Haunted by Our Dark Side: Chicago Ghosts, Gangsters, and True Crime Tour
Explore the Dark Side of Chicago • 2 Hours • 1.75 Miles • All Ages
What to Expect
A Ghosts & Gangsters & True Crime Tour Perfect for Autumn!
If you love ghost stories, gangster legends, and true crime TV, or even if you simply savor that eerie feeling of crisp autumn evenings, this is the Chicago tour for you. For two chilling hours, we’ll peel back the glamorous façade of the Windy City to uncover its darker side—where mobsters ruled, tragedies struck, and restless spirits still make their presence known.
On this 2-hour walking tour (just under 2 miles at an easy pace), you’ll hear real stories of rival gangsters gunning each other down right after church, psychopaths hiding in plain sight, and the unforgettable disasters that scarred Chicago’s past—from the Haymarket Affair to the Iroquois Fire to the Eastland Disaster. Along the way, you’ll step inside a few historic interiors where gangsters once gathered and where ghosts are still said to roam.
We’ll also dive into the origins of ghost lore: are people really seeing specters, or does the strange design of some buildings simply play tricks on the mind? You’ll learn why certain spots get labeled “haunted,” and decide for yourself if Chicago’s spookiest stories are fact, fiction, or something in between.
Perfect for fall evenings and curious minds alike, this tour combines a little taste of Chicago’s gangster history with spine-tingling true crime and ghost tales. You’ll leave with a deeper appreciation of the city’s past—and maybe a few goosebumps, too.
Ready to explore Chicago’s dark side? Join us for a tour that’s equal parts eerie, fascinating, and unforgettable.
Tour Details
- Runs rain or shine! We will be in touch in case of severe weather.
- Meeting Location: At the corner of Eric & Dearborn, in front of the Fedex Store at 34 W. Erie St.
Duration
2 Hours *1.75 miles on foot*
Address
River North & Chicago Loop
Pricing
| Adult | $35 |
| Child | $30 |
| Senior | $30 |
Cancellation Policy
For public tours booked directly through us, we generally issue a full refund for tours that are cancelled at least 72 hours before the tour date/time. That said, we rely on something of an “honor system” for cancellations, and we do ask that guests be sensitive to a small business’ difficulty selling tickets for their cancelled spots at the last minute, and ask that guests only cancel in case of emergency.
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