Chicago: Guided Gangsters & Food Walking Tour

Chicago Guided Gangsters and Food Walking Tour

Discover the dark history and delicious flavours that shaped Chicago on this two-hour guided walking tour. You'll explore the streets where Al Capone's associates built their criminal empire whilst sampling the city's most famous dishes. This small-group tour combines fascinating crime stories with authentic Chicago cuisine, taking you to historic sites that still bear the marks of the Prohibition era.

Your expert local guide leads you through a neighbourhood once dominated by speakeasies and gangster operations. Visit underground tunnels hidden beneath former bootlegging establishments, stand outside grand mansions that operated as brothels during Prohibition, and see the cathedral marked by violent gangster history. Between historical stops, you'll taste traditional Chicago deep dish pizza, crispy tavern-style pizza, authentic Chicago hot dogs, and prime steak at classic local eateries.

The tour goes beyond Al Capone legends to reveal modern stories, including how a restaurant owner's actions led to dismantling Chicago's last mafia groups in the early 2000s. Each carefully chosen stop provides authentic insights into how culinary traditions became intertwined with the gangs that once controlled these streets.

What is Included

• Expert local guide
• Traditional Chicago deep dish pizza tasting
• Crispy tavern-style pizza sample
• Authentic Chicago hot dog
• Prime steak tasting
• Small group experience
• Historical site visits including underground tunnels and former speakeasies

Good to Know

The tour lasts approximately two hours with moderate walking and regular food stops for breaks. Arrive at the meeting site at least 10 minutes before departure. The tour discusses historic crime and is most suitable for older children and adults.

Vegetarian food options may be available if you notify your guide in advance. No alcoholic beverages are included in the tastings. Follow your guide's instructions throughout the tour for group safety, and remember that food tastings are exclusively part of the tour experience.

If you're exploring more of Chicago's attractions, consider booking the Chicago Architecture Foundation River Cruise to see the city's famous skyline from the water. For more Chicago tours that showcase the city's unique character, the Chicago Food Walking Tour in West Loop offers another delicious perspective on the city's culinary scene.