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Hidden Gems in Chicago

Hidden Gems in Chicago

Chicago’s urban sprawl can be intimidating for visitors, but some of the Windy City’s best surprises are hidden in its diverse neighborhoods—each with a character all its own. Explore beyond the downtown Loop with these insider experiences that take you from 1920s gangster hideouts and back-alley art galleries to pizza parlors and heated underground tunnels.

Unexpected Chicago

Surprising adventures in the Windy City.

Speakeasies & Secrets

Go underground at Prohibition-era hot spots.

Gangsters and Ghosts Tour in Chicago
Historical Tours
Chicago Night Crimes Bus Tour
Bus Tours
  • star-4.5
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From
$50.00

Neighborhood Haunts

Explore Chicago's diverse "villages" with a local.

Deep Dishes

Taste true Chicago pizza, hot dogs, and more.