Chicago
Chicago is located in the Midwest. It is the third largest city in the United States with a population approaching 3 million. Chicago is a huge vibrant city and a metropolitan area that sprawls over 10,874km². It's well known for house music, blues, jazz…
Read More ›Best Time To Go
Apr-Sep
Best Places To Stay
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Chicago, IL -
Chicago, IL -
Chicago, IL -
Chicago, IL -
Chicago, IL -
Chicago, IL -
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Chicago, IL
Trip Guides
- Trip Guide
Beaches, beef and the Bean: 48 Hours in Chicago
- 15 Places
- Trip Guide
The top things to do on a U.S. Route 20 road trip
- 23 Places
- 60:25
- 3,576 mi
- Trip Guide
- 1 Week
The top things to do on a Route 66 road trip
- 41 Places
- 38:08
- 2,284 mi
- Trip Guide
Ultimate Offbeat Guide to Chicago, Illinois
- 15 Places
- Trip Guide
Everything awesome you never knew about Christmas Vacation
- 5 Places
- 04:32
- 286 mi
- Trip Guide
A holly, jolly guide to Christmas movie filming locations
- 25 Places
- Trip Guide
"Planes, Trains, and Automobiles" filming locations
- 6 Places
- 16:45
- 1,037 mi
- Trip Guide
Get your kicks on Illinois's Route 66
- 24 Places
- 06:35
- 323 mi
- Trip Guide
Cruise through the Land of Lincoln on IL's Route 66
- 15 Places
- 05:16
- 290 mi
- Trip Guide
America's sexiest hostels are as cool as any boutique hotel
- 9 Places
- Trip Guide
These are America's 8 most iconic road trips
- 15 Places
- Trip Guide
U.S. Route 12 Road Trip
- 51 Places
- 46:22
- 2,661 mi
