Haunted by Our Dark Side: Chicago Ghosts, Gangsters, and True Crime Tour

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.

Duration

2 Hours

1.75 miles on foot

Highlights of the Tour

• Sites of major Chicago disasters, all avoidable and tragic;
• Architecture that feels "ghostly" because of its design;
• Cold spots and stories of sightings at famously haunted places;
• Infamous gangster shoot-outs and hideouts...

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.

What to Bring:

• Comfortable clothing and shoes
• Camera
• Umbrella if needed
• Bottle of water if needed
• Extra cash for gratuities for your guide (optional, but appreciated!)

Please arrive at least 5 minutes prior to the scheduled tour time. Your guide will be carrying a binder.

Tours generally run rain or shine, but are possibly canceled in case of extreme weather -- we will call customers the day of the tour if weather prohibits an enjoyable experience, and offer them either a reschedule or refund.