Chicago Crime Mob Bus Tour: Al Capone, Massacre

★★★★★★★★★★ 4.60 (3,558 reviews) 77% rated it 5 stars

Free cancellationTravelers' pick

1/15

Duration1h 30m–2h

GroupUp to 37

LanguagesEN

Mobile ticketAccepted

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.

1h 30m–2h

Step-by-step itinerary

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.

Good to know

Easy physical levelStroller 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.