Chicago: Gangsters and Food Tasting Walking Tour

Delving into Chicago’s storied past, the Chicago: Gangsters and Food Tasting Walking Tour offers an unparalleled glimpse into the city’s notorious criminal underworld. Combining the city’s iconic culinary delights with its captivating gangster history, this unique experience transports participants back in time, unveiling the secrets and scandals that once gripped the Windy City. Led by expert guides, the tour takes visitors on a journey through the very streets that once bore witness to the tumultuous reign of Al Capone and his contemporaries, leaving them hungry for more.

Key Points

• This 2-hour walking tour in Chicago offers participants the opportunity to explore the city’s notorious gangster history and sample iconic local cuisine.
• The tour covers approximately 1 mile and visits infamous gangster hangouts, including Al Capone’s secret tunnels and a brothel mansion used for illicit activities.
• Participants will taste classic Chicago foods such as deep-dish pizza, tavern-style pizza, Chicago hot dogs, and prime steak, showcasing the city’s renowned culinary heritage.
• The expert local guide provides captivating tales about the city’s most notorious mobsters and the turbulent Prohibition-era history.
• The tour meets at Hoyts Restaurant on the Chicago River and includes food tastings, water, and soft drinks, with gratuities and alcoholic drinks not included.

You can check availability for your dates here:

Overview of the Tour

The Gangsters and Food Tasting Walking Tour in downtown Chicago offers participants the opportunity to explore the city’s rich history of organized crime and iconic local cuisine over the course of a two-hour excursion.

Highlights include learning the backstories behind classic Chicago foods, sampling deep-dish pizza, Chicago hot dogs, and prime steak, and visiting infamous gangster hangouts like Al Capone’s secret tunnels.

Along the way, the expert local guide will regale travelers with captivating tales of the city’s notorious mobsters.

The tour covers about a mile of ground, and the food tastings are substantial enough to serve as a hearty lunch.

Comfortable shoes are recommended, as the tour operates rain or shine.

Iconic Chicago Foods Tasted

Participants on the Gangsters and Food Tasting Walking Tour get to sample some of Chicago’s most iconic culinary delights, including deep-dish pizza, tavern-style pizza, Chicago hot dogs, and prime steak.

The deep-dish pizza, a Chicago specialty, features a thick, buttery crust loaded with toppings and tomato sauce.

The tavern-style pizza, on the other hand, has a thinner, crispier crust and is cut into squares.

The classic Chicago hot dog is a must-try, with its all-beef frank, neon green relish, onions, tomatoes, a dill pickle spear, and a dash of celery salt.

Finally, the tour offers a taste of prime steak, showcasing the city’s reputation for quality meat.

These iconic bites provide an authentic flavor of Chicago.

Gangster Hideouts Visited

On the tour, visitors explore old gangster hideouts, including an underground tunnel once used by Al Capone to evade the authorities. They also see locations associated with notorious gangsters, such as a mansion that served as a brothel and a cathedral where gangsters were gunned down in a violent altercation. These sites provide a glimpse into Chicago’s turbulent past, when the city was plagued by gang violence and criminal activity.

Gangster Hideout	Historical Significance
Al Capone’s Underground Tunnel	Used to transport illegal goods and escape authorities
Brothel Mansion	Housed illegal activities and exploitation
Cathedral Shootout Site	Scene of a deadly clash between rival gangs
Speakeasies	Served as fronts for illicit alcohol sales during Prohibition

Mansion Used as Brothel

A notorious mansion, once used as a brothel, stands as a grim reminder of Chicago’s seedy underbelly during the Prohibition era.

This opulent residence, now a shell of its former glory, was allegedly a hub for illicit activities and a favorite haunt of Al Capone and his gang.

The tour guides recount tales of lavish parties, where wealthy patrons indulged in forbidden pleasures.

Although the mansion’s glory days are long gone, the crumbling walls still whisper secrets of the past, offering a glimpse into the city’s dark history.

As the tour continues, participants are left to ponder the contrasts between the city’s infamous criminal underworld and its vibrant, modern-day charm.

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Cathedral With Gangster Shootout

Looming over the city’s skyline, the cathedral stands as a grim backdrop to one of Chicago’s most notorious gangster shootouts.

During the Prohibition era, this hallowed ground witnessed a bloody clash between Al Capone’s henchmen and their rivals, leaving a trail of bodies in its wake.

The tour guide recounts the chilling details of the incident, painting a vivid picture of the chaos that unfolded within the cathedral’s sacred walls.

Bullet holes still pockmark the edifice, a haunting reminder of the violence that once gripped the city.

As the group stands in solemn silence, they can almost hear the ghostly echoes of the gunfire that shattered the peace on that fateful day.

Tour Duration and Distance

The Gangsters and Food Tasting Walking Tour in Chicago spans a distance of about one mile and lasts for a duration of two hours. Participants will have the opportunity to taste a variety of iconic Chicago foods, including deep dish pizza, tavern-style pizza, Chicago hot dogs, and prime steak.

The tour also includes visits to old gangster hangouts and locations associated with famous criminals like Al Capone. Throughout the experience, the expert local guide will share stories and insights about Chicago’s notorious gangster history.

The tour operates rain or shine, and comfortable shoes are recommended. While food tastings are included, gratuities and alcoholic drinks aren’t part of the tour package.

Meeting Point and Inclusions

The Gangsters and Food Tasting Walking Tour in Chicago meets at Hoyts Restaurant at the Royal Sonesta Hotel on the Chicago River (Wacker and Wabash).

This 2-hour tour includes several delectable tastings:

1. Deep dish pizza
2. Tavern-style pizza
3. Chicago hot dog
4. Prime steak

Along with the food, the tour also provides water and soft drinks to keep guests refreshed.

An expert local guide leads the group, sharing stories about famous gangsters and taking them to old hideouts, including an underground tunnel used by Al Capone.

Comfortable shoes are recommended, and the tour operates rain or shine. Gratuities and alcoholic drinks aren’t included in the tour price.

Additional Tour Information

The tour covers approximately 1 mile with 4 stops, allowing participants to comfortably experience the highlights.

Food tastings add up to a good lunch meal, so guests needn’t worry about going hungry.

Regardless of weather conditions, the tour operates rain or shine, so attendees should dress appropriately.

While gratuities and alcoholic drinks aren’t included in the tour price, guests are welcome to provide tips for the expert local guide at their discretion.

Comfortable shoes are recommended to fully enjoy the walking portion of the experience.

Recap

The Chicago: Gangsters and Food Tasting Walking Tour offers an unparalleled opportunity to explore the city’s infamous criminal past and indulge in its renowned culinary delights.

Combining captivating tales of mobsters with a tantalizing sampling of classic Chicago foods, this immersive experience promises an unforgettable adventure for visitors seeking to explore the vibrant history and culture of the Windy City.

You can check availability for your dates here: