Chicago Mobs and Haunts Walking Tour
Recommended by 94% of travelers
Badge of Excellence
Chicago, USA
- 1 hour 30 minutes to 2 hours (approx.)
- Mobile ticket
- Offered in: English
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Overview
Lovers of history, true crime, and haunted mysteries rejoice—skip the generic sightseeing tours and learn about Chicago’s dark underbelly with this mob history tour. Follow your guide through historic streets and alleys from Grant Park to the “Alley of Death”—also known as West Couch Place—as you learn about the city’s gritty mobsters, doomed ghosts, crime, and vice.
- A mob history walking tour through central Chicago
- Learn about the city’s mobsters, ghosts, and all-around vice
- Skip generic sightseeing tour for something edgier
- Visit the Chicago Loop, Buckingham Fountain, and more
What's Included
- Professional, entertaining, local guide
- Gratuities
Meeting and Pickup
Meeting point
- The Congress Plaza Hotel & Convention Center520 S Michigan Ave, Chicago, IL 60605, USA
Meet your tour guide in front of the Congress Plaza Hotel & Convention Center. The hotel address is 520 S. Michigan Ave, Chicago, IL 60605. Your guide will be wearing an orange hat that says “ExperienceFirst”.
End point
- North Michigan Avenue & East Wacker DriveN Michigan Ave & E Wacker Dr, Chicago, IL 60601, USA
This tour ends near N. Michigan Avenue and Wacker Drive.
Itinerary
1
The Congress Plaza Hotel & Convention Center
15 minutes • Admission Ticket Free
2
Exchequer Restaurant & Pub
15 minutes • Admission Ticket Free
3
Chicago Loop
15 minutes • Admission Ticket Free
4
West Couch Place
15 minutes • Admission Ticket Free
Additional Info
- Confirmation will be received at time of booking
- Not wheelchair accessible
- Service animals allowed
- Near public transportation
- Infants must sit on laps
- Not recommended for travelers with back problems
- Not recommended for pregnant travelers
- No heart problems or other serious medical conditions
- Most travelers can participate
- This tour/activity will have a maximum of 20 travelers
Supplied by
Cancellation Policy
You can cancel up to 24 hours in advance of the experience for a full refund.
Traveler Photos
Reviews
4.7
based on 403 reviews
Lynn_H, Apr 2026
Lark was a fantastic tour guide- knowledgeable, enthusiastic, and genuinely engaging. Our group was small, which made the experience feel personal and easy to connect with. We were able to ask plenty of questions, and Lark handled each one with ease and insight. His depth of knowledge about Chicago's history was especially impressive. He shared fascinating stories and facts that we never would have discovered on our own. The places we visited were rich with historical significance, and his storytelling made each stop come alive. We absolutely recommend Lark to anyone looking for a fun and informative tour of the city.
Sven_Z, Mar 2026
Bryson is a great guide who enthusiastically engaged in riveting stories about Chicago. Living in Chicagoland for 20+ years, this experience is not only for tourists and visitors - you learn about the hidden sides of Chicago. I am somewhat glad that I didn't live in the 1920's Chicago.
Debbie_L, Feb 2026
Very informative and lots of fun. Ben did a great job explaining everything and keeping everyone engaged
Gustavo_L, Feb 2026
Great way to know the city. For first timers this is the tour to take and walk the city of Chicago and it's misteries
Rob_M, Feb 2026
Lark was a very knowledgeable tour guide! We enjoyed all the Chicago fun facts he shared. We’ll definitely book another tour.
Dennis_W, Feb 2026
If in winter months dress warm!
You will learn of Chicago history from a talented story teller.
Our tour guide, Mitchell, was very accommodating.
Christa_C, Jan 2026
Mitch was a terrific tour guide. Great insider stories about ghosts...and more importantly...the mob within the historical context of Chicago. Learned much and also got to see some of the more interesting architectural and historic Chicago landmarks.
Janelle_D, Dec 2025
Unfortunately was not what I expected. Lots of talking & walking. No actual indoor sight visits just from afar.
Guide spoke too fast.
Response from Host, Jan 2026
Hi Janelle,
Thanks for reaching out. As it states in the title, this is a walking tour so there is a fair amount of walking. Unfortunately, we are not allowed to enter any of the buildings on the tour as they are private buildings. We feel our guides do their best to paint vivid pictures of the stories that are told on this tour. We appreciate your feedback and will definitely take what you said under consideration.
Thank you.
Carla_T, Dec 2025
Great historical perspective on origins of Chicago . Lark was professional and entertaining and showed us the core of the city.
Mytalya_T, Nov 2025
I thought it would’ve been more interesting not enough exploring actual spots the mobsters frequent.
