Chicago's Dark Side: Ghosts, Gangsters, and True Crime Tour
Overview
Available languages
2 hours
Mobile ticket
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.
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
Cancellation Policy
For a full refund, cancel at least 24 hours before the scheduled departure time.
What‘s Included
Expert guide
Gratuities
What To Expect
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.
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.
Options
Chicago's Dark Side: Ghosts, Gangsters, and True Crime Tour
Reviews
24 reviews
Total reviews and rating from Viator & Tripadvisor
They has us go inside...
Kylie G,
Nov 9, 2025
- Review from Viator
4.00They has us go inside places to see cool things and outside to see cool buildings. It was unfortunately raining or it would’ve been better but that’s nobody fault
Great Tour (rain or shine)
FellowTraveler698459,
Nov 8, 2025
- Review from Tripadvisor
5.00I really loved this tour, and it was much more than the organized crime history I thought I was in for. It really looks at tragedy throughout the city and its effects on the city itself. The weather was terrible, it was pouring rain and windy the whole time. Our guide never waivered though, and at point was shouting above the weather. Thank you Scott, incredible job! I booked this experience through Airbnb.
Great storytelling!
meredithmL7178SX,
Nov 8, 2025
- Review from Tripadvisor
5.00Scott was awesome! Really great at keeping the group interested and doing justice to the stories. You could tell he was knowledgeable and cared a lot about everything he was sharing. Will absolutely be going down a rabbit hole online to dig deeper into all the stories he shared. Very dark but interesting! My 13 and 14 year old nieces enjoyed it a lot.
A cool way to see Chicago
I1401BXtomd,
Nov 7, 2025
- Review from Tripadvisor
5.00Scott was great and the tour was awesome. My wife and I have lived here for a year and saw a lot of things that we previously hadn’t seen before.
Great tour w Scott!
Reaughstar,
Nov 7, 2025
- Review from Tripadvisor
5.00awesome way to experience Chicago history on foot. Saw places and heard history I would’ve missed otherwise. Thanks, Scott!
Very enjoyable tour!
Anonymous,
Nov 4, 2025
- Review from Viator
5.00Very enjoyable tour to do. Our guide, Scott was very knowledgeable and shared many old stories about the area. We went along the river walk for a bit and were in and out of hotels and restaurants spotting pieces of Chicago history. I highly recommend this tour!
Disappointing tour
Stewart P,
Nov 4, 2025
- Review from Viator
3.00Felt the tour lacked focus. Tried to cover too much and ultimately didn’t really cover any topic properly. Some interesting sections but overall a disappointment
Not spooky but interesting
Casey G,
Nov 1, 2025
- Review from Tripadvisor
5.00Scott was great! I will say that this is more history than spooky but was still a good time. Wear gym shoes - about a 2 hour tour
Perfect tour
lynnw846,
Nov 1, 2025
- Review from Tripadvisor
5.00Scott was an amazing tour guide! So much information was shared. Good walking pace and amount of time to fit it all in in the 2 hours. Highly recommend!
Scott and Tour are amazing!!!
carmenmP2049JQ,
Nov 1, 2025
- Review from Tripadvisor
5.00The tour was absolutely amazing. Scott is incredible and so excited about his subject. Highly recommend going on this tour.
From $35.00
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Operated by Inside Chicago Walking Tours