Chicago Gangsters and Ghosts Tour – Late Night Halloween Special
About this Event
Delve into the dark secrets of the South Loop, once a vice district, as your historian guide shares captivating tales of Al Capone and the city’s infamous past. Explore haunted locations like the Palmer House and the Chicago Theatre, and hear eerie stories of spirits that linger in Death Alley and along the Chicago Riverwalk. This tour culminates at the Congress Hotel, renowned for its ghostly sightings, making it the perfect way to experience Chicago's haunted history at midnight.
- Late-night Halloween walking tour through Chicago's South Loop, ending at midnight.
- Hear true stories about notorious gangsters like Al Capone
- Visit haunted spots including the Chicago Theatre and Palmer House
- End your tour at the Congress Hotel, one of Illinois' most haunted locations
Agenda
🕑: 10:00 PM - 10:20 PM
Chicago Riverwalk
Host: Expert tour guide
Info: As we cruise along the historic Chicago Riverwalk, look down at the dark waters that hold some of the city's deepest secrets. During the roaring 1920s, this waterfront was the lifeblood of Al Capone’s bootlegging empire
🕑: 10:20 PM - 10:30 PM
Chicago Theatre
Host: Expert tour guide
Info: Snap a photo under one of the most iconic landmarks in the United States, the glowing, six-story-high "CHICAGO" marquee
🕑: 10:30 PM - 10:40 PM
"Death Alley"
Host: Expert tour guide
Info: Step into the chilling shadow of "Death Alley," a narrow brick passageway where the lingering terror of over 600 lives lost in the 1903 Iroquois Theatre fire still hangs heavy in the air. Deep in the darkness of Chicago's Loop, feel the temperature plunge as phantom hands brush past you and panicked whispers echo off the cold, scorched walls.
🕑: 10:40 PM - 11:00 PM
Palmer House
Host: Expert tour guide
Info: Step inside the breathtaking, gold-leafed lobby of the Palmer House, a masterpiece of Gilded Age opulence. While it looks like a royal palace today, this historic hotel holds a dark and legendary past.
🕑: 11:00 PM - 11:20 PM
Cloud Gate "The Bean"
Host: Tour Guide
Info: Looming under the pitch-black sky of Millennium Park, the seamless silver curve of "The Bean" glows with an eerie, otherworldly light, twisting Chicago’s night skyline into a distorted nightmare. From across the dark lawn, the cold, silent monolith reflects the city's pale lights, staring back like a massive, alien eye watching your every move.
🕑: 11:20 PM - 11:40 PM
The Art Institute of Chicago
Host: Expert tour guide
Info: Guarded by its two iconic bronze lions, The Art Institute of Chicago looms under the dark skyline, where centuries of haunted lore wait in the shadows. As you stand before its dimly lit facade, you'll hear chilling tales of spectral footsteps pacing empty galleries and restless spirits trapped alongside the ancient masterpieces within.
🕑: 11:40 PM - 11:59 PM
The Congress Hotel
Host: Expert tour guide
Info: Looming large at the edge of Grant Park, The Congress Plaza Hotel stands as the tour's final and most heavily haunted stop. Known as one of the most paranormal locations in America, its dark windows hold terrifying tales of Al Capone’s ghost, the notorious room 441, and the restless spirits of tragic guests who never checked out.
Where is it happening?
Event Location & Nearby Stays:
USD 45.00



















