Discover Chicago’s Dark Side: Ghosts, Gangsters & True Crime
See more
Explore the hidden, darker side of Chicago on the Chicago's Dark Side: Ghosts, Gangsters, and True Crime Tour. Over two hours, you'll walk just under 2 miles through some of the city's most mysterious neighborhoods, uncovering stories of notorious gangsters, tragic events, and restless spirits lurking behind Chicago's glamorous facade.
Visit historic interiors where gangsters once gathered and hear tales of ghostly encounters that may make your hair stand on end. From hidden mob headquarters to haunted sites, this tour blends true crime, gangster history, and ghost stories into an unforgettable experience. Perfect for fall nights or anyone curious about Chicago’s shadowy past.
Throughout the tour, you'll learn whether ghost sightings are real or just clever architecture tricks. With surprises at every turn, this adventure invites you to decide what’s fact and what’s fiction. Join us and see Chicago's dark side in a whole new light.
Frequently asked questions
How long is the tour?
The tour lasts approximately 2 hours and covers just under 2 miles at a relaxed pace.
What languages are available?
The tour is conducted in English.
What is the group size?
Groups are limited to up to 10 participants.
Is the tour suitable for children?
Yes, children aged 5-10 can join, but they should be accompanied by an adult. The tour is suitable for ages 11-64, and seniors up to 110 years old.
Is the tour accessible?
Infants and small children can ride in a stroller or pram. Participants should have at least a moderate level of physical fitness.
What’s included and what’s not?
The tour includes an expert guide. Gratuities are not included.
Free cancellation
Cancel at least 24 hours before the scheduled departure for a full refund.
Reserve now
Check a date here, then finish booking with our partner. Payment options are confirmed at checkout.
Duration 2 hours
Check availability to see start times.
Live tour guide
English
Key facts
What's included
Included
- Expert guide
Not included
- Gratuities
Itinerary
-
Stop 1
We’ll surprise you with our itinerary—half in River North, half in Chicago's Loop. Visit sites like the hotel where a serial killer stayed after his crimes and a gangster hangout with a hidden vault.
-
Stop 2
The second half is full of surprises—ghost stories, tales of disasters, and dark history. From cold spots to eerie energies, you'll get a taste of Chicago’s haunted side.
Meeting point & pickup
Meet at the starting point
We meet directly in front of the FedEx store near the corner of Erie & Dearborn. Please check in with your guide upon arrival.
Open in Google MapsCancellation & confirmation
Free cancellation
Cancel at least 24 hours before the scheduled departure for a full refund.
- 100% refund if canceled at least 1 day prior
- No refund if canceled within 0–1 days
- Tour may be canceled due to bad weather
Instant confirmation
Your booking is confirmed immediately after checkout.
From $35.00 per person
- Free cancellation
- Secure checkout with our booking partner
