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Cultural History Tour for Chicago, IL

Untouchable Tours offers an unforgettable cultural history tour that brings to life the dramatic, high-stakes world of 1920s and 1930s Chicago, IL. Our historical tours take you deep into the heart of the Prohibition Era—a time of speakeasies, bootlegging, organized crime, and the relentless lawmen who fought to restore order. Whether you’re visiting from out of town or rediscovering your city, this is a Chicago experience like no other.

An Authentic Glimpse Into the Roaring Twenties

Our expert guides present an accurate account of the events that shaped Chicago during the Prohibition Era. You’ll hear real stories about infamous figures such as Al Capone, Bugs Moran, and John Dillinger, alongside context about the social climate and law enforcement’s efforts to curb crime. This isn’t just about gangsters—it’s about how crime, culture, and politics collided to shape a city’s identity.

Our historical tours visit iconic sites, including the scene of the St. Valentine’s Day Massacre, the Biograph Theater, and Holy Name Cathedral. Each stop adds layers of authenticity and intrigue to your journey through Chicago’s past.

History That’s Entertaining and Alive

What truly sets Untouchable Tours apart is our incredible team of Gangster Guides. These aren’t your average tour guides—they’re professional actors in costume who take on the personas of 1920s-era gangsters. Their performances are full of energy, humor, and dramatic flair, transforming history into an immersive experience. Our tours are both educational and wildly entertaining, making them ideal for families, groups, or solo travelers.

Comfortable, Engaging, and Unmissable

Each tour lasts nearly two hours, with guests comfortably seated for the duration. We begin and end in front of the McDonald’s at 600 North Clark Street, near the intersection of Clark & Ohio in downtown Chicago, IL.

Whether you’re a tourist or a curious local, Untouchable Tours offers a cultural history tour that’s rich in storytelling and historical insight. Discover Chicago’s legendary past with the most unique historical tour in town.

Reserve your seat today—history is waiting!