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

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.

Step-by-step itinerary

Stops and time spent at each2 stops

1. Lincoln Park and Zoopassing by
2. Biograph Theater10m

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.

Information

Lasts 2h–2h 30m, runs Thursday and Friday at 19:30, from US$ 55 per person, with a live guide in English and with free cancellation up to 24 h before.

Days and timesThursday and FridayDeparts at 19:30Another day? ›

GroupUp to 39

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 6 days ago

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 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.

Traveler reviews

4.82★★★★★★★★★★

524 verified traveler reviews

5 ★460

4 ★44

3 ★15

2 ★1

1 ★4

Read all the reviews ›

Top questions

How long is the Chicago night crimes tour?

The tour runs 2 to 2.5 hours total, including on-and-off-bus stops at crime scenes.

Where does the bus pick up and drop off?

Pick-up and drop-off are at 163 E. Pearson Street, on the southeast side of Michigan Avenue and Pearson Street, across from a Chicago landmark building.

What crime scenes do you visit?

The tour includes the St. Valentine's Day Massacre site, Biograph Theater, the garage where Dillinger was shot, the corner where Hymie Weiss died, and Nitti's Vault, a crime museum with a historic bootlegging tunnel.

What's included in the tour?

Inclusions are a live interactive guide, historic video footage, entry to Nitti's Vault, a crime quiz, a keepsake brochure with photos, and a Prohibition Era personality profile.

Can you get off the bus during the tour?

Yes, the tour includes stops where you get off the bus to walk and explore historic crime scenes up close.

Is there a restroom break?

No, there are no restroom breaks on the tour. You should use the restroom before checking in at the bus.

Can you eat or drink on the bus?

No eating or drinking is allowed on the bus during the tour.

What if I arrive late?

Guests cannot join the tour after the bus departs. You must arrive at least 15 minutes early for check-in.

Is the tour suitable for children?

Yes, infants and small children can ride in a pram or stroller. The tour is suitable for all physical fitness levels.

Does the bus have accessibility features?

The bus has five steps to board and is not equipped with an electronic lift. There is limited storage for a folding wheelchair or stroller, and some stops off the bus include stairs.