Chicago: Gangsters and Food Tasting Walking Tour





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
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.
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.
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
What's included
Traveller Ratings
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)
It was a great experiance. Peyton was very knowledgeable.
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!
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.
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.
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
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.
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 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.
Peyton was fantastic! She was knowledgeable and entertaining! Tour was fun! Food was good. Harry Carrey basement was my fav.
Talia was an awesome guide. I learned so much about Chicago history and the food here. 10/10 would recommend this tour for others.



