Chicago Tours
Chicago: Gangsters and Ghosts Walking Tour
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Chicago: Gangsters and Ghosts Walking Tour

By Chicago Gangsters and Ghosts Tours
Recommended by 94% of travellers
94% of reviewers gave this product a bubble rating of 4 or higher.
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Combine a Chicago history lesson with supernatural tales for an ideal day or evening activity. Go back in time on this gangsters and ghosts tour to hear about Chicago in the Roaring Twenties when speakeasies around The Loop attracted notorious bootleggers and gangsters including Al Capone. See former gangster hangouts and haunted places like Congress Hotel, Palmer House, and Death Alley, with lively commentary from your historian guide. Upgrade to experience the tour by minibus.
Lowest price guaranteeReserve now & pay laterFree cancellation

Ages 0-100, max of 20 per group
Duration: 2h
Start time: Check availability
Mobile ticket
Live guide: English
More

Highlights
  • Walking tour of Chicago with a ghost and gangster theme (minibus tour upgrade available)
  • Insightful commentary shared by the guide
  • Mixture of historical fact and ghost stories makes for a fun tour
  • Discover a side of Chicago that many other tours overlook

  • Walking tour of Chicago’s gangsters and ghost stories
  • Expert Guide
What's not included
  • Gratuities


Start:
  • 71 E Wacker Dr, Chicago, IL 60601, USA
    Walking tour meeting location: The tour meets outside of "Hoyt's Tavern", your guide will be waiting for you here!
End:
  • 520 S Michigan Ave, Chicago, IL 60605, USA

  • Not wheelchair accessible
  • Near public transportation
If you have questions about accessibility, we’d be happy to help. Just call the number below and reference the product code: 61552P8

  • Confirmation will be received at time of booking
  • Travellers should have a moderate physical fitness level
  • This experience requires good weather. If it’s cancelled due to poor weather, you’ll be offered a different date or a full refund
  • This tour/activity will have a maximum of 20 travellers

  • For a full refund, cancel at least 24 hours in advance of the start date of the experience.

If you have questions about this tour or need help making your booking, we’d be happy to help. Just call the number below and reference the product code: 61552P8

