The Dark Side of the Architecture
Chicago’s architectural history is inseparable from its criminal history — the same city that produced the skyscraper also produced Al Capone, the St. Valentine’s Day Massacre, the gangland wars of Prohibition, the serial killings of H.H. Holmes (whose “Murder Castle” was built for the 1893 World’s Columbian Exposition), and a century of organised crime that shaped the city’s politics, its architecture (speakeasies hidden behind legitimate facades, tunnels beneath the streets, buildings designed for surveillance), and its popular mythology.
A ghost and crime tour explores this darker narrative — visiting the sites of notorious events (the Biograph Theater where John Dillinger was shot by FBI agents in 1934, the site of the St. Valentine’s Day Massacre on North Clark Street, the former locations of Capone’s operations), the haunted buildings (the Congress Plaza Hotel, Bachelor’s Grove Cemetery), and the architectural connections between the built environment and the criminal underworld.
What You Will See
The Biograph Theater — the movie palace (now a venue and theater) where FBI agents ambushed and killed bank robber John Dillinger on 22 July 1934, after being tipped off by the “Lady in Red.”
The site of the St. Valentine’s Day Massacre — on 14 February 1929, seven members of Bugs Moran’s gang were murdered in a North Clark Street garage by gunmen posing as police officers, in a hit ordered by Al Capone. The garage has been demolished, but the site and the story remain.
H.H. Holmes and the Murder Castle — Holmes built a hotel near the 1893 World’s Fair site that was designed with hidden rooms, soundproofed chambers, gas lines for asphyxiation, and a basement crematorium. The building was demolished, but the story — and the site — are covered on guided tours.
The Congress Plaza Hotel — one of Chicago’s most famous haunted buildings, with reported ghostly activity on several floors. Ghost tours visit the hotel and narrate the stories associated with its history.
Frequently Asked Questions
Are the ghost and crime tours historically accurate?
The crime history (Capone, Dillinger, the St. Valentine’s Day Massacre, H.H. Holmes) is well-documented and the guides present accurate historical accounts. The ghost stories are presented as reported experiences and folklore — whether you believe in ghosts is your prerogative; the guides present the material with appropriate ambiguity.
Are ghost tours suitable for children?
The crime content includes murder, organised violence, and serial killing. The ghost content includes haunting narratives that may frighten younger children. Most operators recommend ages 12+ for crime tours and 10+ for ghost tours. Check the specific operator’s content and age guidance.
How long is a ghost and crime tour?
Typically 1.5–2.5 hours, usually conducted in the evening (the atmosphere is better after dark). Walking tours cover 2–3 kilometres. Bus tours cover more ground and reach sites outside the central area.
Do ghost tours relate to architecture?
Yes — many of Chicago’s significant buildings have crime or ghost stories attached. The Congress Plaza Hotel, the Excalibur nightclub (a former historical society building with reported hauntings), and the speakeasy architecture of the Prohibition era are all architecturally significant. The best ghost and crime tours integrate the building history with the narrative.