Top 15 road trips from Chicago

Chicago to Madison
starting from Chicago
36 minutes → Arlington Heights
1 hour → South Beloit
60 minutes → Lake Kegonsa State Park
21 minutes → Madison





3 hours of driving
Chicago to Indianapolis
starting from Chicago
38 minutes → Gary
53 minutes → Wheatfield
45 minutes → Remington
41 minutes → Triple XXX Family Restaurant
35 minutes → Frankfort
52 minutes → Indianapolis Museum of Art
10 minutes → Indianapolis


4.5 hours of driving
Chicago to Ann Arbor
starting from Chicago
50 minutes → Indiana Dunes State Park
56 minutes → Saint Joseph
57 minutes → Kalamazoo
39 minutes → Marshall
57 minutes → Waterloo State Recreation Area
35 minutes → Ann Arbor



5 hours of driving
Chicago to St. Louis
starting from Chicago
1 hour → Morris
55 minutes → Pontiac
46 minutes → Bloomington
1 hour → Springfield
52 minutes → Carlinville
1 hour → St. Louis



6 hours of driving
Chicago to Detroit
starting from Chicago
50 minutes → Indiana Dunes State Park
56 minutes → Saint Joseph
1 hour → Fairfield Inn Kalamazoo West
52 minutes → Marshall
57 minutes → Waterloo State Recreation Area
1.5 hours → Detroit



6 hours of driving
Chicago to Traverse City
starting from Chicago
50 minutes → Indiana Dunes State Park
1.5 hours → South Haven
57 minutes → Grand Rapids
1.5 hours → Evart
1.5 hours → Traverse City




6 hours of driving
Chicago to Columbus
starting from Chicago
1.5 hours → Remington
1.5 hours → Indianapolis
1.5 hours → Richmond
47 minutes → Dayton
1 hour → Columbus




6 hours of driving
Chicago to Louisville
starting from Chicago
38 minutes → Gary
53 minutes → Wheatfield
45 minutes → Remington
1 hour → Crawfordsville
53 minutes → Indianapolis
41 minutes → Taylorsville
47 minutes → Scottsburg
35 minutes → Louisville

6.5 hours of driving
Chicago to Lexington
starting from Chicago
1.5 hours → Remington
1.5 hours → Indianapolis
1.5 hours → Scottsburg
1.5 hours → Frankfort
43 minutes → Lexington




6.5 hours of driving
Chicago to Cincinnati
starting from Chicago
38 minutes → Gary
53 minutes → Wheatfield
45 minutes → Remington
41 minutes → Triple XXX Family Restaurant
1.5 hours → Indianapolis
57 minutes → Greensburg
1 hour → Creation Museum
25 minutes → Cincinnati

6.5 hours of driving
Chicago to Des Moines
starting from Chicago
1.5 hours → Sycamore
1 hour → Rock Falls
1 hour → Moline
1 hour → University of Iowa
1 hour → Brooklyn
1.5 hours → Des Moines



7 hours of driving
Chicago to Cleveland
starting from Chicago
50 minutes → Indiana Dunes State Park
57 minutes → South Bend
1.5 hours → Coldwater
1 hour → Rodeway Inn
48 minutes → Toledo
1 hour → Sandusky
1 hour → Cleveland


7.5 hours of driving
Chicago to Nashville
starting from Chicago
50 minutes → Indiana Dunes State Park
2 hours → Triple XXX Family Restaurant
1.5 hours → Indianapolis
1.5 hours → Sellersburg
2 hours → Mammoth Cave National Park
1.5 hours → Nashville



9 hours of driving
Chicago to Minneapolis
starting from Chicago
55 minutes → The Vine - Martini & Wine Bar
1 hour → South Beloit
1 hour → Madison
1 hour → Wisconsin Dells
45 minutes → Tomah
1 hour → Neillsville
1 hour → Eau Claire
1.5 hours → Afton State Park
39 minutes → Minneapolis
9.5 hours of driving
Chicago to Charleston
starting from Chicago
2 hours → Triple XXX Family Restaurant
1.5 hours → Indianapolis
2 hours → Dayton
4 hours → Yellow Springs
2 hours → Wellston
1.5 hours → Charleston



13 hours of driving

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Find day trips near Chicago and explore nearby destinations that are easily drivable. Once you've picked a place, you can search for alternate routes that might have more interesting stops along the way. If you're looking for all the possible destinations, try searching for a radius of 100 miles from Chicago up to 400 miles from Chicago or anything in between. Did you mean to drive to Chicago instead? Plan a longer getaway and do a road trip to Virginia from Chicago.