Chicago's ghost stories come with names attached: Al Capone, H.H. Holmes, Resurrection Mary. Between the Great Fire of 1871, the gangland 1920s and a cemetery the city literally built a park over, the Windy City gives its guides more documented material than almost anywhere in the Midwest. This guide compares twelve Chicago ghost tours, on foot, by bus, by bike and by Segway, so you can pick the format and the era that suit you.
1. Chicago: Gangsters and Ghosts Tour Walking Tour
A historian guide takes the Loop back to the roaring twenties, when the neighborhood ran on bootleggers, speakeasies and Al Capone. Stops include onetime gangster hangouts and reputedly haunted addresses like the Palmer House, the Congress Hotel and Death Alley.
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2. Chicago Hauntings Original Ghost Bus Tour
The cover-the-city option: three hours by bus with a historian guide, reaching the old City Cemetery grounds, the Levee vice district, Prairie Avenue and the site of the St. Valentine's Day Massacre, places too far apart to walk in one night.
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3. Haunted Chicago Booze and Boos Ghost Walking Tour
A mile-long crawl with a guide costumed as a flapper or a 1920s gangster, threading stories of forgotten cemeteries and lingering spirits between three bar stops, drinks at your own expense. History first, happy hour a close second.
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4. Medieval Torture Museum Ticket with Audio Guide and Ghost Hunting
Not a tour so much as a destination: advance tickets to the Medieval Torture Museum, with an audio guide covering the practices and devices, realistic models to drive the point home. Book ahead for a smooth visit.
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5. Embers of the Windy City: Chilling Chicago Ghost Tours
A small-group walk through Lincoln Park after dark, passing pubs and theaters said to be haunted, with macabre legends and unexplained happenings from the era of gangsters, bootleggers and jazz along the way. The five points the listing names are all pass-bys, and none of them is a former burial ground.
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6. Lincoln Park Hauntings Ghost Investigation Tour
A paranormal investigator walks you through Lincoln Park's layered history, the Great Fire of 1871, Suicide Bridge, the St. Valentine's Day Massacre and the old City Cemetery beneath the park, and hands you the ghost-detecting equipment to run your own readings.
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7. Chicago: Prairie Ave Historic District History and Ghost Tour
Prairie Avenue became the city's millionaires' row after the Great Fire of 1871, home to the Armour, Field, Kimball and Pullman families, and six blocks of it survive rather than the whole street. This one pairs that Gilded Age history with a ghost investigation among houses where the former owners are said to linger.
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8. Chicago Private Smartphone Scavenger Hunt Game and Tour
A private phone-based scavenger hunt that strings the city's haunted locations into a story. Solve a puzzle, unlock the next chapter, follow the directions to the next stop. Go whenever you like, at whatever pace your group argues its way into.
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9. The Devil in the White City: A Haunting History Tour
A three-hour deep dive inspired by the book, covering the 1893 World's Columbian Exposition and the crimes of H.H. Holmes. The listed stops are the Prairie Avenue Historic District, Jackson Park and its Japanese Garden, the Union Stock Yard Gate and the Museum of Science and Industry. The operator's description also names Midway Plaisance Park and the so-called Murder Castle site, which was demolished in 1938. The one to book if you read the book.
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10. Haunted Ghosts and The Chicago Outfit Segway Tour
Gliding through the city by moonlight behind a costumed local guide in a small group, covering the sites of some of Chicago's grimmest murders and disasters while the skyline does its nighttime show. It was bookable and flagged likely to sell out at our July 30, 2026 check, with a minimum age of 12 and a 100-pound minimum rider weight.
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11. Chicago: Halloween Ghost Stories Evening Small-Group Bike Tour
An evening ride through the city's scary heritage with professional actor guides playing the ghosts to life, in a group kept small. The route covers Resurrection Mary, the notoriously haunted Levee District and the story of H.H. Holmes, the city's most infamous killer. A Halloween-season special.
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12. Chicago: Private Haunted History Ghost Tour
The private option covers three headline locations in one go, the Murder Castle site, Death Alley and the old Congress Hotel, with Al Capone woven through, and a guide whose attention belongs entirely to your group.
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Questions people ask
Is Chicago haunted?
The city's claims rest on documented disasters and crimes: the Great Fire of 1871, the St. Valentine's Day Massacre, H.H. Holmes and the fact that Lincoln Park sits atop the old City Cemetery. Whether the reported activity follows from all that is the question every tour lets you test.
What is the most haunted place in Chicago?
The Congress Hotel and Death Alley behind the old Iroquois Theatre site take the most votes downtown, while Resurrection Mary owns the roadside-legend category and Lincoln Park's buried cemetery unsettles everyone who learns about it.
Are ghost tours in Chicago worth it?
Yes, especially for true-crime and history readers; Chicago's material is unusually well documented. Choose the bus to cover the whole map, a Loop walk for the gangster era, or an investigation tour if you want equipment in hand.
Should I take a walking tour or the ghost bus?
Walk if you want the Loop's density, the Palmer House, the Congress Hotel and Death Alley sit within blocks of each other. Take the bus for the far-flung sites like the Levee district and Prairie Avenue, and dress in layers either way; the lake wind is not a legend.
Keep reading
Trading lake wind for desert sky sometime? Freaky Foot Tours runs walking tours in three Arizona towns; see our locations page.
