Chicago: Gangsters and Ghosts Walking Tour

Badge of ExcellenceChicago, USA
Gangsters and Ghosts Tour in Chicago
  • 2 hours
  • Mobile ticket
  • Offered in: English


Experience a colorful side of Chicago history with this gangsters and ghosts tour. With a historian as your guide, you’ll step back to the Roaring Twenties, when the Chicago Loop was a hub for bootleggers, speakeasies, and gangsters like the infamous Al Capone. Visit onetime gangster hangouts and haunted sites like the Palmer House, Congress Hotel, and Death Alley.
  • Experience the Windy City's dark past, right in the Loop
  • Historian guide with expert knowledge of city history
  • Learn the true tales behind Chicago’s gangster past
  • Listen to ghost stories and visit spooky haunted sites

What's Included

  • Walking tour of Chicago’s gangsters and ghost stories
  • Expert Guide
  • Gratuities

Meeting and Pickup

Meeting point

  • 71 E Wacker Dr, Chicago, IL 60601, USA

    The tour meets outside under the "Hoyt's" sign in front of Hoyt's Restaurant at The Wyndham Grand Riverfront Hotel.

End point

  • 520 S Michigan Ave, Chicago, IL 60605, USA

What To Expect

Start this Chicago gangsters and ghosts tour by meeting your historian guide and group at the designated meeting spot in the city. Start by exploring the Chicago Loop with your guide as you hear stories of mobsters, gangsters, ghosts, and more spooky tales.

Follow your guide to see sights such as Millennium Park, Downtown’s Palmer House hotel, the Riverwalk, and many other major landmarks as well as lesser-known corners. Your guide shows you places that were old gangster hangouts, where ghosts have been reported, and even where Al Capone set up his own personal headquarters.

After walking the city with your guide, say goodbye near the Congress Plaza Hotel and Convention Center.

The Loop

1 hour Admission Ticket Free

Millennium Park

15 minutesAdmission Ticket Free

Palmer House Hilton Historic Lobby

20 minutesAdmission Ticket Free

Chicago Riverwalk

15 minutesAdmission Ticket Free

Cloud Gate (Pass By)

The Chicago Theatre

15 minutesAdmission Ticket Free

The Congress Plaza Hotel & Convention Center

15 minutesAdmission Ticket Free

Additional Info

  • Confirmation will be received at time of booking
  • Not wheelchair accessible
  • Near public transportation
  • Travelers should have a moderate physical fitness level
  • This tour/activity will have a maximum of 20 travelers
Operated by Chicago Tours

Cancellation Policy

You can cancel up to 24 hours in advance of the experience for a full refund.

  • For a full refund, you must cancel at least 24 hours before the experience’s start time.
  • If you cancel less than 24 hours before the experience’s start time, the amount you paid will not be refunded.
  • Any changes made less than 24 hours before the experience’s start time will not be accepted.
  • Cut-off times are based on the experience’s local time.
  • This experience requires good weather. If it’s canceled due to poor weather, you’ll be offered a different date or a full refund.

