Chicago Gangsters and Ghosts Tour launched in 2017 as a hybrid product designed to capture two distinct visitor markets in a single ninety-minute walk. The walking tour begins at the Royal Sonesta Hotel at 71 East Wacker Drive — a 1929 art deco tower built as the Mather Tower's neighbor — and threads through the Loop and River North.
Guides cover the Chicago Outfit's central figures — Jim Colosimo, Johnny Torrio, and Al Capone — at the addresses they actually used: speakeasies, hotel suites, and corners where contract hits were carried out. The tour also stops at sites with documented paranormal reports, including buildings tied to the Eastland disaster of 1915 and the Iroquois Theatre fire of 1903.
A seated minibus version departs from the Palmer House Hilton at 17 East Monroe Street, the lobby of which has its own history as a 1920s political and gangland meeting place. Tours run daily with four departures — 11 am, 1 pm, 4 pm, and 8 pm — with seasonal adjustments. Pricing is $36 for adults, $34 for seniors, $26 for youth, and free for children under six.
Sources
- https://gangstersandghosts.com/
- https://www.choosechicago.com/articles/holidays/chicago-haunted-tours-for-halloween/
Phantom smellsPhantom voicesPhantom footstepsCold spotsApparitionsResidual haunting
The tour's ghost stops are anchored to addresses with documented mass-casualty events. The Iroquois Theatre fire of December 30, 1903, killed at least 602 people in a Loop theater built only weeks earlier; the alley behind the modern Nederlander Theatre, once nicknamed Death Alley by the press, is included on the route. Guides reference reports collected from theater workers and pedestrians since the 1920s, including the smell of smoke in the alley on still days.
The Eastland disaster of July 24, 1915, killed 844 Western Electric employees and family members when their excursion steamer rolled in the Chicago River. The tour visits riverbank stops where bodies were temporarily stored and where later building occupants — most notably the staff of Harpo Studios in the 1990s — described phantom voices and footsteps.
The gangster sites are presented in parallel. The Lexington Hotel, Capone's Prohibition-era headquarters, was demolished in 1995, but its former site at Michigan and Cermak is referenced. Hotel rooms in the existing Palmer House and Congress Plaza are included as buildings where staff have reported recurring activity. The minibus version expands the route to additional locations including former speakeasy sites along the Loop.