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

5.0
(13 reviews)

2 hours (approximately)
Offered in: English

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
Gratuities

Meeting and pickup

Meeting point
34 W Erie St

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

End point
The Congress Plaza Hotel & Convention Center

This tour ends near (or inside) the most haunted hotel in the country!

Itinerary

Duration: 2 hours (approximately)
  • 1
    River North

    We will surprise you with our itinerary -- half in River North, half in Chicago's Loop neighborhood. We will visit various dark sites in both neighborhoods, including the hotel where a psychopathic serial killer stayed after committing his crimes, and a gangster hangout with a hidden vault.

    1 hour Admission ticket free
  • 2
    Chicago

    We are purposely giving a vague description of where we'll be so that you'll be surprised at every turn with the tales of ghosts, gangsters, disasters, and more! From cold spots, to dead energy, to stories of the macabre, this tour will show you the darker side of Chicago.

    1 hour Admission ticket free

Additional info

  • 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
Supplied by Inside Chicago Walking Tours

Tags

Private and Luxury
Architecture Tours
Walking Tours
Ghost Tours
Likely to Sell Out
Crime Tours
Seasonal
Best Conversion
Low Supplier Cancellation Rate
Low Last Minute Supplier Cancellation Rate
Short term availability

Cancellation Policy

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

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Rating

5.0 Based on 13 13 reviews
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Likely to sell out
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