and entertaining options on the drive. You'll have a newfound love and appreciation for Lake Erie after this sensational road trip.

Drive Time: 4 Hours to Toledo

On the Way: University of Notre Dame, Shipshewana, RV/MH Hall of Fame & Museum

What to Do: Marblehead Lighthouse State Park, Cedar Point Amusement Park, Rock n' Roll Hall of Fame, and Fairport Harbor Marine Museum and Lighthouse.

Where to Eat & Drink: Dock's Beach House Restaurant in Port Clinton, New Sandusky Fish Company, Mary's Kitchen in Geneva-on-the-Lake, Old Prague in Vermilion, Madsen Donuts in Geneva, and White Turkey Drive-in.

Where to Stay: Waterfront Property near Cedar Point

best road trips starting in chicago


Bloomington tops the list of coolest college towns in the Midwest. There's always something going on between outdoor festivals, sports games, and music events.

Take a tour of one of the most beautiful campuses in the nation, go brewery hopping, or explore the area's natural beauty.

There's a reason Bloomington is referred to as the "Gateway to Scenic Southern Indiana," just twenty minutes away is the beautiful Lake Monroe and the Hoosier National Forest.

Drive Time: 4 hours

What to Do: Hickory Ridge Fire Tower, B-Line Trail, Indiana University Tour, and Tibetan Mongolian Buddhist Cultural Center.

Where to Eat & Drink: Nick's English Hut on Kirkwood, Laughing Planet Cafe, Oliver Winery, Crazy Horse, Cardinal Spirits, Upland Brewing Company, and Switchyard Brewing.

Where to Stay: Nice Hotel Walking Distance to University with Free Breakfast

best road trips starting in chicago


The river town of Hannibal is all about Mr. Samuel Clemens, aka Mark Twain. The prolific American writer grew up in this charming small town and many of his tales were inspired here.

Take a ride on the Mississippi, tour Twain's boyhood home and climb in the caves he played in and helped shape his imagination.

If you want to make your trip extra memorable, visit Memorial Day Weekend when the family-friendly Twain on Main Festival takes place featuring an arts and craft event, live music, Mark Twain performers, and a wine & beer garden with local favorites.

Drive Time: 4 1/2 hours

On the Way: Route 66 (see below for stops) to Springfield (Lincoln attractions)

What to Do: Mark Twain Boyhood Home & Museum, Mark Twain Cave, Lovers Leap, Mississippi Riverboat, Memorial Lighthouse, and Cave Hollow West Winery.

Where to Eat & Drink: Fiddlesticks Food & Spirits Company, Mark Twain Brewery, Becky's Old Fashioned Ice Cream Parlor and Emporium, Becky Thatcher's Diner.

Where to Stay: No-frills Chain with Indoor Pool and Free Breakfast

Unique and Romantic B&B with Breakfast and Full Bar

best road trips starting in chicago


Route 66 is the most popular road in the United States and it begins in Chicago! For a fun weekend getaway, take a ride to the state capital of Illinois.

On the way, you'll find quirky roadside attractions along with interesting small towns. There are a ton of fun photo opportunities, colorful murals, and historical places along the route.

Once you arrive in Springfield, learn about one of America's most beloved presidents, Abe Lincoln, and see where he lived and worked.

Read here for a complete Springfield Itinerary to make the most of your time in the city.

Drive Time: 5 hours

On the Way: Old Joliet Prison, Gemini Giant, Launching Pad, Funks Grove Pure Maple Sirup, Route 66 Hall of Fame, World's Largest Covered Wagon, and Paul Bunyan Statue.

What to Do: Lincoln Home, Abraham Lincoln Presidential Museum, Lincoln Tomb, Ergadoozy Creative Play Center (kids under 12), Henson Robinson Zoo, Illinois State Capitol, and Knight’s Action Park.

Where to Eat & Drink: Cozy Dog Drive-In, Obed and Isaac's Brewery, Incredibly Delicious, Engrained Brewery & Restaurant, Mel-O-Cream Donuts, and Route 66 Motorheads.

Where to Stay: Downtown Hotel with Indoor Pool

best road trips starting in chicago


Saint Louis has it all - good food, unique museums, craft breweries, and outdoor activities.

This Midwest destination is easy on the pocketbook too with most of the attractions and museums being free.

Don't miss the Gateway Arch; one of our newest national parks with a new state-of-the-art visitor center, the City Museum; the wackiest "museum" I've ever been to, and Anheuser Busch Brewery; a tour where you can also see the famous Clydesdales.

St. Louis is a great destination for couples, families, and solo travelers with an array of vacation activities to choose from.

On the Way: For a delightful lunch on the way down, stop halfway in Bloomington at Rosie's Pub. It's a popular restaurant serving up delicious sandwiches and burgers in one of the oldest buildings in town.

What to Do: St. Louis Zoo, The Arch, City Museum, Anheuser-Busch Brewery, Forest Park, Cathedral Basilica of St. Louis, Ballpark Village, and the Missouri Botanical Garden.

Where to Eat & Drink: Bogart's Barbecue, The Fountain on Locust, Crown Candy Kitchen, Hodak's Restaurant and Bar, Civil Life Brewery, and 360 rooftop bar.

Where to Stay: Well Reviewed Hotel near the Arch with a Free Hot Breakfast & Swimming Pool

best road trips starting in chicago


Cleveland provides an array of attractions from action-packed sporting events to interesting museums and even a few quirky stops like Ralphie's house in A Christmas Story.

Progressive Field, the Cleveland Indians' turf, is right near the pedestrian-friendly East 4th street which is the entertainment district downtown lined with restaurants and pubs. Down the street, take your chances with Lady Luck at a casino which also happens to be in the department store where the infamous 1983 Christmas movie was filmed.

And no visit to Cleveland would be complete without the Rock and Roll Hall of Fame experience . The museum launches visitors through the evolution of the shake-rattle-and-roll era that exploded in America.

And lastly, only 20 miles south is a national park to check off your list, Cuyahoga Valley. You can explore the park on a side trip from Cleveland or Akron.

Drive Time: 5 hours 20 minutes

On the Way: Cedar Point Amusement Park

What to Do: James A Garfield Memorial, Cleveland Botanical Garden, Cultural Gardens, Rock & Roll Hall of Fame, and A Christmas Story House.

Where to Eat & Drink: Collision Bend Brewery, West Side Market, Mabel's BBQ, Great Lakes Brewery, Lindey's Lake House, Alley Cat Oyster Bar, and Fat Cats.

Where to Stay: Reasonably priced 4-star hotel with indoor pool and lake views

best road trips starting in chicago


You won't believe you're still in the Prairie State once you arrive in Shawnee National Forest. It is one of the best-kept secrets in Illinois.

It's a great destination to unplug and get back to nature. Start with the 1.7 mile Rim Rock Trail which will guide you through 300-year-old oak trees and narrow crevices to a beautiful canyon.

Explore the Cave-in-Rock overlooking the Ohio River, the historic cavern provided a safe haven for frontier outlaws back in the day. Take the Cave in Rock Ferry across the river to the small Amish village in Marion.

Don't miss a sunset at Garden of the Gods and a hike up Triggs Tower for more beautiful views.

What to Do: Rim Rock Recreation Trail, Burden Falls, Triggs Tower, Bell Smith Springs Recreation Area, Cave-in-Rock, Inspiration Point, and Garden of the Gods.

Where to Eat & Drink: The Diver Down, Garden of the Gods Outpost, E'Town River Restaurant, and Hogg Hollow Winery.

Where to Stay: A Beautiful Cabin with Private Bathroom and Deck

best road trips starting in chicago


One of the best road trips from Chicago during Covid we took was to Patoka Lake. It is a destination that offers outdoor activities, that isn't very busy especially midweek, and where you can get out on a lovely lake.

Combine the trip with visiting the small towns of French Lick, known for its historic mineral springs, and Jasper, home to the Indiana Hall of Fame.

Make sure to rent a pontoon for a day on the lake and to take a walk through the stunning French Lick Resort and West Baden Springs Hotel for a glimpse into the past.

Drive Time: 5 1/2 hours

On the Way: Stop for lunch in a booming college town - either Lafayette or Bloomington.

What to Do: French Lick Casino, French Lick Scenic Railway, and Patoka Lake State Park.

Where to Eat & Drink: Patoka Lake Winery, 33 Brick Street, German Cafe, and French Licks Ice Cream.

Where to Stay: A 3-bedroom Country Cabin on the Lake

best road trips starting in chicago


If you are looking for a fun wholesome summer trip for the family, head over to Santa Claus, Indiana.

With free soft drinks, free parking, free sunscreen, and free Wi-Fi, you can't go wrong with a visit to Holiday World and Splashin' Safari.

Home to the world's longest water coaster and America's only launched wing coaster, both amusement parks will keep the whole family entertained.

In between, make sure to track down all the festive spots that'll have you celebrating Christmas in July.

On the Way: Lincoln Boyhood National Memorial

What to Do: Holiday World Amusement Park, Splashin’ Safari Water Park, Lincoln State Park, Santa Claus Christmas Store, Santa’s Candy Castle, Santa’s Stables, Santa Claus Museum, and Holiday Drive-In.

Where to Eat & Drink: Frosty's Fun Center

Where to Stay: Santa's Lodge just not far from the Amusement Park

Rental RVs and Holiday Cabins

best road trips starting in chicago


Where should I go for a weekend getaway from Chicago? Let me introduce you to South Bass Island in Ohio that is home to the small charming village of Put-in-Bay.

Even though there's plenty to do for families, this Midwest must-experience destination is best for couples or friend getaways. It's where golf carts roam and drinks flow with over 25 bars, breweries, and wineries.

From boating to paddle boarding, water activities are one of the best things to do when visiting. Along with catching a sunset at South Bass Island State Park, touring the wineries, and eating and drinking your way through town.

Drive Time: 5 1/2 Hours

On the Way: Shipshewana, Indiana's cutest Amish town.

What to Do: Observation Deck at Perry’s Victory and International Peace Memorial, island tour by tram, bike, or golf cart, Heineman’s Winery and Cave Tour, the monument view from Oak Point State Park, swimming at The Sand Bar, and the Massie Cliffside Preserve.

Where to Eat & Drink: Put-in-Bay Brewery, Chocolate Cafe & Museum, The Forge, Put-in-Bay Winery, Biergarten at the Boathouse, The Boardwalk, and Topsy Turvey's Bar & Grill.

Where to Stay: A Private Guesthouse with Free Bikes and a Fabulous Breakfast

best road trips starting in chicago


Where can I go 6 hours from Chicago? Akron, Ohio that's where!

This is a city that surprised us in so many ways, not to mention, it's right next door to one of the few national parks in the Midwest.

Catch a minor league baseball game, tour an incredible historic mansion, chase waterfalls in Cuyahoga National Park, and visit an impressive art museum.

Drive Time: 6 hours

What to Do: Akron Art Museum, Cuyahoga Valley National Park, Akron Rubber Ducks, Stan Hywet Hall, and Akron Civic Theatre.

Where to Eat & Drink: The Peanut Shoppe, Mr. Zub's Deli & Bar, Lock 15 Brewing Company, and El Patron Tequileria & Cuisine.

Where to Stay: Modern Hotel with Lounge and Indoor Pool

best road trips starting in chicago


Saint Paul and Minneapolis, commonly called the Twin Cities, have a lot to offer for a vacation.

St. Paul is a little quieter with the state capitol and more daylife. While Minneapolis is where you go for art, theater, and nightlife. Both have a ton of breweries and great food options.

Discover the area through fun attractions like the Mall of America, the Science Museum of Minnesota, Como Zoo, Can Can Wonderland, and the Walker Art Sculpture Garden.

And do not miss the most beautiful places like the Cathedral of Saint Paul, the Minnesota State Capital, Como Conservatory, the historic homes of Summit Avenue, Lake Phalen, and Minnehaha Falls.

On the Way: Eau Claire, an Underrated Wisconsin Destination.

Where to Eat & Drink: Band Box, Summit Brewing Company, Keg and Case Market, Bad Weather Brewing, The Anchor Fish & Chips, and The Nook.

Where to Stay: Hotel with a Free Shuttle and Modern Rooms

best road trips starting in chicago


Clear Lake is a little hidden gem in the state of Iowa and it's another destination only 6 hours away from Chicago.

Cruise the Lady of the Lake, an authentic paddlewheel boat, while taking in the sights and learning some fun facts about the area.

Take in a show and tour The Surf Ballroom, where Buddy Holly, Ritchie Valens, and JP “The Big Bopper” Richardson played their last concert. Frozen in time, it'll transport you right back to 1959.

Eat, drink, and shop along Main Avenue, the hub of this friendly lakefront community.

And before you leave, drive north to Buddy Holly's Crash Site, you can't miss the giant Holly's iconic black eyeglasses.

On the Way: Galena's Helluva Half Mile Main Street

What to Do: Lady of the Lake Cruise, The Surf Ballroom & Museum, Clear Lake State Park, and Central Gardens of North Iowa.

Where to Eat & Drink: Cabin Coffee, Starboard Market, PM Park, South Shore Donuts, Lake Time Brewery, and Sevens Steak House.

Where to Stay: Adorable Rental with Free Bicycles walking distance to the Surf & Downtown

best road trips starting in chicago


Michigan's Upper Peninsula is pleasant in the spring and summer, but it is also one of the best fall road trips from Chicago. And no trip there is complete without a visit to the Porcupine Mountains Wilderness State Park.

With 60,000 acres of old-growth forest, meandering rivers, jaw-dropping vistas, and flowing waterfalls, the “Porkies” will impress any traveler. It's kind of hard to believe you can find these views in the Midwest!

Drive Time: 6 hours 40 minutes

On the Way: Oshkosh, Wisconsin.

What to Do: Bond Falls, Lake of the Clouds, Escarpment Trail, Presque Isle Falls, Summit Peak Observation Tower, Big Carp River Trail, Union Spring Trail, and Porcupine Mountains Chairlift.

Where to Eat & Drink: White Pine's Yooper Diner, Antonio's Restaurant, and Hoop'n Holler Tavern.

Where to Stay: Chain Hotel only 15 minutes from the Park

best road trips starting in chicago


Listed on the National Register of Historic Places and a National Natural Landmark and National Archaeological District, Red River Gorge is a place that should not be overlooked as a road trip from Chicago.

Located in the Daniel Boone National Forest, there are over 100 natural sandstone archways, waterfalls, dense woodlands, exposed limestone ledges, tunnels, and bridges. 

Red River Gorge is an outdoor enthusiast's dream destination.

Drive Time: 7 hours

On the Way: Kentucky Horse Park in Lexington

What to Do: Nada Tunnel, Sheltowee Trace National Recreation Trail, Gladie Historic Site and Visitor Center, Sky Bridge Trail, Angel Windows Trail, Chimney Top Rock Trail, Cliff Trail, and Hidden Arch.

Where to Eat & Drink: Sky Bridge Station, Red River Rockhouse, Thatcher Barbecue Company, and Miguels Pizza.

Where to Stay: Great Resort surrounded by Natural Beauty

best road trips starting in chicago


We are moving onto longer drive times so anything below here are my recommended best road trips from Chicago for a week or more.

Kansas City has culturally rich areas, bold and modern architecture mixed with distinguished historic buildings, a flourishing arts scene, and finger-licking-good barbecue.

If that doesn't convince you, it is also home to the best World War I Museum in the country and a highly rated art museum admired by all that visit.

Drive Time: 7 hours 45 min

On the Way: Springfield, Illinois.

What to Do: Crossroads Art District, National World War I Museum, Nelson-Atkins Museum of Art, City Market, Rose Garden at Loose Park, and Country Club Plaza.

Where to Eat & Drink: Arthur Bryant's, Cinder Block Brewing Company, Gillis Cafe and Hangout, Pigwich, Joe's Kansas City Bar-B-Que, and Boulevard Brewing Company.

Where to Stay: Hotel with Ideal Location and Free Breakfast

best road trips starting in chicago


Branson is probably one of the most underrated road trips from Chicago for families.

It's not just cheesy musicals and religious shows, there's a lot of natural beauty, fun attractions, and cool things to do for kids and adults alike. 

Drive Time: 8 hours

On the Way: St Louis and the quirky stop of Uranus.

What to Do: Titanic Museum, Silver Dollar City Amusement Park, Table Rock Lake Trail, Dick’s 5 & 10 Store, Top of the Rock, Shepherd of the Hills Fish Hatchery, and Branson Landing.

Where to Eat & Drink: Danna’s BBQ & Burger Shop, White River Fish House, Andy’s Frozen Custard, The Paddlewheel, Clockers Cafe, and Mel's Hard Luck Diner.

Where to Stay: Modern Hotel on the Branson Landing

best road trips starting in chicago


If you are interested in 10 hour road trips from Chicago, Finger Lakes is the place to go especially if you enjoy hiking, lakes, and drinking.

The region is renowned for its wine trail but it also has more than 75 craft breweries! Don't miss the wonderful state parks and the interesting towns of Hammondsport and Corning.

Drive Time: 10 1/2 hours

On the Way: Rock n Roll Hall of Fame in Cleveland.

What to Do: Watkins Glen State Park, Corning Glass Museum, Hammondsport, Robert H. Treman State Park, and Mark Twain's Study and Burial Site.

Where to Eat & Drink: Market Street Brewing Company and Restaurant, Glenora Wine Cellars, Rooster Fish Brewing Tasting Room, Nickel's Pit BBQ, and Wagner Vineyards Estate Winery.

Where to Stay: Inn with a Beautiful Grounds & a Free Breakfast

best road trips starting in chicago


If you're planning a 2 week road trip from Chicago, head to the beautiful Black Hills of South Dakota.

You'll find scenic drives, history, wildlife, and natural beauty throughout the entire region. And, some goofy roadside attractions on the way!

Drive Time: 14 hours

On the Way: Austin, Minnesota

What to Do: Wildlife Loop in Custer State Park, Mount Rushmore, Wind Cave National Park, Evans Plunge Hot Springs, Crazy Horse Memorial, and Badlands National Park.

Where to Eat & Drink: Chuck Wagon Dinner Show, Baker’s Bakery & Cafe, Black Hills Burger & Bun Co, Wall Drug, and Legion Lake Lodge. 

Where to Stay: Bavarian Inn with an Outdoor Pool

best road trips starting in chicago


If you like cool roadside attractions, quirky vibes, outdoor adventure, and getting off the beaten path then this is one of the best long road trips from Chicago.

Don't put off North Dakota as your last state because it has a lot going for it. The Theodore Roosevelt National Park has sprawling natural beauty with winding waterways and painted canyons along with free-roaming bison and wild horses.

The neighboring town of Medora is one of my favorite small towns in the U.S. with an authentic Western energy. Visit the Cowboy Hall of Fame to learn about cowboy culture, catch a show at the famous Medora Musical, an outdoor extravaganza with the real badlands as its backdrop, and stroll the streets of this tiny charming town.

On the Way: Fargo-Moorhead Visitors Center, Fargo Air Museum, Frontier Village, World's Largest Buffalo, Lewis and Clark Riverboat, Fort Abraham Lincoln State Park, North Dakota Heritage Center and State Museum, North Dakota State Capitol, and the Enchanted Highway.

What to Do: The Medora Musical, Chateau de Mores State Historic Site, Pitchfork Steak Fondue, ND Cowboy Hall of Fame, South Unit 36-mile Loop Drive, Sunset at Wind Canyon, Painted Canyon Visitor Center Overlook, Ridgeline Nature Trail, Roosevelt’s Maltese Cross Ranch Cabin, Boicourt Trail, Buck Hill Trail, Oxbow Overlook, River Bend Overlook, Cannonball Concretions Pullout, and 14-mile North Unit Scenic Byway at the Theodore Roosevelt National Park.

Where to Eat & Drink: Sandy's Donuts, Drekker Brewery, Tower Travel Center, Little Missouri Saloon & Dining Room, Medora Uncork'd, and Hidden Springs Java.

Where to Stay: Ranch Cabin in the Heart of Medora

Hotel with Free Breakfast and Indoor Pool

One of the most beautiful Midwest states is just a short drive from Chicago, here are fun day trips in Michigan to help you plan. 

I hope you enjoyed my favorite road trips from Chicago 2021 edition! If you have any other recommendations, please let us know in the comments below!

The top picture is a sweeping view of a valley filled with trees with fall color in Porcupine Mountains Wilderness State Park and the bottom is a lake in Illinois with cypress trees that have orange and green leaves with a text overlay that says the best road trips from Chicago.

  • About Author
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Angela E. is a travel writer from the Chicagoland area who has visited all 50 states in the US and has traveled extensively around the world. She is passionate about exploring the great outdoors and hiking in particular. Her love for nature has taken her to some of the most beautiful locations on the planet. She has written extensively about her travels on her own website, Dang Travelers, and has been published in collaboration with other travel websites and multiple visitor bureaus around the country.

Latest posts from Angela

  • The Best Road Trips from Chicago with Itineraries - April 15, 2024
  • The Best Restaurants in Celebration, Florida - January 15, 2024
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6 Best Road Trips From Chicago

Waterfalls, storybook towns, incredible food, and more await just a short drive from Chicago.

Cities can sometimes feel like endless stretches of concrete — especially in the hot summer months — and Chicago is no exception.

