- Overview
- Essential Info
- Trip Guides
- Hotels
- Things To Do
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
59 °F
Clear
Best Places To Stay
-
Chicago, ILFastBook$$$
Click to discover a
great deal! -
Chicago, ILFastBook$$
Click to discover a
great deal!
Trip Guides
A holly, jolly road trip to holiday movie filming locations
- 9 Places
- 57:06
- 3,562 mi
The ultimate road trip guide to I-90, from Boston to Seattle
- 47 Places
- 60:51
- 3,500 mi
The most epic American road trip
- 28 Places
- 191:21
- 11,212 mi
The coolest retro neon signs along Route 66
- 17 Places
- 34:05
- 2,156 mi
Pun-tastic Restaurants
- 16 Places
Chicago to New Orleans Road Trip
- 19 Places
- 19:28
- 1,068 mi
Library Lust
- 7 Places
Get your kicks on Illinois's Route 66
- 24 Places
- 07:05
- 335 mi
U.S. Route 12 Road Trip
- 51 Places
- 47:15
- 2,642 mi
Keep exploring with the Roadtrippers mobile apps.
Anything you plan or save automagically syncs with the apps, ready for you to hit the road!
Connect with us and hit up #roadtrippers
Tall tales, trip guides, & the world's weird & wonderful.