Chicago Gangster and Food Walking Tour

The Chicago Gangster and Food Walking Tour provides a unique blend of Prohibition-era history and the city’s iconic culinary delights. Participants explore the River North neighborhood, visiting historic gangster hideouts while savoring tastings of prime cut steak, Chicago hot dogs, and deep-dish pizza. With a maximum of 15 travelers, this intimate tour offers personalized attention from knowledgeable guides, ensuring an engaging experience. Guests enjoy a full lunch, alcoholic beverages, and gratuity, making it a memorable exploration of Chicago’s rich history and flavors.

This experience made our article of The 16 Best Walking Tours In Chicago.

Key Points

• Uniquely combines Prohibition-era history and Chicago’s iconic culinary delights on a walking tour.
• Visits historic gangster hideouts in the River North neighborhood.
• Includes tastings of classic Chicago foods like prime cut steak, hot dogs, and deep-dish pizza.
• Offers a small-group format for a personalized experience, with lunch, beverages, and gratuity included.
• Starts at Hoyts Tavern and ends near the Magnificent Mile, providing convenient access to public transportation.

Tour Overview

The Chicago Gangster and Food Walking Tour is a unique combination of Prohibition-era history and Chicago’s renowned culinary delights.

Located in Chicago, USA, the tour has earned a 96% recommendation rate from 469 traveler reviews, with a Badge of Excellence.

Highlights include visits to historic "gangster" hideouts in the River North neighborhood and tastings of Chicago specialties like prime cut steak, hot dogs, and deep-dish pizza.

The small-group format ensures personalized attention, and the tour includes lunch, alcoholic beverages, and gratuity for the guide.

Meeting and end points are conveniently located near public transportation.

Tour Highlights

Combining Prohibition era history with Chicago’s famous foods, the tour visits River North neighborhood and historic "gangster" hideouts.

Guests enjoy tastings of Chicago Prime Cut Steak, Chicago Hot Dog, and Deep Dish Pizza.

The small-group format allows for personalized attention, with a maximum of 15 travelers. Included features are lunch, three different tastings, alcoholic beverages, and tour guide gratuity.

The tour starts outside Hoyts Tavern and ends at Mister Js, two blocks from the Magnificent Mile.

Included Features

The Chicago Gangster and Food Walking Tour includes a range of features to enhance the overall experience.

Travelers can expect:

• A full lunch
• Three different food tastings, such as Chicago Prime Cut Steak, Chicago Hot Dog, and Deep Dish Pizza
• Alcoholic beverages to complement the historical insights
• Gratuity for the knowledgeable tour guide who brings the Prohibition era to life through captivating storytelling.

These included features ensure that guests enjoy a well-rounded culinary and cultural exploration of Chicago’s iconic gangster history and local delicacies.

Meeting and End Points

The meeting point for the Chicago Gangster and Food Walking Tour is located outside Hoyts Tavern, situated at 71 East W Wacker Dr, Chicago, IL 60601.

The tour concludes approximately two blocks from the Magnificent Mile at Mister Js, located at 822 N State St, Chicago, IL 60610.

The tour’s end point is conveniently located near public transportation, allowing participants to continue exploring the city after the tour.

The tour’s meeting and end points provide a seamless experience, allowing participants to enjoy the city’s rich history and culinary delights throughout the duration of the tour.

Tour Experience and Reviews

What do travelers say about the Chicago Gangster and Food Walking Tour experience?

Reviews from past participants describe the tour as a captivating blend of Prohibition-era history and culinary delights. Guides are praised for their extensive knowledge and engaging storytelling abilities.

Highlights include:

• Visiting historic "gangster" hideouts in the River North neighborhood
• Sampling Chicago’s signature dishes like prime cut steak, hot dogs, and deep-dish pizza
• Exploring the secret tunnel at a local steakhouse
• Learning about Harry Caray’s basement connection to the city’s notorious past

Booking Information

Priced from $75.00 per person, the Chicago Gangster and Food Walking Tour offers free cancellation up to 24 hours before the scheduled departure.

Confirmation is received at the time of booking. The tour is near public transportation, though it is not wheelchair accessible. Infants must sit on laps. Service animals are allowed.

Reviews highlight the knowledgeable and engaging tour guides, with an overall rating of 4.8 based on traveler feedback.

The small-group format, historical insights, and diverse food tastings contribute to the positive tour experience.

Gangster Hideouts and Historical Insights

Chicago’s Prohibition-era history comes alive during the Chicago Gangster and Food Walking Tour. Guests explore the River North neighborhood, visiting former speakeasies and gangster hideouts once frequented by notorious figures like Al Capone.

The tour highlights:

• The steakhouse with a secret tunnel used for bootlegging
• The basement of Harry Caray’s, the legendary baseball broadcaster
• Insights into Chicago’s underground mob operations and notable crime scenes
• Vivid storytelling from knowledgeable guides who bring the city’s storied past to life

These historical elements are seamlessly woven with tastings of Chicago’s famous food, creating an immersive experience for travelers.

Culinary Delights of Chicago

While exploring Chicago’s gangster history, the tour also delights participants with tastings of the city’s renowned culinary offerings.

The tour features three distinct tastings, including a juicy Chicago Prime Cut Steak, a classic Chicago Hot Dog, and a slice of savory Deep Dish Pizza.

These iconic dishes showcase the city’s diverse food culture and allow travelers to indulge in the flavors that have made Chicago a celebrated culinary destination.

The small-group format ensures a personalized experience, where guides provide insights into the history and traditions behind these beloved local specialties.

Frequently Asked Questions

Is the Tour Appropriate for Children?

The tour may not be suitable for children due to its focus on gangster history and potential adult themes. However, the tour provider should be consulted for specific policies regarding the appropriateness of the tour for minors.

What Is the Tour’s Dress Code?

There is typically no strict dress code for walking tours. However, participants are advised to wear comfortable walking shoes and weather-appropriate clothing to ensure they can fully enjoy the tour experience.

Can Special Dietary Requirements Be Accommodated?

The tour operator is generally able to accommodate special dietary requirements with advance notice, such as vegetarian, vegan, or gluten-free options. Travelers should communicate any needs at the time of booking to ensure appropriate arrangements can be made.

Is Photography Allowed During the Tour?

Photography is typically allowed during tours, but visitors should check with the tour operator for any specific policies or restrictions. Some tour providers may have guidelines in place to ensure the comfort and experience of all participants.

What Happens in Case of Inclement Weather?

In the event of inclement weather, tour operators typically provide rain ponchos or cancel the tour and issue refunds. Guests should check the weather forecast and prepare accordingly, as the tour itinerary may need to be adjusted based on prevailing conditions.

The Sum Up

The Chicago Gangster and Food Walking Tour offers a captivating blend of Prohibition-era history and the city’s iconic culinary delights. Participants explore historic gangster hideouts while savoring prime cut steak, Chicago hot dogs, and deep-dish pizza. With personalized attention from knowledgeable guides, the tour provides an engaging and memorable experience for guests seeking to enjoy Chicago’s rich history and flavors.