Tours/Chicago/Chicago: Gangsters and Food Tasting Walking Tour
Viator · group up to 25 pax

Chicago: Gangsters and Food Tasting Walking Tour

4.6(23)Chicago1 hour
VIATOR4.2(5)TRIPADVISOR4.7(18)

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.

Tour Options

Chicago: Gangsters and Food Tasting Walking Tour

Itinerary

30 min

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.

30 min

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.

30 min

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.

Highlights

Expert tour guide
Meals

What's included

Included
Expert tour guide
Meals
Not included
Alcoholic Beverages
Gratuities

Traveller Ratings

4.6
23 reviews
5
18
4
1
3
4
2
0
1
0

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

Reviews(23)

G
Guide10421202628
August 19, 2026
Factual tour of old Chicago.

It was a great experiance. Peyton was very knowledgeable.

4
433spencerc
August 17, 2026
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
shotty3388
August 17, 2026
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.

M
MiamiFan123
August 16, 2026
Good time!

Despite less than ideal weather, walking tour was great. Moved along well. While the food was good, the tour guide, Talia, really made the day. She was exceptional in her presentation and lots of fun.

J
J646IOelainea
August 8, 2026
Missing a second pizza

So the tour description stated that we would get 2 different types of pizza but we only had one. It also stated that we would see a mansion that was once a brothel which we did not. Kind of disappointing

1 people found this helpful
M
Megan_D
August 5, 2026
Fun but Incomplete

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.

T
Theresa_W
August 2, 2026
Hamsters and Food

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

H
helen_b
August 2, 2026
A quick tour with some...

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.

C
candicef356
July 30, 2026
Loved it!

Peyton was fantastic! She was knowledgeable and entertaining! Tour was fun! Food was good. Harry Carrey basement was my fav.

C
Cayla_m
July 24, 2026
Fun introduction to Chicago

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

You might also like...

4.6(23)
Book now