Fortunately, there's a whole world out there beyond the city limits. While it doesn't always feel like it, there are so, so, so many worthy escapes within a few hours' drive of Chi-town: storybook towns studded with ice cream parlors, lakeside cities with entirely different cultures, and even places where you can connect with nature among waterfalls and lush trees. Waterfalls! Outside Chicago!

The Windy City's location, in this case, is your ally. Pack your car with some picnic accoutrements, and maybe some hiking gear just in case, and head off. You're within driving distance of some truly great, out-of-the-ordinary places that make for wonderful road trips. Here are six of them.

Madison, Wisconsin

Imagine a state already known for its beer and cheese having to cater to over 30,000 college students, and you've got some idea of the earthly delights that await in Madison, Wisconsin. This state capital could have been a destination in its own right for its unique geography — located on a narrow isthmus surrounded by two large lakes, it's beautiful even during cold Wisconsin winters — or its remarkable breadth of shopping, cultural events, and festivals, and architecture, but its food scene is virtually unrivaled for a city of its size.

The streets are filled with an eclectic mix of professors, politicians, businesspeople, street performers, and health nuts, and if you ask any of them for their favorite spot, you'll likely get a range of answers as large as the city's 250,000-plus population: American small bites at the new and renowned Mint Mark, tacos and margaritas at Canteen, Lao-Thai noodles from Vientiane Palace, and the list goes on and on.

Most students, however, will drive you toward craft-beer watering holes like The Malt House or Dotty Dumpling's Dowry, which purportedly serves one of the best burgers anywhere. Wash it down with some Wisconsin beer from New Glarus as well as some fried cheese curds, and you'll have yourself a real Madison, Wisconsin, night.

Madison is about two and a half hours from Chicago.

Starved Rock State Park, Illinois

Yes, Illinois isn't known for its natural beauty like some other states. Yes, its highest natural point is Charles Mound, a diminutive 1,235-foot hill. But that doesn't mean that hidden gems don't exist here. For a true escape from Chicago's steel-and-stone skyscrapers that is still within the state limits, drive to the area around Starved Rock State Park.

Visitors expecting more flat Illinois farmland will be surprised to find an incredible valley around the Illinois River, with lush trees, striking bluffs, and 14 gorgeous waterfalls feeding into the roaring waters. Starved Rock is a choice destination for camping, hiking, kayaking, and white-water rafting, and after you're exhausted from a day of physical exertion, it's also got a place to hang your hat: the Starved Rock Lodge .

However, if you feel like experiencing a bit more of the local flavor, the towns around the river valley provide it in buckets. Tiny, charming Utica is home to the August Hill Winery and some wonderful antique stores, while the historic towns of Oglesby and Ottawa are chock-full of Americana: small museums, galleries, and great food, particularly at the Red Dog Grill in Ottawa and The Rootbeer Stand in Oglesby.

Starved Rock State Park is about an hour and a half from Chicago.

Allegan County, Michigan

Lake Michigan is huge. And in the summertime, when the heat gets a little unbearable, you could easily just jump into the lake in Chicago. But there's something to be said for taking a jaunt out to Michigan to visit a string of lakeside towns that bring some truly unique qualities to the mix.

Douglas, Saugatuck, and Holland — and Fennville, though it's not right on the water — epitomize small-town charm, while still offering some truly city-sized amenities for city-sized appetites. Fennville is known as the fruit basket of Michigan, with apple orchards, vineyards, and berry farms alongside delightful creameries and even corn mazes, while Saugatuck and Douglas consistently take the cake as two of the best lakeside towns in the Midwest, with incredibly charming downtown areas, gorgeous undulating sand dunes, pristine blue water, and more art galleries than you can shake a stick at. In fact, it's here that two School of the Art Institute of Chicago instructors founded their own art school and residence, Ox-Bow, establishing an artists' colony right on the shores of Lake Michigan. Their legacy endures to this day.

Further up the road, you'll find a truly unique destination in Holland, where Dutch colonists established a foothold in the 1800s, bringing with them their culture, architecture, pastries (check out DeBoer Bakkerij), and even fields' worth of tulips, which you can find at Veldheer Tulip Gardens.

Fennville is about two hours from Chicago.

Indianapolis, Indiana

Among the many types of travelers out there — people who crave solitude, people who don't want to leave the 100-foot radius of their resort's pool — there are those who are fascinated by city life, jumping from one urban area to another. If you count yourself among them, a road trip from Chicago to Indianapolis is certainly warranted.

First off, it's the 15th-largest city in America, with a vast population and penchant for festivals, parties, and overall pageantry (it is the Racing Capital of the World, after all, and its famous month of May includes tons of smaller celebrations leading up to the Indy 500). No matter the time of year, though, you'll find Indianapolis in full swing, whether you're in the midst of its rollicking IndyFringe Festival in August and September or its Wine & Food Festival in June. It's also a museum hub, with the world's largest children's museum, several art museums with broad and granular focuses, and small museums focusing on its favorite children, from Vonnegut to President Benjamin Harrison.

But one of the main reasons visitors flock to Indianapolis is its incredible food scene, which has, in recent years, exploded into national prominence. Hot new restaurants like Bluebeard, Milktooth, Crispy Bird, Oca, and more have all contributed to its reputation as a gastronomical powerhouse, while iconic institutions like Workingman's Friend have been, well, working behind the scenes to keep Hoosiers well-fed for decades. It's about time their city gets noticed.

Indianapolis is about three hours from Chicago.

Traverse City, Michigan

If you're craving a real getaway, you can't do much better than northern Michigan — it's still within driving distance of Chicago and not as remote as the state's Upper Peninsula, while still providing a wilderness-tinged escape for city dwellers. The de-facto capital of the region, Traverse City, is a city in name, but its population of around 15,000 means it's got small-town charm and accessibility, making it a perfect gateway to the region's breathtaking sights. Stop in for a glass of beer or wine at one of the many famous wineries and brewpubs, like Mari Vineyards or Mackinaw Brewing Company, before heading into the wilderness.

From Traverse City's quaint streets, you can head north and explore the Leelanau Peninsula, or veer west to Sleeping Bear Dunes National Lakeshore. Better yet, take scenic M-22 to tick off both boxes. Sleeping Bear Dunes is one of the country's best stretches of shoreline, with incredible dunes and westerly views that mean it's got some of the best sunsets east of the Mississippi.

From there, mosey up M-22 to continue exploring the Leelanau Peninsula, where wilderness encroaches a bit further and small towns, each with a population under 1,000, dot the roads. Hike through the dense forests, pick apples and berries at the region's many farms, and be sure to grab a heaping sandwich from the Village Cheese Shanty in the county seat of Leland (population 377).

Traverse City is about five hours from Chicago.

Galena, Illinois

In rare cases, a road trip doesn't just mean traveling great distances — it can also mean traveling back in time. That's what's figuratively the case when you drive west from Chicago to Galena, consistently rated as one of the best small towns in America. For decades, Galena has been on a mission to preserve its rich history, meaning it has one of the most unspoiled historic town centers in the country.

The town's good fortune started back in the mid-1800s, when it was the beneficiary of government grants to begin mining precious minerals located under the town. Since then, the town has focused on maintaining the buildings from that boom time, and there are architectural landmarks around every corner. The Galena Historic District is a particular delight, comprising more than 1,000 buildings, including the home of Ulysses S. Grant, a prime example of the Italianate style and now a dedicated memorial to his legacy. The town even has trolley tours that take you to its major historical and architectural benchmarks, contributing to its overall throwback feel.

Galena's best eating institutions don't necessarily date all the way back to 1850, but that doesn't mean they aren't also great — Durty Gurt's Burger Joynt was founded in 2007 and serves gigantic, almost architecturally impressive stacks of meat and cheese. Looks like everyone's concerned with building a legacy here.

Galena is about three hours from Chicago.

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best road trips starting in chicago

The Best Road Trips From Chicago To Take This Spring

The best is yet to come, especially when you're going on an adventure. It's time to load up the car and head to one of these vibrant Midwest states for spectacular culture, art, and a culinary scene.

Tori Levy

Fall is here, so it’s time to get away! While we adore our beloved Chicago, the Midwest is sprawling with beautiful and scenic cities within just a few hours of the city. Whether you want to get away to explore a stunning hiking trail or just spend the weekend roaming a charming town with cobblestone streets, there are tons of amazing things you can experience, so check out the best road trips from Chicago!

1. Madison, Wisconsin

Madison, Wisconsin, USA downtown skyline at dusk on Lake Monona.

First on our list is where Wisconsin’s capital is located, and it happens to be the second largest city in the state. Madison lies in the south-central part of the state and is centered on an isthmus between Lakes Mendota and Monona.

The proximity to the lakes makes waterside adventures a must; there are endless activities to participate in, between boating, kayaking, and swimming. After, take a stroll through the charming streets and head to one of the many breweries, or for an evening filled with serenity, head to the Olbrich Botanical Gardens , where Oblrich’s Thai Pavilion is located and is the only one in the US, and the only one outside of Thailand surrounded by a garden.

🚗 Distance from Chicago : 148 miles

🕐 Arrival Time: 2 hr and 23 mi

2. Holland, Michigan

Windmill in Holland Michigan - An authentic wooden windmill from the Netherlands rises behind a field of tulips in Holland Michigan at Springtime.

When people think of Holland, what usually comes to mind is the Keukenhof Tulip Gardens in Amsterdam, Holland. However, you don’t need to buy an international plane ticket when another Holland is only a few hours away. This road trip from Chicago will be your new favorite getaway.

While in Holland, you’ll be able to indulge in Dutch experiences such as sprawling tulip gardens , cobblestone streets, and the picturesque Tunnel Park. With over 100 specialty shops, breweries, and restaurants, this is the perfect place to head on a road trip.

🚗 Distance from Chicago : 150.8 miles

🕐 Arrival Tim e : 2 hr 25 min

3. Traverse City, Michigan

fall foliage surrounding Downtown Traverse City Michigan with a lake in the background

One of our favorite Chicago trips, known as the “Cherry Capital” of the world, it’s easy to get lost in the beauty of Traverse City. Stroll along the shoreline at Grand Traverse Ba y and glance at the fluid waves as you take in a majestic sunset.

While there are many things to do in Traverse City, some of our highlights include touring the wineries, scaling a dune at the Sleeping Bear Dunes National Lakeshores, picking out some blum cherries, and immersing yourself in the beautiful lakeside town.

🚗 Distance from Chicago : 318.6 miles

🕐 Arrival Time : 4 hr 55 min

4. St. Louis, Missouri

St. Louis, Missouri, USA downtown cityscape on the river at dusk.

One of the major cities in Missouri, St. Louis, lies along the Mississippi River and displays an iconic 630-foot Gateway Arch built in the 1960s. St. Louis is a quintessential city to visit, with a vibrant arts and culture scene, lively bars, and acclaimed restaurants.

This is also one of the best road trips from Chicago if you’re a fan of Chicago baseball. With Busch Stadium nearby, schedule your road trip for a game between the Cardinals and the Cubs, one of the best rivalries.

🚗 Distance from Chicago : 298.8 miles

🕐 Arrival Time: 4 hr 28 min

5. Bloomington, Indiana

iew of Kirkwood Street across from the college campus of Indiana University Bloomington (IU), a major public research university located in the US midwest.

Bloomington is most notably known as the home for students of Indiana University . Nestled in the rolling hills of southern Indiana, the city has spectacular foliage surrounding the town as you drive in.

Along with the visually stunning scenery , there is vibrant art, spectacular shopping, and notable restaurants—all of which support the thriving local business scene. However, it wouldn’t be right to mention Bloomington without mentioning sports. With the Big Ten, rowdy football and basketball games are an innate part of the town.

🚗 Distance from Chicago : 232.3 miles

🕐 Arrival Time : 3 hr 48 min

6. Columbus, Ohio

Columbus, Ohio, USA skyline on the Scioto River with tall buildings and green grass

Along with Bloomington, Columbus is a celebrated city with a younger population due to the booming tech industry and innovative arts scene. As Ohio’s state capital , it’s one of the largest college campuses in the country.

This is one of the best road trips from Chicago if you’re looking for lively nightlife . Walking down High Street, you’ll be surrounded by reverberating music and packed patios, especially if the Buckeyes are playing.

🚗 Distance from Chicago : 356.5 miles

🕐Arrival Time: 5 hr 27 min

7. Wisconsin Dells, Wisconsin

downtown of the Wisconsin Dells, which is a major tourist attraction in the US state of Wisconsin

Situated in southern Wisconsin, the Dells lies on the Wisconsin River in a region of glacier-carved sandstone formation and might be one of the most exhilarating cities on this lift. This is the best road trip near Chicago for any family planning an adventure-filled weekend .

There are numerous theme parks and entertainment centers, including Noah’s Ark Water Park and Mt. Olympus Water and Theme Park, both indoor and outdoor, spanned with waterslides, lazy rivers, rafts, and more! It’s one of the ideal road trips from Chicago for a family outing.

🚗 Distance from Chicago : 193.5 miles

🕐 Arrival Time : 2 hr 59 min

8. Saugatuck, MI

Sunset over the water on Lake Michigan at Saugatuck Michigan

If you’re looking for award-winning beaches , scenic waterways, and verdant dunes, take a road trip to Saugatuck, Michigan. This is the ultimate escape for a quiet, luxurious weekend, with an animated art scene and renowned culinary restaurants. It’s a place that seamlessly switches from exploration to recreation for people visiting—making it one of the best road trips from Chicago.

🚗 Distance from Chicago : 145.8 miles

🕐 Arrival Time : 2 hr 19 min

9. Ann Arbor, MI

Historic Michigan Theater, built in 1928, located on East Liberty St in Downtown, Ann Arbor

While many of the Michigan cities listed here are located along Lake Michigan, Ann Arbor is one the few recognized as an urban oasis in the middle of the state. The downtown scene is from a storybook with a red-brick main street filled with independent bookstores, locally-made candle shops, home goods, and more.

While there’s a lot to do downtown, head outside the city to explore the nature parks surrounding the town, which have some of the most scenic hiking trails.

🚗 Distance from Chicago : 241.3 miles

🕐 Arrival Time : 3 hr 45 min

10. Sheboygan, Wisconsin

Beautiful walkway through the natural sand dunes along the Great Lake shores. The Kohler Andrea park is in the area around Sheboygan and Wilson Wisconsin. Small trees and Juniper bushes along path.

Deemed the “Malibu of the Midwest, ” Sheboygan, Michigan, might not have five-foot waves like the West Coast. Still, it’s a freshwater haven for anyone who loves fishing, sailing, and surfing, from outdoor recreational activities like golfing and biking to events and festivals that highlight the art scene, cultural heritage, and vibrant music, it’s no wonder it’s one of the best road trips from Chicago.

🚗 Distance from Chicago : 147.6 miles

🕐 Arrival Tim e: 2 hr 24 min

11. Cincinnati, Ohio

Cityscape of Cincinnati's Roebling bridge.

Cincinnati is a beloved Midwestern city—right on the border of Northern Kentucky—some say it’s where metropolitan vibrancy meets Kentucky’s southern flair . From a wild sports fandom, you can catch Joe Burrow throwing a football or Joey Votto singing his bat, all less than a 1/2 mile from each other. However, besides athletics, there are splendid places to explore within Cincinnati, and it’s one of the ideal road trips from Chicago.

🚗 Distance from Chicago : 295.4 mi

🕐 Arrival Tim e: 4 hr 32 min

best road trips starting in chicago


  • National Parks
  • Tiny Houses

10 Best Weekend Road Trips From Chicago, Illinois

Posted by Brittany Varano June 01, 2021 Updated May 21, 2024

Sometimes you need a change of scenery, and these weekend road trips from Chicago make it easy to get away from the bustle of the Windy City.

Perfectly perched within reach to four different states, Chicago conveniently sits at the crossroads to destinations in Wisconsin, Michigan, Indiana, Iowa, as well as the rest of Illinois.

Its prime location means endless weekend road trips that range from city escapes to small-town excursions and outdoor getaways. And you’ll have your choice of several sandy beach towns lining the shores of neighboring Lake Michigan.

Below, you’ll find a diverse list of the best weekend road trips from Chicago to inspire your next adventure out of the city.

Related Read: The 10 Best Illinois Glamping Rentals

1. Milwaukee, Wisconsin

milwaukee road trip from chicago

Milwaukee is an easy weekend trip just north of Chicago over the Wisconsin border. Known for its craft breweries and local eats, there’s a lot to do and see in this smaller midwestern city. If you’re interested in learning about the local history, make time to visit Milwaukee’s beloved museums like the historic art museum or the Harley Davidson Museum to marvel at one of Elvis Presley’s classic motorcycles.

If you’re a sports fan, make time to catch a Milwaukee Bucks basketball game or tailgate outside of Miller Park before watching the Brewers play ball. The end of summer is also a fantastic time to visit Milwaukee as Summerfest is in full swing. Summerfest is a music festival held along the picturesque shores of Lake Michigan in downtown Milwaukee and brings notable acts each year.

Distance from Chicago: 93 miles (approx. 1 hour and 30 minutes)

Related Read: 11 Best Cabin Rentals in Illinois For an Outdoor Getaway

2. Starved Rock State Park

starved rock state park from chicago

If peace in nature is what you’re seeking, Illinois’ Starved Rock State Park is a beautiful outdoor getaway known for scenic sandstone canyons, numerous waterfalls, and miles of hiking trails. The park’s top sights include Lover’s Leap Overlook (a lookout point offering clear views of the Starved Rock Dam) as well as the Wildcat, French, and St. Louis canyons.

Summertime is the best time to visit, bringing sunshine and warm weather. Winter is also not a bad time to visit, when the canyon falls freeze over in a spectacular show of ice and snow. Many visitors opt to camp out in the state campground, where reservations can be made up to six months in advance. The park is on the Illinois River southwest of Chicago.

Distance from Chicago: 94 miles (approx. 1 hour and 30 minutes)

Related Read:   9 Fabulously Unique Places to Stay in Illinois

3. Indianapolis, Indiana

indianapolis 500

Indianapolis is an excellent weekend road trip from Chicago for city dwellers and racing fans. Home to the world-famous Indy 500 and the Indianapolis Motor Speedway Museum , car lovers can cheer on their favorite drivers and learn a bit about the sport’s history.

No visit to Indy is complete without sampling some local cuisine, including local specialities like pork tenderloin sandwiches and shrimp cocktail. The city was named as an ‘Underrated Food City in America’ by Condé Nast Traveler for its rich and diverse restaurants and dishes. Other popular things to do in Indianapolis include walking the eight-mile Indianapolis Cultural Trail that stretches through downtown or visiting the iconic Monument Circle.

Distance from Chicago: 184 miles (approx. 3 hours)

Related Read:   10 Romantic Getaways Near Chicago, Illinois

4. Galena, Illinois

galena roadtrip from chicago

For a taste of small-town living, look to Galena, Illinois . The city has consistently been ranked as one of America’s most livable cities and offers a lovely weekend trip from the big city. Galena is known for its quaint main street lined with historic brick buildings dating to the 1800s.

Visitors can tour the former home of Ulysses S. Grant and visit the beautiful grounds of the Dowling House, the oldest home in the city. Rolling hills and Native American effigy mounds surround Galena, such as the Horseshoe Mound, a nature preserve boasting views of three nearby states. The best way to experience Galena is to stay in a charming bed and breakfast or a local vacation rental.

Distance from Chicago: 164 miles (approx. 2 hours and 45 minutes)

5. Indiana Dunes National Park

Indiana Dunes National Park from Chicago

Boasting the shortest distance of all the road trips from Chicago, the Indiana Dunes National Park is a convenient road trip from Chicago to northwestern Indiana. The park protects over 15,000 acres of diverse landscapes that include sunny beaches, sand dunes, wetlands, and forests.

The park is a four-season destination offering wildflowers in the spring, water fun in the summer, fiery colors as the leave change in the fall (and sunsets are great), and cross-country skiing in the winter.

Most people opt to camp out in the national park campground or stay in nearby vacation rentals. Besides the outdoor adventures inside the park, make time to shop at the Saturday European Market in Chesterton, visit the Old Lighthouse Museum , and indulge in Indiana comfort food.

Distance from Chicago: 49 miles (approx. 56 minutes)

6. Grand Rapids, Michigan

Frederik Meijer Gardens Sculpture Park

Get a feel for Michigan city life with a weekend in Grand Rapids . About three hours north of Chicago, the city was once a hub for furniture manufacturing, securing the nickname “Furniture City.” Today, locals and visitors alike enjoy strolling the downtown riverwalk along the Grand River, eating out at hip restaurants like Divani and Stella’s Lounge,  and shopping at the Grand Rapids Downtown Market.

The Frederik Meijer Gardens & Sculpture Park is another must-see stop, with walking trails meandering through nearly 160 acres of colorful gardens and sculptures. In the evening, sip cocktails as the sun sets at the New Hotel Marten’s hip rooftop.

Distance from Chicago: 177 miles (approx. 3 hours)

7. Madison, Wisconsin

monona terrace madison wi

Home to the majestic Wisconsin state capitol building, Madison is a charming city best known for its location on an isthmus surrounded by four scenic lakes. The University of Wisconsin Madison campus sprawls through the downtown area, bringing with it a vibrant artistic atmosphere as well as hip bars and restaurants. Along the pedestrian friendly State Street, boutique shops and charming cafes lead the way to the capitol building.

