Chicago Gangsters and Food Tasting Walking Tour
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Discover the vibrant history and flavors of Chicago on this Gangsters and Food Tasting Walking Tour. As you stroll through one of the city’s most stylish and notorious neighborhoods from the Prohibition era, you'll get to sample some of Chicago’s most famous foods.
Taste two types of pizza—deep dish and historic tavern-style—along with a prime steak and the legendary Chicago hot dog. Your guide will share stories of the gangsters who once ruled these streets and the city’s culinary secrets.
Highlights include visiting an old tunnel used by Prohibition gangsters, exploring a mansion once operated as a gangster brothel, and seeing the cathedral where gang violence once erupted. You’ll also learn about a restaurant connected to the man who took down the Chicago mafia in the early 2000s.
Whether you're a foodie or history buff, this tour offers a unique glimpse into Chicago’s past, with plenty of tasty bites along the way. Dietary options like gluten-free and vegetarian are available—just let us know in advance!
Frequently asked questions
How long is the tour?
The tour lasts approximately 2 hours.
What languages are spoken?
The tour is conducted in English.
What is the group size?
Groups are limited to up to 15 people.
Is the tour suitable for children?
Yes, it’s suitable for infants (0-3), youth (4-12), and adults (13-64).
Is the tour accessible?
Yes, it’s wheelchair accessible, and infants or small children can ride in a stroller or pram.
Are dietary restrictions accommodated?
Yes, gluten-free options are available at all three food stops, and vegetarian/vegan options are available at one stop. Please notify us in advance of any dietary needs.
Free cancellation
For a full refund, cancel at least 24 hours before the scheduled departure time.
Reserve now
Check a date here, then finish booking with our partner. Payment options are confirmed at checkout.
Duration 2 hours
Check availability to see start times.
Live tour guide
English
Key facts
What's included
Included
- Expert tour guide
- Meals
Not included
- Alcoholic beverages
- Gratuities
Itinerary
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Stop 1
Begin at Harry Caray's Italian Steakhouse on West Kinzie Street, a building linked to mob boss Frank Nitti. Enjoy a steak tasting while your guide shares stories of Chicago’s gangster and culinary history. Meat options can be gluten-free.
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Stop 2
Visit Pizzeria Due on North Wabash Avenue for authentic Chicago deep-dish pizza. Savor a slice while hearing tales of Chicago’s mobster past. Gluten-free options are available, cooked in a shared oven.
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Stop 3
Stop at Mister J's on North State Street for a classic Chicago-style hot dog. Enjoy this local favorite and learn about the city’s gangster history. Hot dogs can be served bunless for gluten-free options.
Meeting point & pickup
Meet at the starting point
Please meet your guide outside 'Hoyt's Tavern' 15 minutes before the tour begins: 71 E Wacker Dr, Chicago, IL 60601.
Open in Google MapsCancellation & confirmation
Free cancellation
For a full refund, cancel at least 24 hours before the scheduled departure time.
- 100% refund if cancelled at least 1 day before
- 0% refund if cancelled within 0–1 day
Instant confirmation
Your booking is confirmed immediately after checkout.
From $79.99 per person
- Free cancellation
- Secure checkout with our booking partner
