Innovation and Midwest friendliness collide in America’s Second City (technically its third largest). If you’re unmoved by Chicago’s 27 miles of shimmering lakefront, majestic city skyline and patchwork of walkable neighborhoods, there’s just no pleasing you. As for its harsh weather, just do as the locals do—slap on an extra layer or two, and quit complaining. Free cancellation on most hotels. Because flexibility matters.
Car rentals
Compact 2/4Door Car
$25
Midsize Special
$35
Economy Special
$33
Compact 2/4Door Car
$21
Midsize Special
$35
Economy 2/4Door Car
$44
Travel tips
9 travel myths you shouldn’t believe
How to show off your hometown
6 tips for exploring a city like a local
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