×
Menu
Search

Private Gangster Tours

Private Gangster Tours

Today, Chicago is celebrated for its vibrant craft brewing scene, enchanting locals and tourists with its unique and flavorful beers. However, many may not realize that this city also boasts a rich and glamorous history, marked by a lively gangster culture from the 1920s and 1930s. Enter The Barrel Run, where you can journey back in time to explore the Prohibition era, filled with speakeasies and infamous crime figures. Our Private Gangster Tours offer an exhilarating mix of history, craft brewing, and adventure, providing an unforgettable glimpse into Chicago’s captivating past. Don’t miss out on this thrilling experience!

WHY GO ON A PRIVATE GANGSTER TOUR?

Our Private Gangster Tours offer a unique and immersive experience that cannot be replicated by simply reading about Chicago’s gangster history. By going on one of our tours, you will not only learn about the city’s notorious past but also see it come to life through expertly crafted narratives and visual aids. Our knowledgeable tour guides provide an insider’s perspective, taking you to the very locations where some of the most infamous events in Chicago’s gangster history took place. You’ll feel like you’re stepping back in time as you walk through these iconic streets and buildings.

What You’ll Experience

On your journey, you’ll travel around Chicago in our infamous Barrel Bus and visit notorious gangster hideouts and significant locations, including:

  • Holy Name Cathedral – Learn about the assassinations of Dion O’Banion and Hymie Weiss.
  • Chicago River – Hear tales of smuggling and clandestine meetings.
  • St. Valentine’s Day Massacre Site – Uncover the chilling details of the infamous massacre.
  • Biograph Theater – Walk the grounds where John Dillinger met his end.
  • Streeterville – Explore the neighborhood once controlled by George “Cap” Streeter.

Upon reaching each location, our tour guides will allow you to take photos and ask in-depth questions. You’ll also have the opportunity to stop at some of Chicago’s best craft breweries along the way, trying out a range of delicious beers while soaking in the city’s lively atmosphere. It’s an experience that combines education, entertainment, and indulgence all in one!

Enhance and Customize

The best part about our Private Gangster Tours is their complete customizability, tailored to match your interests and preferences for a truly personalized experience. You have the option to enhance your tour by adding delightful stops, such as a luxurious dinner at The Green Door Tavern, one of Chicago’s historic speakeasies. This charming venue is steeped in history and offers a sumptuous menu, providing the perfect setting to unwind and savor a meal after immersing yourself in Chicago’s thrilling gangster past. You can also enjoy extra time at the speakeasy with a completely open bar, allowing you to try everything this iconic venue has to offer. Our team is dedicated to ensuring your tour is not only informative and exciting but also perfectly aligned with your interests, adding exclusive touches that make your journey truly memorable.

Book Your Private Gangster Tour Today

Ready to step into the intriguing world of Chicago’s notorious gangsters? Don’t miss out on this incredible opportunity to explore the city’s darker side in style. Discover the history behind the infamous crime families, navigate the hidden speakeasies, and learn about the legendary figures who shaped the city’s underworld. Contact us today to start planning your adventure – it’s an experience you won’t soon forget!

What is Lorem Ipsum?

Lorem Ipsum is simply dummy text of the printing and typesetting industry. Lorem Ipsum has been the industry’s standard dummy

What is Lorem Ipsum?

Lorem Ipsum is simply dummy text of the printing and typesetting industry. Lorem Ipsum has been the industry’s standard dummy

What Our Clients
Think of The Barrel Run

testi-image

BOOK A TOUR

Available
Unavailable