Chicago Gangster and Food Walking Tour
Chicago, USA
Chicago Gangster and Food Walking Tour
Recommended by 96% of travelers
Badge of Excellence
Chicago, USA
- 2 hours (approx.)
- Mobile ticket
- Offered in: English
Overview
This tour stands out by pairing Chicago Prohibition era history with the city’s most famous foods—a rare combination. Tour the fashionable River North neighborhood while sampling local specialties at historic “gangster” hideouts: think of a steakhouse with a secret tunnel, and deep dish pizza in an old “gangster’s” mansion.
- A small-group “gangster” and food walking tour in Chicago
- Visit a historic steakhouse, deep-dish pizza spot, and more
- Travel with a guide: Learn about Chicago’s “gangster” history
- Small group ensures more personalized attention from your guide
What's Included
Meeting and Pickup
Itinerary
Additional Info
Cancellation Policy
You can cancel up to 24 hours in advance of the experience for a full refund.
Traveler Photos
Reviews
4.8
based on 474 reviews
Chantal_B, Dec 2024
Give Ty a big Bonus!! He was awesome! Very informative, knew the subject, added his own twist.
Chantal and Jill.
Debbie_P, Dec 2024
Had a great tour with Baylor. We were the only ones on this tour so had all of her knowledge directed at us only. Interesting tour and Baylor was very chatty and friendly!
Jessica_G, Dec 2024
My husband booked a last minute tour and our guide Avery was great! He was so knowledgeable about the history of Chicago and we learned so much. It was so nice meeting new people and exploring a little! I highly reccomend this tour. The food we sampled was also excellent!
Suzanne_H, Dec 2024
Avery was awesome, he went above and beyond
Great tour, wonderful tour guide
We all had a great time
Loved it
Sue Hockman
Valerie_M, Dec 2024
Taka was great! Knowledgeable and kept us moving with lots of super info! Delicious food too— definitely could make it a lunch or early dinner!
Jason_C, Dec 2024
Taka was an amazing tour guide! Very knowledgeable and friendly. We all had a great time and we would all highly recommend!
Regina_L, Nov 2024
Taka is a great story teller! We throughly enjoyed our time exploring the city with a fun gangster twist and food. Loved the Chicago Hot Dog the best!
Cristine_L, Nov 2024
Loved learning the history of the Irish North and Italian South gangs and the clever ways they stuck it to each other. Pizza was phenomenal, and Harry Carrys basement was so interesting with the tunnels!
Rachel_W, Nov 2024
We booked this tour for a client and they absolutely loved it! They could not say enough good things about their tour guide, Avery. He was so knowledgeable about the city's history, the architecture, and they said that he was the reason they had such a great time. He kept them entertained, and because it was a small group of 4 people, he got to know them and made the experience much more personal than if they were to have been in a big group. They could not recommend him enough!!
Tera_S, Nov 2024
Had a wonderful tour with Taka! She took the time to answer our questions and gave an informative tour!
Steve_K, Nov 2024
Harry karry's steak and basement vault.
Tour guide was very good, but the event was priced too high.
JASON_C, Nov 2024
Alan was very knowledgeable about the history of Chicago and how the gangsters & mafia were part of the early history. A nice bonus was the delicious eats along the way! Thanks Alan for a great tour & experience!
Melody_M, Nov 2024
Avery was a great tour guide. Was flexible and very knowledgeable and personable. Was a very fun tour learning about the Chicago Mobs and eating great food.
Amanda_B, Nov 2024
The food tour was well thought and fun! Our guide, Baylor, was super nice and made our experience memorable!
ktdid04, Nov 2024
It was informative, filling, and fun! Baylor was our guide and she was knowledgeable and friendly. It was the perfect length of time to get in some good food and gangster history.
Shane_O, Oct 2024
Excellent tour, Taka was a fab guide, would highly recommend taking it. Interesting history combined with local food
Mark_J, Oct 2024
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!
Kathy_R, Oct 2024
Sarah our guide was funny and entertaining. Walk was easy. Stories were fun and interesting. Weather was fantastic. Food was ok
Nathan_C, Oct 2024
Sarah was a great tour guide. The food was awesome except the steak portion was underwhelming. Fun activity.
Christine_S, Oct 2024
Sarah was a fantastic guide! Very knowledgeable and a great story teller. Food and stories were great, would absolutely recommend!
Roberta_B, Oct 2024
The gangster stories were interesting, the steak was tasty, but minimal, the pizza was really bland, the hot dog was tasty with all the dondiments.
Kodi_M, Oct 2024
Watching my boys try new foods. Very much enjoyed the gangster story telling- Alan did a nice job! I would recommend this tour
Brianne_P, Oct 2024
We had a great time doing the Gangster Food Walking tour with Alan! He was super entertaining and full of knowledge and the food was amazing! My 3 kids (ages 6,9,9) loves it!
Megan_M, Oct 2024
Great experience and afternoon. Great food and info. Sarah was a great host and couldn’t ask for a better afternoon
Nikki_M, Oct 2024
Baylor was a fantastic guide. She was engaging and kept up with our large group. The food on the tour was tasty and held us over until dinner. Baylor also gave us spot-on recommendations for dinner and drinks near Second City.
John_C, Oct 2024
We had an enjoyable time. Karinna was awesome and the food was good. Info on gangsters was interesting
Cesar_R, Oct 2024
The tour guide was nice, but this was extremely underwhelming. The last stop or we have the loaded hotdog, most of us did not enjoy and could easily be replaced by visiting Mr. beef not too far from that location.
Crystal_R, Oct 2024
Sarah was an incredible guide. We had such a great time learning about the history of Chicago and its Gangster underground. The food was delicious and she did a great job keeping us all engaged.
Marshall_E, Oct 2024
Avery was an awesome tour guide. We learned a lot about the history of Chicago and the food was great. Don’t hesitate to book this tour. You won’t regret it.
Dalena_R, Oct 2024
Avery was a great tour guide very knowledgeable! Food was good we really suggest this tour. The pizza was my favorite, it was so filling!
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