Traveler Photos

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5,541 reviews
Total review count and overall rating based on Viator and Tripadvisor reviews
Reviews by Viator travelers.
Showing 1-10 of 5,541 reviews
Avery was great! So much...
Robert_S, Apr 2024
Avery was great! So much fun. He was knowledge, enthusiastic and very funny. Would definitely recommend any tour he gives.
8pm tour
Amy_B, Apr 2024
We had so much fun. Thank you Avery for being such an enthusiastic storyteller! We learned a lot & would check out other tours
"Five-Star Experience with Chicago Gangsters and Ghosts Walking Tour led by Baylor!
Ruriko_Y, Apr 2024
Attending the Chicago Gangsters and Ghosts Walking Tour with Baylor was an unforgettable experience! From the moment the tour began, Baylor's passion for the city's history and storytelling prowess shone through, captivating the entire group. The tour provided fascinating insights into Chicago's notorious past, from the era of gangsters like Al Capone to tales of mysterious hauntings and paranormal activity. Baylor's knowledge and enthusiasm brought each stop along the tour to life, making it both educational and entertaining. Exploring the city streets under the cover of night added an extra layer of intrigue to the experience. From iconic landmarks to hidden alleyways, every corner revealed new secrets and stories from Chicago's past. Baylor's engaging narration, combined with her ability to engage with the group, made the tour a highlight of my visit to Chicago. I highly recommend the Chicago Gangsters and Ghosts Walking Tour to anyone interested in delving into the city's rich history and darker side. Five stars all the way!" 🌃👻
Interesting stories.
Erin_P, Apr 2024
Avery was a great tour guide. Gave great stories and history of the area. Great solo or with friends.
Worth it
Tyler_B, Apr 2024
Wasnt sure what to expect but ended up learning so much about Chicago history and archetecture. Avery had such good energy and explained everything so well.
Interesting way to see the city
keriane_f, Apr 2024
I had a friend come into town and as a recent transplant my self we thought this would be a fun way to explore the city. Our guide Sarah was great. She is very knowledgeable about the area ( Actual Native Chicagoan), and somehow found a way to inject humor into a tour that many times talks about some grisly events. Definitely doit, even better if you have a sunny day like we did.
Walking Tour
Dara_F, Apr 2024
Interesting stories. Tour guide Grant was very helpful. Would recommend and good value for money. 2 hours in total to complete the tour.
Highly recommend!
Nick_S, Apr 2024
Baylor had great energy and knowledge! Fascinating site stops and facts. Excellent pacing. Would highly recommend!!
Great tour
Kadi_P, Apr 2024
Ty was an excellent guide. He was funny, engaging, and knew how to give the tour "space" so we could ask questions, take a breather, etc. Highly recommended!
An absolutely amazing experience!
Melissa_S, Apr 2024
Ty was very informative and friendly. They knew several random facts as well as passed on the gangsters and ghosts tales we were all craving. Ty also made a point of interacting personally in some way with each group on the tour which was very sincere and kind. Ty also had great jokes that they easily slipped in around the tales to break up the transitions between locations but also offer a teaser about future parts of the tour. I had an amazing time, and honestly I expected it to be like most walking tours: following some “guide” around as they parrot trained facts and phrases while actively avoiding conversation or extra details just trying to get through the day. This felt more like a group of friends walking the area, joking around and seeing the sights while learning interesting facts that interest all of us along the way. I absolutely will be booking again when I return in a few weeks with my other sister and friends as I’m certain it will be just as entertaining and fun. Please tell Ty how they made the end of our trip an absolute delight and finished it on a very high note.
Gangster/Cappone Tour
MaryAnn_K, Apr 2024
Tour was great but leaned heavily on the Cappone story. It was very light on ghosts. Great tour though.
Great trip, very glad we did it.
Marlin_W, Apr 2024
Excellent trip and wonderful guide in Takka. Not alot of real "ghost stuff", but the information and Capone stuff was excellent. We would do it again.
Amazing experience!
Lynne_S, Apr 2024
Ty was an amazing tour guide. He was funny and very informative about the mob and ghosts in the area. We would all recommend this tour to others!
Sarah rocks!
Amanda_H, Apr 2024
Sarah was amazing!!! She was well done, funny, projected her voice over the loud city! And was very knowledgeable!
A Must Do
Suzette_M, Apr 2024
This was my second time on this tour. Even though my last tour was amazing, I learned more history with our guide, Taka. She is amazing at projecting her voice. She speaks clearly and loudly which is key to any tour. Her directions are precise and she handled our group impeccably. She was funny, friendly and very professional. On top of all that, she knows her stuff. She explained the history in an entertaining manner. The tour flew by, and I loved it.
Hope you get Sarah as your tour guide. She's outstanding at te
Brian_S, Apr 2024
Sarah really brought the past gangster aspect of Chicago and ghost stories to life. She really knows the topic and it's obvious that she enjoys the work.
Great tour!!
Lorraine_C, Apr 2024
This was an amazing tour! We leaned so much about Chicago. This was my first time visiting. Thank you.
Al Capone and ghosts
kelsey_g, Apr 2024
Sarah was amazing! Very knowledgeable, friendly, and funny! Definitely recommend as a tour guide!!!!
Chicago ghosts and gangsters walking tour
Donita_C, Apr 2024
Palmer hotel was an amazing place for a break and the history there! Wow!! Loved taking pictures inside the lobby.
Highly recommend 10/10!
Amy_H, Apr 2024
Taka was great. Very informative, enthusiastic! This was a great tour, especially for someone who wants to know some fun facts about Chicago history!

From $35.00

up to 24 hours before the experience starts (local time)

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