One of the best things to do in Madison includes visiting the Saturday farmers market, where 150 vendors line the capital square selling locally sourced produce, flowers, and sweet treats. Grabbing a pitcher of beer at the Union Terrace along Lake Mendota and visiting the admission-free Henry Vilas Zoo are also popular things to do. That said, Madison is a very outdoorsy city, so you’ll find plenty of options for everything from paddling to hiking, biking, and outdoor movies and festivals.

Distance from Chicago: 147 miles (approx. 2 hours and 20 minutes)

8. Lake Geneva, Wisconsin

lake geneva road trip from chicago

Lake Geneva is a four-season resort destination in south-central Wisconsin. The city is named after the large 5400-acre Geneva Lake that attracts fishing and boating enthusiasts. The city’s Big Foot Beach State Park is one of the best places to go for swimming, sun tanning, and kayaking. If you enjoy casual walks, take a stroll along the Geneva Lake Shore Path that circles the lake for 21 miles.

While summer is an ideal time to make the most of the lake and surrounding beaches, winter also offers a unique weekend getaway. Every year, the Geneva National Resort and Club hosts the award-winning Ice Castles festival, where ice sculptures and structures amaze winter visitors. Prices and hotels cross into a variety of budget and lux options, but in general, it’s one of the cheaper towns for a summer getaway near Chicago.

Distance from Chicago: 83 miles (approx. 1 hour and 30 minutes)

Related Read:   13 Exciting Things to Do in Lake Geneva, Wisconsin

9. Saugatuck, Michigan

Saugatuck state park Michigan

Saugatuck, Michigan , is an artsy beach destination best enjoyed in the summer. This small town is on Lake Michigan and Kalamazoo Lake, offering fantastic water fun like fishing, swimming, and boating. The area is also famous for its idyllic grassy dunes, Mount Baldhead Park hiking, river cruises, and the Dutch windmills and gardens in nearby Holland, MI.

The city’s center features Butler Street, where visitors can enjoy up-and-coming gourmet restaurants and boutique shops. Don’t forget to pack your swimsuit for a trip to Oval Beach. For the best experience, opt for a cozy B&B along the water or in the downtown area, but be sure to plan ahead as lodging fills fast in the summer.

Distance from Chicago: 141 miles (approx. 2 hours and 15 minutes)

10. The Wisconsin Dells

Wisconsin Dells Road Trip from Chicago

Known as the waterpark capital of the world, the Wisconsin Dells is a resort town with 20 different indoor and outdoor water parks and resorts. It’s a perfect weekend road trio from Chicago for families looking for something fun but family-friendly – and the area offers more to do than just waterparks. Take a tour along the Wisconsin River and surrounding forests on a Wisconsin Duck, an amphibious truck that dates back to WWII.

Be sure to check out other popular activities such as local winery tours, the hiking trails through nearby Devil’s Lake State Park, and the vibrant nightlife of downtown. When visiting, there are plenty of cozy Wisconsin Dells cabins to stay at if resort living isn’t for you.

Distance from Chicago: 195 miles (approx. 3 hours)

Explore More in the Midwest

10 Best Lake Camping Destinations in Wisconsin

11 Peacefully Secluded Cabin Rentals in Wisconsin

10 Awesome Glamping Getaways in Michigan

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Posted by Brittany Varano

Brittany is a freelance travel writer and avid photographer with a love of hiking and nature. Originally from Wisconsin, she fell in love with travel blogging after living and teaching English in South Korea. She’s now location independent and enjoys slow travel to new and exciting places.

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Mom Van Up

Where to Road Trip from Chicago: 12 Interesting Destinations

  • Date: July 18, 2022
  • Time to read: 6 min.

There are a lot of great destinations from Chicago! If you have a day or a week, these interesting cities and attractions are great places to visit  on a road trip this summer. 

When you are planning a vacation on a budget there there three factors to consider:

You have control over all these costs, but gas will cost what gas will cost. You have find something closer to home. 

I have a list of destinations that can be exciting no matter how close or far from home your budget can carry you. 

Day Trips from Chicago

These trips will take about an hour from the city and include some really cool sites to see. 

The Vine Martini and Wine Bar

In Greyslake Illinois The Vine is a very popular bar. The relaxed atmosphere of The Vine makes it a great place to visit from Chicago. 

Right down the street there is a great burger place, Twisted Burger and Emil’s Tavern. A great place to spend the evening with friends. 

Cedar Lake (Indiana) 

Cedar Lake is a great trip for hunting for antiques. The Old Goat’s market is a good first stop and you can enjoy learning about the area at the Cedar Lake Historic Museum. 

There are a number of other antique and resale shops for a day of deal hunting. 

Cedar Lake Shopping for Antiques

Michigan City

Michigan City is just a short drive from Chicago and you can find Casinos, restaurants, outlet shopping and you will cross state lines! 

If you are not into gambling, the lighthouse museum is a high quality educational trip and the outlet shopping is a great girls trip idea. Michigan city is an exciting day trip from Chicago. 

2-3 Hour Trips from Chicago

A two hour trip is a really good distance for traveling with kids or young babies. Experienced travelers often travel for 2-3 hours max between stops. 

Take a page from their book and stop before you get too tired of driving. 

Menomonee Falls

Menomonee Falls is a beautiful destination. The falls are man made waterfall located in Mill Pond Park. The city was once home to a large sugar mill. 

There are a lot of beautiful walking trails, ponds and river walks to enjoy in Menomonee Falls. There are also sunset beer garden events in warm weather. 

Crane Orchards U-Pick and Corn Maze, Fennville, Michigan 

A great fall destination , the Crane Orchards and Corn Maze in Fennville Michigan is a destination worth the drive. 

Be sure to pack your walking shoes and enjoy picking cherries, peaches, apples and pumpkins in season. You can find their seasonal fruit page to let you know what is available to pick. 

I love marking apple picking on my family’s calendar each fall. It is a beautiful memory and such a fun day. 

u-pick Orchard

Davenport Iowa

Right on the banks of the Mississippi Davenport is a great small city. Davenport is considered one of the Quad Cities. 

This area offers riverfront dining, walking trails, shopping, theater and museums. 

The Adler Theater offers comedian tours, live music and Broadway shows. Follow up your show with a river cruise and dinner. 

This vacation is really shaping up and you drove less than 150 miles! 

Indianapolis, Indiana 

There is a large museum in Indianapolis that contains the best preserved T-rex in existence, your dino lover will never forget this three hour drive out of Chicago. 

The museum associate with the Indianapolis Speedway is engaging even if you have never seen a race. When the track is not in use you can take the bus tour of this iconic track. 

Monument circle in the heart of town hosts a farmer’s market, food trucks, coffee and restaurants. This busy area of town has plenty to see and do. 

3-5 Hour Trips from Chicago

Three to five hours is the longest drive I would recommend that you drive without stopping, but you will feel like you really got away. 

If you are traveling with kids I recommend that you read this post about how to plan stops with kids . 

Bowling Green, OH

Bowling Green is a great place to attend really great events and festivals. The National Tractor Pulling competition is hosted here and the Great Black Swamp Art Festival.

They have a wonderful summer activity calendar that is sure to offer something worth seeing.   

Bloomington, IN

If you would like a slower paced trip, head to Bloominton. The small town feel offers plenty to see and do. 

Art museums, sculpture gardens and science museums offer plenty of things to do for the whole family. 

The Wonder Lab Science Museum is a hands-on science museum for the whole family and it would make a great family event. 

St. Louis, MO

Our family has taken several trips to St. Louis and you can read about our favorite STL destinations in the linked post. There is no limit to what you can do in St. Louis. 

When you visit St. Louis you will want to see the Arch, the gateway to the West. The improved grounds are a lovely place to walk and read more about American history. 

There are also a few foods you will want to try while visiting the city:

Frozen Custard

Toasted Ravioli 

St. Louis Style Pizza

The first time I tried pizza from Imo’s Pizza I was surprised. It is a memorable experience, give it a try. 

St. Louis is great for familes!

6-8 Hour Trips from Chicago

Chicago is a great starting point when you want to explore America. If you can budget to drive six to eight hours you will be able to visit some iconic American cities and attractions. 

Erie has the best city website I have seen. There is so much to do in Erie, water parks, historic tours of Lake Erie and AA baseball. 

Request a guide to Erie on their city website. It will give you the most information about how to spend your time in this vibrant diverse city. 

Nashville, TN

Nashville is an unforgettable trip. There is so much to see and hear in Music City. 

The Nashville Zoo is great day or night. Their night light display is a stunning event and a low stress evening event. 

You may also choose to schedule your trip around their incredible Food and Wine Festival. The city has the best hotels and restaurants for any budget. 

You will want to hear some music and venues abound. Check out the calendars for: 

Storytellers Hideaway

Grand Ole Opry 

Ryman Auditorium 

RCA Studio A 

Mammoth Cave National Park

Mammoth Cave National Park is a beautiful destination for camping, hiking, exploring and soaking in nature. 

National Parks can book up quickly so check out my handy guide to when to book your road trip lodging. 

Large families or large groups will enjoy the flexible lodging options in National Parks. I highly recommend this for a family vacation. 

Niagara Falls

Niagara Falls is a bucket list item for many people and it is just a few hours from Chicago!

This popular international tourist destination should be planned well in advance. Check lodging prices frequently and plan accordingly. 

One tip for creating a low stress vacation plan is to hire a local guide. I highly recommend that you consider planning this trip with a travel agent or local guide company so that you can avoid getting stuck in a crowd and missing the experience you dreamed about. 

Memphis, TN

Memphis is the home of bluegrass, soul music and rock and roll. This is an incredible destination for music lovers. 

This is about as far south as you can drive from Chicago in 8 hours , so if you are looking to warm up Memphis is a great destination. 

Festivals, concert cities and museums are all waiting in memphis. 

They have several immersive art experiences as well as a trolly tour that is sure to delight. 

Planning a Road Trip From Chicago

When you are planning a road trip from Chicago I recommend that you start at this site will allow you to explore different travel radius options from your city.

This can help you uncover hidden gems that you may never have thought of in your area. 

Follow up with this Road Trip Planning guide with a few printable worksheets that can help you stay organized and on budget.

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red barn and corn field on the side of the road, a typical midwest road trip itinerary view

13 Marvelous Midwest Road Trips (Itinerary Ideas + Tips!)

Of all the regions of the USA, there’s a good chance that (for non-locals) the Midwest is the most surprising–and that alone is an excellent reason to plan a Midwest road trip!

Packed with diverse national and state parks, incredible beaches (yes, beaches!), interesting cities, a seemingly endless array of quaint lighthouses and charming small towns, and so much more, the Midwest is far more than “flyover country”.

Sure, many of the best road trips in the Midwest require a lot of time on the interstate.

And yes, visiting in winter probably isn’t optimal for most first-time visitors.

But, if you’ve never visited the region before, any of these incredible Midwest road trip routes–many of them written by locals–are bound to leave you enchanted.

kate storm jeremy storm and ranger storm posing on the cleveland sign at edgewater park during a midwest road trip itinerary

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We asked several other travel bloggers to share their favorite Midwest USA road trip ideas with us, and they delivered a remarkably diverse set of routes, perfect for everything from weekend getaways to long vacations.

From the wide-open spaces of Theodore Roosevelt National Park in North Dakota to the stunning architecture of Chicago to the historic charm of Mackinac Island, there are so many incredible places to visit in the Midwest.

We have offered suggestions for the best hotels in each place but if you are doing this as a true road trip it is really cool to do it in an RV. You can rent incredible RVs and camper vans from Outdoorsy, book here for your next road trip!

Here are some of the best Midwest road trip itineraries to consider for your next vacation!

Table of Contents

Quick Tips for Taking Your Midwest Road Trip

Single-state midwest road trip itineraries, multi-state road trips in the midwest.

straight 2 lane road leading through the landscape of badlands national park, one of the best road trips midwest usa

Don’t underestimate the driving distances.

The Midwest is an expansive region with lots of wide open spaces, and that can lend itself to drives that are longer than some visitors might expect!

Be sure to check estimated driving times carefully when planning your route, and build in plenty of stops to stretch your legs.

… And also to check out the many quirky roadside attractions in the region, like the Corn Palace in South Dakota or the American Gothic House in Iowa!

front facade of the american gothic house iowa

If you’re renting a car, shop around.

The best company to rent a car from for your Midwest road trip will likely vary dramatically depending on where and when you’re traveling.

Sometimes large international carriers offer the best prices, sometimes local outfits. Sometimes one company has an excellent base price, but terrible rental requirements.

The best way to find your rental car is to search through  Discover Cars , which will sift through dozens of companies to find the best combination of low prices and reasonable rental terms for your road trip route.

Browse rental cars  for your Midwestern USA road trip today!

view of fall foliage with lake in the foreground on michigan upper peninsula

Read the rental requirements carefully.

Especially make sure you know how many miles you’ve been allotted (or ideally, if they’re unlimited), if you need to return the car empty or full of fuel, what to do if the car breaks down, and what damages you’re liable for in the event of an accident.

Make sure you pack the right gear.

From safety gear to snacks, a road trip in the Midwest requires bringing the right tools along, whether you’re taking a short vacation, trying out van life, or something in between.

We recommend taking a look at the suggestions on  our road trip packing list  before you go!

jeremy storm and ranger storm in cleveland ohio galleria

Don’t overextend yourself.

Exploring all of the incredible places to visit in the Midwest is a project for a lifetime, not one trip!

As tempting as it is to add on additional driving to stop at just one more waterfall, lighthouse, or small town, make sure that you leave enough time to thoroughly explore each destination rather than spending the entirety of your vacation driving from one spot to the next.

Be prepared to be surprised!

If this is your first trip to the Midwest, there’s a good chance that its diversity and beauty will enchant you in all the best ways.

When exploring the Midwest, beautiful beaches, delicious food, gorgeous fall foliage, incredibly warm people, and dynamic cities–among many other treasures–are just around the corner.

white sand beach at indiana dunes with bright blue water on the right

South Dakota State + National Parks Road Trip

From Allison of Eternal Arrival

One of the best Midwest road trips is a loop from Rapid City, South Dakota making stops in its two national parks, as well as Custer State Park!

This is an easy road trip that you can do in as little as 4 days, but you can also make it part of a larger  South Dakota road trip itinerary .

Start in Rapid City to begin your trip and then make your way first to Wall, SD.

This fun little town is a great place to stop at Wall Drug Store for scenic photos in an Old West-feeling setting.

From there, head through Badlands National Park from the Northeast Entrance, taking the 30-mile Badlands Loop Road and stopping at as many overlooks as possible!

Depart via the Pinnacles Entrance and then make your way to Wind Cave National Park.

interior of wind cave in south dakota, a fun stop on a road trip in the midwest america

Wind Cave National Park is beautiful but there must be some advance planning as you need advance reservations to visit Wind Cave.

Book your reservation for one of the 3 tours, ranging from moderate to hard difficulty, on the  NPS website here . 

After visiting Wind Cave, swing up north towards Custer State Park for one of the final stops on this South Dakota tour.

Custer State Park in the Black Hills is home to lots of stunning wildlife, including bison, pronghorn antelope, and elk. Bring your binoculars and a zoom lens!

Finally, drive back to Rapid City to end your road trip.

Driving Distance

Recommended road trip length.

At a minimum, you should spend at least 2 days in Badlands National Park, 1 day in Wind Cave National Park, and 1 day in Custer State Park.

This road trip can be done easily in 4 days, but you can stretch it out to a week and visit other sites like Mt. Rushmore, the Black Hills National Forest, Keystone, and Crazy Horse.

view of cylvan lake with rock formations in the background in south dakota

Ohio Road Trip Along Lake Erie’s Coast

From Theresa of Fueled By Wanderlust

One of the Midwest’s best road trips is  driving Ohio’s Lake Erie coast   from Cleveland to Marblehead for gorgeous lake views, beautiful sunsets, and lots of local history.

Beginning in downtown Cleveland, spend a day exploring the Rock n Roll Hall of Fame, Old Arcade, and West Side Market. 

Depart Cleveland the next day via Route 2, with several lakefront parks to your right. 

Edgewater Park and Lakewood Park offer Cleveland skyline views, while Edgewater Park and Huntington Reservation have pretty beaches. 

Continue for thirty minutes towards Lorain, OH, transitioning over to Route 6. 

While being a rust belt city, Lorain also offers a broad beach at Lakeview Park and the charming Lorain Harbor Lighthouse. 

Literature fans may also know it as Toni Morrison’s hometown and the setting of  The Bluest Eye .

Vermilion, the next town over, is a quaint location for an overnight stay. 

Its small downtown has an old-timey feel, with historic storefronts and a soda shop. 

red and white lighthouse in vermilion ohio with lake erie in the background

Take a stroll down Main Street for elegant dining at Chez Francois, and to see tiny Vermilion Lighthouse and its adjacent beach.

After leaving Vermilion, continue down Route 6 for a short rural break until you reach Sandusky. 

After consuming Asian fusion food and craft beer at Small City Taphouse, walk 10 minutes to the Maritime Museum of Sandusky. 

This museum features exhibits on the Battle of Lake Erie and Sandusky’s role in the Underground Railroad. 

If you love roller coasters, plan an extra day in Sandusky to catch thrills at Cedar Point.

Finally, drive 30 more minutes to the tip of the Marblehead Peninsula to reach the 200-year-old Marblehead Lighthouse. 

This beauty is the oldest continuously running lighthouse on the Great Lakes.

With no stops,  this drive  takes a little over 2.5 hours. 

However, I recommend slowing down over a long weekend to fully enjoy each stop.

aerial view of marblehead lighthouse, one of the best places to visit in the midwest usa

North Dakota Road Trip (Fargo to Theodore Roosevelt National Park)

From Anwar of Beyond My Door

Many people overlook North Dakota, however, the state has a plethora of road trip-worthy sites.

Starting in Fargo, visiting the town that is unfairly characterized by the movie of the same name, visitors can enjoy this hip small city of the north.

Be sure to check out the Plains Arts Museum and the wonderful contemporary, traditional, and folk art of the region.

For those with more time, a quick stop in adjacent Moorhead MN, and the Hjemkomst Center, visitors can connect with the local Scandinavian culture through this incredible boat journey.

From Fargo, head west stopping in Jamestown, to see the old wild west town and the largest buffalo.

Similar to many other big roadside attractions throughout the state.

From here, visitors can detour slightly north and visit interesting Lewis and Clark expedition sites such as Fort Mandan (where Lewis and Clark wintered) and the nearby Knife River Indian Villages known as the birthplace of Sacajawea.

best road trips starting in chicago

Both can easily be visited on the same day before heading on towards Bismarck.

Bismarck, the capital but smaller and sleepier than Fargo has a cute downtown as well as beautiful nature nearby.

But if you are pressed for time save the nature exploration until you head to  Theodore Roosevelt NP , 2 hours west of the capital.

Named for the 26th president, the park protects North Dakotan Badlands and local flora and fauna such as bison.

The park is divided into two non-connected units and at least 2 days are worth spending in the park.

river running through the plains in north dakota road trip

But if you have very limited time, the South Unit has more diversity of sights.

For those with more time and desire to explore local history, a quick stop at Fort Union Trading Post (90 minutes from the north unit) is worth a look at the fur trade and one of the most important forts in the mid-1800s.

About 550 miles, plus time in the national park. 

This Midwest road trip can be anywhere from 4 to 8+ days.

It’s recommended to spend at least 2 days in Fargo, a day en route to Bismarck, 1-2 days in and around Bismarck, and another 2-3 days in Theodore Roosevelt NP. 

buffalo in theodore roosevelt national park, an amazing stop on a road trip in the midwest

Minnesota’s Iron Range

From Susan of This Big Wild World

Have you heard of Minnesota’s Iron Range ?

Stretching from central Minnesota and north to the border of Canada, the region is home to some of the best mountain biking in the country, excellent hiking, and the pristine wilderness of the Boundary Waters Canoe Area.

This Midwest road trip itinerary starts and ends in Minneapolis, which is a city worth exploring!

Enjoy an afternoon at a Minnesota Twins baseball game or paddling the lakes in the heart of the city. 

Next, head to Crosby which is part of Cuyuna Country. What once were mining pits are now crystal clear lakes surrounded by mountain biking trails for all levels.

Spend a day paddle boarding or kayaking the lakes or cruising the trails. Gear rentals are available in Crosby.

From there, drive to Ely which is a gateway into the Boundary Waters.

person in red sweatshirt at the front of a canoe on minnesota boundary waters

This area is among the most beautiful and remote wilderness in the US, best explored by canoe. Find guides and outfitters in Ely for gear and permits.

For hiking, try the Norberg Lake Trail at nearby Bear Head Lake State Park or the Bass Lake Loop Trail. 

Duluth is a harbor town on Lake Superior, offering easy access to popular destinations along Minnesota’s north shore.

Be sure to watch for the big ships entering the harbor near Canal Park, relax on the beach at Park Point, and stop at one of the many breweries in town.

Ursa Minor and Bent Paddle are local favorites!

These destinations are just 2-3 hours apart and have tons to explore.

Spend a minimum of 1 day in each of the 4 destinations for a 4-5 day trip.

