Chicago's Dark Side: Ghosts, Gangsters, and True Crime Tour
Description
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.
Tour Options
Itinerary
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.
Highlights
What's included
Traveller Ratings
Important Information
- 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
Reviews(64)
Incredibly disappointing. After reading so many amazing reviews, we were excited to book directly with the tour operator. Unfortunately, our experience with Scott was nothing like what others described. From the beginning, he was unfriendly, disengaged, and seemed to have little interest in making our experience enjoyable. Nearly every question we asked was met with “I don’t know,” even when the questions were directly related to the tour. Based on the dramatically different experiences described in other reviews, we were left feeling as though our family was being treated differently. We specifically purchased every available spot so that the tour would be private. We were traveling with older children, including our daughter, who has a profound cognitive disability, and having a private experience allowed us to accommodate her needs without affecting other guests. Instead of feeling welcomed and supported, our family felt uncomfortable and dismissed. We paid a premium for what we expected would be a personal, engaging, and memorable experience. Sadly, Scott’s attitude and lack of effort overshadowed the entire tour. Families especially those traveling with a disabled child deserve to be treated with patience, dignity, and respect. We left feeling deeply disappointed and questioning whether our family had been discriminated against. I cannot recommend this experience based on the way we were treated.
Hi Shelly, I'm going to reach out to you privately to get more details about this. I'm absolutely shocked and saddened to hear that you felt this way. I've talked with Scott, who is equally shocked and upset, as he had no idea that you and your family were not enjoying the tour. I do know him to be an incredibly friendly and sweet person, and he always goes above and beyond to accommodate guests, like taking more than the usual 2-hour time frame to accommodate a slower pace, like with your group. He let me know that your group often separated into two smaller groups due to a slower pace being needed for your daughter, but that you kept telling him to go ahead and not wait for them. I'm very sorry that you feel like your experience with him was bad. As you mentioned, based on other reviews, your experience is not a typical experience, and Scott really is a wonderful, sweet person, and I know he takes a great amount of pride in his work and in the experience he provides guests. I'll reach out to you privately to get more details.
The tour was fine but I wish there was more information. There were LONG pauses in between stops as we walked to the next one and it felt like there could’ve been more added here. Nothing on this tour felt special and a lot of the stops were public access with signs most likely pointing to what you would want to learn. I think this tour would benefit either some sort of vehicle, being done at night to add spookiness, a microphone, and a refinement of the content. We talked about gangsters for all of two stops and they were barely mentioned again. Most of the stops just BARELY related to the stories that were being told. This tour was a little all over the place, but the tour guide was very sweet and I hope that they continue doing well!!
Thanks for your feedback, Jessica, and I'm sorry this tour wasn't your cup of tea. We do admittedly cover quite a bit of ground physically on this tour, so stopping between our many planned stops would unfortunately add time to our 2-hour tour. To be clear, the tour's content does not prioritize gangster stuff over other content: it's some gangster stuff, but largely true crime, tragedies, and hauntings (which usually have a true crime or tragic story behind them). Chicago's tourism scene is full of gangster tours that make up stories to be entertaining to guests, and the places they stop are often not related to gangsters at all: if you want real gangster stuff, you'd have to go outside of downtown Chicago, and most of what you'd want to see is no longer there. So we cover a bit of real gangster stuff -- like visiting a real old mob headquarters -- but we also focus on the true crime, real history, and ghost stories that fill the downtown area.
This was a magnificent tour. I wish I had done it earlier in my visit to Chicago as it made me want to do some further exploring. Scott was the perfect balance between informative, personable and knowledgeable. Lots of extra tidbits to keep you fascinated. Two hours flew by and the walk was easy. Highly recommend.
Excellent tour! I learned so much about Chicago while also getting to see some beautiful buildings and neighborhoods. Our tour guide was very knowledgeable and had great insights about the city. 10/10 would recommend to anyone who loves a walking tour.
Great experience. Scott is very informative
Very informative tour about disasters and murders in Chicago's history
Scott knew so much information. He was also very friendly on the hottest day ever! We have been on different crime tours but we learned about all new areas of crime on this tour.
This was an unexpectedly amazing experience and our tour guide, Scott, made it so much better! He was so knowledgeable about the dark history of Chicago and answered all of my extra curious questions. I would 100% recommend this tour!
What a wonderful tour! Scott was knowledgeable and so accommodating. Navigating Chicago on my own was tough. Scott called me to see if I was going to make the tour when I missed the start time. He was able to talk me through how to find them so I could catch up. Thank you Scott. Appreciate your commitment to your guests, it meant a lot!
Max was a great tour guide! Very funny and entertaining and knowledgeable!
