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The 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

Whether you seek to commune with nature or an urban escape, the Midwest has a lot to offer. All it takes is a quick road trip from Chicago (these scenic drives are all under six hours) to transport yourself to somewhere completeley different, whether it's sipping bourbon in Louisville, hiking in Eau Claire or sunabathing in Door Country. So if you're not sure where to start when it comes to a Midwestern vacation, 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

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Best road trips 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

5hrs from Chicago

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 boats and has shuttles that will drive you upstream so you can hit the Chippewa River. 


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

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 fienst BBQ in the Midwest at 17th Street BBQ


4hrs from Chicago

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 Bakery Cafe, a family-owned kitchen with a lovely corner porch where everything is made from scratch daily. 

4 hours 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's 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 about half way. 


5 hrs

Kentucky’s largest city, just across the Ohio River from southern Indiana, is steeped in bourbon and long on charm. The home of the old-fashioned and the mint julep embraces its role as the gateway to Bourbon Country. The city now has five tourable distilleries, including Evan Williams, Angel’s Envy and Bulleit. If bourbon and honkeytonk 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

4hrs from Chicago 

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.


4hrs from Chicago 

If you're sticking to less-crowded cities this year, 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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