Chicago's Dark Side: Ghosts, Gangsters, and True Crime Tour
Recommended by 96% of travelers
Badge of Excellence
Chicago, USA
- 2 hours (approx.)
- Mobile ticket
- Offered in: English
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Overview
Lots of tours help you explore Chicago’s historic streets, but most avoid the grittier details that have helped shape the city over the decades. But this small-group walking tour doesn’t shy away from the gruesome details. Listen to tales of gangsters, restless spirits, and local disasters as you navigate some of Chicago’s most popular landmarks.
- Small-group tour: Lots of chances to ask your guide questions
- A walking tour helps you spot details you’d otherwise miss
- Learn facts about Chicago that most travelers don’t get to hear
- Get some handy tips for the rest of your trip
What's Included
- Expert guide
- Gratuities
Meeting and Pickup
Meeting point
- 34 W Erie St, Chicago, IL 60654, USA
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 Center520 S Michigan Ave, Chicago, IL 60605, USA
This tour ends near (or inside) the most haunted hotel in the country!
Start time.4:00 pm
Itinerary
1
River North
1 hour • Admission Ticket Free
2
Chicago
1 hour • Admission Ticket Free
Additional Info
- Confirmation will be received at time of booking
- Not recommended for travelers with back problems
- Service animals allowed
- Near public transportation
- Stroller accessible
- Not wheelchair accessible
- Travelers should have a moderate physical fitness level
- This tour/activity will have a maximum of 20 travelers
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Cancellation Policy
You can cancel up to 24 hours in advance of the experience for a full refund.
Traveler Photos
Reviews
4.9
based on 70 reviews
Sort by: Most insightful
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!!
Response from Host, Aug 2026
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 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!
My family and I really enjoyed this tour. Lots of great history! I’ve lived in IL for over 30 years and still learned a lot of new things.
Super knowledgeable guide. Great walking tour that covers tons of the city.
Be prepared to get your steps in!
Guide was knowledgeable of the history of Chicago, places, people, and the architecture. Went several notable gangsters hideouts.
This tour was excellent. We covered a lot of locations, and Scott went into the best details at each stop. Scott was Fantastic! He was an excellent presenter with lots of interest and passion on the topics .He also wanted everyone to have the best experience by engaging in Questions and Answers. You’ll love this tour and Ieatbed so much!
Our guide was very knowledgeable and spoke loudly enough that I could hear everything. He walked at a moderate speed.
Despite being a cold snowy afternoon and having to navigate the St Paddy’s day activities in the city we had a great time.
Scott was a great guide. He was very knowledgeable on Chicago history. We throughly enjoyed the tour.
Great way to spend an evening and learn about the city. Scott had lots of information and engaged the group. Great fun being able to enter locations we wouldn’t ordinarily go and find new details. Lots of fun.
Very 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!
Felt 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
Response from Host, Nov 2025
Sorry to hear you feel that way. The focus of the 2-hour tour is stated in the title -- ghosts, gangsters, and true crime (with true crime being the source of many of the ghost stories, of course) -- so we do cover these three topics in one tour, as they are related. But I'm sorry this was overwhelming for you. I'm glad you enjoyed at least part of it. For customers reading this, please refer to the multiple positive reviews left by other reviewers (calling it "the perfect tour"), and decide for yourself if this topic suits you.
Our tour was very informative and the guild was great! I would do it again. We got to see really cool building as well.
Haley was our tour guide. She was amazing. She knew a lot about the history of Chicago, and her story telling was very engaging. She made it fun. We enjoyed it very much. We had a nice group. We heard about this from a St. Louis couple who enjoyed it very much while visiting and we are natives of Chicago and had never done this in our hometown so thought this was the perfect time to learn more about our city. So glad we did. The reveal was epic! Must see. You won’t regret it. We plan to do more events in the future.
Member Pricing
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$33.25
per personWas $35.00(-5%)
up to 24 hours before the experience starts (local time)
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Chicago's Dark Side: Ghosts, Gangsters, and True Crime Tour
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