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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
Best Places To Stay
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Chicago, ILFastBook$$
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Trip Guides
Meet "Big Daddy": Roadtripping US-20, the Longest Road
- 23 Places
- 60:25
- 3,576 mi
The Coolest Attractions and Stops Along I-80
- 35 Places
- 53:41
- 3,194 mi
"Planes, Trains, and Automobiles" filming locations
- 6 Places
- 16:45
- 1,037 mi
A neon-fueled road trip along Route 66's most iconic spots
- 41 Places
- 38:08
- 2,284 mi
Get your kicks on Illinois's Route 66
- 24 Places
- 06:35
- 323 mi
Cruise through the Land of Lincoln on IL's Route 66
- 15 Places
- 05:16
- 290 mi
Your road trip guide to every awesome detour off I-70
- 42 Places
- 45:04
- 2,584 mi