Top 10 road trips to Chicago

Madison to Chicago
starting from Madison
1 hour → South Beloit
36 minutes → Harvard
51 minutes → Elgin
51 minutes → Millennium Park
5 minutes → Chicago




3.5 hours of driving
Indianapolis to Chicago
starting from Indianapolis
48 minutes → Frankfort
35 minutes → Triple XXX Family Restaurant
41 minutes → Remington
47 minutes → Wheatfield
48 minutes → Gary
41 minutes → Chicago



4.5 hours of driving
Detroit to Chicago
starting from Detroit
43 minutes → Ann Arbor
1 hour → Marshall
41 minutes → Kalamazoo
57 minutes → Saint Joseph
56 minutes → Indiana Dunes State Park
50 minutes → Chicago



5.5 hours of driving
St. Louis to Chicago
starting from St. Louis
53 minutes → Old 66
1 hour → Springfield
53 minutes → McLean
51 minutes → Pontiac
47 minutes → Morris
55 minutes → Naperville
37 minutes → Chicago


6 hours of driving
Louisville to Chicago
starting from Louisville
37 minutes → Scottsburg
47 minutes → Taylorsville
41 minutes → Indianapolis
1.5 hours → Triple XXX Family Restaurant
41 minutes → Remington
47 minutes → Wheatfield
1 hour → Museum of Science and Industry
15 minutes → Chicago
6 hours of driving
Cincinnati to Chicago
starting from Cincinnati
1.5 hours → Rushville
57 minutes → Indianapolis
1.5 hours → Triple XXX Family Restaurant
41 minutes → Remington
60 minutes → Cedar Lake
57 minutes → Chicago



6.5 hours of driving
Cleveland to Chicago
starting from Cleveland
1 hour → Cedar Point
1 hour → Toledo
48 minutes → Rodeway Inn
1 hour → Coldwater
1 hour → Middlebury
45 minutes → South Bend
57 minutes → Indiana Dunes State Park
50 minutes → Chicago
7.5 hours of driving
Nashville to Chicago
starting from Nashville
1 hour → Bowling Green
2 hours → Louisville
2 hours → Indianapolis
1.5 hours → Triple XXX Family Restaurant
2 hours → Indiana Dunes State Park
50 minutes → Chicago



9 hours of driving
Minneapolis to Chicago
starting from Minneapolis
1.5 hours → Eau Claire
1 hour → Neillsville
1 hour → Tomah
51 minutes → Wisconsin Dells
1 hour → Madison
1 hour → South Beloit
1 hour → The Vine - Martini & Wine Bar
55 minutes → Chicago
9 hours of driving
Columbus to Chicago
starting from Columbus
3 hours → Yellow Springs
4 hours → Dayton
49 minutes → Richmond
1.5 hours → Indianapolis
1.5 hours → Triple XXX Family Restaurant
2 hours → Gary
41 minutes → Chicago


13 hours of driving

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Search for Chicago road trips and plan a quick drive in a weekend or less. Select your hometown as a starting point and explore alternate routes to find the best roads to take for your Chicago vacation. Did you mean to start from Chicago instead? Find routes from Leesburg (Virginia) to Chicago and start planning your trip!