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
Midsize SUV
$71
Economy 2/4Door Car
$59
Economy 4/5Door Car
$28
Travel tips
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6 tips for exploring a city like a local
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