Chicago: Gangsters and Food Tasting Walking Tour

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Chicago, USA

Popular pick

Booked 5+ times last week!

2 hours (approx.)
Mobile ticket
Offered in: English

Overview

What's Included

Meals
Expert tour guide

Alcoholic Beverages
Gratuities

Meeting and Pickup

Meeting point

71 E Wacker Dr, Chicago, IL 60601, USA
Please meet your guide outside "Hoyt's Tavern" 15 minutes before the start time: 71 E Wacker Dr, Chicago, IL 60601, USA.

End point

822 N State St, Chicago, IL 60610, USA
Mister J's Hotdogs is where the tour will end

Itinerary

Harry Caray's Italian Steakhouse

30 minutes • Admission Ticket Free

Pizzeria Due

30 minutes • Admission Ticket Free

Mister J's

30 minutes • Admission Ticket Free

Additional Info

Confirmation will be received at time of booking
Wheelchair accessible
Stroller accessible
Service animals allowed
Near public transportation

Infant seats available
Most travelers can participate
Gluten free food options available at all 3 locations
Vegetarian/Vegan: Available at 1 of 3 stops (Pizza stop only).
This tour/activity will have a maximum of 25 travelers

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Cancellation Policy

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

Traveler Photos

Gallery picture 1 (from a traveler's review)

Gallery picture 2 (from a traveler's review)

Gallery picture 3 (from a traveler's review)

Gallery picture 4 (from a traveler's review)

Gallery picture 5 (from a traveler's review)

Reviews

4.7

based on 31 reviews

Total reviews and rating from Viator & Tripadvisor

We perform checks on reviews

Payton was Great!

Angela_S, Sep 2026

Had a great tour with the best guide full of gangster history and great food. Really enjoyed! Thanks Payton!

Definitely recommend

Delinda_B, Sep 2026

Our guide, Baylor was 5 stars Lots of Chicago gangster history Terrific personality Food was great It was sooo much fun

Fun but Incomplete

Megan_D, Aug 2026

Peyton was fun! She had great energy & loved the vibe but the stops & food did NOT reflect what we read & what was purchased. We did not get to try the Tavern Pizza even though it was listed & we did not visit the gangster mansion that used to be a brothel. The only reason I’m harping on this is because this experience was a tad expensive & it was explicitly listed as being part of the tour. So we are pretty disappointed on not getting those 2 listed things.

Hamsters and Food

Theresa_W, Aug 2026

The walk is short, the food was good and the stories interesting. We took lots of photos had a wonderful time!

A quick tour with some...

helen_b, Aug 2026

A quick tour with some fun facts about the mob influence in Chicago. In regards to the food you will sample 3 Chicago staples that were ok but could have been more authentic. Our tour guide was great and knowledgeable and very animated.

Fun introduction to Chicago

Cayla_m, Jul 2026

Talia was an awesome guide. I learned so much about Chicago history and the food here. 10/10 would recommend this tour for others.

Quick food tour!

Samantha_R, Jul 2026

This was a fun quick tour of a nice part of the city. The food we tried was really good. It was fun learning about gang violence. Would recommend if you want to get a cultural food experience. Payton did a great job and knew her stuff.