Or, take your time and spend up to 3 days in each destination for a 7-10 day road trip.

minneapolis skyline with stone arch bridge in the foreground, one of the best midwestern road trip stops

Badlands National Park Scenic Road Trip

From Theresa of The Local Tourist

At only39 miles, the Badlands Loop State Scenic Byway is a short but mighty road trip in South Dakota. 

Driving through Badlands National Park  is a surreal experience.

You’ll feel like you’re on another planet instead on a road trip in the Midwest USA.

The drive begins in Cactus Flat at Exit 131 off I-90. You’ll know you’re nearing the exit because you’ll begin seeing sand-colored buttes, spires, and cliffs to the south.

After taking the exit, it’s a short distance to enter Badlands National Park.

Before you even get to the Ben Reifel Visitor Center, you’ll see a few overlooks and trailheads.

winding road through badlands national park

The visitor center itself is a great place to get your bearings, take a bathroom break, and get something to eat at the restaurant next door.

From there, you’ll continue west through the otherworldly landscape.

In addition to the unique formations, you’re also likely to encounter pronghorn antelope, bighorn sheep, bison, and prairie dogs.

The road ends at Wall, which is a destination in its own right with its famous, or infamous, Wall Drug.

You could drive straight through in about an hour, but what’s the fun in that?

For a more immersive experience, camp at one of the two campgrounds within the park and take some day hikes.

bighorn sheep seen on a midwest road trip in badlands national park

Michigan’s Upper Peninsula

From Linda of Midwest Explored

Easily one of the best road trips in the Midwest USA, a drive through Michigan’s upper peninsula is a must-do.

Start one of the best Michigan road trips of them all by crossing Mackinac Bridge into the Upper Peninsula.

If you want, leave your car behind and enjoy all that Mackinac Island has to offer before continuing on.

After all, this island is completely car-free and features top attractions like Fort Mackinac and Arch Rock. 

Next, continue onto the peninsula and check out the natural beauty of Kitch-iti-kipi, an incredible local spring with crystal-clear waters.

Then, hop back on the road and drive to Porcupine Wilderness State Park.

view of fall foliage and a lake in porcupine wilderness state park, one of the best stops on a michigan road trip midwest itinerary

It’s a wonderful area with stellar views of Lake Superior, gorgeous local waterfalls, and 90+ miles of trails that will take you through vast old-growth forests. 

From here, drive until you hit Marquettethe.

It’s known for being the largest city in this UP (Upper Peninsula for all the non-Michiganders out there) and is a great place to explore Presque Isle Park, Sugarloaf Mountain, and Lakenenland Sculpture Park. 

Finally, conclude your road trip at the Pictured Lakes National Lakeshore with its dynamic natural landscape.

Be sure to explore the multicolored Pictured Rocks cliffs, Miners Castle, Chapel Rock sandstone formations, and Twelvemile Beach.

While this road trip isn’t long, taking around 2 hours to drive, plan on devoting between 3 and 5 days to this trip.

You could definitely spend an entire day on Mackinac Island alone!

arch rock formation on mackinac island michigan

Mount Rushmore to the Badlands, South Dakota

From Candice of CS Ginger

Mount Rushmore to the Badlands of South Dakota is a fantastic Midwest road trip route.

While there’s a sad story behind the impressive facade of Mount Rushmore, there’s no doubt that visiting the monument and associated museum is an incredible experience.

After visiting Mount Rushmore and touring all it has to offer, you will travel to the Badlands National Park.

Badlands National Park is a very beautiful and unique area.

There are really fun hiking trails in the Badlands , and it is a great place to visit with your family. 

You will be surprised at all the animals the Badlands offer.

You can see big horn sheep, buffalo, and the famous prairie dog area where you will see lots of prairie dogs. You can get very close to the prairie dogs but don’t touch them or get too close!

3 praire dogs in badlands national park, a great stop on a south dakota midwest road trip

If you want to stay in the park, you will need to stay at Cedar Pass Lodge in one of their rental cabins. 

There are some hotels and camping options close by, but the Cedar Pass Lodge is the only option if you are looking at staying inside the park.

This is a classic road trip in the Midwest, and a fantastic way to spend a long weekend (or longer!).

About 80 miles.

We recommend spending at least 3 days enjoying this road trip in South Dakota, though 4-5 days would be better if you have more than a long weekend to work with.

landscape of badlands national park in south dakota, one of the best things to do usa

Missouri + Southern Illinois Road Trip

From Tori of Tori Pines Travels

When planning a road trip in the Midwest, you won’t want to miss Missouri and Southern Illinois.

The perfect road trip includes a variety of cities filled with activities, nature to explore, and delicious food to eat, and you’ll find plenty of that here.

Start in Kansas City, Missouri where you’ll visit the American Jazz Museum and Money Museum.

For the famous Kansas City BBQ, check out Gates Bar-B-Q and order burnt ends.

Spend two nights here, before continuing east across the state to St. Louis. 

A weekend in St. Louis is the perfect amount of time.

Start at the country’s smallest national park, The Gateway Arch National Park, ride the tram to the top for incredible views over the city.

The free museum teaches the history of St. Louis and its title as the gateway to the west.

That night, visit Busch Field for a Cardinals game with the arch as your backdrop.

st louis missouri gateway arch as seen from across the river, a classic stop on road trips in midwest usa

For kids, and kids at heart, spend a few hours at the City Museum, the most unique children’s museum you’ll find.

Fill the rest of your time with visits to the free activities, the St. Louis Zoo, St. Louis Art Museum, and Missouri History Museum!

Eat some of St. Louis’s staples, toasted ravioli, St. Louis Style pizza, St. Louis style ribs, and gooey butter cake.

Finish off the road trip by venturing across the river into Illinois to Shawnee National Forest.

The draw here is the Garden of the Gods which features fun dog-friendly hikes and super unique rock formations.

The whole trip should take about 5 to 6 days, and will only require about 6.5 hours of driving.

sunset over rock formations in garden of the gods illinois, a fun usa midwest road trip destination

Great Cities of the Midwest Road Trip Loop

From Lisa of Waves and Cobblestones

Looking for a fun road trip itinerary in the Midwest?   

Making a round trip from Chicago, Illinois to Milwaukee and Madison in Wisconsin will give you a great sampling of museums, architecture, and natural beauty to enjoy.

Start your road trip in Chicago, Illinois. One of the undisputed best experiences here is the architectural river cruise . 

Your vantage point from the river gives you great views of the skyscrapers, and you’ll learn a lot about Chicago’s architecture and history.

Chicago is also home to several fantastic museums, including the famous Art Institute of Chicago.

The Field Museum is the home of Sue, the largest Tyrannosaurus rex specimen ever discovered.

Chicago Skyline with river filled with sailboats in the center, an excellent view to seek out during 3 days in Chicago

Your next stop is Madison, Wisconsin. This college town is also the capital of Wisconsin. 

The Capitol building is incredible and is free to tour. Be sure to take in the panoramic city views from the observation deck!

One of the  best things to do in Madison   is to visit the Olbrich Botanical Gardens. 

The outdoor areas of the garden are free to visit. Don’t miss the phenomenal Thai pavilion and garden – this is definitely the garden’s highlight!

Continue on to Milwaukee, Wisconsin. 

Enjoy local favorites like bratwurst and fried cheese curds (and perhaps a local beer) at Old World 3 rd  Street. 

Then take a stroll along the downtown Riverwalk and enjoy the public art including ‘The Bronz Fonz’.

milwaukee wisconsin skyline at night

Spend an afternoon at one of Milwaukee’s museums, such as the world’s only Harley-Davidson Museum. 

Be sure to take a look at the amazing architecture of the Milwaukee Art Museum, with its Burke Brise Soleil ‘wings’.

320 miles round-trip.

Recommend Road Trip Length

This Midwest road trip itinerary will take you about a week since you’ll want to spend a minimum of 2 days in each city. 

aerial view of madison, one of the best cities to visit on road trips in midwest usa

Route 66 Road Trip Through the Midwest (Chicago to Oklahoma)

From Kylie of Between England and Iowa

The classic US road trip Route 66 starts in Chicago Illinois and passes through the Midwestern states of Missouri and Kansas before crossing into Oklahoma and continuing west all the way to Los Angeles, California. 

Of course, it’s quicker to travel on the Interstate but the heart of the road trip is to follow the original route across the country.

Travelers could easily spend a couple of days exploring Chicago alone, but it’s at least worthwhile checking out the Route 66 BEGIN sign at E Adams St and S Michigan Ave.

The stretch across Illinois between  Chicago to St Louis   can take upwards of 12 hours, especially if stopping at several of the different points of interest. 

historic route 66 begin sign in chicago, start of one of the top road trips in midwest usa

When the Interstate was built, it bypassed all the small towns along the route.

To encourage travelers to come back many of the towns created unique roadside attractions.

Today, you can find a mixture of historic buildings that were part of the original Route 66 as well as the unique attractions from the time after the Interstate was built.

Some highlights between Chicago, IL, and Catoosa, OK include The Gemini Giant (Wilmington, IL), Pontiac, IL, the Chain of Rocks Bridge, IL, Gateway Arch National Park (St. Louis, MO), the World’s Largest Rocking Chair (Fanning, MO), Cars On The Route (Galena, KS) and the Blue Whale (Catoosa, OK).

Approximately 700 miles.

This road trip could be done in around 3 days (overnight stops in St Louis, MO, and Carthage, MO).

However, with the addition of spending time exploring the larger cities of Chicago and St. Louis, it is better to take around 5 or 6 days.

blue catoosa whale on route 66 in oklahoma, a kitschy tourist attraction in the us

Great Lakes Road Trip in Wisconsin + Michigan

From Jenifer of The Evolista

One of the best Midwestern road trip journeys is a National Lakeshore Road Trip to visit 2 of the best kayaking trips in the US , Apostle Islands National Lakeshore and Pictured Rocks National Lakeshore.

Apostle Islands National Lakeshore is a spectacularly beautiful area in the most northern part of Wisconsin that has a 12-mile stretch of mainland rocky cliffs with sea caves and a chain of 21 islands.

It also has the distinction of having the most lighthouses in the USA.

A kayak tour of the mainland sea caves will take you to the prettiest spots around the reddish sandstone shoreline.

You will cruise through incredible caves in turquoise water and can also hike the Lakeshore Trail through old-growth forest for a different vantage point.

apostle islands national lakeshore as seen from the water at sunset

On your way to Pictured Rocks National Lakeshore, break up the drive with a day at Porcupine Mountains State Park where you’ll find waterfalls, tons of hiking trails, and gorgeous views, especially for fall foliage.

It adds an extra hour of drive time but it’s completely worth it.

When you arrive in Munising, you’ll be treated to Pictured Rocks National Lakeshore’s towering multi-colored cliffs, bright blue waters, and hidden caves.

On a kayak tour, you can paddle to Lovers Leap Arch, Chapel Rock, Battleship Row, and sea caves. Or hike the Chapel Loop Trail to get even more incredible views. 

But this place isn’t all about the rocks. Don’t miss Twelvemile Beach for a traditional beach day or enjoy the sunset at Sandpoint beach.

And you’ll also find beautiful waterfalls at Munising Falls and Miner’s Falls. 

This road trip in the Midwest takes approximately 6 hours of driving.

Plan at least 4 days to be able to do daily activities and a week to enjoy at a more leisurely pace.

arch at pictured rocks national lakeshore, one of the best midwest travel destinations

Kansas City, Omaha + Des Moines Road Trip Loop

From Sage of Everyday Wanderer

There are many things to love about Kansas City — flowing fountains, tree-lined boulevards, and the world’s best barbeque.

So before you head north on this road trip loop through America’s Heartland, be sure you’ve hit all of the highlights in the Chiefs Kingdom. 

Start with the Liberty Memorial. This 217-foot tall limestone tower surrounded by acres of green space honors those who perished in World War I and is home to the only museum dedicated to the Great War.

It’s also one of the best places to view the Kansas City skyline. 

Then head to the Country Club Plaza where you can shop, dine, and admire Spanish-inspired architecture and several of the city’s most renowned fountains.

Then stroll through the sculpture garden, explore the glass maze, and snap a selfie with one of four, oversized badminton shuttlecocks at the Nelson-Atkins Museum of Art.

And you certainly won’t want to leave town without eating your fill of Kansas City barbeque .

plate of smoked barbecue ribs in a restaurant

The next stop is Nebraska’s biggest city, Omaha, about three hours to the north.

Walk across the Missouri River – a natural border between Nebraska and Iowa – on the Bob Kerrey Pedestrian Bridge.

Then enjoy The RiverFront connecting river to Downtown Omaha with lush green space, pet-friendly areas, a sculpture garden, and more.

Fuel up at a cafe or eatery in the Old Market, and don’t miss the world-renowned Henry Doorly Zoo and Aquarium.

The capital city of Des Moines is about two hours east of Omaha.

Stretch your legs after the drive by wandering through Pappajohn Sculpture Park or strolling through the botanical garden.

Tour the gold-domed capitol building, and learn more about Iowa’s biggest city with an interactive scavenger hunt.

skyline of des moines iowa at sunset, a fun stop on midwest road trip itineraries

Outdoor enthusiasts will want to hike or bike the Des Moines River Trail, and foodies will want to compare the barbeque at Flying Mango to what they enjoyed in Kansas City.

On the way back to Kansas City, stop in Pella. With its working grain windmill, Dutch bakeries, and thousands of tulips in the spring, you’ll feel as if you’ve been transported to the Netherlands while exploring the middle of America.

580  miles.

We recommend enjoying this Midwest road trip itinerary over the course of a week, in order to allow about 2 days per city.

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2 photos of the usa midwest, lighthouse and bison in a field. black and red text reads "11 epic midwest road trip ideas"

About Kate Storm

Image of the author, Kate Storm

In May 2016, I left my suburban life in the USA and became a full-time traveler. Since then, I have visited 50+ countries on 5 continents and lived in Portugal, developing a special love of traveling in Europe (especially Italy) along the way. Today, along with my husband Jeremy and dog Ranger, I’m working toward my eventual goal of splitting my life between Europe and the USA.

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Home | Travel guides | Road trips | Road trips USA | Top spots for a road trip from Chicago

Top spots for a road trip from Chicago

  • Saugatuck Dunes State Park
  • Door County
  • Walworth County
  • Table Rock Lake
  • Lake Leelanau
  • Traverse City

Top spots for a road trip from Chicago

The Windy City has plenty to offer all kinds of people, but sometimes you just want some time away from Chicago. If you find yourself longing for an adventure that takes you elsewhere, you won’t have to book a flight or travel the world to find fun. There are numerous exciting destinations well within driving distance of the city. Learn about the top 10 best road trips from Chicago.

1. Explore scenic mountain paths in the  Ozarks

Driving time from Chicago: 8.5 hours Distance from Chicago: 560 miles

If you’re looking for outdoor adventure, there’s nothing quite like the  Ozark Mountains . This stunning mountain range covers almost 47,000 square miles, and all that space is packed with attractions like hiking trails and tranquil lakes for fishing or boating. Don’t forget to visit Buffalo Lookout after your road trip from Chicago to see the tallest point of the Ozarks.

2. Visit Music City in  Nashville

Driving time from Chicago: 7 hours Distance from Chicago: 470 miles

Nashville , Tennessee, is known primarily for its dedication to music, so you’ll be able to find an exciting performance no matter what genres you’re into. Even outdoor performances are prominent, though you can learn all about music history at its local museums as well. Of course, Nashville is also a great place for satisfying Southern cooking.

3. Find family fun in  Branson

Driving time from Chicago: 8 hours Distance from Chicago: 540 miles

If you’re looking for family-friendly fun, you won’t have to look farther than  Branson , Missouri. This wholesome town has something for everyone. Not only is it relatively close to the Ozarks, but the community itself features amusement parks, delicious restaurants, and extensive shopping opportunities. Outdoor fun is especially popular, with zip lines and ropes courses for kids and adults alike.

Beach on Lake Michigan in Saugatuck

4. Relax with a trek through  Saugatuck Dunes State Park

Driving time from Chicago: 2 hours Distance from Chicago: 140 miles

Located on the other side of Lake Michigan,  Saugatuck Dunes State Park  is an incredible destination for travelers looking to relax at the end of their road trip from Chicago. It comprises about 1,000 acres of land and features freshwater coastal dunes, with some more than 200 feet tall. This place is a hiker’s dream, but you can also enjoy the lakefront shoreline.

5. Revel in natural splendor in  Door County

Driving time from Chicago: 3.5 hours Distance from Chicago: 240 miles

Up north in Wisconsin, you’ll find  Door County  after a relatively short road trip from Chicago. Located on a peninsula, this is one of the unique areas where you can watch a coastal sunrise and sunset in the same area. That’s just the beginning, however, as this region is also home to extensive orchards and vineyards. If wine isn’t your thing, numerous breweries call Door County home as well.

6. Discover the charming small town of  Galena

Driving time from Chicago: 2.5 hours Distance from Chicago: 160 miles

The small town of  Galena  is a charming destination for any road trip from Chicago. The main street offers numerous colonial-style buildings with a variety of restaurants that are all locally owned. Additionally, you can enjoy the iconic County Fair, which hosts an impressive craft show, and the annual Halloween Parade.

Walking trail in the woods in Wisconsin

7. Find diverse fun in  Walworth County

Driving time from Chicago: 1.5 hours Distance from Chicago: 90 miles

No matter what kind of fun you’re looking for, you can find it in  Walworth County . This southern Wisconsin region features incredible natural sites as well as charming small towns. You can venture out onto one of the local lakes in a boat, or you can ride a zip line through the forest. Even shoppers can find fun in the Lake Geneva area.

8. Venture through the clear waters of  Table Rock Lake

For a relaxing destination after a long road trip from Chicago, there are few spots better than  Table Rock Lake near Branson. The clear water here offers extensive aquatic activities including swimming, boating, and rafting. Surrounding the lake is vibrant scenery with numerous trails for hikers to enjoy. There are almost 500 miles of shoreline, so you’ll never find yourself short of space or things to do.

9. Experience tranquil comforts in  Lake Leelanau

Driving time from Chicago: 5 hours Distance from Chicago: 330 miles

Road trips from Chicago can lead to many places, but  Lake Leelanau  in Michigan offers a tranquil experience you can’t find anywhere else. The area is fairly remote and sparsely populated, so it’s useful for finding some peace and quiet away from the hustle and bustle of the big city. Don’t think you’ll be isolated, however, as there are plenty of small eateries and shops around the lake.

10. Enjoy endless activities in  Traverse City

Driving time from Chicago: 4.5 hours Distance from Chicago: 320 miles

When you visit  Traverse City , Michigan, at the end of a road trip from Chicago, you can enjoy a wide variety of activities for the whole family. Whether you’re looking to immerse yourself in the local culture of the city or spend time along the water for a scenic sunset, there’s never a shortage of beauty or entertainment here.

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The best driving route around the Great Lakes: hit the road on this epic round trip from Chicago

Apr 14, 2022 • 7 min read

Husband and wife on road trip in van parked on side of road near ocean looking out

This road trip around the Great Lakes is a wonderful way to experience the best of the region © Thomas Barwick / Getty Images

A happy marriage of open road and open water, of blacktop and blue swells, a looping tour of the Great Lakes – beginning and ending in Chicago – can take in five states, four of the lakes, and the birthplaces of two music legends.

As much country as it is town, this road trip delivers all the hazy, lazy romance of a beach holiday while staying firmly inland. Take your time, it's an epic journey.

Find beaches, art, and baseball on the drive from Chicago, Illinois to Toledo, Ohio 

Approximately 250 miles

Stick close to the Lake Michigan shoreline and it’s just 20 miles from downtown Chicago to the Indiana border. A handful more and you’ll be in Gary , a once-prosperous steel town that, though now heavily rusted, still has its fans – most of them musical. One of the few tended properties in a rundown neighborhood is the fenced-off two-bedroom bungalow at 2300 Jackson St. This was home to Michael Jackson and his nine siblings, and is where the Jackson 5 was launched. 

Gary is the western bookend of Indiana Dunes National Park , one of the country's newest national parks and a patchwork of beaches, marshland, prairie, scrub, and forest running for 25 miles alongside Lake Michigan. There you can swim, hike, go horseback riding, spot rare plants and birds, and bed down at Dunewood Campground.

Afterward, head east on Interstate 80, to Toledo , Ohio , at the western tip of Lake Erie . This former industrial metropolis is nicknamed "the Glass City" due to it making a lot of glass in its heyday. It was also something of a safe space for mobsters and bootleggers during Prohibition. More recently, Toledo has recovered its mojo, bringing in art lovers to visit the world-class  Toledo Museum of Art , sports fans who pack out the stadium to see the Toledo Mud Hens  (one of the oldest Minor League Baseball teams), and devotees of the Hungarian hot dog .

Waves lap the banks of Lake Huron; Great Lakes road trip

Stop for some great surf on your drive from Toledo, Ohio, to Bay City, Michigan

Approximately 340 miles

Before you head north up Hwy 23 to the university town of Ann Arbor, where you can fill up on experimental art, vegan cuisine and radical politics, make a detour to Luna Pier , a modest resort town just over the Michigan state line. Here be surfing. Yes, you can surf on the Great Lakes, and at any time of year, but you’re more likely to get the right blustery conditions to do so in fall, winter, and early spring. Lunar Pier has some of Lake Erie’s most popular breaks.

