Chicago’s mobster past is the stuff of legend — bootleggers, speakeasies, and notorious crime bosses who ruled the city during Prohibition. Today, you can relive that era through Chicago’s famous gangster tours, combining history, humor, and a touch of Hollywood drama.

Whether you’re a true crime buff or just looking for a unique way to explore the city, here’s what you can expect from a Chicago Gangster Tour — plus how to make the most of your experience.

🕵️‍♂️ Step Back in Time to the Roaring Twenties

Most gangster tours in Chicago take you on a journey through the city’s most infamous crime scenes and hangouts from the 1920s and ‘30s. You’ll cruise past secret hideouts, historic speakeasies, and landmarks tied to the Chicago Outfit’s rise to power.

Typical highlights include:

• The Biograph Theater – where bank robber John Dillinger met his end.

• Holy Name Cathedral – the site of a famous mob hit targeting Hymie Weiss.

• The St. Valentine’s Day Massacre Site – a chilling piece of true crime history.

• Former speakeasies and mob hangouts once frequented by Al Capone and Bugs Moran.

Each tour mixes dark history with storytelling and local flavor — you’ll hear wild tales of bootlegging, police chases, and the underworld empire that made Chicago famous.

🚐 What Kind of Gangster Tours You Can Take

There’s no one-size-fits-all experience — you can explore the city’s criminal past in several ways:

• 🚌 Classic Bus Tours:
  Join iconic groups like Untouchable Tours or Chicago Crime Tours, known for their costumed guides, humor, and live commentary.

• 🚶‍♀️ Walking Tours:
  Explore the city’s streets up close with guides who uncover hidden stories most visitors miss.

• 🍸 Gangsters & Ghosts Tours:
  A unique mix of mob history and haunted tales — a top-rated evening option in downtown Chicago.

👉 Check current options and reviews on Groupon Chicago Things to Do, where similar city tours often appear at discounted prices.

💡 Insider Tips for the Best Experience

• Book ahead – Gangster tours are especially popular on weekends and around Halloween.

• Dress for the weather – many tours include walking segments.

• Ask your guide questions – most are local historians and storytellers who love to share hidden gems.

• Pair your tour with dinner at a vintage Chicago restaurant — like The Green Mill, a real Prohibition-era jazz club.

📸 Don’t Miss These Photo Ops

Capture your moment in mob history with:

• The Chicago Theater marquee on State Street

• Murals and vintage signs in River North

• A shot in front of the Biograph Theater where Dillinger’s story ended

🕰️ Make It a Full Day of Chicago History

If you’re into the city’s dramatic past, consider pairing your gangster tour with:

• Architectural boat tour on the Chicago River

• Chicago History Museum tickets

• Ghost and True Crime walking tours

• Speakeasy cocktail classes

You can find many of these experiences on Groupon — perfect for building a themed weekend of Chicago history and entertainment.

🧭 Final Thoughts

Chicago’s gangster tours offer the perfect blend of education and entertainment. You’ll uncover real crime stories, visit legendary landmarks, and see the city in a way few travelers do. Whether you hop on a vintage bus or take a twilight walking tour, it’s an unforgettable glimpse into the darker side of Chicago’s past.

👉 Explore related experiences on Groupon Chicago – Things to Do and discover more local adventures for less.