About this experience
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.
At a glance
- Duration: 2 hr
What is included
- Expert guide
Not included
- Gratuities
Itinerary and highlights
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.
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.
Meeting and pickup information
- We meet directly in front of the Fedex store, near the corner of Erie & Dearborn. Please check in with your guide upon arrival!
Languages and tickets
- English — Guide
- Mobile Only
Tour operator
- Inside Chicago Walking Tours
Meeting points and locations
Accessibility and practical details
- 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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