From Ann Arbor, pick up Interstate 69 at Flint and at Port Huron join Hwy 25, which clutches Lake Huron’s supremely scenic western shore – "the sunrise side" – all the way to Saginaw Bay. The coast is punctuated by quaint towns – Lexington and Ports Sanilac, Hope and Austin – and their beaches, lighthouses, marinas, and charter fishing.

Michigan’s Lower Peninsula is often referred to as "the mitten," and Saginaw Bay separates the thumb of that mitten from the rest of it. Bay City, the birthplace of Madonna, sits in the crook of that thumb. It’s one of the better spots for surfing.

The Bavarian-style town of Frankenmuth; Great Lakes road trip

Drive to Frankenmuth and onwards into Michigan's lower northwest for fresh fish and natural wonders

Approximately 360 miles to Mackinac Bridge

Before you head east across "the mitten" on Hwy 10, a visit to Frankenmuth , aka "Little Bavaria," is in order. The area was settled in the 19th century by Lutheran immigrants from Franconia, Germany, and the town – in its timber-framed architecture, beer and sausage festivals, and German spoken as a second language – has retained more than a flavor of the old country.

At the end of Hwy 10, on the east coast of Lake Michigan, is Ludington, one of the state’s best beach towns, with 28 miles of sandy shoreline, community beach bonfires, and a coal-fired car ferry to and from Manitowoc , Wisconsin. More salmon and trout are caught from Ludington each year than anywhere else, so hire a charter boat and get your catch prepped, broiled or poached at one of many local restaurants participating in Michigan’s Catch and Cook program .

A family walks along the lake shore with the Mackinac bridge in the background; Great Lakes road trip

Join Hwy 31, which skirts Lake Michigan for 366 miles and travels north to where the Lower meets the Upper Peninsula , or "the Yoop," via the five-mile Mackinac Bridge, an ethereally elegant piece of engineering that looks plucked from the pages of Greek mythology.

On the way, make time for the myriad virtues of northwest – that is, lower northwest – Michigan. Perhaps you'll stop by the vineyards, wineries and fine-dining establishments in and around Traverse City, a resort town producing 75 percent of the country’s tart Montmorency cherries. Or you could visit the Leelanau Peninsula, Charlevoix, Harbor Springs, Boyne City and Petoskey, all places with beaches that are mobbed in high season, but still feel untamed and isolated.

Special mention must go to the Sleeping Bear Dunes National Lakeshore. Its steeply elevated bluffs – which help make up the largest freshwater dune system in the world – beech and maple woodlands and views of Lake Michigan at its most Mediterranean amount to a natural wonder. The Overlook , an observation point on the Pierce Stocking Scenic Drive , gazes down on a 450ft near-drop. People are warned to not descend because few have the lung capacity to get back up. Surfers are welcome to chance their boards at the public beach in Empire , a candy-colored hamlet of weathered buildings Norman Rockwell could have painted.

The sun sets over the lake; the shore is littered with driftwood

Keep heading north into Michigan's Upper Peninsula for shipwrecks and ghost towns 

Approximately 325 miles

Nicknamed "the Deep North," heavily forested and formerly rich, the Upper Peninsula is a place of mystery and of ghosts. Hear some of their stories at the Great Lakes Shipwreck Museum , at Whitefish Point, west of Munising town. More than 6000 ships and 30,000 lives have been lost on the Lakes, in large part because they lack natural harbors in which vessels can wait out violent storms.

Keweenaw Peninsula , northwest of Marquette, a major port on Lake Superior , is likewise haunted. Native Americans were the first to mine copper in the area, some 7000 years ago, but it took the Ojibwe to sign a treaty in 1842 ceding their mineral-rich lands to the United States for the copper rush, which made more fortunes than California’s gold rush, to gain momentum. Almost all of the mines were shut down during the Great Depression, and relics of the industry – several ghost towns, the erstwhile opera house in Calumet – are all that is now left.

Girl and boy exploring rocks in Cave Point County Park on shores of Lake Michigan

Leave the Upper Peninsula behind for charming small towns and a stop in the cool city of Milwaukee, Wisconsin

Approximately 555 miles

From Keweenaw Peninsula bear south on Hwy 141 and you’ll be in Wisconsin in a couple of hours. Overshoot Green Bay and hang a left on Hwy 57 into Door County , a narrow spit of land – 75 miles long by 3 miles at its tip – that juts out into Lake Michigan. Mesmerizingly tranquil and comfortably affluent, every square inch of this "Cape Cod of the Midwest" seems to carry a divine stamp. It’s a storehouse of biological diversity. And its towns, such as Egg Harbor and Fish Creek , are stuffed with charm, independent stores, and artisanal bakers.

As a way of weaning oneself off the cozy joys of bucolic Wisconsin and easing oneself into the raw excitement of Chicago, Milwaukee , off I-43, makes the perfect transitional stop. Brew City continues to make beer, but it has diversified its appeal, transforming itself into an assuredly cool arts, music, and festival hub , and some of its neighborhoods , such as Bay View , south of the downtown area, are so hip it hurts.

From there, it’s back to the Chicago. But not without a carful of memories, a camera full of photographs, and a head full of beach hair.

You might also like: Top 7 day trips from Chicago    The best time to visit Michigan: a season-by-season guide    Save your money and spend time enjoying free things in Milwaukee   

This article was first published Sep 25, 2019 and updated Apr 14, 2022.

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Road Trips from Chicago: The Most Scenic Drives for Fall Colors

Chicago’s surrounding forests display vibrant fall hues that provide some of the best autumn scenery in the Midwest. The myriad fall hues of maples, oaks, and other trees capture autumn’s essence. This article featuring road trips from Chicago will highlight the prime times to catch peak colors and recommend the top scenic drives within a few hours of the city to marvel at Mother Nature’s paintbrush.

galena IL fall road

When to Catch Peak Fall Foliage Near Chicago

Predicting the ideal timing for a fall colors road trip poses challenges since factors like weather affect peak conditions. In the Chicago area, the explosion of autumn hues typically occurs in mid to late October. Monitoring fall foliage prediction maps can help pinpoint prime times for a road trip based on road trips from Chicago, as they use algorithms based on location, weather, and historical data to indicate the status of change across regions. Apps like Forest Service Fall Colors and SmokyMountains’s Fall Foliage Map provide weekly forecasts so leaf peepers can plan outings during optimal conditions. Being flexible by a week or two will maximize your chances to see nature’s fleeting brilliance.

Top Scenic Drives Less Than 2 Hours from Chicago

Venturing just a short drive from Chicago opens up many options to immerse in the lush palette of fall. These routes offer stunning vistas and quintessential Midwest autumn charm less than 120 minutes away.

Oglesby IL

Starved Rock State Park

This park, located just 90 minutes southwest of Chicago in Oglesby, IL, shines like a beacon for leaf peepers. Its eponymous 125-foot sandstone bluff overlooks the brilliant wooded ravines flanking the Illinois River. Maples, oaks, hickories, and other trees display a spectrum of colors along the park’s 13 miles of trails.

Kettle Moraine Scenic Drive – Wisconsin

A quick 60-minute drive north enters Wisconsin’s picturesque Kettle Moraine forest. This 100-mile stretch of gloriously winding roads offers continuous gorgeous vistas. Rolling glacial terrain and kettles dot the landscape. You’ll want to stop at scenic overlooks like Lookout Tower and Greenbush Kettle Bowl.

Illinois River Road Scenic Byway

Meandering riverside offers ever-changing colors along this National Scenic Byway just 90 minutes west of Chicago. The route follows the curves of the Illinois River past Peoria and the remnants of colonial forts and villages.

Top-Rated Scenic Drives Accessible with Road Trips from Chicago

For those willing to venture further afield, magical autumnal wonderlands await within half a day’s drive of Chicago. Here are some beloved destinations for experiencing fall’s vibrant colors.

Door County, Wisconsin

Situated along the shores of Lake Michigan, Door County boasts quintessential New England vibes with historic lighthouses, quaint coastal towns, and fish boils. The four-hour drive rewards visitors with bucolic countryside awash in red and gold hues, especially throughout Peninsula State Park.

Michigan Upper Peninsula

Michigan’s remote upper region transforms into a kaleidoscope of autumn majesty as crimson and copper colors illuminate dramatic shorelines, deep forests, and thundering waterfalls. Places like Tahquamenon Falls State Park and Pictured Rocks National Lakeshore offer extraordinary beauty just 4 hours northwest of Chicago.

Brown County State Park, Indiana

Rolling hills cloaked in autumnal splendor give Brown County its reputation as “Little Smokies.” Just 3.5 hours southeast of Chicago near Nashville, Indiana, this 16,000-acre park comes alive in the fall. Miles of hiking trails thread through maples and oaks decked out in their seasonal best.

car trip autumn

Maximizing Your Fall Foliage Road Trip from Chicago

When chasing fall colors, flexibility and patience pay off. Here are some tips for making the most of your leaf-peeping drives from Chicago:

  • Allow ample time for frequent photo stops and short walks, as peak colors demand admiration.
  • Bring snacks and drinks to enjoy extended stays at scenic overlooks.
  • Remain open to shifting your trip dates a few days or weeks if weather delays peak conditions.
  • Travel mid-week to avoid crowds that flock during busy weekends.
  • Have binoculars and bird books handy, as bird migration overlaps with foliage season.

Top Stops to Make Along Chicago Fall Color Routes

While simply driving through areas bursting with autumn’s canopy provides pleasure, taking time to explore on foot injects a deeper appreciation for the fleeting beauty. Here are some recommended stops along a few of the featured drives from Chicago:

Door County – Sample apple pie in Fish Creek, and capture the iconic Eagle Bluff Lighthouse. Traverse trails in Peninsula State Park through maple groves.

Starved Rock – Explore seasonal waterfalls like French Canyon Falls, and weave through the diverse flora on Wildcat Canyon Trail.

Brown County – Take Abe Martin Lodge tours, visit rustic shops and eateries in Nashville, and hike along sycamore-lined trails like Fire Tower Loop.

Where to Stay on Your Fall Foliage Road Trip

Having lodging options near prime leaf-peeping locations allows you to maximize time among the trees and minimize long drives back to Chicago at night. Here are some cozy accommodations to bookend your days spent enveloped in autumn’s splendor:

Door County – Country House Resort in Sister Bay offers charming cottages. The Blacksmith Inn B&B in Baileys Harbor provides fireside relaxation.

Starved Rock Area – Starved Rock Lodge inside the park welcomes wooded lodge appeal. Hotel Veruca in downtown LaSalle provides contemporary elegance.

Brown County – Salt Creek Golf Retreat features secluded cabins near Nashville. Story Inn immerses guests in a historic cottage ambiance.

For a truly immersive fall camping experience, reserve one of the wooded and secluded RV or tent sites at Nicolet Bay Campground in Door County’s Peninsula State Park. Nestled right along the shore of Green Bay, the campground provides immediate trail access into maple forests resplendent with autumn hues. Build a campfire and cook meals surrounded by the glow of fall colors. Here are some camping breakfast ideas for some inspiration.

Autumn Landscape

Ways to Embrace the Spirit of Fall

In addition to beholding the beauty of fall foliage, consider incorporating these quintessential autumn activities into your road trip:

  • Indulge in apple and pumpkin treats from roadside stands and farms.
  • Peruse farmer’s markets showcasing peak produce and seasonal crafts.
  • Attend a local harvest festival with activities like hayrides and corn mazes.
  • Hike or bike with the crunch of leaves accompanying each footfall.
  • Photograph pumpkins, hay bales, and sunflower fields.

Fall Road Trip Gear Essentials

Appropriate equipment enhances time spent reveling amidst autumn’s temporary wonders. Be sure to pack:

  • Warm layers like fleece jackets, vests, hats, and gloves for crisp days
  • Hiking shoes or boots with traction for trails
  • A blanket or portable seat for comfortable scenic stops
  • Snacks and refillable water bottles
  • Phone power bank and car phone charger
  • Binoculars for birdwatching
  • Camera gear like extra batteries and memory cards
  • Collapsible wagon for hauling picnic supplies

By following the road trips from Chicago outlined above, Chicagoans can fully embrace fall’s fleeting grandeur through delightful weekend road trips or extended foliage forays. Don’t miss seeing nature’s autumn masterpiece firsthand by heading out among the fall splendor. The snapshot views and insider knowledge shared here aim to ignite inspiration to seek out your adventures amidst the blazing colors waiting to be discovered near the city. So, pack your car with the essentials, roll down the windows, and drive out to find that perfect patch of fall majesty.

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A scenic view of the 60-ft high granite sculpture of the four presidents of the United States in the Black Hills with a green forest at the foot of the mountain in a sunny morning in Mount Rushmore National Memorial Monument in South Dakota

Road Trip From Chicago To Mount Rushmore

Mount Rushmore, one of the most incredible sights in the entire world, yet one that doesn't draw anywhere near the number of people you would expect for such a famous and iconic location. Why is that, you ask? Well, it's all to do with the location.

It will take a solid 14 hours to drive the road trip from Chicago to Mount Rushmore in the Black Hills of South Dakota before adding time for fuel, food, and rest stops. Take 3 to 4 days to explore the best of Iowa and South Dakota's wilderness.

The long drive may put many off going, but for real road-trippers like us, it presents an opportunity - a chance to hit the road and explore some lesser-known gems in this part of the country.

How far is Mount Rushmore from Chicago and how long will it take to get there?

Ok, so this trip isn't going to be for the faint of heart or those that aren't fond of being in a car. The distance from Chicago to Mount Rushmore is almost exactly 1,000 miles, so it's a trip you're probably going to want to break into stages.

Following the fastest route, the journey can be made in around 14 hours. However, that's almost exclusively on the freeway, with very little in the way of attractions to see along the way.

With that in mind, we're going to take a slightly different route that, while it will bump the traveling time up to 16 hours, will be much more rewarding overall.

Best road trip route from Chicago to Mount Rushmore

The start of the trip is very straightforward. Head off on the I-88 where it begins and follow it to its conclusion, just before the Iowa state line.

From here take, take the I-80 west until you reach Omaha. Don't worry if it sounds like we've already been driving for an age - there's plenty of sights to see and stop at along the way, including the famous Iowa cornfields that we'll get to in the next section.

A row of windmills in the cornfield in a blue sky with uniformed blue-gray fuzzy clouds in Iowa

From Omaha, take the I-29 north to Junction City. This is where we get to see even more of the rural beauty of the area as we get off the interstate and join US-50, still going west.

Follow this until it meets the I-90, just outside Pukwana, which you'll follow almost the rest of the way to Rapid City.

From Rapid City, it's just a short trip to Mount Rushmore down US-16 and 16A.

Best places to stop between Chicago and Mount Rushmore

So, while you could technically make the journey in one day, I think it's clear it will be more enjoyable to break it up into chunks and make the most of your time in an area you may not get the chance to come back to again.

Looking at the length of our journey, I'm going to break it up into three even parts.

A relaxing stay in Des Moines, Iowa

The first stop on our list will have us staying in the capital city of Iowa, Des Moines.

There's not much to see between here and Chicago, so making the journey in one hit will give us plenty of time to explore the city.

The stunning Des Moines Botanical Garden Environmental Center in Iowa with made of a glass dome and a series of beautiful flowers around it during summer

A beautiful city that's often overlooked due to its location, Des Moines has plenty of things to keep you entertained for an afternoon. See the Iowa State Capitol, the Botanical Gardens, and the Kruidenier Trail Bridge, before relaxing in one of the many great bars and restaurants throughout the city.

Just a short drive south-west, there's also the town of Winterset, home to the birthplace of the legendary movie star John Wayne and featuring a museum of his life in the house he was born in.

As this is certainly going to be a trip to remember, why not do it in style and treat yourself to a stay in Hotel Fort Des Moines, Curio Collection By Hilton ?

With a central location in Des Moines, you will be in the center of the action with Pappajohn Sculpture Park and Science Center of Iowa at your doorstep within walking distance of the hotel.

There are plenty of restaurants and bars nearby, but we highly recommend booking a table at the restaurant on-site to treat yourself to a delicious meal once you are done exploring.

Experience life on an Indian Reservation

For many of us, life on an Indian reservation is something we won't really understand. We'll have seen it in films and heard about it in the media, but until you've visited one, you won't get a true feeling of what they're actually like.

Considering our route takes us directly through the Yankton Reservation, home to legendary figures such as Chief Running Bull, there will never be a better time to experience it than this.

See the stunning wildlife and beautiful landscapes, learn about the rich history and culture of the area and talk to the people for whom this is their lives.

An experience we thoroughly suggest everyone has at least once in their lifetime, you get to tick it off without even making a detour. Now that's a win if ever we saw one.

While visiting, we recommend making the Fairfield by Marriott Inn & Suites Yankton your home away from home. This modern hotel has all the amenities you will need, including a fabulous indoor pool and a fitness center if you are looking to keep active during your road trip.

Make sure to take advantage of the delicious continental breakfast on offer before you hop back on the road.

A not-so-rapid stay In Rapid City

Bronze statues in the "City of Presidents", Rapid City, South Dakota

The final stop on our journey, Rapid City, is great in its own right but is often used as a place to stay on the way to other sights and destinations.

Within 50 minutes of the city, there is an incredible number of sights and attractions to see.

You have national parks, historic towns, tourist attractions, festivals, and even Mount Rushmore itself is less than 30 minutes away. If you wanted to drive a little further, there's also the site of the famous Wounded Knee Massacre under 90 minutes from the city.

With so much in the vicinity and all the time you've taken to get here, I'd highly recommend staying for at least 4-5 nights to make sure you don't go away feeling like you've missed out on anything.

With a longer stay here, you're also going to want to make sure you get your accommodation just right. Well, when you've traveled all this way to visit Mount Rushmore, it's only fitting to stay at the beautiful Summer Creek Inn .

This lovely inn has all the luxury you might need after a long drive, or a day spent outside exploring Mount Rushmore. We highly recommend booking a treatment at the spa on-site to pamper yourself and unwind in style.

The next day, you will be able to enjoy a delicious breakfast and admire the views of a waterfall and beautiful gardens on the sun terrace before setting off on the next leg of your adventure in Rapid City. Both Hill City and Deadwood are manageable drives from the property.

Things to see on a road trip from Chicago to Mount Rushmore

So, we've said we're making three stops along the journey, but that doesn't mean there are only 3 things to see. It doesn't even mean we'll only be stopping for three nights.

There's plenty to do and see along the route, with some being short stops and others being locations you may want to spend more time in. Your own personal preferences will dictate how long you stay at each of our overnight spots.

With that in mind, some of the sights you can look forward to seeing along the way include:

  • Iowa Cornfields - Famed for its sprawling cornfields, experience driving through the countryside with them spreading out as far as the eye can see in every direction.
  • Des Moines - The capital and most populous city in the state of Iowa.
  • John Wayne Birthplace Museum - Just down the road from Des Moines, in Winterset, is the birthplace of a legend. Visit the childhood home of the duke, restored to how it would have looked at the time of his birth in 1907, and learn his history as it's now a museum dedicated to his life and works.
  • Omaha - The capital city of Nebraska, Omaha is home to dozens of historic landmarks and districts. Take the opportunity to get out and explore some of the area's culture on your way through and see attractions such as the Henry Doorly Zoo and the Old Market.
  • Yankton Reservation - Experience the landscape, history, and culture of what a modern-day Indian Reservation looks like.
  • Wall Drug - A famous attraction located adjacent to Badlands national park, Wall Drug features a large collection of Wild West-themed stores, including souvenir shops, restaurants, and, as you might expect, a drug store. There's also a large art gallery and a Brontosaurus sculpture to show the culture and history of the area, which you can further explore in….
  • Badlands National Park – A beautiful national park covered with sprawling prairies and canyons. Make the most of your chance to get back to nature for a while and see if you can spot some of its famous bison or bighorn sheep. It's also home to one of the world's richest collections of fossils, and there are paleontologists on-site to teach you about them.
  • Wind Cave National Park – One of the longest and most complex cave systems in the world lies beneath great pine forests and grassy prairies. Whether you're more interested in being above or below ground, this is an adventure not to be missed.
  • Deadwood - The second-largest Wild West town still in existence (behind Tombstone, AZ), walk the same streets as the legendary lawman Wyatt Earp, see the spot where Wild Bill Hickok was killed, and get a real feel of what made the American frontier famous.
  • Sturgis Festival - If you're lucky enough to be in the area during the first weekend in August, experience the largest motorcycle rally in the world. Featuring live bands, organized rides, and stalls selling all manner of products, it's definitely a unique event.
  • Crazy Horse Monument - Expected to be one of the largest carvings in the world upon completion, see the monument to the legendary native war chief as it's being built. Visitors are even given a piece of the mountain that has been removed to take home as a souvenir, free of charge.

An empty curve road leading to Mount Rushmore National Monument in South Dakota and a view of the carved faces of the Four US Presidents in the mountain and green trees

Best time to go on a road trip from Chicago to Mount Rushmore

While you can go at any time of year, as this isn't a beach destination that relies on the weather, you must be aware that the surrounding area operates on a traditional tourist season.

While it's certainly enjoyable to see the mountain without swarms of tourists all around, many of the attractions near Mount Rushmore will be closed. When I visited in February, for example, only one store was open in the town of Keystone at the base of the mountain.

With that in mind, if you're looking to experience everything the area has to offer, I'd suggest visiting at the start of August. Not only do tourists thin out just a little compared to the previous month, but it also gives you the opportunity to experience the Sturgis festival while you're there.

