Discover the dark side of Chicago on this 2-hour walking tour. Explore sites of death, tragedy, and hauntings, and learn about the city’s darkest characters and stories.
Discover the dark side of Chicago on this 2-hour walking tour. Explore sites of death, tragedy, and hauntings, and learn about the city’s darkest characters and stories.
- River North - Prepare to be amazed by our itinerary, which is split between River North and Chicago’s Loop neighborhood. Explore intriguing dark sites in both areas, including the hotel where a notorious serial killer stayed after his crimes, and a gangster hideout featuring a secret vault.
- Chicago - We’ve intentionally kept the details vague…
- River North - Prepare to be amazed by our itinerary, which is split between River North and Chicago’s Loop neighborhood. Explore intriguing dark sites in both areas, including the hotel where a notorious serial killer stayed after his crimes, and a gangster hideout featuring a secret vault.
- Chicago - We’ve intentionally kept the details vague to ensure surprises at every corner with stories of ghosts, gangsters, disasters, and more! From chilling cold spots to eerie energy and tales of the macabre, this tour reveals the darker side of Chicago.

- Expert guide
- Expert guide
- Gratuities
- Gratuities
Uncover the mysterious side of Chicago with a spine-tingling 2-hour walking tour. Covering nearly 2 miles at a leisurely pace, this tour unveils tales of gangsters, tragedies, and restless spirits lurking behind the city’s glamorous exterior. Discover hidden mob hideouts, psychopaths in plain sight, and calamities like the Iroquois Fire and Eastland…
Uncover the mysterious side of Chicago with a spine-tingling 2-hour walking tour. Covering nearly 2 miles at a leisurely pace, this tour unveils tales of gangsters, tragedies, and restless spirits lurking behind the city’s glamorous exterior. Discover hidden mob hideouts, psychopaths in plain sight, and calamities like the Iroquois Fire and Eastland Disaster.
Join the exploration of historic sites where gangsters once convened and where ghosts are rumored to linger. Along the journey, delve into the origins of ghost lore—are they genuine sightings or architectural illusions? Determine for yourself whether Chicago’s most haunted stories are fact or fiction. Ideal for autumn evenings and inquisitive minds, this tour combines true crime, gangster history, and ghost stories into an unforgettable adventure.
For a full refund, cancel at least 24 hours before the scheduled departure time.
For a full refund, cancel at least 24 hours before the scheduled departure time.