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Chicago's Dark Side: Ghosts, Gangsters, and True Crime Tour

4.9(82)Rated 4.9 out of 5 from 82 reviews2 hFree cancellationBy Inside Chicago Walking Tours
Chicago's Dark Side: Ghosts, Gangsters, and True Crime Tour

About this activity

Discover Chicago’s dark side on a chilling 2-hour walking tour. Strolling just under 2 miles at an easy pace, we reveal stories of gangsters, tragedies, and restless spirits hidden behind the city’s glamorous façade. Hear of hidden mob headquarters, psychopaths in plain sight, and disasters like the Iroquois Fire and Eastland Disaster.

Join us in exploring historic interiors where gangsters once gathered and ghosts are said to linger. Along the way, explore the roots of ghost lore—are they real sightings or tricks of architecture? Decide for yourself if Chicago’s most haunted tales are fact or fiction. Perfect for fall nights and curious minds, this tour blends true crime, gangster history, and ghost stories into an unforgettable experience.

What's included

  • ✓Expert guide

Not included

  • ✕Gratuities

Meeting and pickup

  • We meet directly in front of the Fedex store, near the corner of Erie & Dearborn. Please check in with your guide upon arrival!

Good to know

  • Not recommended for travelers with spinal injuries
  • Service animals allowed
  • Public transportation options are available nearby
  • Infants and small children can ride in a pram or stroller
  • Travelers should have at least a moderate level of physical fitness

Cancellation policy

For a full refund, cancel at least 24 hours before the scheduled departure time.

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