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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, ILFastBook$$
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Chicago, ILFastBook$$
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great deal!
Trip Guides
The top things to do on a U.S. Route 20 road trip
- 23 Places
- 60:25
- 3,576 mi
The top things to do on a Route 66 road trip
- 41 Places
- 38:08
- 2,284 mi
Everything awesome you never knew about Christmas Vacation
- 5 Places
- 04:32
- 286 mi
"Planes, Trains, and Automobiles" filming locations
- 6 Places
- 16:45
- 1,037 mi
Get your kicks on Illinois's Route 66
- 24 Places
- 06:35
- 323 mi
Cruise through the Land of Lincoln on IL's Route 66
- 15 Places
- 05:16
- 290 mi
U.S. Route 12 Road Trip
- 51 Places
- 46:22
- 2,661 mi