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
Tour/Activity Deals
Tour/Activity Deals
Chicago
Trip Guides
- 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
- Trip Guide
Drive This, Not That: I-80 Chicago/Cleveland
- 17 Places
- 09:17
- 419 mi
- Trip Guide
U.S. Route 12 Road Trip
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- 51 Places
- 46:22
- 2,661 mi
- Trip Guide
Drive down 5 of America’s most haunted roads, if you dare
- 5 Places
- Trip Guide
Ultimate Offbeat Guide to Chicago, Illinois
- 18 Places
- Trip Guide
So, axe throwing is a thing now, and it looks kinda fun
- 6 Places
- Trip Guide
Meet the "Big Daddy": Roadtripping US-20, the Longest Road
- 23 Places
- 60:25
- 3,576 mi
- Trip Guide
"Planes, Trains, and Automobiles" filming locations
- 6 Places
- 16:45
- 1,037 mi
- Trip Guide
Ferris Bueller's Day Off Filming Locations Day Trip
- 7 Places
- 01:48
- 63 mi