Response from Host, Nov 2025
Hi,
Thank you for taking the time to share your feedback with us. We’re sorry to hear the tour didn’t meet your expectations, especially in terms of exploring more of the locations associated with the mobsters.
Your comments help us improve our routes and storytelling, and we’ll review this internally to see how we can enhance the experience for future guests.
Thank you again for your input, and we hope to have the chance to give you a more engaging experience next time.
Adrian_N, Nov 2025
It’s just a great tour, takes you around the city hotspots of where things happened in history, the tour guide was very knowledgable about the city
Stacey_S, Nov 2025
Ben was exceptional, energetic and full of knowledge. I loved listening to him talk. Had a wonderful time.
AmyJo_H, Nov 2025
Filled with history facts about Chicago as well as mysterious lore! Great story telling and wonderful to learn some Chicago history! Lark was an awesome guide!
Melissa_C, Nov 2025
Great tour. Bryson was an amazing guide and storyteller. Despite the cold, it was a fun way to see the city.
Eric_M, Oct 2025
Ben was extremely knowledgeable and funny. We definitely it. We did the 4:00 one and it got a little cold when the sun went down. We loved the Al Capone history
debbiedoherty62, Oct 2025
Very interesting tour and the guide was very helpful & adapted to our specific interests.
Highly recommend.
Terrance_T, Oct 2025
had Alyssa. She was a great guide. Very knowledgeable and excited to share the information. She was very personable as well. Tour stuck to the theme very well and there were plenty of interesting facts that I was never aware of. The history of Chicago is very rich. Would 100% recommend to other tourists or people who love history. Plenty of different people in my tour group, from couples to people with kids. Alyssa was welcoming to all. Ran into sooo many problems on my trip in Chicago, this tour was by far the highlight of my trip. I will definitely be doing something similar whenever I come back.
Blakeley_M, Oct 2025
This was a very informative tour led by Alyssa, who is very knowledgeable about all things Chicago!!
Elizabeth_J, Oct 2025
Be prepared to walk and learn. This was a good tour although I wished we had a few more indoor spots only because it was hard to hear our guide sometimes due to traffic. But the historical stories were really interesting. Alyssa was engaging and knowledgeable. Kept the stories entertaining.
Sandra_D, Oct 2025
Knowledgeable guide, relevant topics covered made an enjoyable night out for locals and tourists alike
Eleanore_F, Sep 2025
Very interesting and Bryson was great!
The walk was fun and hearing stories at the location was perfect.
kevin_D, Sep 2025
Guide tried hard but he can only play with the cards he is dealt. There would appear to be little left of 20s Chicago so the gangster part was pretty brief compared to what I hoped for.
No mention of Dion O’Bannion or John Dillinger which I felt was poor.
The ghost stories were interesting up to a point but I would struggle to recommend this tour unless my friends wanted tales of disaster and death
Derek_J, Sep 2025
Tyson was a fantastic guide! Very knowledgeable with a side of humor! The tour was well worth it! Our family continues to talk about what we learned!
Karin_D, Sep 2025
Very enjoyable and informative tour. Bryson did a really good job. We particularly enjoyed the story at the Nederlander theatre.
Julie_R, Sep 2025
This tour doesn’t match the description. The content was informative but it seemed fragmented. You had to make your own connections to the theme. Left with unanswered questions.
Response from Host, Sep 2025
Thank you for your feedback. We're glad you found the content informative, and we’ll work on improving the flow and clarity to better align with expectations. Your comments are valuable and will help us improve the structure and clarity of future tours.
Joseph_I, Sep 2025
Kevin was friendly and did a great job. Very knowledgeable and full of interesting stories. I would recommend this tour.
Roxanne_S, Sep 2025
Great experience! Our guide, Justin, was very entertaining and knowledgeable. The walking was not extensive.
Christine_C, Aug 2025
The tour guide was excellent. We really appreciated that he spoke up since it was a big group. I would give 5 stars for him. One hour of the tour was around the subway tracks and he had to keep stopping for them to pass. This made the tour awful. It would of been a nice tour if it wasn't for that. I think the tour guides name was Mitchell.
Response from Host, Aug 2025
Thank you for your feedback! We're so glad to hear you enjoyed Mitchell’s guiding, he’ll be thrilled to know he made a great impression.
We’re sorry the subway noise affected your experience, and we appreciate you pointing it out. We’ll definitely take this into account as we look to improve the tour route.
Chris_B, Aug 2025
Nice history of the mobster’s era in Chicago with haunted history mixed in. Right in the middle of the south side of the river walk
Shana_R, Aug 2025
It was a great tour full of history and crazy stories about notorious mobsters of Chicago. Lark did a wonderful job!
From $34.00
per personup to 24 hours before the experience starts (local time)
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Chicago Mobs and Haunts Walking Tour
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