Perfect for getting everything out of an area that many will only get to visit once in a lifetime.

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best illinois road trips

Illinois Road Trip Ideas: 11 Best Road Trips + Itinerary

best road trips starting in chicago

Melissa Mahoney

I'm an east coast girl living in a west coast world. I grew up in New England before moving to SoCal for several years. I then lived in NYC or a year before moving to AZ in 2009. I worked in the entertainment industry for many years of my adult life and have a deep love for photography, writing, and traveling around the U.S. as well as to far-flung locations around the world. Travel is my life and writing about it is a dream!

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With so many cities, small towns, and wide open spaces, the Land of Lincoln is a great state for a road trip. Whether you have a few hours, a day, a few days, or longer, check out these Illinois road trip ideas for your next adventure. These are some of the best Illinois road trips you can take!

1-Day Road Trip In Illinois

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best road trips starting in chicago

  • Route: Burden Falls > Jackson Falls > Cache River Basin Vineyard & Winery > Ferne Clyffe State Park > Feather Hills Vineyard and Winery
  • Distance: 64 miles
  • Trip Time: 1 hour 38 minutes

best road trips starting in chicago

  • Route: Gold Pyramid House > Leaning Tower of Niles > Gemini Giant > Hippie Memorial > Two Story Outhouse > World's Largest Wind Chime > World's Largest Catsup Bottle > America's Largest Cross > Piasa Bird > Superman Statue
  • Distance: 823 miles
  • Trip Time: 13 hours 43 minutes

best road trips starting in chicago

  • Route: Pomona Natural Bridge > Pomona Winery > Dixie Barbecue > Ozark Hills Nature Preserve > Annabelle Market > Barkhausen Cache River Wetlands Center
  • Distance: 51 miles
  • Trip Time: 1 hr 20 min

best road trips starting in chicago

  • Route: RavenStone Castle > Aurora Sunken Gardens > Allerton Park and Retreat Center > Castle Of Palmyra > Villa Kathrine > Boo Castle Park
  • Distance: 649 miles
  • Trip Time: 11 hours 42 minutes

best road trips starting in chicago

  • Route: Ferne Clyffe Waterfall Trail > Kinkaid Lake Spillway > Cedar Falls > Little Pakentuck Waterfall Trail > Jackson Falls > Burden Falls
  • Distance: 119 miles
  • Trip Time: 3 hours

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Get Away From It All At This Remote And Beautiful Campground In Illinois

Get Away From It All At This Remote And Beautiful Campground In Illinois

The Breathtaking Scenic Drive Through Illinois That Runs Along The Ohio River

The Breathtaking Scenic Drive Through Illinois That Runs Along The Ohio River

The Magnificent Lakefront Airbnb In Illinois That Is Perfect For A Spring Retreat

The Magnificent Lakefront Airbnb In Illinois That Is Perfect For A Spring Retreat

best road trips starting in chicago

  • Route: Sunrise Park > Three Oaks Recreation Area > Anderson Japanese Gardens > Fox Hollow Tubing Adventure > I & M Canal Boat > Starved Rock State Park > Grand View Drive
  • Distance: 250 miles
  • Trip Time: 5 hours 25 minutes

best road trips starting in chicago

  • Route: Long Hollow Scenic Overlook > Mississippi Palisades State Park > Black Hawk Statue > Lowden - Miller Forest >
  • Distance: 77 miles
  • Trip Time: 1 hour 43 minutes

best road trips starting in chicago

  • Route: Chicago Botanic Garden > Lincoln Park Zoo > Starved Rock Lodge > Folepi's Winter Wonderland > McIntosh Christmas Road > Shelbyville Festival of Lights
  • Distance: 331 miles
  • Trip Time: 6 hours 10 minutes

best road trips starting in chicago

  • Route: Junction Diner > Lincoln Park Zoo > Leaning Tower of Niles > Great Wolf Lodge > Jurassic Gardens > Illinois Railway Museum > Pilot Pete's
  • Distance: 137 miles
  • Trip Time: 3 hours 27 minutes

best road trips starting in chicago

  • Route: Illinois Beach State Park > Mississippi Palisades State Park > Starved Rock State Park > Matthiessen State Park > Pomona Natural Bridge > Giant City State Park > Ferne Clyffe State Park > Cache River Natural Area > Garden of the Gods > Cave-in-Rock State Park
  • Distance: 733 miles
  • Trip Time: 3 hours 23 minutes

best road trips starting in chicago

  • Route: Clarendon Hills > Harvard > Woodstock > Cherry Valley > Galena > Mount Carroll > Fulton > Morrison > Franklin Grove > Sycamore
  • Distance: 365 miles
  • Trip Time: 8 hours

Which of these Illinois road trip ideas do you like the best? There’s so much to see in this state that it’s a good idea to go with an itinerary. Tell us, which road trip adventure will you take first?

OnlyInYourState may earn compensation through affiliate links in this article. As an Amazon Associate, we earn from qualifying purchases.

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Illinois road trip ideas.

What are the most popular landmarks to visit in Illinois?

Some of the most popular landmarks to visit in Illinois are the following:

  • Millennium Park and Cloud Gate in Chicago
  • Navy Pier in Chicago
  • Chicago Riverwalk
  • Illinois’ Historic Route 66 (there’s nothing quite like driving along the Mother Road)
  • Lincoln Home National Historic Site in Springfield. This historic site is the home that Abraham Lincoln once owned.
  • The Dana-Thomas House in Springfield which was designed by Frank Lloyd Wright
  • Wrigley Field in the Windy City
  • Grand View Drive, a gorgeous scenic drive in Peoria
  • The Great River Road which follows the Mississippi River and runs through Illinois from the borders of Wisconsin and Iowa, between Illinois and Missouri, and down to Kentucky. This route is a great midwestern scenic byway.

What are the most popular state parks to visit in Illinois?

Some of the most popular state parks to visit in Illinois include:

  • Starved Rock State Park which is filled with canyons and waterfalls
  • Ferne Clyffe State Park
  • Matthiessen State Park
  • Cave-in-Rock State Park
  • Mississippi Palisades State Park
  • Garden of the Gods Recreation Area
  • Shawnee National Forest

What are the major highways in Illinois?

Some of the major highways in Illinois include:

  • Business Loop 55
  • In addition, for road trippers, there’s Historic Route 66 and the Great River Road

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10 Best RV Road Trips From Chicago

Published on September 20th, 2021 by Ray & Tammy Roman This post was updated on March 14th, 2022

What makes the best RV road trips from Chicago is the distance to the destination, attractions, accessibility, and food and hotel options.

Whether you are traveling with children, a group of adults, or a significant other, there are many places to make memories that last a lifetime.

best rv road trips from chicago

To choose your road trip destination, you could throw a dart at a map. If you are a terrible dart thrower, we are here to help. These are some of RV best road trips from Chicago to ten of the most popular locations ranked by distance:


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Gurnee, illinois – six flags.

(Approximately 40 miles or 1 hr. drive)

Thrill-seeking families rave about Six Flags Great America . While the tickets to the park and purchases inside are expensive, it is a memory-making road trip like no other. The attractions like the Superman roller coaster and Tornado water raft tunnel are endless.

This location incorporates the requirements of the Americans with Disabilities Act (ADA).

Food inside the park is pricey. However, the location is close to Chicago, so you won’t need to pay for a hotel.

Indiana Dunes, Indiana

Budget-conscious travelers flock to this stunning outdoor destination for its affordability and beauty. If you love playing in the sand, swimming in the lake, or napping with the breeze in your hair, this location is for you. When you are ready to stretch your legs, there are easy hiking and cycling trails.

This location strives to provide handicap access throughout the park. Beach wheelchairs are available at the lifeguard station at West Beach. At Lake View, the picnic areas and overlooks are handicap accessible.

There are hundreds of restaurants at this location offering almost any type of cuisine to satisfy your hunger. The site is close to Chicago, so you won’t need to pay for a hotel.

Lake Geneva, Wisconsin

(Approximately 80 miles or 1.5 hr. drive)

Active outdoor visitors and laid-back tourists alike swoon over this road trip destination. It offers hot air balloon rides, ziplining, beaches, and trails. It provides pontoon boats, kayaks, and wave runners for rent. If you want to relax, there are calmer attractions in town and places to kick back by the lake.

This location offers ADA accessibility and features such as an exercise facility, guest rooms, parking, entrances, swimming pool, transportation, and alarms.

Lake Geneva has dozens of eating establishments offering many types of cuisine. The location is close to Chicago, so you won’t need to pay for a hotel.

Oglesby, Illinois – Starved Rock State Park

(Approximately 95 miles or 1.5 hr. drive)

Outdoor enthusiasts adore this destination for its cycling, camping, and hiking adventures. It offers attractions like waterfalls, a winding river with stunning cliffs, and incredible natural rock formations. This location is a geologist’s dream come true.

The lodge incorporates the requirements of the ADA. However, accessibility to the nature trails presents challenging obstacles.

The Veranda at Starved Rock Lodge offers Americana cuisine. The nearby towns of Utica, Peru, LaSalle, and Oglesby have many restaurants to satisfy whatever you crave. The location is close to Chicago, so you won’t need to pay for a hotel.

Saugatuck, Michigan

(Approximately 140 miles or 2.5 hr. drive)

Saugatuck is another outdoor lover’s adventure destination, but so much more. Gorgeous Oval Beach offers kayak and sailboat rentals, paddleboat rides, and dunes where you can frolic. On the other hand, the art scene here is astounding. With dozens of galleries and shops, you can spend a day just wandering through the downtown district. If you visit during the town’s seasonal events, you might find yourself enjoying a craft beer, harvest dinner, or getting lost in a corn maze.

This location offers handicap accessibility on some of its beaches with beach wheelchairs and ramps.

This location provides numerous restaurants serving Americana, Thai, French, and Italian gastronomic experiences. The area is relatively close to Chicago, so you may not want to pay for a hotel. If you do, there are options to suit any budget.

Galena, Illinois

(Approximately 165 miles or 3 hr. drive)

History buffs and power walkers enjoy this road trip location because of its famous Historic District and cobblestone streets. Galena also offers rafting trips on the great Mississippi River, a ski resort at Chestnut Mountain, and hiking trails for on-the-move visitors. One of the most popular laid-back attractions is viewing the brilliant colors of autumn leaves.

This location offers handicap accessibility to many of its businesses. Also, Hartig Drug Store provides wheelchair rentals.

From high-rated pizzerias to Mexican, Italian, and Japanese culinary choices, this location offers plenty of restaurant experiences. The site is reasonably close to Chicago, so you may not want to pay for a hotel. There are options for any reasonable budget if you choose to stay.

Door County, Wisconsin

(Approximately 245 miles or 4 hr. drive)

Known as the “Cape Cod of the Midwest,” Door County includes several small towns on a peninsula extending into Lake Michigan. With a multitude of public beaches and state parks, there are attractions for everyone. The most popular activities are viewing fall colors, exploring open spaces, and visiting roadside farm stands and farmers’ markets.

This location incorporates the requirements of the ADA and offers numerous handicap accessibility opportunities on the beaches and in the parks.

The cuisine scene at this destination boasts more than wine bars. It also offers farm-to-table dining with Swedish, Americana, and Wisconsin culinary experiences. The average hotel cost runs $100 – $260 per night.

Traverse City, Michigan

(Approximately 320 miles or 5 hr. drive)

Without a doubt, Sleeping Bear Dunes National Lakeshore is a must-see when visiting Traverse City . It offers miles of fantastic coastline, dunes, forests, and towering bluffs. An added attraction to this destination is its proximity to highway M-22, which winds along the coast, boasting one of America’s “most scenic drives.” You won’t want to miss out on this extraordinary adventure in the fall.

This location incorporates the requirements of the ADA and offers numerous handicap accessibility opportunities. Sand wheelchairs are available.

Traverse City has dining options, from pizzerias and breweries to fine dining and bar bites. The average hotel cost runs $90 – $250 per night.

Shawnee National Forest, Illinois

(Approximately 350 miles or 5.5 hr. drive)

Outdoor folks and wine tasters declare this as one of their best road trips from Chicago because of its enchanting natural beauty and numerous award-winning wineries. The Garden of the Gods Wilderness is the perfect quiet getaway to meditate and self-heal, while the Shawnee Hills Wine Trail leads you over the countryside to explore 11 unique wineries.

This location offers limited handicap accessibility on some nature trails.

Whether you are hungry for Cajun flavor, whole organic foods, or barbeque, you will find what you crave here. The average hotel cost runs $60 – $170 per night.

Nashville, Tennessee

(Approximately 475 miles or 7 hr. drive)

Music City is one of the hottest road trip destinations from anywhere in the nation. It offers attractions like the Country Music Hall of Fame, the Grand Ole Opry, historic music studios and museums, bus tours, bars, and nightlife with live music like the Wildhorse Saloon, and the Nashville’s Children’s Theater.

This location offers handicap accessibility at many of its businesses and numerous accessibility opportunities throughout the city.

The sky is the limit when it comes to Nashville’s dining options. Anything you want, you will find here. The average hotel cost runs $70 – $300 per night.

Best RV Road Trips From Chicago Final Thoughts

Chicago is a great city but for those who want to experience something outside the city limits these 10 roads trip from Chicago are excellent weekend trips, you’ll enjoy.

If you like this article I also wrote about the best walkie-talkies for road trips , and here are 11 RV membership sites to save you money.

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The Best Weekend Escapes from Chicago

Whether your idea of unwinding involves wine tasting, hopping onto a boat, wandering antique stores or strolling art galleries, we’ve got you covered.

best road trips starting in chicago

While there’s plenty to do in Chicago , sometimes you need a weekend away from the hustle and bustle. Whether your idea of unwinding involves wine tasting, hopping onto a boat, wandering antique stores or strolling art galleries, there are plenty of getaways surrounding Chicago where you can do just that—and they’re all within a five-hour drive. Blessed with the Great Lakes and many smaller, inland lakes, as well as rivers, chances are you will wake up by the water.

Getting away from the city, however, doesn’t mean losing access to culture. In fact, many of these small towns near Chicago thrive on fine dining, art and natural parks that will make you want to whip out your phone to capture the striking images. Be sure to pack hiking boots, too, to explore gorgeous trails, and sandals to walk on the beach or stroll around town. That this part of the Midwest isn’t super spread out also means you don’t need to drive very far for a weekend escape, which translates to spending less time in the car and more time enjoying your vacation.

Here are five destinations to check out, ensuring you come back to the city relaxed and reinvigorated. If a road trip is calling and you’re not sure where to go, this cheat sheet will help.

best road trips starting in chicago

Lake Geneva, Wisconsin

1.5-Hour Drive

Architecture geeks and The Gilded Age fans will love the grand, historic estates dating back to the late 1800s and early 1900s that surround Geneva Lake, accessible via a stroll around a section of the 26-mile Lake Shore Path or aboard a narrated Geneva Cruise Line boat tour . Dine with a lake view on the patio at Barrique Bistro & Wine Bar or linger over Italian-American food like wild-boar Bolognese pasta at Sopra Bistro on Main Street. Shop downtown for cheese curds and cheddars flavored with whiskey, dill and more at Hill Valley Dairy’s storefront , and poke into the Lake Geneva Public Library , designed by Frank Lloyd Wright protégé James Dresser and featuring stained-glass windows from Wright’s now-demolished Lake Geneva Hotel. For whimsical décor finds and entertaining frills, head to the other side of the lake to Fontana Home . The best design-oriented spot for a beer is at Topsy Turvy Brewery , within a 1910 former church.

best road trips starting in chicago

Where to Stay

Featuring an outdoor pool with striped umbrellas and a speakeasy-style bar, Maxwell Mansion ’s 28 rooms are divided between the main house and former horse stables. For a full-service experience that includes a spa, steakhouse, Italian restaurant and outdoor pool, try the  Grand Geneva Resort & Spa , whose interconnected buildings were once home to the Playboy Club. Today, you can sip cocktails in the lobby’s sunken lounge.

best road trips starting in chicago

Saugatuck, Michigan

2.5-Hour Drive

Hugging Lake Michigan’s western shoreline, Saugatuck, fittingly known as “The Art Coast,” is home to dozens of galleries. Most are sprinkled downtown near shops and restaurants, although the two-story, 12,000-square-foot J. Petter Galleries just outside of town is worth a trip, and hosts a wine bar within. In nearby Douglas, one of the nation’s oldest artist residencies— Ox-Bow , affiliated with the School of the Art Institute of Chicago, also a destination for art and writing classes—hosts an art gallery and boutique (Ox-Bow House) in an adorable white church dating back 152 years. Modales Wines in Fennville pours wines crafted by its Napa Valley-born winemaker, formerly of Duckhorn. Explore further on a vertical hike down sand dunes at Opal Beach, or rent a 1950s electric boat from Retro Boat Rentals to cruise along the Kalamazoo River to live our your IRL Emily Henry novel dreams.

best road trips starting in chicago

Owned by Chicago design firm Soucie Horner , the 11-room Wickwood Inn  is a new, modern revamp of The Silver Palate Cookbook author Julee Rosso ’s inn. Rosso also owned a gourmet-foods shop of the same name in New York City. Antiques and artwork tie into a clear coastal vibe that includes outdoor s’mores and French bistro chairs on the patio.

best road trips starting in chicago

Kohler, Wisconsin

This company village town—nearly everyone works for the luxury plumbing manufacturer—also excels at hospitality. The Immigrant Restaurant has long been considered one of Wisconsin’s best fine-dining restaurants; it embraces early-American art and décor while serving a five-course tasting menu, plus delicacies like caviar and 16 artisan Wisconsin cheeses. At the three-level, 36,000-square-foot Kohler Design Center , rooms by celebrity designers can be toured and the design staff is available to chat. Then, at Kohler Waters Spa, hydrotherapy treatments incorporate Kohler’s Vichy shower. On your way into town, swing by Art Preserve , a museum dedicated to artist-built environments by folk artists. Tours of the Kohler factory across the street from the hotel are led by retired employees.

best road trips starting in chicago

The American Club is the most luxurious of the three Kohler properties, with 241 rooms. Built in 1918 for single male immigrant employees, it’s now one of Wisconsin’s most coveted properties, with a spa, yoga studio, multiple restaurants, golf courses and shops all within a short walk and managed by the resort.

best road trips starting in chicago

Galena, Illinois

3-Hour Drive

Situated along the Mississippi River, Galena boasts an adorable downtown dotted with antiques stores (like the 200-some vendors at Elizabeth’s Grand Antique Co. in a former school) and unique boutiques along Main Street. That includes Galena Apothecary (formerly of Chicago, the owner opened the shop in her favorite weekend-getaway town), Galena Book & Paper (books and stationery) and Galena River Goods (candles, skincare products, barware and clothing). Sip bubbles in Champagne on Main ’s outdoor courtyard and choose your dinner spot after a walking tour with Galena Foodie Adventures , visiting five different eateries.

best road trips starting in chicago

Tuck in at night at Goldmoor Inn , a castle-like structure just outside of town with 13 suites and breakfast included. Massages are also available on-site, in the inn’s dedicated spa room, including a hot-stone massage to work out the kinks.

best road trips starting in chicago

Traverse City, Michigan

5-Hour Drive

This emerging wine region is also a great spot to hike; make sure to take in the soaring bluffs at Sleeping Bear Dunes National Lakeshore and to sail. The Wind Dancer , offers sunset sails nearly daily as well as Champagne Sails on Sunday afternoons. Short on time but still want to experience a local winery? Head to the 155-acre Brys Estate Vineyard & Winery , where the vineyard views from an elevated deck are nothing short of picturesque, with vistas of a lavender field and gardens blooming with flowers and herbs. The winery also serves frosé, plus cheese and charcuterie boards. Perusing downtown Traverse City’s shops, including two bookstores, can easily fill an afternoon. History buffs will love Trattoria Stella ’s cave-like environment, located at The Village at Grand Traverse Commons , a former state-run mental hospital with a philosophy that a beautiful environment is healing.

best road trips starting in chicago

 Delamar Traverse City ’s perch above the West Arm of Grand Traverse Bay means water views for days and the on-site yoga studio puts wellness within easy reach, plus a restaurant wildly popular with locals. Or, wake up next to the grapes at the 10-room Inn at Black Star Farms , which also hosts private yoga classes in its vineyard.

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best road trips starting in chicago

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23 Incredible Road Trips in the U.S.

Whether you’re looking for sweeping views of the pacific ocean or a multiday adventure through national parks, these road trips provide plenty of opportunities to explore the united states..

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A highway leading toward mountains

Glacier National Park is one of many scenic places you can visit on an American road trip.

Photo by Zack Frank / Shutterstock

In a country as large as the United States, there’s no shortage of destinations and detours to explore by car . Whether your idea of the perfect American road trip entails an epic, cross-country journey or a shorter jaunt through a few of its most iconic national parks , your options are as large and varied as the country itself.

Even if you don’t have the time to drive cross-country, there are plenty of road trip routes (ranging from three days to a week or longer): classic California itineraries , New England routes that shine especially well in the fall, scenic East Coast adventures, and a variety of Midwest journeys for folks farther from the coasts.

No matter your mode of transportation—be it van, RV, motorcycle, or four-door sedan—these are 21 of the best road trips in the nation to consider.

