Chicago Night Crimes Tour: St Valentine's Day Massacre & Gangster Sites

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Free cancellationExcellent quality

1/12

Duration2h–2h 30m

GroupUp to 39

LanguagesEN

Mobile ticketAccepted

The St. Valentine's Day Massacre Wasn't the Only Body That Fell

You ride a climate-controlled bus through Chicago's mob neighborhoods, stopping to walk the sites where Al Capone, John Dillinger, and Hymie Weiss operated and died. The tour includes entry to Nitti's Vault, historic video footage, a crime quiz, and a keepsake pamphlet with photos. It runs 2 to 2.5 hours and departs from Michigan Avenue and Pearson Street, so arrive fifteen minutes early.

2h–2h 30m

Step-by-step itinerary

Explore Chicago crime history by bus

Start outside 163 E. Pearson Street
Learn about famous gangsters and mobsters
See St. Valentine's Day Massacre site
Visit Biograph Theater and Harry Caray's Steakhouse
Pass by Museum of Contemporary Art
View John Hancock Center in Streeterville
See the Magnificent Mile
Drive by Lincoln Park and Zoo
Pass by Lakeshore Drive beach
Drive by Oz Park to massacre site
Visit Jewelers Building landmark
Enjoy views from State Street Bridge
Enter Nitti's Vault crime museum
Walk last steps of Hymie Weiss
Conclude near Historic Water Tower

The Experience

The bus pulls up at Michigan Avenue and Pearson Street, and your guide starts talking about Al Capone before you've even sat down. Two to two and a half hours later, you'll have walked the exact corner where Hymie Weiss took his last steps, stood outside the Biograph Theater where John Dillinger's body hit the pavement, and seen the garage on North Clark Street where seven men died in a single burst of gunfire on Valentine's Day 1929. This Chicago night crimes tour moves fast — you're on and off the bus at actual crime scenes, not just driving past them.

The guide knows the stories in a way that feels lived-in, not rehearsed. You get the names straight: Dean O'Banion, Frank Nitti, Bugs Moran. There's historic video footage playing on screens, a crime quiz that's harder than it sounds, and the tour includes a souvenir pamphlet with photos so you can place the faces to the places. The bus itself is climate-controlled and moves through Streeterville, past the John Hancock Center and down Lakeshore Drive, so you're seeing the city's geography shift as the stories unfold. It's not a museum tour — it's the actual streets where this happened, and the difference matters.

One stop takes you inside Nitti's Vault, a small crime museum where you can see the bootlegging tunnel that ran under the city during Prohibition. Another has you standing in front of the Jewelers Building, another at the State Street Bridge looking at the Chicago River and the speakeasy views. The tour ends near the Historic Water Tower, one of the few buildings that survived the Great Chicago Fire of 1871. The whole thing moves on schedule — the bus departs on time, so you need to be there fifteen minutes early and ready to go when it leaves. No restroom breaks, no eating on the bus, and you can't join once it's rolling.

What’s included

Your tour includes a live interactive guide in English, historic video footage of the Prohibition Era, entry to Nitti's Vault (a crime museum with a bootlegging tunnel), a crime quiz, a keepsake brochure with photos and special offers, and a Prohibition Era personality profile.
The bus is climate-controlled and departs from Michigan Avenue and Pearson Street.
All inclusions are subject to availability.

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 if you want Chicago's mob history told on the actual streets where it happened, with stops to walk the crime scenes themselves — the fixed 2.5-hour schedule and included guide mean you don't have to research the stories or navigate the neighborhoods alone.