Chicago Gangsters and Ghosts Tour: Al Capone and mob history
Bullet scars on cathedral stone, secret mob tunnels, and the river's deadliest night
This minibus tour traces Chicago's gangster era and paranormal history through nine stops across the city, led by an expert guide in English. You'll start at the Palmer House, where Al Capone operated from the Empire Ballroom, then move through Grant Park to learn about H.H. Holmes and the 1903 Iroquois Theatre fire. The route includes the actual bullet scars on Holy Name Cathedral, a hidden underground tunnel beneath Harry Caray's building, and ends with a ghost-hunting photo opportunity along the Chicago River.
Step-by-step itinerary
Explore Chicago's gangster and ghost history
- Start outside Palmer House
- Visit haunted Congress Hotel
- Drive through Grant Park
- Stop at Mob daylight hit site
- Pause at Iroquois Theatre fire site
- Cross LaSalle Street Bridge
- Explore Harry Caray’s building
- Inspect Holy Name Cathedral bullet scars
- Photo and ghost hunt at Chicago River
- Palmer House Hilton 5m
- Grant Park passing by
- Chase Tower 5m
- Holy Name Cathedral 5m
- Chicago Riverwalk 10m
What’s included
- Expert tour guide leading the minibus.
- stops at the Palmer House, Grant Park, the Iroquois Theatre site, Holy Name Cathedral, and the Chicago Riverwalk.
- access inside Harry Caray's building to view the hidden tunnel and secret vault.
- paranormal photo opportunity along the Chicago River.
- Tuesday, Friday, Saturday and Sunday 18:00
- Wednesday and Thursday 18:00 20:00
Information
Minibus tour through Chicago's gangster era and haunted sites, starting at the Palmer House where Al Capone ran his speakeasy, with stops at Grant Park.
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The experience
The Palmer House opens the tour as the entry point to Chicago's underworld. Al Capone used the Empire Ballroom as his personal speakeasy, and you'll hear how the hotel became a nexus of mob activity. From there, the minibus moves to a second haunted landmark where Capone managed his criminal empire from an 8th-floor suite, with documented ghost stories tied to the building's violent past.
Grant Park becomes the setting for darker chapters: the 1893 World's Fair that drew millions into the city and directly into the path of H.H. Holmes, documented as America's first serial killer. The tour then shifts to the Loop, where you'll learn about the Tony Lombardo assassination: a daylight mob hit on busy city streets. The Iroquois Theatre stop centers on the 1903 fire that killed more people in a single building than any other fire in U.S. history, with the rear alley still known as "Death Alley." At Harry Caray's building in River North, you step inside to see the hidden underground tunnel and secret vault that once belonged to Frank Nitti, Al Capone's enforcer.
The final stops bring you to Holy Name Cathedral, where you can inspect the actual bullet scars embedded in the cornerstone from a gangland shooting, and then to the Chicago Riverwalk for a paranormal photo opportunity. Here the guide explains the river's role in the Great Chicago Fire of 1871 and the maritime disaster of July 24, 1915, when the LaSalle Street Bridge crossing became the site of Chicago's worst water tragedy. The two-hour tour wraps at the river's edge.
Top questions
Can children come?
Yes. Ticket types: Child (4 to 12 years). Children under 4 can't be included in the booking.
What is the story behind the bullet scars on Holy Name Cathedral?
Holy Name Cathedral's cornerstone still bears the actual bullet scars from a gangland hit, a physical record of mob violence carved into the building's stone in River North. The guide explains the circumstances of the shooting during the tour's stop there.
Can I go inside the buildings on this tour, or do we stay on the bus?
You get off the bus at several stops. At Harry Caray's building, you step inside to view the hidden underground tunnel and secret vault that once belonged to Frank Nitti. At the Chicago Riverwalk, you step out for photos and to participate in the ghost-hunting activity along the water.
What happened at the Iroquois Theatre that makes it part of this tour?
The Iroquois Theatre fire of 1903 was the deadliest single-building fire in U.S. history. The tour pauses at the site and explains the tragedy, including the rear alleyway that has been known as "Death Alley" ever since the disaster.
Does the tour cover Al Capone's actual locations in Chicago?
Yes. The Palmer House is where Capone frequented the Empire Ballroom as his personal speakeasy, and a second stop is the hotel where he managed his criminal empire from an 8th-floor suite. The tour also covers other mob-related sites across the city, including the Tony Lombardo assassination location in the Loop.
What is the paranormal photo opportunity at the end?
At the Chicago Riverwalk, you step out along the water for photos and active ghost hunting. The guide explains how the river played a deadly role in the Great Chicago Fire of 1871 and discusses the spirits said to haunt the waters, including those from the 1915 maritime disaster.
Operated by Empire Tours - Chicago. Explorevia does not run this tour: we compare it with similar options, and you book it with our booking partner.
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Chicago Gangsters and Ghosts Tour: Al Capone and mob history
2h · EN
from US$ 65 per person
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