From
$59.93
per adult
Select date and travellers

Similar experiences

Itinerary
  • 71 E Wacker Dr, Chicago, IL 60601, USA
    Walking tour meeting location: The tour meets outside of "Hoyt's Tavern", your guide will be waiting for you here!
  • 1
  • 2
  • 3
  • 4
    Pass by
    Cloud Gate
  • 5
  • 6
  • 7
  • 520 S Michigan Ave, Chicago, IL 60605, USA
About the operator
Don’t take it from us – here’s what people have to say about this operator:
  • Chicago Gangsters and Ghosts Tours
    4,631
    Chicago, United States
    Joined in January 2018
  • Flyer03913251950
    0 contributions
    5.0 of 5 bubbles
    10/10
    Ty was an excellent guide, he told us in detail several stories about the city and also gave us excellent recommendations. Its a tour that is very worthwhile if you visit Chicago.
    Written 10 November 2024
  • Curiosity35740107977
    0 contributions
    5.0 of 5 bubbles
    Must do in Chicago
    Fantastic tour guide Baylor. 2 hour walking tour visiting 3 food places and learning lots of history. Recommend to anyone visiting Chicago
    Written 2 November 2024
  • SteveJ0910
    0 contributions
    5.0 of 5 bubbles
    Ghosts and gangsters and more ghosts..
    Part of Chicago's past are stories from its underbelly and those people both well known, and not, that are part of the city's history. Max did a great job shepherding us in and around the neighborhood spinning tales. Who's to tell whether they're true or not when you're talking about spirits doing and undoing as well as the turf wars of those trying to exert power. Enjoyed this very much!
    Written 31 October 2024
  • Nicole E
    0 contributions
    5.0 of 5 bubbles
    Great evening activity
    Allen was great! We thought we already knew a lot about Chicago history but we learned a lot more!! Definitely fun for the whole family and the bus was very comfortable with opportunities to get out and see things.
    Written 29 October 2024
  • L4410ELjaneta
    0 contributions
    5.0 of 5 bubbles
    Best walking tour and guide- Sophia
    Sophia was our guide and she was amazing. Lots of information, energy and very interesting. The walk was so much fun, I very well may do it with other family or friends.
    Written 29 October 2024
  • MarkJaycock
    0 contributions
    5.0 of 5 bubbles
    Wonderful Tour!
    What a great tour, first off, our guide Allan was wonderful, kind, friendly, informative, and fun. The tour was a couple hours of walking, highlighting some key locations in gangster history, and Allan was awesome about linking many of the locations together, and sharing the stories. Food was great, nice piece of steak, chicago pizza, and chicago dog, each of which were in neat locations with neat history. Would highly recommend this tour, well worth it and so much fun! Thanks Allan!
    Written 29 October 2024
  • JoshFlanders
    0 contributions
    5.0 of 5 bubbles
    Engaging and creepy tour of Chicago 100 years ago
    Karinna was a delightfully energetic and engaging tour guide of Chicago ghost and gangster stories. She led us to many wonderful stops including the best view of the city from the Planetarium, a hidden gangster tunnel under Harry Caray's, and the Alley of Death. Karinna captivated with creepy tales of ghosts, murderers, and disasters that lingered long after the tour was over. A great way to learn about Chicago!
    Written 27 October 2024
  • Peter P
    0 contributions
    5.0 of 5 bubbles
    This tour was excellent. Our tour guide Matthew Schlerf did a fantastic job. Thank you for a great tour.
    This tour was a very interesting tour of the city. Our tour guide Matthew Schlerf was excellent and did a great job of telling the stories of the city. We really enjoyed it.
    Written 24 October 2024
  • B7809IGjeremyw
    0 contributions
    5.0 of 5 bubbles
    Don’t miss out
    What a fun and amazing trip. Guide was energetic and very informative. Highly recommend.we did ours at 6 during the week a perfect time I think.
    Written 23 October 2024
  • Geonavy
    0 contributions
    5.0 of 5 bubbles
    Chicago Mobsters and Food Tour!
    Sarah did a wonderful job providing information on the history of the Irish vs Italian gang wars of Chicago. As for the food portion of the tour, we were surprised at how much we received. We thought we were only going to get a “taste” of several Chicago staples, however we received a decent steak sample at Harry Cary, a full slice of deep dish pizza at Pizzeria Duo and a complete Chicago dog at Jay’s. Definitely was worth it!
    Written 22 October 2024
  • X8490FNmichaeld
    0 contributions
    5.0 of 5 bubbles
    Great tour!
    Avery was amazing. I’ve lived in the Chicagoland area all my life and this was the first time I’ve heard some of the stories shared on this tour. Highly recommend taking this tour.
    Written 19 October 2024
  • jeannefE3020RC
    0 contributions
    5.0 of 5 bubbles
    Excellent experience
    Al was a great tour guide and very enthusiastic about Chicago and its history. The three food stops were delicious !! Highly recommend this food tour.
    Written 19 October 2024
  • Paradise47541335218
    0 contributions
    5.0 of 5 bubbles
    Great Host
    Great host. Leant a lot about gangs in Chicago in 20s..Alan was fun and knowledgeable . The food at the steakhouse and Pizza due was really good
    Written 15 October 2024
  • mimiw519
    0 contributions
    5.0 of 5 bubbles
    Great food and history combo!
    What a great combination of seeing historical sites and eating amazing food! Our tour guide was knowledgeable and easy to talk with during the tour. We are still talking about it, days later!
    Written 14 October 2024
  • Lisa_David_2011
    0 contributions
    5.0 of 5 bubbles
    Loved this mob and ghost tour!
    Alan is such a great storyteller! We enjoyed the tour. The bus was very comfortable and the stops really brought the stories to life!
    Written 13 October 2024
See all 4,631 reviews
These reviews are the subjective opinions of Tripadvisor members and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

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5.0
5.0 of 5 bubbles3,934 reviews
Excellent
3,491
Very good
231
Average
117
Poor
41
Terrible
54

ChiGal
Chicago, IL22 contributions
5.0 of 5 bubbles
Oct 2020
Spent Halloween night on this walking tour with Olivia as our guide, who did an awesome job telling the tragic and spooky tales and describing Chicago's gangster past. The 1.5 mile walk in Chicago Loop at night afforded views of the city lights. I highly recommend this as a unique and fun activity still available to us during this time when many activities are not available.
Written 2 November 2020
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

psuf
Atlanta, GA16 contributions
5.0 of 5 bubbles
Our friendly guide Olivia was quite passionate about the stories, good narrator, and knowledgeable. My wife and I enjoyed the early afternoon tour, about 1.5 hrs of leisurely walking pace and frequent stops for a story or two. Chicago has plenty, and each adds color to some of the city landmarks and landscapes. Our group had about 10 people, easy to stay together and hear our guide even in the hustle of downtown.

