About the Guided Gangsters & Food Walking Tour

Step back into Chicago’s storied past and explore the vivid intersection of history and food on this immersive walking tour. Led by an expert local guide, your journey will wind through a neighborhood once rife with Prohibition-era intrigue, revealing the enduring influence of notorious gangsters and the legendary flavors that define the city.

Walk Through History

Stroll along the very streets where Al Capone’s associates forged their reputations, visiting sites that still echo the city’s turbulent past. From historic tunnels hidden beneath speakeasies to grand mansions that once doubled as brothels, you’ll see the shadowed corners where the city’s most notorious figures once walked.

• Visit a tunnel deep beneath a renowned establishment, a relic from Chicago's bootlegging days

• Stand at a mansion that operated as a prominent brothel during Prohibition

• See the iconic cathedral marked by a violent chapter in gangster history

Sample Iconic Chicago Cuisine

No trip to Chicago is complete without tasting its most distinguished dishes. This tour goes beyond sightseeing, offering you the chance to savor:

• Traditional Chicago deep dish pizza known for its gooey cheese and thick crust

• Crispy tavern-style pizza, a local favorite often overlooked by visitors

• The city’s famous hot dog, dressed the authentic Chicago way

• Succulent prime steak, a staple in the city’s classic eateries

Between tastings, listen as your guide shares tales of gang wars, Prohibition exploits and the legendary figures who shaped Chicago’s criminal underworld. Learn how culinary traditions became intertwined with the very gangs that once ran the city’s streets.

Discover Hidden Stories

The narrative goes beyond legends like Capone. Uncover tales of modern law enforcement and the restaurant owner whose actions led to the dismantling of Chicago’s last standing mafia groups in the early 2000s. Each stop is carefully chosen to give you an authentic perspective on Chicago’s colorful past and vibrant food scene.

Perfect for Foodies and History Buffs

This two-hour guided tour is designed for small groups, creating an engaging experience filled with flavor, intrigue and unforgettable stories. Whether you’re fascinated by crime history or eager to savor the city’s culinary highlights, this tour delivers an insightful and delicious introduction to Chicago’s unique culture.

Book your Chicago: Guided Gangsters & Food Walking Tour tickets now!