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Chicago Night Crimes Bus Tour Including St Valentine's Day Massacre and Holy Name Cathedral
day_trips

Chicago Night Crimes Bus Tour Including St Valentine's Day Massacre and Holy Name Cathedral

by Chicago Crime Tours and Experiences LLC

2 hours
$49.50$55 on ViatorSave 10%/person
From
$49.50$55 on ViatorSave 10%per person

Choose from 1 available option

2 hours
Starting time
Friday 11 September 2026
Language
English
Free cancellation until 10 Sept 2026.
$99$110Save 10%
2 guests × $49.50
All taxes and fees included

How do you want to book?

Confirmation before Wed, 9 Sept - card's only charged if it's a yes. If it's a no, still time to book on Viator.

Book on Viator Confirmed right away, but you pay full price.$110

Overview

This bus tour in Chicago lasts about two to two and a half hours and focuses on the city’s crime history. The tour begins and ends outside 163 E. Pearson Street, near Michigan Avenue. You will travel on a luxury, climate-controlled coach while listening to live commentary from a guide who shares true crime stories about figures like Al Capone, John Dillinger, Frank Nitti, and Bugs Moran. The route includes stops where you can get off the bus to explore and photograph famous crime scenes such as the St Valentine's Day Massacre site, the Biograph Theatre, and Holy Name Cathedral. You will also see landmarks like the historic courthouse, the John Hancock Center, the Magnificent Mile, and Oz Park during the drive-by segments. At Nitti's Vault, the tour includes a visit inside a crime museum and bootlegging tunnel. Additional features include historic video footage, a crime quiz, and a souvenir pamphlet with photos. The guide’s commentary is interactive and in English. Throughout the tour, you will learn about the paths gangsters followed and the locations of key events in Chicago’s criminal past. The tour operates on a fixed schedule and requires arriving early for check-in.

Highlights

Bus tour lasting about 2 to 2.5 hours
Stops at St Valentine's Day Massacre, Biograph Theatre, Holy Name Cathedral
Live English commentary with interactive crime quiz
Visit inside Nitti's Vault crime museum and bootlegging tunnel
Photos allowed at infamous crime scenes
Souvenir brochure with historic photos included

What's included

Profile of Prohibition Era personalities
Photo opportunities at well-known crime locations
Access to mini mob museum
Live interactive English-speaking guide
Historic video footage during the tour
All listed inclusions depend on availability
Participation in exclusive crime quiz
Keepsake brochure offering special deals

What's not included

Gratuity recommended at about $5 per person via cash or Venmo
No translations, audio guides, or headphones provided

Itinerary

1

Chicago Crime Tours and Experiences

The tour starts and ends outside 163 E. Pearson Street, near Michigan Avenue. Here, the guide introduces the histories of key gangsters like Al Capone, John Dillinger, Frank Nitti, Dean O'Banion, and Bugs Moran. Guests can disembark to explore crime scenes such as the St. Valentine's Day Massacre site, the handshake murder location, and the safe and tunnels used by 'The Enforcers.'

15 min

2

Pick-up and Drop-off Location

The bus pick-up and drop-off point is directly across from the Chicago Landmark at 163 E. Pearson Street.

3

Museum of Contemporary Art Chicago

The route passes by the Museum of Contemporary Art, located close to the tour's starting point, adding an architectural and cultural landmark to the journey.

4

John Hancock Center

The bus travels through the historic Streeterville neighborhood, offering views of the John Hancock Center.

5

The Magnificent Mile

The tour includes a drive along the Magnificent Mile, a well-known Chicago shopping and cultural district.

6

Abraham Lincoln Park

The bus passes Abraham Lincoln Park en route to several historic crime sites across Chicago.

7

North Avenue Beach

The route includes a drive along Lakeshore Drive with views of North Avenue Beach.

8

Biograph Theatre

Guests see the Biograph Theatre and Harry Caray's Italian Steakhouse. The bus departs on schedule and late arrivals cannot join the tour once it has left.

10 min

9

Oz Park

The bus drives past Oz Park as it approaches the site of the St. Valentine's Day Massacre in the Lincoln Park area.

10

Thirty Five E Wacker

The tour passes by the Jewelers Building, a historic landmark.

5 min

11

Chicago River

The bus crosses the State Street Bridge, providing views of the Chicago River, the city skyline, and a historic speakeasy.

12

Nitti's Vault

The tour includes a visit inside Nitti's Vault, a crime museum featuring a historic bootlegging tunnel.

10 min

13

Holy Name Cathedral

Guests walk the final steps of Northside gangster Hymie Weiss at Holy Name Cathedral.

5 min

14

Historic Water Tower

The tour concludes across from the Historic Water Tower, a surviving structure from the Great Chicago Fire of 1871, often open to visitors before or after the tour.

Meeting point

Bus pickup OUTSIDE 163 E. Pearson (SE side of Pearson St and Michigan Ave). Report 15 minutes early for check-in. Bus departs on time. Look for the tour guide at the bus.

End point

Bus pickup OUTSIDE 163 E. Pearson (SE side of Pearson St and Michigan Ave). Report 15 minutes early for check-in. Bus departs on time. Look for the tour guide at the bus.

Languages

English (guide)

Cancellation policy

  • Cancel at least 24 hours before start for a full refund.

Additional info

1–15 travelers per booking
Mobile ticket
Pushchair and stroller friendly
Service animals are welcome
Reachable by public transport
Suitable for all fitness levels
The bus leaves on time; guests should arrive at least 15 minutes early for check-in and call the number on the ticket if the bus is not visible 10 minutes before departure.
Joining the tour after the bus departs is not allowed; seating is on a first-come, first-served basis without guaranteed joint seating.
There are no restroom breaks during the tour; guests should use facilities before boarding.
Eating and drinking are not permitted on the bus.
There is no onsite office for this tour.
The bus has five steps and some stops require stairs; no electronic lift is available; limited storage for folding wheelchairs or strollers is provided.
Audio and video recording or services require written permission from Chicago Crime Tours and Experiences.
Passengers should kindly refrain from talking or translating on the bus during the tour.
Total
$99Save 10% vs Viator