Top 6 weekend trips from Chicago

  1. Traverse City / Ann Arbor
  2. Detroit / Columbus
  3. Nashville / St. Louis
  4. Des Moines / Minneapolis
  5. Indianapolis / Cleveland
  6. Cincinnati / Lexington

For any of these trips, you could visit just the first or second destination if you want to do less driving and spend more time in the area.

The longest trip is about 22.5 hours of total driving, so you may want to plan to do this over a long weekend.


Trip idea #1: Chicago → Traverse City → Ann Arbor → Chicago


Chicago to Traverse City
leave Chicago on Friday
50 minutes → Indiana Dunes State Park
1.5 hours → South Haven
57 minutes → Grand Rapids
1 hour → Stanwood
1 hour → Cadillac
1 hour → Traverse City (stay Friday night)
view all routes
6.5 hours of driving

Traverse City to Ann Arbor
leave Traverse City on Saturday
1.5 hours → Roscommon
30 minutes → West Branch
38 minutes → Pinconning
46 minutes → Frankenmuth
1 hour → Wixom
38 minutes → Ann Arbor (stay Saturday night)
view all routes
5 hours of driving

Ann Arbor to Chicago
leave Ann Arbor on Sunday
57 minutes → Waterloo State Recreation Area
39 minutes → Marshall
57 minutes → Kalamazoo
56 minutes → Saint Joseph
50 minutes → Indiana Dunes State Park
36 minutes → Chicago (back home)
view all routes
5 hours of driving

Total driving time for this trip is about 16.5 hours of driving.


Trip idea #2: Chicago → Detroit → Columbus → Chicago


Chicago to Detroit
leave Chicago on Friday
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 (stay Friday night)
view all routes
6 hours of driving

Detroit to Columbus
leave Detroit on Saturday
1 hour → Toledo
53 minutes → Fostoria
37 minutes → Upper Sandusky
44 minutes → Mount Gilead
50 minutes → Dublin
22 minutes → Columbus (stay Saturday night)
view all routes
4.5 hours of driving

Columbus to Chicago
leave Columbus on Sunday
55 minutes → Dublin
49 minutes → Bellefontaine
1 hour → Lima
49 minutes → Fort Wayne
1.5 hours → Warsaw
50 minutes → Indiana Dunes State Park
22 minutes → Chicago (back home)
view all routes
6.5 hours of driving

Total driving time for this trip is about 17 hours of driving.


Trip idea #3: Chicago → Nashville → St. Louis → Chicago


Chicago to Nashville
leave Chicago on Friday
50 minutes → Indiana Dunes State Park
2 hours → Triple XXX Family Restaurant
1.5 hours → Indianapolis
1.5 hours → Sellersburg
1.5 hours → Mammoth Cave National Park
1.5 hours → Nashville (stay Friday night)
view all routes
9 hours of driving

Nashville to St. Louis
leave Nashville on Saturday
53 minutes → Clarksville
40 minutes → Hopkinsville
53 minutes → Grand Rivers
59 minutes → Shawnee National Forest
1 hour → Burton's Cafe
47 minutes → Nashville
60 minutes → St. Louis (stay Saturday night)
view all routes
6 hours of driving

St. Louis to Chicago
leave St. Louis on Sunday
52 minutes → Carlinville
1 hour → Springfield
46 minutes → Bloomington
47 minutes → Pontiac
1 hour → Morris
1 hour → Chicago (back home)
view all routes
5.5 hours of driving

Total driving time for this trip is about 21 hours of driving.


Trip idea #4: Chicago → Des Moines → Minneapolis → Chicago


Chicago to Des Moines
leave Chicago on Friday
1.5 hours → Sycamore
1 hour → Rock Falls
1 hour → Moline
1 hour → University of Iowa
1 hour → Brooklyn
1.5 hours → Des Moines (stay Friday night)
view all routes
7 hours of driving

Des Moines to Minneapolis
leave Des Moines on Saturday
38 minutes → Ames
48 minutes → Webster City
41 minutes → Iowa Falls
1 hour → Clear Lake
39 minutes → Albert Lea
41 minutes → Waseca
1 hour → Eagan
22 minutes → Minneapolis (stay Saturday night)
view all routes
6 hours of driving

Minneapolis to Chicago
leave Minneapolis on Sunday
1.5 hours → Afton State Park
1 hour → Eau Claire
1 hour → Neillsville
42 minutes → Oakdale
1 hour → Wisconsin Dells
1.5 hours → Madison
1 hour → Rockford
55 minutes → The Vine - Martini & Wine Bar
39 minutes → Chicago (back home)
view all routes
9.5 hours of driving

Total driving time for this trip is about 22.5 hours of driving.


Trip idea #5: Chicago → Indianapolis → Cleveland → Chicago


Chicago to Indianapolis
leave Chicago on Friday
38 minutes → Gary
45 minutes → Cedar Lake
60 minutes → Remington
41 minutes → Triple XXX Family Restaurant
35 minutes → Frankfort
52 minutes → Indianapolis Museum of Art
10 minutes → Indianapolis (stay Friday night)
view all routes
4.5 hours of driving

Indianapolis to Cleveland
leave Indianapolis on Saturday
1.5 hours → Richmond
47 minutes → Dayton
1 hour → Columbus
48 minutes → Mount Gilead
2 hours → Brecksville Nature Center
23 minutes → Cleveland (stay Saturday night)
view all routes
6 hours of driving

Cleveland to Chicago
leave Cleveland on Sunday
1 hour → Sandusky
48 minutes → Toledo
1.5 hours → Rodeway Inn
46 minutes → Middlebury
57 minutes → South Bend
50 minutes → Indiana Dunes State Park
1 hour → Chicago (back home)
view all routes
7.5 hours of driving

Total driving time for this trip is about 18 hours of driving.


Trip idea #6: Chicago → Cincinnati → Lexington → Chicago


Chicago to Cincinnati
leave Chicago on Friday
38 minutes → Gary
1 hour → Remington
41 minutes → Triple XXX Family Restaurant
1.5 hours → Indianapolis
57 minutes → Greensburg
1 hour → Hebron
30 minutes → Cincinnati (stay Friday night)
view all routes
6.5 hours of driving

Cincinnati to Lexington
leave Cincinnati on Saturday
29 minutes → Hebron
23 minutes → Walton
18 minutes → Crittenden
16 minutes → Williamstown
15 minutes → Corinth
17 minutes → Sadieville
19 minutes → Georgetown
29 minutes → Lexington (stay Saturday night)
view all routes
3 hours of driving

Lexington to Chicago
leave Lexington on Sunday
1.5 hours → Frankfort
60 minutes → Scottsburg
1 hour → Nashville
1.5 hours → Indianapolis
1.5 hours → Remington
43 minutes → Chicago (back home)
view all routes
7.5 hours of driving

Total driving time for this trip is about 16.5 hours of driving.



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Discover weekend getaways from Chicago and explore places that are easily drivable for a short 3-day trip or a longer weekend if there's a holiday or you can get time off. Once you've picked a destination, you can search for alternate routes that might have more interesting stops along the way. If you're looking for all of the possible destinations, try searching for a radius of 50 miles from Chicago up to 200 miles from Chicago or anything in between. If you don't have enough time for a long weekend, try searching for day trips from Chicago, or you can make Chicago your destination instead. If you have more time, you can plan a drive from Chicago to Kentucky.