Put a New Twist on Route 66—Make It an American Whiskey Road Trip

Plan your next Route 66 trip around thirst-quenching stops.

Photo by Peek Creative Collective/Shutterstock

There are many ways to do a cross-country road trip in the USA, but these two itineraries will take you through some truly iconic American places.

1. Chicago to Los Angeles: A Whiskey Road Trip on Route 66

It doesn’t get more American than a 2,000-mile drive along the entirety of Route 66. There are endless ways to take this legendary trip (including an EV version —but to take your cross-country road trip to the next level, we recommend exploring another American pastime: whiskey.

Starting in Chicago and ending in L.A., you’ll stop by some of the leading craft distilleries in the United States, like Few Spirits in Chicago, Still 630 in St. Louis, and Red Fork Distillery in Tulsa. In between tastings, make time for detours to natural attractions, like the Grand Canyon, and quirky roadside curiosities, like Cadillac Ranch in Amarillo, Texas. Just remember to drink responsibly—this is a road trip after all.

Plan your trip

The full itinerary: Put a New Twist on Route 66—Make It an American Whiskey Road Trip

People biking on a busy street

No cars are allowed on Mackinac Island, so you need to park before taking the ferry to this spot.

Photo from Shutterstock

2. Bangor, Maine, to Seattle, Washington: The Great Northern on U.S. Route 2

Covering both the U.S. and Canada, a cross-country trip along U.S. 2 is ideal for anyone who wants to experience the vast diversity and expansiveness of North America. This drive runs the entire top border of the U.S. and showcases otherworldly natural wonders like Acadia National Park in Maine, the Apostle Islands National Lakeshore in Wisconsin, and Mackinac Island in Michigan. The route also passes through Canada, taking road-trippers through Ontario into Quebec—this route may focus on nature, but you won’t want to miss a stop in Montreal or Ottawa.

You’ll also get to explore Montana and Glacier National Park ( reservations may be required ) before passing the Columbia Plateau and ending in the Pacific Northwest’s largest city, Seattle. Don’t miss spending time in the Olympic Peninsula (home to Olympic National Park) for a peek at one of the most scenic places on the West Coast.

3. Dana Point to San Francisco: Driving California’s Pacific Coast Highway

The seemingly endless views of the Pacific Ocean along Highway 1 (also known as the Pacific Coast Highway) are what road trip dreams are made of, and exactly what makes this California road trip so popular. However, with so many stops along the 655-mile stretch, we pulled together a list of the ones well worth pulling over to view. Don’t miss the perfect surfing waves in Santa Cruz, seasonal cuisine in Malibu, an afternoon a the boardwalk in Santa Monica, or a night in Big Sur as you drive between Dana Point (just south of Los Angeles) and San Francisco.

  • The full itinerary: The Best Stops for a Road Trip on the Pacific Coast Highway
  • The AFAR Guide to San Francisco

Wooden pier with shops on top juts out into the ocean

The seaside town of Monterey was the setting for John Steinbeck’s Cannery Row .

Photo by Denise Lett/Shutterstock

4. Big Sur to Mono County: A Literary Road Trip Through Northern California

Yes, this itinerary requires you actually put down your book to drive, but seeing some of the pivotal places that shaped American authors will be so worth it. Follow in the footsteps of writers like Jack Kerouac, Maya Angelou, and Amy Tan on this road trip that takes you through literary landmarks in Northern California, such as Caffe Trieste, a meeting place for Jack Kerouac, Allen Ginsberg, Alan Watts, and other bohemian writers and thinkers. This 12-stop itinerary is perfect if you live in the San Francisco Bay Area because you’ll be able to stay make these trips in one or two days.

The full itinerary: The California Road Trip All Book Lovers Should Take

Wide shot of a red canyon with a river running through it

Arizona may take its nickname from the Grand Canyon, but the state has far more natural wonders than just that one.

Courtesy of Shutterstock

5. Phoenix to the Grand Canyon: An Iconic Arizona Road Trip

This 240-mile Arizona road trip takes travelers along some of the state’s most iconic highlights, including its most famous one, the Grand Canyon. A great itinerary for first-time visitors and returning travelers alike, it offers plenty of opportunities for scenic drives, hiking, and biking—as well as tasty food along the way. Hike the 2,704-foot-tall Camelback Mountain in Scottsdale or take in the beautiful red rocks of Sedona on a hike to Cathedral Rock while exploring the Grand Canyon State.

  • The full itinerary: The Classic 5-Day Arizona Road Trip
  • Grand Canyon guide: The First-Timer’s Guide to the Grand Canyon
  • Where to eat in Phoenix: A Chef’s Guide to the Best Restaurants
  • Where to stay: The Best Hotels in Arizona ; The Best Airbnbs in Sedona

The Delicate Arch living up to its name in Utah's Arches National Park

The Delicate Arch living up to its name in Utah’s Arches National Park

Photo by tusharkoley / Shutterstock

6. Zion to Grand Canyon: A National Parks Road Trip in the Southwest

If you’re looking to visit as many national parks as possible in one road trip, this southwestern itinerary is for you. This journey through Utah and Arizona lets you hike Angel’s Landing in Zion, feel tiny under Delicate Arch in Arches National Park, explore Fairyland Loop Trail in Bryce Canyon, and, of course, raft down the Colorado River in the Grand Canyon. Most visitors to the Grand Canyon remain on the rim, but take at least four days to venture within the canyon and take advantage of the trails and river rafting.

  • The full itinerary: The Ideal Road Trip Through U.S. National Parks
  • Utah’s 8 Best National Parks and Monuments
  • 10 Best National Parks and Monuments in Arizona
  • The First-Timer’s Guide to the Grand Canyon

Couple sitting in front of a curving road

Stop and admire the winding roads of the San Juan Skyway.

Photo by Anh Luu/Shutterstock

7. San Juan Scenic Skyway Road Trip: An Adventure Through Southwestern Colorado

This Colorado trip takes you along the 232-mile loop of the San Juan Scenic Skyway, where you will see plenty of alpine forests, mining towns, and craggy peaks. And for anyone looking to enjoy refreshments after a long day of driving, this route features many opportunities to stop at some of the best breweries in Colorado , such as Ska Brewing Co. in Durango.

  • The full itinerary: The Ultimate Southwestern Colorado Road Trip
  • Five Classic Colorado Road Trips To Take This Year

In small-town Buena Vista, the riverfront Surf Hotel offers front-row seats to Colorado-style adventure seekers.

In small-town Buena Vista, the riverfront Surf Hotel offers front-row seats to Colorado-style adventure seekers.

Courtesy of the Surf Hotel

8. Denver to Montrose: A 420-Mile Road Trip Through Colorado

Want to explore even more of the Centennial State? Head out on this weeklong road trip where you can fish for salmon in Colorado’s largest reservoir, visit numerous small towns, like Paonia and Crawford, with thriving art scenes along the Colorado Creative Corridor , and explore Black Canyon of the Gunnison National Park, one of the least visited national parks in the nation.

  • The full itinerary: Art Stars, High-Altitude Wines, and a Remote National Park: The Ultimate Colorado Road Trip
  • Where to stay: The Best Hotels in Colorado
  • The AFAR Guide to Denver

Woman walking by a mural of a river and bridge

Portland may be Oregon’s largest city, but with a population of some 652,000 (or 2.5 million in the larger metropolitan area), it isn’t intimidatingly large.

Photo courtesy of Travel Portland

9. Portland to Astoria: An Oregon Coast Road Trip for Outdoor Lovers

If you love the outdoors, then this six-day road trip along the coast of Oregon is for you. After driving to Coos Bay from Portland, travelers will meander along Oregon’s dramatic, rocky coastline, discovering some quintessentially Pacific Northwest vistas along the way: evergreen forests, seaside dunes, and marine ecosystems. Between stops, there are ample opportunities to stretch your legs hiking, kayaking, or strolling around the region’s small towns—like the historic old town in Florence.

Of course, it wouldn’t be an Oregon road trip without a stop (or three) at a craft brewery, such as Fort George Brewery in Astoria, or cozy coffee shop, like Bread & Roses in Yachats.

  • The full itinerary: An Outdoor Lover’s Road Trip on the Oregon Coast
  • The AFAR Guide to Portland

The State Capitol Building in Nashville marks the end of this road (trip).

The State Capitol Building in Nashville marks the end of this road (trip).

Photo by / Shutterstock

10. Seneca Falls, New York, to Nashville, Tennessee: Follow the Path of the Women’s Suffrage Movement

Starting in New York’s Finger Lakes region and ending at the State Capitol Building in Nashville, this road trip traces the route of the national women’s suffrage movement. Highlights include stops at the Susan B. Anthony Museum & House ; Union Square in New York City, which was the site of the first suffrage march; and the Belmont-Paul Women’s Equality National Monument in Washington, D.C.

  • The full itinerary: Celebrate Women’s Suffrage on an Epic, Self-Guided Road Trip
  • Where to stay: The Best Hotels in Nashville
  • The AFAR Guide to Nashville
  • The AFAR Guide to Washington, D.C.

A long shot of a mountain-backed city, framed by flowers and trees

Asheville is one must-stop on a North Carolina road trip.

Courtesy of

11. Charlottesville to Asheville: A Scenic Road Trip Through Virginia and North Carolina

The Blue Ridge Parkway is one of the most scenic drives in the country. Beginning in the soft hilly meadows of the Appalachian Mountains from Shenandoah National Park down into the Blue Ridge Mountains, then into the Great Smoky Mountains, this five-day road trip is best done at a slower pace, which is perfect for admiring the dramatic outlooks and green plateaus. This eclectic itinerary features stops at an art museum, a dairy farm, and plenty of hiking trails.

  • The full itinerary: The Ultimate Blue Ridge Parkway Road Trip
  • Where to stay: 12 Dreamy Blue Ridge Mountain Cabins You Can Rent on Airbnb and Vrbo
  • 8 U.S. National Park Road Trips to Take in Your Lifetime

Dowa:kwe dance group from Zuni Pueblo in 2019

Dowa:kwe dance group from Zuni Pueblo in 2019

Courtesy of Indian Pueblo Cultural Center

12. Albuquerque to Las Cruces: Discover New Mexico on This Three-Day Road Trip

This route steers you away from New Mexican tourist hot spots like Taos and Santa Fe and instead takes you on a three-day adventure with places that teach you about Pueblo history. You’ll stop at Indian Pueblo Kitchen (formerly known as Pueblo Harvest), a restaurant inside the Indian Pueblo Cultural Center that features Indigenous cuisine ; pick up peppers at Three Brothers in Hatch; and slide down the dunes in White Sands National Park.

  • The full itinerary: This New Mexico Road Trip Is the Perfect Introduction to the Land of Enchantment

Green tree near brown house during daytime

Historic Fort Martin Scott is one of the places travelers can visit to learn about Fredericksburg’s history.

Photo by Mark König/Unsplash

13. A Five-Day Scenic Road Trip Through Texas Hill Country

This Texas road trip starts and ends in San Antonio with stops in small towns like Bandera, Boerne, and consider a stop in Fredericksburg, which is one of AFAR’s best places to go in 2024 ). Over five days, you’ll find opportunities to stroll in a Japanese tea garden in San Antonio, relax along the Sabinal and Frio Rivers by inner tube, and eat as many tacos as you want. Seriously: You could eat tacos for every meal on this road trip and not get tired of them.

  • The full itinerary: Tree Houses, Tubing, and Tacos: The Ultimate Texas Hill Country Road Trip

Mount McKinley looms large on a drive through Denali National Park.

Mount McKinley looms large on a drive through Denali National Park.

Photo by warnsweet / Shutterstock

14. A Weeklong Road Trip Through Alaska’s Most Majestic Sights

This weeklong drive in Alaska starts and ends in Anchorage. You travel along four scenic byways; explore Wrangell–St. Elias wilderness, the largest U.S. national park; catch sight of Denali, the tallest peak in North America; and enjoy the surprisingly stellar food scene of McCarthy, a one-road town with only a couple dozen residents.

  • The full itinerary: Glaciers, Mountain Peaks, and Organic Farms: The Ultimate Alaska Road Trip
  • Which Alaska National Parks Should You Visit?

More than geothermal pools, Kirkham Hot Springs features a piping-hot waterfall.

More than geothermal pools, Kirkham Hot Springs features a piping-hot waterfall.

Courtesy of Idaho Tourism

15. Boise to Sun Valley: Explore Idaho’s Scenic Byways

Even a short road trip can be packed with adventure, good food, and scenery, which is exactly what this trip from Boise to Sun Valley along Idaho’s Ponderosa Pine Scenic Byway offers. Although the drive only takes six hours, we recommend taking a few days to explore all the stops and detours along the way. One can’t-miss spot is the Kirkham Hot Springs , where you can stand under a waterfall that will splash you with 135-degree mineral water year-round.

  • The full itinerary: The Little-Known Idaho Road Trip You Need to Drive
  • Things to do: The Best Outdoorsy Things to Do in Idaho

Grand Portage State Park is the only state park jointly managed by a state and a Native American band.

Grand Portage State Park is the only state park jointly managed by a state and a Native American band.

Photo by Shutterstock/QZ

16. Duluth to Grand Portage State Park: A Scenic Minnesota Sampler

Although there are many appealing road trips throughout the Midwest, this 143-mile, three-hour circuit, which starts and ends in Duluth, Minnesota, is worth keeping in mind. Meandering north on MN-61 with this itinerary, you will enjoy prime views of Lake Superior and towns like Grand Marais, as well as Grand Portage State Park, home to waterfalls, hiking trails, and opportunities to learn about the Ojibwe community who occupy the land today. Once back in Duluth, enjoy a beer at Canal Park Brewing Company before checking into the waterfront Canal Park Lodge nearby.

  • The AFAR Guide to Minnesota

Overhead view of curvy Kancamagus Highway through fall forest

Wind your way through colorful foliage in New Hampshire.

Photo by Shutterstock

17. Kancamagus Highway: A Quintessential New England Drive

Yes, you can take a road trip in New England at any time of the year , but this region shows off its best colors in the fall, when locals and tourists alike head out into the country to view the changing colors of the trees. Join other admirers of fall foliage on this popular, 34.5-mile road trip along New Hampshire’s Kancamagus Highway, colloquially known as the “Kanc,” for picturesque ponds, hiking trails, and scenic overlooks.

  • Plan Your Fall Getaway With This Peak Foliage Prediction Map

Red boat beside a wooden dock in a cove

Ogunquit is home to the small, postcard-perfect harbor of Perkins Cove.

Photo courtesy of QualityHD / Shutterstock

18. Maine’s “Lobster Trail”: Travel Route 1 Along the Coast

Traveling Route 1, affectionately known as “the lobster trail,” along Maine’s jagged coastline is an exercise in indulgence. Sample lobster dishes in all forms—buttered, steamed, on a roll, or even in a decadent mac-and-cheese.

The trip starts in the quaint small town of Ogunquit , with its rare (for the area) 3.5 miles of white-sand beach. Make your first lobster of the journey count, steamed with a side of drawn butter at Barnacle Billy’s in picturesque Perkins Cove harbor. Stop at Big Daddy’s for a cone on your way to the shipbuilding center—and summer home of George H. W. Bush—Kennebunkport. Stay at the recently redesigned 150-year-old classic White Barn Inn , and consider a sailing trip for an afternoon. With lobsters cooked in ocean water, the legendary lobster roll at the Clam Shack is a must.

  • 8 Scenic East Coast Road Trips to Take This Year

Interior of Leah & Louise restaurant in Charlotte

Throughout North Carolina’s Piedmont region, innovative restaurants, shops, and restaurants like Leah & Louise in Charlotte, above, are creating a buzz.

Photo by Peter Taylor Photography

19. Raleigh to Charlotte: A 4-Day Trip Through North Carolina’s Reinvented Core

North Carolina’s Piedmont region extends from the coastal plain to the Blue Ridge Mountains, and includes farmland and rolling wooded hills, especially on the 1-40 stretch near Hillsborough. Starting in Raleigh, drive the short distances to Greensboro, Winston-Salem, and Charlotte to see how these cities are innovating through art, food, and a celebration of the past. Take your time—four days should do—to experience downtown arts districts, James Beard Award–winning restaurants, and civil rights museums that speak truths. Plan your trip

  • A Road Trip Through North Carolina’s Reinvented Core

The Florida Road Trip You’ve Been Missing

Scenic South Walton is part of the Emerald Coast of Florida.

20. Scenic Highway 30A: A Sunday Drive Through South Walton, Florida

Florida is full of places to cruise with the top down, but it’s hard to beat a Sunday (or any day) drive along Scenic Highway 30A through northwest Florida, home to a postcard-perfect stretch of seaside towns known as South Walton.

The roughly 28-mile route through South Walton County kisses the coast for nearly all its length, taking you through gorgeous residential Gulf-front communities like Rosemary Beach, Grayton Beach, and Blue Mountain Beach . Roll down the windows and let the emerald-hued views in.

Pull over to explore, too—maybe to admire the New Urbanism architecture in Alys Beach or to swim in the clear waters at Grayton Beach State Park . (The beach here has been lauded among the best in the world.)

  • The full itinerary: The Florida Road Trip You’ve Been Missing

Two stand-up paddleboarders on the water at sunset

Stand-up paddleboarding is just one way to enjoy a Florida Keys sunset.


21. The Florida Keys: An Island-Hopping Getaway

For a sunny road trip itinerary in Florida, skip Miami and head farther south. Beginning in Key Largo and ending in Key West, the Florida Keys Scenic Highway is often overlooked for more well-known routes up north, but it is well worth going out of your way to experience.

As the name suggests, this route is very scenic, so plan to spend at least a few days exploring it and numerous stops along the way. Some highlights include driving across the impressive Overseas Highway, stopping to admire art in the town of Islamorada, and enjoying the historic sites, food, and (of course) beaches in the city of Key West.

  • The full itinerary: How to Road Trip in the Lesser-Known Florida Keys

A brick building with an oversized guitar hanging off the side and a sign that says "Sun Studio"

Sun Studio in Memphis was the site of the famous Million Dollar recording session that brought together Elvis Presley, Jerry Lee Lewis, Carl Perkins, and Johnny Cash.

Photo by f11photo on Shutterstock

22. Memphis to Bristol, Tennessee: A Music-Driven Adventure

If you have about a week to spare and a deep appreciation for music, take a road trip from one side of Tennessee to the other, starting in Memphis and ending in Bristol. The eastbound trip spans genres, including rock ( Graceland ), blues ( Beale Street) and, of course, country (did you really go to Tennessee if you didn’t go to Dollywood ?). Nashville serves as the halfway point on your journey—so consider penciling in an extra 48 hours to fully explore the state capital’s greatest hits.

  • The full itinerary: 5 Great American Road Trips For Music Fans

The stunning coastline near Cueva del Indio has been the backdrop of star-studded films.

The stunning coastline near Cueva del Indio has been the backdrop of star-studded films.

Photo by

23. Arecibo to Condado, Puerto Rico: A Lesser-Known Side of a Well-Loved Island

In the minds of many, trips to Puerto Rico bring images of stunning beaches , delicious foods , and maybe a bioluminescent bay or two . But there’s plenty of history to be found here, too, as Puerto Rico was home to an Indigenous population known as the Taino, a heritage many Puerto Ricans embrace. That history can be explored via a road trip. Starting in the northern town of Arecibo, travel south to Ponce, then back north to Condado—along the way you’ll encounter petroglyphs, Indigenous sites, and breathtaking natural spots.

  • The full itinerary: A Puerto Rico Road Trip That Puts Indigenous Culture First

Additional road trip planning resources Picking the route for your road trip is only one part of your planning. From what snacks to pack to which podcasts to listen to, these additional resources will help you prepare for your next adventure:

  • Best road trip snacks
  • Road trip planning apps
  • Podcasts and audiobooks to download
  • What to pack for a road trip

This article originally appeared online in August 2020. It was most recently updated on April 4, 2024, to include current information. Additional reporting by Jessie Beck, Erika Owen, Ray Rogers, Terry Ward, and Sheryl Nance-Nash.

The City center, cathedral, city hall and the old main bridge across the Main river at night time in Germany, Lower Franconia, Würzburg

  • Travel recommendations
  • The taste of travel
  • Tips & tricks
  • Travel experiences


How to plan a road trip, from cross-country journeys to weekend getaways

best road trips starting in chicago

Driving is embedded into American culture, which is why road-tripping is so popular across the U.S. Whether you're looking to visit cities for history and culture or national parks for access to the great outdoors, a road trip can take you there. If you're not sure where to start, here's how to plan a road trip.

In this post

How do you plan a road trip for beginners?

When is the best time to start planning a road trip, how many days should you plan for a road trip, how to determine the best itinerary to take, how to choose when to take a road trip, how to plan a road trip on a budget, what is an appropriate/realistic driving time for each section of the trip, what are the best road trip tools/apps to use, what are the essentials to buy and pack, what are the main steps in the road trip planning process.

A family of four cheering in the car and excited to go on a road trip.

If you've never planned a road trip before, there are a few things you'll want to discuss with your travel companions before you start crafting a turn-by-turn itinerary. Start with where you want to go. We're talking big picture, like a region or a state, not every single stop along the way (we'll offer tips for how to plan a road trip with stops later on). Then think about how long you want to go for. And finally, consider your budget. Once you nail down those three things, you can start looking at the details.

