Chicago Gangsters and Ghosts Minibus Tour

Discover Chicago's landmarks connected to local crime history & haunted legends on a guided Gangsters & Ghosts minibus tour. Learn about Prohibition-era figures, historic rivalries, & city mysteries.
Begin your journey aboard a minibus at the historic Palmer House, where you'll be introduced to Prohibition-era Chicago history and Al Capone. Discover his origins, his rise through the underworld alongside Johnny Torrio, and the secret escape doors he used to flee the hotel's Empire Ballroom during its speakeasy era.

Tour Highlights & Key Stops:

- Congress Hotel: Ride past this historic hotel, famous for its supernatural legends and haunting accounts. Hear reported ghost stories and unexplained encounters connected to Room 441, the 12th-floor "Ghost Boy," and local lore surrounding Capone's 8th-floor business suite.

- Grant Park & H.H. Holmes: Step back in time to the 1893 Chicago World's Fair and trace the history of H.H. Holmes. Learn about his life in Chicago, his complex financial schemes, and his ultimate downfall before transitioning into the backstory of Prohibition-era organized crime.

- Dearborn & Madison (Chase Tower): Look out from your minibus to the site of historic gangland rivalries and explore the high-stakes conflict between competing Chicago syndicates.

- Death Alley & LaSalle Bridge: Drive past the site of the Iroquois Theatre Fire to learn about the historic tragedy and the resulting global fire safety codes. At LaSalle Bridge, uncover the story of the SS Eastland disaster, one of the deadliest maritime accidents in American history.

- Harry Caray’s Italian Steakhouse: Stretch your legs at the former apartment building of Frank Nitti. Go inside to inspect the hidden tunnels and vault discovered beneath the building.

- Holy Name Cathedral: Step off the minibus in River North to stand near the site of historic Prohibition-era standoffs and inspect the architectural markings left on the cathedral’s stone facade.

- Chicago River Stop: Capture photos, hear about local ghost stories, and learn about the Great Chicago Fire. Before reboarding, take in views of the landmark Tribune Tower and the Jewelers Building, home to the former rooftop speakeasy, the Stratosphere Lounge.

Finally, sit back in comfort on the drive back to the Palmer House as your guide details the conclusion of Al Capone's career, from the St. Valentine's Day Massacre to his federal prosecution by the Untouchables, his prison sentence, and his final years.

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