Chicago Crime Mob Bus Tour: Al Capone, Massacre

Step off the bus at real crime scenes and walk the streets where Chicago gangsters fell

A 1.5- to 2-hour bus tour of Chicago's crime and mob history with a live guide, departing from Water Tower Place in the Near North Side. You ride a climate-controlled coach through Streeterville, River North, Lincoln Park and the Loop, get off at historic sites like the Biograph Theater and the St. Valentine's Day Massacre location, and hear documented stories of Al Capone, John Dillinger, Frank Nitti, Bugs Moran and other Prohibition-era figures. The tour includes a mini mob museum, crime trivia, historic video footage and a souvenir brochure.

Step-by-step itinerary

Stops and time spent at each3 stops

1. Water Tower Placepassing by
2. Lincoln Park and Zoopassing by
3. Biograph Theater10m

Chicago crime and mob bus tour

• Meet guide near Water Tower Place
• Board luxury climate-controlled bus
• Drive by Museum of Contemporary Art
• See the Magnificent Mile
• View John Hancock Center in Streeterville
• Drive through Lincoln Park neighborhood
• Stop and explore Biograph Theater crime scene
• Drive by St. Valentine's Day Massacre site
• Enjoy views from State Street Bridge
• See Jewelers Building landmark
• Visit Nitti's vault and mob museum
• Pass Holy Name Cathedral and massacre site
• Walk areas linked to Dillinger and Weiss
• Return to Near North Side
• Conclude tour near Historic Water Tower

The experience

The tour meets across from Water Tower Place and runs 1.5 to 2 hours round-trip on a single luxury coach. Your guide narrates the route through neighborhoods where Chicago's underworld operated (Streeterville, River North, the Gold Coast, Lincoln Park, Old Town and the Loop), and stops the bus at key sites so you can step out and explore on foot. You'll see the Biograph Theater where John Dillinger was shot, pass the Holy Name Cathedral near the St. Valentine's Day Massacre location, and visit Nitti's vault inside a historic landmark building where bootlegging tunnels still run beneath the street.

The stories center on documented figures and events: Al Capone's South Side gang versus Bugs Moran's North Side operation, the 1929 massacre that killed seven mobsters, Frank "The Enforcer" Nitti's operations, and the paths John Dillinger and Hymie Weiss walked before their deaths. You'll also hear about Leopold and Loeb, H.H. Holmes, Cap George Streeter and Dean O'Banion. The guide offers in-depth narration from the bus and at stops, and you get a souvenir brochure with special offers, a Prohibition Era personality profile, a crime trivia quiz and access to a mini mob museum inside one of the tour stops.

Arrive 15 minutes early for check-in at Water Tower Place. The bus departs on time and does not wait for late arrivals. The coach has five steps to board, and some stops include stairs. There is no electronic lift and limited storage for a folding wheelchair or stroller. No restroom breaks are scheduled, so plan accordingly. The bus is climate-controlled, seating is first-come first-served, and no eating, drinking, recording or side conversations are permitted during the tour.

What’s included

• The tour includes a live guide in English narrating the full route.
• entry to a mini mob museum.
• a Prohibition Era personality profile and exclusive crime trivia quiz.
• historic video footage.
• a souvenir brochure with special offers.
• and photo opportunities at famous crime scenes like the St. Valentine's Day Massacre site and the Biograph Theater.

Information

Lasts 1h 30m–2h, runs every day, 6 start times, from US$ 49 per person, with a live guide in English and with free cancellation up to 24 h before.

Days and timesMonday to Friday: 10:00, 12:00, 14:00 and 16:00Saturday: 10:00, 12:00, 14:00, 16:00, 18:00 and 20:00Sunday: 10:00, 12:00, 14:00, 16:00 and 18:00

GroupUp to 37

Live guideEnglish

Meeting point and pickupNo hotel pickup: you go to the meeting point. Ends back at the starting point.

Book up toStart time

Cancellation and refundsFree cancellation up to 24 h before the start. After that, no refund.

Prices and times updated yesterday

Good to know

Low physical effortStroller-friendlyPets welcomePublic transport nearby

Operated by Chicago Crime Tours and Experiences LLC

Is this one for you?Book this tour if you want to hear Chicago's crime stories from a live guide who knows the neighborhoods and can point out the exact sites where events happened: the bus and walking stops let you see the places instead of just reading about them, and the museum and video footage add depth to what your guide explains.

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Top questions

What exactly is the St. Valentine's Day Massacre and why does it matter to Chicago's crime history?

The St. Valentine's Day Massacre was a 1929 shooting in which Al Capone's South Side gang murdered seven members of Bugs Moran's North Side gang, marking the peak of Prohibition-era gang violence in Chicago. The tour passes the Holy Name Cathedral near the massacre site and explains the conflict between the two gangs that led to this brutal killing.

Do I get to go inside buildings or just see them from the bus?

You ride the bus for most of the tour but get off to explore historic crime scenes on foot at several stops. You'll go inside to see Nitti's vault and the bootlegging tunnels, and you can visit the mini mob museum included with your ticket. Other landmarks like the Biograph Theater and Cook County Criminal Court House are viewed from the bus or from outside.

Is there a guide on the bus, and does the tour work if I don't speak English?

A live guide in English narrates the entire tour from the bus and at walking stops. There are no translations, audio guides or headphones, so the tour is conducted in English only.

How much time do I spend walking versus sitting on the bus?

Most of the 1.5- to 2-hour tour is spent on the climate-controlled bus, with stops to get off and walk at key crime scenes like the St. Valentine's Day Massacre site and the Biograph Theater. The exact balance depends on traffic and how long you spend at each stop.

What's included in the ticket price?

Your ticket includes the bus ride, live guide narration, entry to the mini mob museum, a Prohibition Era personality profile, a crime trivia quiz, historic video footage, a souvenir brochure with special offers, and photo opportunities at famous crime scenes. A $5 per person gratuity (or more) is recommended separately via cash or Venmo.

Can I bring children or a stroller on this tour?

Infants and small children can ride in a pram or stroller, and the tour is suitable for all physical fitness levels. The bus has five steps to board, and some stops include stairs, so plan for that if you're using a stroller. There is limited storage space available for a folding stroller on the bus.