A happy gay couple is sitting in the dining area and holding a laptop in front of them.

The earlier the better! Planning a road trip can take quite a bit of time and effort, so allowing yourself at least a few weeks to put together a full itinerary is a good idea. You'll also want to leave enough time between planning and departure to get your car checked out by a mechanic. No one wants to break down on the road!

And if you're renting a car instead of driving your own, you'll want to book your rental car in advance to ensure there's inventory (say, the right type of rental car available).

The duration of your road trip is entirely up to you. The two important things to consider are where you want to go and what you want to do along the way. If you're looking for recommendations for how to plan a cross-country road trip, give yourself at least two weeks if you want to make a few sightseeing stops. If you want to take the trip at a more leisurely pace and spend more time sightseeing than driving, four weeks is more reasonable. Regional road trips, however, can be as short as a few days. Or you could really take your time and stretch them out over a week or more.

A tall arch bridge across a ravine between two cliffs overlooking the ocean.

Choosing a road trip itinerary largely depends on your personal preferences, but in all cases, you should start by thinking about where you want to go, considering who you'll be traveling with. If you're planning a family road trip , that might take you to different destinations than if you were traveling with a group of friends or by yourself.

Once you have your general destination in mind, whether that's a region or a state or a full cross-country journey, you'll want to start selecting points of interest within that region. Plot these points on a map, then connect the dots! This is a good starting point for route planning, but now comes the laborious part: checking drive times between those points. It'll take a bit of finagling to create an itinerary that works in your favor.

As you're planning your road trip itinerary, you'll also need to consider your overnight locations. Some remote destinations might not have accommodations at all , and more popular accommodations may book up months in advance.

You should always consider seasonality for road trips. When you pick a destination, look at the typical weather for each season. In general, it's usually wise to avoid snowy destinations in the winter (some roads close seasonally) and extremely hot destinations in the summer (extreme heat can affect your car).

You can do a road trip on any budget, but no road trip will be free. You always need to consider the cost of gas and food. One way to save money, however, is on accommodations. Hotels are often more expensive than campsites, but campsites frequently book up in advance, particularly in the summer.

a smiling woman in a colorful outfit behind the wheel in a car

If you have more than one driver, you could take shifts and have a longer driving time each day. But an individual driver should typically not drive more than six to eight hours in one day. More experienced drivers, however, might have a higher limit of say, 10 to 12 hours. Drowsy driving is extremely dangerous, though, so make sure the drivers are well rested before each segment, and take breaks every 2 hours.

Every road tripper has their preference of apps, but these are tried-and-true favorites.

  • Google Maps
  • Roadtrippers
  • Triptik by AAA
  • iOverlander
  • Atlas Obscura

Here's a quick and easy packing list for a road trip.

  • First aid kit
  • Tire pressure gauge
  • Jumper cables
  • Ice scraper (if traveling during winter)
  • Portable phone charger
  • Paper towels or toilet paper
  • Bottled water

A family of four takes their bags and the kid's toys from the back of their car.

2 months before departure: Start looking at the points of interest you want to visit, consider the duration of your road trip, and determine your budget

1 month before departure: Get your car checked out or rent the relevant car for your itinerary and book your accommodations

2 weeks before departure: Buy the essential items

1 week before departure: Do a “test” pack to ensure everything fits in your car, or in your luggages if you are planning a road trip abroad

A road trip is an ideal way to see a destination, but it takes some careful planning to ensure you have a safe and enjoyable trip. While planning is important, always leave spare time in your itinerary. You never know what you might discover along the way!

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best road trips starting in chicago

Where It Starts & Ends: 12 Things You Can Still See On Old Route 66

  • Lou Mitchell's in Chicago is a classic American diner and the perfect place for travelers wondering where to start a Route 66 road trip.
  • The Gateway Arch in St. Louis is easily one of the most iconic landmarks on Route 66 to see.
  • Santa Monica Pier is the perfect final stop on Route 66 to celebrate completing a cross-country journey.

Lore and myth have been built around Old Route 66 and the people who traveled it. From quirky diners and kitschy motels to breathtaking natural wonders and landmarks, the stops along Old Route 66 encapsulate that classic Americana culture and invoke a strong sense of nostalgia.

Forever immortalized in movies, songs, and books, Route 66 continues to fascinate travelers from around the globe. It remains one of the most famous road trips in the United States , even though this road was technically decommissioned in the 1980s to make space for America's current interstate system. Luckily, many of the original stops on Route 66 from its heyday can still be visited. For adventures with their hearts set on precisely that, here are some of the things to still see on Route 66.

UPDATE: 2023/12/27 11:45 EST BY NOAH STAATS

Route 66 Remains A Southwest Staple

This article has been refreshed with even more stops along Old Route 66, plus additional information on existing hotels, restaurants, and attractions. Whether road-trippers come in the summer, fall, winter, or spring, there's always something to see here; have fun!

Related: Road Trip Worthy: Explore These Scenic Drives Across The Southwest U.S.

Lou Mitchell's (Chicago, Illinois)

Get comfy at this classic american diner on route 66, serving hearty grub since 1923.

Though there are plenty of historic stops and fun attractions on Route 66 in Illinois , grabbing a meal at Lou Mitchell's is the hearty way to commemorate the journey. Route 66 officially starts in Chicago, and Lou Mitchell's diner has been there from the start, serving classic American diner fare to hungry drivers.

Colloquially known as "the first stop on the Mother Road," starting a journey on Route 66 with a big breakfast at Lou Mitchell's is a rite of passage. Since 1923, Lou Mitchell's has been in business, and the establishment quickly became an iconic Chicago diner for weary travelers looking for a hearty breakfast to start their Route 66 adventure.

  • Address: 565 W Jackson Blvd, Chicago, IL 60661
  • Hours: Open daily from 6 AM to 2 PM (opens 7 AM on weekends)

Related: 10 Road Trips From Chicago That Will Have You Ready To Hit The Gas

The Gateway Arch (St. Louis, Missouri)

As one of the united states' most iconic landmarks, this arch stands over a midwest gem.

The iconic Gateway Arch in Missouri proudly stands as a monument to America's westward expansion. A feat of engineering, this colossal arch stands at 630 feet, welcoming visitors who are eager to explore the city of St. Louis .

Whether road-trippers are just passing by or riding the tram that takes passengers smoothly up the arch , the Gateway Arch is a classic American landmark that has long greeted those traveling through Route 66.

  • Address: Gateway Arch, St. Louis, MO 63102
  • Hours: Open daily from 5 AM to 11 PM

Meramec Caverns (Sullivan, Missouri)

See the underground caves under route 66 and learn about geological and native american history.

When passing through Missouri, road-trippers on Route 66 must stop at Meramec Caverns . This impressive series of underground caves is home to out-of-this-world rock formations and underground lakes.

Guided tours provide a fascinating glimpse into the area's geological formation and Native American history.

  • Address: 1135 Hwy W, Sullivan, MO 63080
  • Hours: Open daily from 9 AM to 4 PM
  • Tickets: $27

The Cadillac Ranch (Amarillo, Texas)

Super quirky, this is one of the most instagrammable stops on route 66.

Cadillac Ranch is a unique public art installation in Amarillo, Texas, that features 10 Cadillac cars half-submerged in the ground and covered in graffiti. Along with serving as an incredible photo opportunity, this spot on Old Route 66 is a notable example of American pop art and, to this day, continues to be one of the best stops on a Route 66 road trip .

Designed in the 1970s by a group of artists known as the Ant Farm, visitors are encouraged to climb on top of the cars and even add their own graffiti before continuing their journey along Route 66.

  • Address: 13651 I-40 Frontage Rd, Amarillo, TX 79124
  • Hours: Open 24 hours

Midpoint Café (Adrian, Texas)

Established in 1928, this cafe is route 66's midpoint at 1,139 miles from chicago and los angeles.

The Midpoint Café proudly declares itself as the midpoint of the original Route 66. At precisely 1,139 miles from both Chicago and Los Angeles, this restaurant was open 24 hours a day during the height of travel on Route 66.

Established in 1928, this diner served hungry travelers on Route 66. Its slogan was "When you're here, you're halfway there." Along with serving delicious pies and traditional American comfort food (and being the Old Route 66 halfway point), the Midpoint Café has an antique shop and souvenir store for Route 66 enthusiasts.

  • Address: 305 Historic Rte 66, Adrian, TX 79001
  • Hours: Open daily from 8 AM to 4 PM

Historic El Rancho Hotel (Gallup, New Mexico)

This famous route 66 hotel welcomed many of hollywood's golden age legends.

Built in 1936, the El Rancho Hotel was the place Hollywood stars stayed while filming on location in Gallup, New Mexico. From John Wayne and Humphrey Bogart to Katherine Hepburn and Joan Crawford, the El Rancho Hotel played host to countless film legends, forever linking it with the history of the Golden Age of cinema.

One of the most famous hotels on Route 66, the accommodation eventually became a popular stop on Old Route 66 for tourists. Its Western-style architecture and old Hollywood charm make it a sought-after lodging choice for travelers seeking a touch of Hollywood glamor mixed with a large dose of Old Western nostalgia.

  • Address: 1000 E Hwy 66, Gallup, NM 87301

Painted Desert (Arizona)

Stop off and soak up the otherworldly desert scenery.

Few places on Earth can beat the views found in the Painted Desert , which is probably why this stop just slightly off Route 66 was such a popular spot for road-trippers passing through Arizona.

This mesmerizing landscape, adorned with colorful layered rock formations, showcases nature's breathtaking beauty. The Painted Desert is a photographer's dream and worth the stop on Route 66.

  • Address: Painted Desert, AZ, 86031
  • Area: 93,500 acres
  • Length: 160 miles
  • Borders on: Little Colorado and Puerco Rivers

Petrified Forest National Park (Holbrook, Arizona)

Ancient trees, petroglyphs, a ruined village, and epic hikes year-round.

Known as one of Route 66's most natural stops, Petrified Forest National Park is well worth the trip. Here lies the old forest boasting ancient trees, critters, art, and trails to hike throughout the year.

Because Arizona remains fairly stable climate-wise, Petrified Forest National Park is a great year-round destination. It boasts the petroglyphs of Newspaper Rock and the ruined village of Puerco Pueblo. There is the Painted Desert Inn and the Rainbow Forest Museum here as well.

  • Established: December 9, 1962
  • Hours: Open daily from 8 AM to 6 PM
  • Entry Fee: $15-$25

Wigwam Village Motel (Holbrook, Arizona)

There's an authentic native american-style wigwam motel on route 66.

The Wigwam Village Motel in Holbrook allows guests to spend the night in cozy teepee-shaped cabins.

Interestingly, it's one of just three Wigwam Villages left in the country, and it is a nostalgic throwback to the whimsical motor courts and unique accommodations that were once synonymous with the Route 66 experience.

  • Address: 811 W Hopi Dr, Holbrook, AZ 86025

Debate over the cultural appropriation surrounding these Wigwam Villages exists. However, some of the remaining motels have tried in recent years to educate guests about these villages' history and place in American history as a roadside attraction.

Twin Arrows Trading Post (Flagstaff, Arizona)

A perfect spot to pull off route 66 along flagstaff and winslow.

For those between Flagstaff and Winslow, Arizona, visiting the Twin Arrows Trading Post is worth the trip. This is the perfect place to pull off Route 66 and snap a shot, as there are two massive arrows positioned in the ground (it's one of the many quirky roadside attractions on Route 66!).

What was once a fairly busy area in the Arizona desert, Twin Arrows Trading Post now currently sits pretty quiet, as much of this route does.

  • Address: Flagstaff, AZ 86004

There are many other scenic small towns in Arizona worth seeing for those looking to extend their trip or check out a few detours while driving Route 66.

Oatman Ghost Town (Oatman, Arizona)

An old mining town of the wild west where wild burros roam the streets.

Once a bustling mining town, Oatman is now one of the many ghost towns on Route 66 to visit; it's completely frozen in time, providing travelers with a glimpse into the past. The town of Oatman is the real deal; it comes complete with saloons, wooden sidewalks, and Western-themed shops.

Oatman isn't one of the amazing historic ghost towns of the American West with nothing going on, though; visitors can also stop to pet the beloved local burros that roam the streets or enjoy one of the daily gunfight reenactments that pay homage to the long-gone days of the Old Wild West.

  • Address: Oatman, AZ, 86433

Related: Quirky & Historic: 10 Route 66 Attractions That Are Worth Pulling Over For

Santa Monica Pier (Santa Monica, California)

Amusement park rides, hotels, restaurants, and more await at the end of route 66.

There's no better way to end a journey across Old Route 66 than by gazing into the waters of the Pacific Ocean. Indeed, visiting the Santa Monica Pier is the perfect end for road-trippers to celebrate completing their cross-country journey.

The Santa Monica Pier isn't just the penultimate of California's Route 66 portion; it's an important historic landmark that features a magnificent view of the Pacific Ocean, a vibrant amusement park, and numerous restaurants and hotels where travelers can unwind. The ultimate family-friendly stop on Route 66, there are tons of exciting things to do on the Santa Monica Pier for all ages.

  • Address: 200 Santa Monica Pier, Santa Monica, CA 90401

Where It Starts & Ends: 12 Things You Can Still See On Old Route 66

AAA forecasts nearly 44M travelers for Memorial Day weekend: See best times to travel

best road trips starting in chicago

Memorial Day weekend marks the unofficial start of summer, which means people will be flooding highways and airports this weekend looking to get away for some rest and relaxation.

The American Automobile Association is projecting nearly 44 million travelers will head 50 miles or more from home over the Memorial Day holiday travel period, which is defined by the organization as the five-day period from Thursday, May 23 to Monday, May 27.

"We haven't seen Memorial Day weekend travel numbers like these in almost 20 years," said Paula Twidale, senior vice president of AAA Travel, in a news release. "We're projecting an additional one million travelers this holiday weekend compared to 2019, which not only means we're exceeding pre-pandemic levels but also signals a very busy summer travel season ahead."

The organization projects over 38 million people will travel by car over Memorial Day weekend, over 3.5 million will travel by air and nearly 2 million will travel by other modes of transportation, including buses, cruises and trains.

The 38 million drivers is the highest number for Memorial Day since AAA began tracking data in 2000 and is up 4% compared to last year. The 3.5 million air travelers is an increase of nearly 5% over last year and, according to AAA, this will be the most crowded Memorial Day weekend at airports since 2005.

Learn more: Best travel insurance

When is Memorial Day?: Here's when the holiday falls and what to know about its history.

Best, worst times to travel for Memorial Day weekend

Drivers leaving Thursday or Friday should hit the road early to avoid mixing with commuters, AAA said, citing data from transportation data and insights provider INRIX. Drivers going back home Sunday or Monday should avoid the afternoon hours when return trips will peak.

“Travel times are expected to be up to 90% longer than normal. Travelers should stay up to date on traffic apps, 511 services, and local news stations to avoid sitting in traffic longer than necessary,” said Bob Pishue, transportation analyst at INRIX, in the news release.

Here's a breakdown of the best and worst times to travel by car depending on which day you are traveling:

Thursday, May 23

  • Best travel time: Before 11 a.m. and after 7 p.m.
  • Worst travel time: Between noon and 6 p.m.

Friday, May 24

  • Best travel time: Before 11 a.m. and after 8 p.m.
  • Worst travel time: Between noon and 7 p.m.

Saturday, May 25

  • Best travel time: Before 1 p.m. and after 6 p.m.
  • Worst travel time: Between 2 p.m. and 5 p.m.

Sunday, May 26

  • Best travel time: Before 1 p.m.
  • Worst travel time: Between 3 p.m. and 7 p.m.

Monday, May 27

  • Best travel time: After 7 p.m.

Gas prices continue to decrease heading into Memorial Day weekend

According to AAA, the national average for a gallon of gasoline has fallen four cents since last week, to $3.60. The primary reasons are weak domestic demand and oil costs below $80 a barrel, according to the organization.

“Barring some unforeseen event, this pokey drop in pump prices is not likely to change anytime soon,” said Andrew Gross, AAA spokesperson, in a news release. “There are seven states with county gas averages at less than $3 a gallon. This trend will likely accelerate as more gas outlets east of the Rockies drop their prices.”

This Memorial Day weekend, drivers can expect similar gas prices as last year when the national average was about $3.57.

"Pump prices rose this spring but have held somewhat steady in recent weeks," AAA said in the news release, while also noting that prices may creep higher as the summer driving season gets underway.

The wildcard remains the cost of oil, according to the organization, and unlike last year, there are now two wars – in the Middle East and Ukraine – that could roil the oil market.

Gabe Hauari is a national trending news reporter at USA TODAY. You can follow him on X  @GabeHauari  or email him at [email protected].

Watch CBS News

Memorial Day weekend 2024 could break travel records. Here's what to know.

By Emily Mae Czachor

May 20, 2024 / 5:04 PM EDT / CBS News

Despite another month of spring technically still ahead, travelers often view Memorial Day weekend  as an unofficial kickoff to the summer season — and traffic notoriously reflects that . Based on current forecasts, travel around the upcoming 2024 holiday next Monday, May 27, is not expected to relieve Memorial Day of its bad reputation for drivers and airline passengers. They may actually find themselves on some of the busiest highways and flights they've seen in decades.

The American Automobile Association, or AAA, warned of potentially unprecedented congestion on roads this weekend, along with airports that could be even more crowded than in years past. The organization, which looks at various economic factors and partners with other groups to project travel conditions, announced earlier this month that an estimated 43.8 million people across the United States would likely travel at least 50 miles from Thursday to Monday. That would mark a 4% increase in overall travel compared with 2023, according to AAA. It would also come close to the busiest Memorial Day weekend on record, which happened in 2005 when 44 million people left home for the holiday.

"We haven't seen Memorial Day weekend travel numbers like these in almost 20 years," said Paula Twidale, the senior vice president of the travel division at AAA, in a statement. "We're projecting an additional one million travelers this holiday weekend compared to 2019, which not only means we're exceeding pre-pandemic levels but also signals a very busy summer travel season ahead."  

For those planning to hit the road or board a plane this weekend, here's what to know.

Prepare to hit traffic

Memorial Day weekend in 2024 is expected to set a new record for road trips, according to AAA. The organization has estimated that 38.4 million people will travel in cars over the course of the weekend, which would be the biggest number recorded around this particular holiday since the group first started keeping track of Memorial Day travel patterns in 2000. 

Car rental company Hertz told AAA that demand for rentals this year will be highest in Atlanta, Boston, Las Vegas and Orlando, with most renters scheduled to pick up their cars on Thursday and Friday.

In general, drivers hoping to beat the traffic, or at least face less of it, should avoid the roads during afternoon hours on any day of the long weekend. Citing transit data from INRIX , AAA said the worst times to travel by car , in any U.S. time zone, are between 12 p.m. and 6 p.m. on Thursday, between 12 p.m. and 7 p.m. on Friday, between 2 p.m. and 5 p.m. on Saturday, between 3 p.m. and 7 p.m. on Sunday, and between 3 p.m. and 7 p.m. on Monday. 

The best times to drive will be before 11 a.m. or after 7 p.m. on Thursday, before 11 a.m. or after 8 p.m. on Friday, before 1 p.m. or after 6 p.m. on Saturday, before 1 p.m. on Sunday, and after 7 p.m. on Monday.

Airports will be crowded

Airports across the country are bracing for another spike in travelers, following an upward trend in flights booked around Memorial Day since last year's air travel numbers exceeded pre-pandemic levels. An estimated 3.51 million people are projected to fly this weekend, according to AAA, which is up from 3.35 million who traveled on planes to their destinations last year. If as many people fly as expected, this will be the most crowded Memorial Day weekend at airports since 2005, when AAA said 3.64 million people caught flights for the holiday.

United Airlines said more than 500,000 people are expected to fly each day from Thursday to Tuesday, which would be the airline's busiest Memorial Day weekend on record. Delta said 3 million people are expected to fly on its planes over that six-day period and American Airlines said it expects 3.9 million people to fly over the weekend.

Public transportation tips

Any of the projected 1.9 million people who use public transit systems to get to where they're going this weekend can plan ahead, too. INRIX projections show metro riders will face a degree of congestion in major cities, including Atlanta, Boston, Chicago, Denver, Detroit, Houston, Los Angeles, Minneapolis, New York, Philadelphia, Portland, Oregon, San Diego, San Francisco, Seattle, Tampa and Washington, D.C. Congestion on metros is expected to peak in those places in the late afternoon, early evening and mid-morning each day between Thursday and Monday. 

Forecasts suggest D.C., Los Angeles, Houston and Tampa will see the largest jumps in metro crowding compared with their respective norms. The worst is projected for one route from Gainesville to Tampa, where INRIX said metro congestion on Sunday at 9 a.m. local time could be 88% higher than usual.

Kris Van Cleave contributed reporting.

  • Memorial Day

Emily Mae Czachor is a reporter and news editor at She covers breaking news, often focusing on crime and extreme weather. Emily Mae has previously written for outlets including the Los Angeles Times, BuzzFeed and Newsweek.

More from CBS News

43.8 million travelers are predicted to return home this Memorial Day. Here's how it looks in Baltimore

Busy travel weekend for Maryland as Memorial Day holiday draws to a close

Maryland Weather: Afternoon showers & storms Wednesday

Memorial Day tornado warnings activated in Maryland as severe storms sweep region


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