M
GANGSTERSwalk
Overall food experience was 10/10 portions were not too fulfilling. Intense history but well enough for kids. And walking was not an issue at all.
Chicago: Gangsters and Food Tasting Walking Tour
+36 photos
At a glance
- Duration
- 2 hours
- Price from
- $80 / person
- Rating
- 4.7 / 5 · 30 reviews
- Languages
- EN
- Group
- Small group, up to 25
- Cancellation
- Free cancellation
- Meeting point
- Please meet your guide outside "Hoyt's Tavern" 15 minutes before the start time: 71 E Wacker Dr, Chicago, IL 60601, USA.
- Confirmation
- Instant
Prices checked on Sep 11, 2026Things to do in Chicago
Description
Taste some of Chicago's most iconic foods while walking through one of the Prohibition Era’s most fashionable and notorious neighborhoods. Learn about Chicago's world-famous cuisine and the gangsters who ate it all in one special unique tour! Sample two types of pizza - Chicago’s deep dish and historic tavern-style – as well as prime steak and the world famous “Chicago hot dog" all while treading the streets of Capone’s closest friends and dreaded enemies. Highlights include a visit to an old tunnel used by prohibition gangsters in the basement of one of the establishments; a mansion once used a a brothel for gangsters; the Cathedral where gangsters were gunned down by Capone’s men; and a restaurant owned by the man who brought down what was left of the Chicago mafia in the early 2000’s. Gluten-Free: Available at all 3 food stops (shared oven/prep spaces used). Vegetarian / Vegan: Available at 1 of 3 stops (Pizza stop only). Please notify us in advance of any dietary needs!
Tour Options
Itinerary
Step into the historic Harry Caray's Italian Steakhouse on West Kinzie Street—a building famously tied to notorious mob boss Frank Nitti. Savor a delicious, perfectly prepared steak tasting while your guide shares captivating tales of Chicago's rich culinary and gangster history. Meat options can be made gluten-free
Stop at the famous Pizzeria Due on North Wabash Avenue for the ultimate Chicago experience: authentic deep-dish pizza! Savor a mouth-watering slice of this iconic, thick-crusted masterpiece while your guide shares captivating stories of the city's rich culinary and mobster history. Gluten-free option available. Please note: It is cooked in a shared oven with non-GF ingredients
Stop at Mister J's on North State Street for an authentic, fully loaded Chicago-style hot dog. Savor this quintessential local bite while your guide shares thrilling stories of the city's notorious gangster history. Gluten-free? We've got you covered, just ask for your hot dog served bunless!
Highlights
Expert tour guide
Meals
What's included
Included
Expert tour guide
Meals
Not included
Alcoholic Beverages
Gratuities
Traveller Ratings
4.7
30 reviews
Important Information
- Wheelchair accessible
- Infants and small children can ride in a pram or stroller
- Service animals allowed
- Public transportation options are available nearby
- Specialized infant seats are available
- Suitable for all physical fitness levels
- Gluten free food options available at all 3 locations
- Vegetarian/Vegan: Available at 1 of 3 stops (Pizza stop only).
Frequently asked questions
How long does Chicago: Gangsters and Food Tasting Walking Tour take?
Chicago: Gangsters and Food Tasting Walking Tour lasts about 2 hours. The itinerary has 3 stops.
How much does Chicago: Gangsters and Food Tasting Walking Tour cost?
Prices start at $80 per person for this Chicago experience, booked through Viator with the price shown before checkout. There is 1 booking option, so the final price depends on the option you choose.
Can I cancel Chicago: Gangsters and Food Tasting Walking Tour for free?
Yes. Cancel at least 1 day before the start for a full refund. Later cancellations are non-refundable.
Where does the tour start?
The meeting point is Please meet your guide outside "Hoyt's Tavern" 15 minutes before the start time: 71 E Wacker Dr, Chicago, IL 60601, USA.. Hotel pickup is not part of this experience.
What languages is Chicago: Gangsters and Food Tasting Walking Tour offered in?
The experience is available in EN.
Is this a private or a group tour?
It is a small-group experience with a maximum of 25 participants.
Is the tour suitable for children?
Infants and small children can ride in a pram or stroller Specialized infant seats are available
Is the tour wheelchair accessible?
Wheelchair accessible
Reviews(30)
D
Definitely recommend
Our guide, Baylor was 5 stars Lots of Chicago gangster history Terrific personality Food was great It was sooo much fun
D
Loved gangster good tour
Baylor was greet She knows her Chicago gangster history and it was so great to visit Harry Carays steakhouse The food at all three restaurants were so good I would say this is a must to do when visiting Chicago What a great city I can’t wait to come back
9
All Chicago Favs in one tour: Mobsters, pizza, steak and Chicago Dog!
I loved this tour! Our guide, Baylor, was a fantastic storyteller with the right mix of history storytelling and humor😊 She made sure that the group stayed together and had conversations with each of us. There were nine in our group. The food was outstanding and I'm very grateful to the venues we went to. The layout of the tour was perfect: walk a some, learn something new and eat fantastic food! I say a must to do if you're in Chicago! Thank.you for a memorable experience!
G
Fabulous
Baylor was a great guide, very interesting stories, she was really knowledgable and fun, I noticed she took great care to make sure we stayed together and she spent time with each of us, really appreciate having her as our guide.
8
Awesome tour!
Baylor was a great guide and very friendly!
S
Fun Facts About Chicago Gangsters!
This food tour focussed on the River North area, which was the site of gangster activity in the early 1920s and 1930s. Our tour guide, Peyton, was very knowledgeable and added some humor - she did a great job! The tour was just the right amount of walking for our group, and the destinations were so interesting! It was also the right amount of "tastings". However, the description indicated 2 types of pizza; our group had only one. Just a minor suggestion: add a sweet tasting to the tour!
G
Factual tour of old Chicago.
It was a great experiance. Peyton was very knowledgeable.
4
Our guide Talia was wonderful!
Talia is a phenomenal storyteller and a wealth of knowledge about mob and mafia history. We had a great time, and the food was excellent!
S
Good but maybe not worth the money
Our guide was phenomenal and the food was good. The only complaint is the length for the price. It should have been longer, with more stories, for the cost.
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