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 -
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Chicago, IL -
Chicago, IL -
Chicago, IL
Trip Guides
- Trip Guide
Beaches, beef and the Bean: 48 Hours in Chicago
- 16 Places
- 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
Ultimate Offbeat Guide to Chicago, Illinois
- 18 Places
- Trip Guide
These are America's 8 most iconic road trips
- 15 Places
- Trip Guide
U.S. Route 12 Road Trip
- Illinois, US
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- Indiana, US
- United States of America
- Billings, MT
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- 51 Places
- 46:22
- 2,661 mi
- Trip Guide
Pun-tastic Restaurants
- Illinois, US
- Maryland, US
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- United States of America
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- Bay Area
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- 16 Places
- Trip Guide
Check out Chicago's epic lazy river ice skating rink
- 10 Places
- Trip Guide
These are America’s most adorably whimsical bookstores
- 15 Places
- Trip Guide
Get your kicks on Illinois's Route 66
- 24 Places
- 06:35
- 323 mi
- Trip Guide
- 2 Weeks
The ultimate road trip guide to I-90, from Boston to Seattle
- 48 Places
- 61:26
- 3,560 mi
- Trip Guide
The best stops along I-65 from Chicago to Birmingham
- 49 Places
- 17:22
- 874 mi
