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Photograph: ShutterstockThe John A. Roebling Bridge was built in 1866 to connect Covington, Kentucky to Cincinnati, Ohio. It spans the Ohio River.

The 14 best road trips from Chicago

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

Written by
Sarah Medina
Contributor
Lindsay Eanet
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No coast? No problem. Summer is approaching, and it's the perfect time to embark on a scenic road trip from Chicago to transport yourself to somewhere completely different. Whether you prefer sipping bourbon in Louisville, hiking in Eau Claire or sunbathing in Door County, there's a perfect mini-vacation here for everyone. So if you're not sure where to start when it comes to a Midwestern trip, we recommend you load up the car and hit the road—one of these road trips from Chicago could quickly turn into your favorite weekend getaway

RECOMMENDED: The best day trips from Chicago

Best road trips from Chicago

Driving time from Chicago: 4 hrs 30 min

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 at Wilmington, IL to see a roadside attractions called the Gemini Giant, or in Atlanta, IL to take a photo with Paul Bunyon holding a massive hotdog. 

Discover the best things to do in St Louis

Driving time from Chicago: 5 hrs

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. 

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Driving time from Chicago: 5 hrs

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. 

Discover the best things to do in Traverse City

Cincinnati, OH
Photograph: Shutterstock

4. Cincinnati, OH

Driving time from Chicago: 5 hrs 

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.

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Driving time from Chicago: 6 hrs

Not going to make it to Napa this year? Opt for the just-as-beautiful Shawnee Hills Wine Trail instead. The 35-mile scenic drive meanders through Shawnee National Forest in southern Illinois and features 11 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

Driving time from Chicago: 4 hrs

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; see the Morgan-Monroe State Forest wildflowers; admire the Cedar Bluffs Nature Preserve limestone bluffs; go 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. 

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Driving time from Chicago: 4 hrs 30 min

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. 

Driving time from Chicago: 5 hrs 

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 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

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Saugatuck, MI
Photograph: Courtesy Saugatuck Michigan

9. Saugatuck, MI

Driving time from Chicago: 2 hrs 30 min

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. Whether it’s hiking the Saugatuck Dunes, window shopping on Butler Street or 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. 

Driving time from Chicago: 4 hrs

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.

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Detroit, MI
Photograph: Shutterstock

11. Detroit, MI

Driving time from Chicago: 4 hrs 30 min

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 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

Driving time from Chicago: 4 hrs 

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 pletehora 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). 

Discover the best things to do in Ann Arbor

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Shipshewana, IN
Photograph: Shutterstock

13. Shipshewana, IN

Driving time from Chicago: 2 hrs

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
Photograph: Shutterstock

14. Des Moines, IA

Driving time from Chicago: 5 hrs

There's a surprising amount to explore in 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.

Need more travel inspiration?

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