Chicago: Gangsters and Food Tasting Walking Tour
Overview
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 Chicago’s deep dish – 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 as 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/vegan/vegetarian options are available (please reach out prior to the tour to inform us of any dietary requirements.)
What's Included
- Meals
- Expert tour guide
- Alcoholic beverages Alcoholic Beverages
- Gratuities
Meeting Location
71 East Wacker Drive
Chicago, IL 60601, USA
Detailed check-in instructions, including the exact address, are provided with your booking confirmation.
822 North State Street
Chicago, IL 60610, USA
Mister J's Hotdogs is where the tour will end
What To Expect
Book Online
Safe & secure Easy breezy Hassle‑free
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 is instant and will be received at time of booking
- Service animals allowed
- Public transportation options are available nearby
- Suitable for all physical fitness levels
- Infants and small children can ride in a pram or stroller
- Specialized infant seats are available
- Gluten-free/vegan/vegetarian options are available (please reach out prior to the tour to inform us of any dietary requirements.)
- This tour/activity will have a maximum of 25 travelers
Frequently Asked Questions (7)
Q: What is the cancellation policy for the Chicago: Gangsters and Food Tasting Walking Tour?
Cancellation Policy
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Activity code: C-5669845P2
Traveler Photos
Reviews
Average 4.71 out of 5 stars based on 51 traveler reviews collected by City Sky Diving and partner sites such as Cool Destinations and TripAdvisor
Additional Info
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Frequently Asked Questions (7)
The answers provided below were previously given in response to questions from City Sky Diving customers.
Filter by:
- For a full refund, you must cancel at least 24 hours before the tour start time.
- If you cancel less than 24 hours before the tour start time, the amount you paid will not be refunded.
- Any changes made less than 24 hours before the tour start time will not be accepted.
- Cut-off times are based on the tour local time (CST).
- Meals.
- Expert tour guide.
- Alcoholic beverages. Alcoholic Beverages.
- Gratuities.
There is no minimum age for this tour, so bring your wee one along for an adventure. This tour requires at least one adult to accompany children..
Apr 2025If a date or time is not listed on the calendar, it’s sold out or unavailable for another reason. Support cannot assist further if a date or time is not on the calendar.
If you find a date and time that works for you, book it NOW because things always sell out at this time of year.
Apr 2025Accessibility information for the Chicago: Gangsters and Food Tasting Walking Tour is as follows:
- Service animals allowed
- Public transportation options are available nearby
- Suitable for all physical fitness levels
Detailed check-in instructions – including meeting point address, Google map, and parking information – for Chicago: Gangsters and Food Tasting Walking Tour will be included in your confirmation email from City Sky Diving. Please be sure to double and triple check your email address is correct at checkout so this important email makes its way to you!
Mar 2024Once your refund is processed, it usually shows on your card statement within 5–10 business days. The exact timing depends on your bank or card issuer.
Want it sooner? When you cancel, choose Receive a refund to my wallet instead. The credit is in your Wallet straight away and is applied automatically at checkout on your next booking when you’re signed in with the same email. You can see your balance any time in My Wallet.
If you paid part of your booking with Wallet credit, that part always goes back to your Wallet. Trip protection isn’t refundable.
Oct 2026What's Included
- Meals
- Expert tour guide
- Alcoholic beveragesAlcoholic Beverages
- Gratuities
Additional Info
- Confirmation is instant and will be received at time of booking
- Service animals allowed
- Public transportation options are available nearby
- Suitable for all physical fitness levels
- Infants and small children can ride in a pram or stroller
- Specialized infant seats are available
- Gluten-free/vegan/vegetarian options are available (please reach out prior to the tour to inform us of any dietary requirements.)
- This tour/activity will have a maximum of 25 travelers
