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
-
Chicago, IL -
Chicago, IL -
Chicago, IL -
Chicago, IL
Tour/Activity Deals
Tour/Activity Deals
Chicago
Trip Guides
- Trip Guide
These are America's 8 most iconic road trips
- 15 Places
- Trip Guide
U.S. Route 12 Road Trip
- Illinois, US
- Minnesota, US
- Idaho, US
- Wisconsin, US
- Washington, US
- North Dakota, US
- Michigan, US
- Montana, US
- Indiana, US
- United States of America
- Billings, MT
- Bozeman, MT
- Chicago, IL
- Detroit, MI
- Madison, WI
- Minneapolis, MN
- Seattle, WA
- Spokane, WA
- St. Paul, MN
- Fargo
- Olympia
- Eau Claire
- Kalamazoo
- Bismarck
- Aberdeen
- Coeur d'Alene
- Ann Arbor
- 51 Places
- 46:22
- 2,661 mi
- Trip Guide
Pun-tastic Restaurants
- Illinois, US
- Maryland, US
- Connecticut, US
- California, US
- Oregon, US
- Washington, US
- Texas, US
- Tennessee, US
- New York, US
- Missouri, US
- Montana, US
- District of Columbia, US
- United States of America
- Austin, TX
- Chicago, IL
- Los Angeles, CA
- Missoula, MT
- Oakland, CA
- Port Angeles, WA
- Portland, OR
- Sacramento, CA
- Syracuse, NY
- Bay Area
- Washington
- Nashville
- Berkeley
- 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
- Trip Guide
Drive This, Not That: I-80 Chicago/Cleveland
- 17 Places
- 09:17
- 419 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
