Illinois
Finding stuff to do in the Windy City is a breeze- they've got two baseball teams, legendary museums (and an aquarium and a planetarium and zoos) and some of the best regional eats in the country. But once you've had your fill of Chicago (and deep dish p…
Read More ›Best Time To Go
May-Jun, Sep-Oct
Current Weather
53 °F
Windy
Best Places To Stay
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Chicago, IL -
Chicago, IL -
Chicago, IL -
Chicago, IL -
Springfield, IL -
Chicago, IL -
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Chicago, IL
Trip Guides
- Trip Guide
A road trip inspired by 'Pee-wee's Big Adventure'
- 15 Places
A holly, jolly road trip to holiday movie filming locations
- 9 Places
- 57:06
- 3,562 mi
- Trip Guide
Pay Tribute and Reflect at These US Monuments and Memorials
- 14 Places
- 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 12 most important Route 66 road trip photo ops
- 12 Places
- 23:05
- 1,491 mi
- 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 country's most retro-tastic drive-in theaters
- 13 Places