Also kudos to a small business to keep operating, safely and responsibly, during these crazy COVID-19 times. They deserve our patronage and recommendations.
Written 16 October 2020
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

Harrison
Taipei, Taiwan1 contribution
5.0 of 5 bubbles
Aug 2021
Not a Chicago native but have been to Chicago multiple times. While I know a little bit about the city, the tour introduced us to Chicago's rich history and our tour guide, Caleb, kept us entertained throughout the way. Girlfriend was hesitant to go at first because we knew it was going to be a lot of walking, but once the tour started, she was enthralled by our tour guide as he took us around the loop experiencing different parts of the city. We also got several chances to take small rests while taking photos and a larger interlude at the Palmer House Hilton Hotel where we got to enjoy its famous ceiling even though the girlfriend wasn't quite as impressed. All in all a very worth-it experience at only $27 per person for 2 hours of an intriguing enthralling tour.
Written 23 August 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

Katie V
1 contribution
5.0 of 5 bubbles
Aug 2020
I took the tour during COVID _and_ on an unexpectedly rainy night. Not only did Lauren roll with it like a pro, she kept the group laughing and intrigued with her great storytelling the entire time. The tour itself highlights some great landmarks and historical points I otherwise wouldn't have known. From someone interested in history, architecture, and great stories, this tour was an A+ experience.
Written 10 August 2020
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

JJ Miran
1 contribution
5.0 of 5 bubbles
Aug 2020
I took the old axiom that one should be a tourist in their own town and I booked this guided tour, hoping that it would reveal unknown layers to a city I've explored up and down across my life. I am happy to report that the tour suspended my view of the city and I was able to see it in a new light, as if for the first time, even discovering things I had overlooked in the many years I've walked its streets. One has to almost play the tourist to appreciate all the heritage, artistry, culture, and significant historical events layered into the gleaming towers and peering statues. Led by our gregarious, comical, and knowledgeable guide, Dylan, this tour was an illuminating and enjoyable experience. My view of the city will never be the same again and I value my newfound insights. I will recommend it to friends and family.
Written 23 August 2020
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

Archie
Glenmoore, PA7,745 contributions
4.0 of 5 bubbles
We booked this tour online about $40 per person for 4 pm. We were requested to meet 30 min before at a hotel. We were waiting on the wrong side and walked over. There were some guides around. We checked in with one of them. The first guide felt like a school teacher and so when we were asked to swap out to another guide we took the opportunity. We went with Kai, she was informative and funny. We walked around, took opportunities for photo shots. We learnt about Al Capone, ghosts in the river, serial killer and infamous hotels around the area. We stopped at Palmer hotel to enjoy the decor. It was interesting. Definitely carry water, wear good shoes, sunglasses.
Written 30 May 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

Passenger23331
26 contributions
4.0 of 5 bubbles
Oct 2022
Our tour guide, Lizzy , was very knowledgeable and described the people and events in an engaging and entertaining way that kept my attention and interest. I enjoyed learning more about this time period in Chicago's history; however, I would have liked more emphasis on the mob history and seeing more of the buildings and places that mob activity took place, as that was my main interest and reason for taking the tour, and less "ghosts". I do know that time is limited and it is hard to get everything in. All in all I did enjoy the Gangsters and Ghosts tour- the tour was well organized, Lizzy is a great guide, I learned some new things about the mobs in Chicago, and I enjoyed the ghost stories. One frustration was that when I booked the tickets there was no mention of different rates for different ages. Only one rate was shown. Even though we had a toddler with us I ended up paying the same for his ticket as no other options were shown on the "booking" site. But on my confirmation email it said I had purchased all adult tickets, and i later learned that children under 6 were free. So we ended up paying $35 extra for our tour.
Written 2 November 2022
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

Benjamin S
1 contribution
5.0 of 5 bubbles
Dec 2019
We definitely recommend going on this tour. It is a great way to learn about the amazing gangster history of the city - also worth mentioning the great ghost stories from our guide Connar. The only negative thing is, that we had a 20 minutes toilet and drink break inside the two hour trip. This was not necessary at all and we would prefer using the time on more fantastic stories!
Written 11 January 2020
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

Reid
3 contributions
5.0 of 5 bubbles
Aug 2021
We had a fantastic time on our tour! Kai, our tour guide, was incredibly knowledgable and charismatic. Not only did she know her history up and down, she was able to maximize our tour with pieces of history and fun facts even between "stop zones" where we got the real meat of the tour. It was an incredibly unique and fun way to see downtown Chicago, and I would recommend this tour to anyone who wants to know more about the gangster (and ghost!) history of Chicago.
Written 25 August 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

MD
1 contribution
5.0 of 5 bubbles
May 2021
I have lived in Chicago for four years now. I just recently went on this tour when a friend was visiting and I thought that Lizzy did an amazing job. She kept the energy level high the whole time, and was able to teach me so much about the city that I never knew. I would 100% recommend this to anybody who would like a new perspective or anyone who would like to take an immersive tour of the city. Thank you so much.
Written 9 May 2021
This review is the subjective opinion of a Tripadvisor member and not of Tripadvisor LLC. Tripadvisor performs checks on reviews as part of our industry-leading trust & safety standards. Read our transparency report to learn more.

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