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
Current Weather
32 °F
Heavy Snow
Best Places To Stay
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Chicago, IL -
Chicago, IL -
Chicago, IL -
Chicago, IL -
Chicago, IL -
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Chicago, IL -
Trip Guides
A holly, jolly road trip to holiday movie filming locations
- 9 Places
- 57:06
- 3,562 mi
- Trip Guide
- 2 Weeks
The ultimate road trip guide to I-90, from Boston to Seattle
- 47 Places
- 60:51
- 3,500 mi
- Trip Guide
Uncover the mystery of the strange, bizarre Toynbee Tiles
- 28 Places
- Trip Guide
The most epic American road trip
- 28 Places
- 191:21
- 11,212 mi
- Trip Guide
13 times in your life to go on a road trip
- 14 Places
- Trip Guide
These are America's 8 most iconic road trips
- 15 Places
- Trip Guide
The coolest retro neon signs along Route 66
- 17 Places
- 34:05
- 2,156 mi
- Trip Guide
Pun-tastic Restaurants
- 16 Places
Chicago to New Orleans Road Trip
- 19 Places
- 19:28
- 1,068 mi
- Trip Guide
Library Lust
- 7 Places
- Trip Guide
Get your kicks on Illinois's Route 66
- 24 Places
- 07:05
- 335 mi
- Trip Guide
U.S. Route 12 Road Trip
- 51 Places
- 47:15
- 2,642 mi