Gangsters and Ghosts Tour in Chicago

Badge of ExcellenceChicago, United States

From $35.00

Select Date and Travelers

Free cancellation
Up to 24 hours in advance.
  • 2 hours (approx.)
  • 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 20’s, 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 dark past of one of Chicago’s most frequented areas, 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
  • Gratuities

Meeting And Pickup

Meeting point

  • 71 E Wacker Dr
    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
    520 S Michigan Ave, Chicago, IL 60605, USA

What To Expect

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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Traveler Tips

The tour is a walking one so be prepared to be on your feet and keep an eye on the weather as well.
It is a lot of walking be prepared wear comfortable clothes and shoes.
3,670 reviews
Total review count and overall rating based on Viator and Tripadvisor reviews
Reviews by Viator travelers.
Showing 1-10 of 3,670 reviews
Chicago - Gangster Tour
Dalibor_S, Mar 2023
Great tour as well as the tourguide - Sarah. Very knowledgeable and expirienced and a very interesting story ... Will definitely book the tour or a similar one ... Thansk again!
Awesome Experience
Ryan_W, Mar 2023
Ty, our tour guide, was a fantastic story teller. He provided extremely interesting information on this history of Chicago and major events involving ghosts, tragedies and gang activity in the 1920s. Would highly recommend the tour and especially Ty as a guide.
arthur_h, Mar 2023
The stories were very interesting and it kept you ingrained during the tour the tour guide was very knowledgeable
Fun and informative walking tour
Juliana_P, Mar 2023
The tour guide, Andre, was very knowledgeable. We were able to walk around the city and see famous places where gangsters and ghost roam the city. The tour ended 30 minutes early. I was under the impression that it would be the full 2 hours. I enjoyed myself, but I would have liked to have seen more. We focused on Scarface and his Era. It would have been interesting to also learn about John Dillinger. Otherwise, it was very informative.
Rudy_M, Mar 2023
All of the unfortunate events in addition to Al Capone’s career. Chicago has a painful as well as a violent, gangster history.
Baylor was a great tour...
David_L, Mar 2023
Baylor was a great tour guide. Lots of fun, very informative, and scary at the same time. It was very interesting walking through death alley and I think there were ghosts there!
Worth the value
Michelle_M, Mar 2023
Baylor was an amazing and informative guide! Stories and history were great. Walk was manageable and the group size was good. It was more Mobster than Ghost tour but that was fine with me.
Learn how to be a mafioso in the 1920's manual guide!
Jorge_L, Mar 2023
Learning about H H. Holmes an Capone, and stories of ghost in the congress hotel. Ty was well-documented and he told us a thorough story of Capone, from his early beggining in NY. He was a charismatic tourguide, humorous and engaging with his audience. Despite the cold, I enjoyed Ty's stories like a kid. Will definetely recommend him to my friends coming over to visit!
Get To Know The Chicago Loop
Stuart_B, Mar 2023
There’s no better way to spend a cold and cloudy evening than walking around the Loop with Ty. We’re long-time Chicago residents but Ty was still able to make us say “huh, I didn’t know that” several times throughout our tour. This tour is engrossing and engaging and great value for money. Highly recommended.
Naomi_P, Mar 2023
Baylor was incredible tour guide! Such a fun experience with some cool stories from Chicago’s vast history. 10/10 would recommend.
Gangsters and ghost tour
Lizzy_G, Mar 2023
Rosa was a knowledgeable tour guide and a captivating story teller. We learned a lot about the dark history of Chicago. A fun way to explore the city!
I had Conner as a guide....
Sean_P, Mar 2023
I had Conner as a guide. I had a great time walking around the city and hearing stories of the area.
Great experience!
Kevin_A, Mar 2023
Connor was a phenomenal guide. Extremely engaging, entertaining, and enthusiastic. He was very knowledgeable and proud of the City of Chicago. Thank you Connor!
Gangsters and Ghosts Tour
Dianna_H, Mar 2023
Such a fun and informative tour! Baylor was an excellent tour guide and really knew her Chicago history. I definitely learned a lot~
Ty our guide was very...
Melissa_B, Mar 2023
Ty our guide was very good at telling the gangster story and interesting facts about Chicago. I would recommend this tour
Well worth activity!
SharonRenee_K, Mar 2023
Great experience and the tour guide was awesome (I think his name was Brayden). I would definitely recommend.
Meredeth_B, Mar 2023
The guide was friendly and entertaining made the tour a lot of fun, very interesting and kept track of all of his flock
James_H, Mar 2023
The palmer house was just beautiful. The rest of the tour was also interesting, particularly the death alley part.
Fun and interesting Chicago experience
Colleen_W, Mar 2023
Our tour guide, Andre was great. So well-informed and personable. He checked in with us prior and the meet up was easy. Saw some great sights that we otherwise would have missed and definitely learned some cool facts about the history of the Chicago gang wars. Fun and different way to experience "the loop".
Great tie in of sites and stories
Elbert_H, Mar 2023
we enjoyed seeing the sites of Loop area and the stories gave it some depth. We had a fun and knowledgeable guide, Braeden.