Chicago’s long and fascinating history — and that includes quite a few ghost stories. This Halloween, explore the city’s spooky side, from supernatural sites to true crime scenes, with these haunted tours of Chicago.

Chicago Ghost Tours from Free Tours by Foot

Hear all about Chicago’s spooky side on this walking ghost tour of the Loop. Highlights include the haunted Congress Hotel, Chicago’s old Red Light District, “Death Alley” outside the former Iroquois Theatre, the site of the S.S. Eastland Disaster, tales of H.H. Holmes and John Wayne Gacy and more. Tours take approximately 2 hours.

Haunted Tours of Historic Prairie Avenue

Glessner House

Tales of strange sounds, unexplained sightings, and untimely endings await as you explore Prairie Avenue after dark. This one-hour evening tour will cover the mysterious deaths and lingering ghosts of the historic district. Tours begin at Glessner House and cost $15 per person. Groups are limited to six people to ensure social distancing.

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Ghosts and Gangsters kayak tour

Learn about the city’s “Wild West” early days as you kayak down the Chicago River at night. Hear about the rise of powerful mobsters like Al Capone and discover the most haunted areas of the Chicago River. Tours are approximately 2 hours, with a 25-minute pre-launch orientation. Your ticket includes either a single or double kayak, life vest, paddle, guide, and paddling lesson.

Graceland Cemetery in ChicagoGraceland Cemetery © Eric Allix Rogers

Chicago Ghost Tours with Nightly Spirits

Nightly Spirits Chicago has explored some of the most haunted bars, alleys, and buildings in the city to create one of the best ghostly pub tours of Chicago. Visit Prohibition era sites frequented by John Dillinger, Al Capone, and rumored supernatural encounters. The tour begins at one of the city’s most haunted bars, Red Lion Pub in Lincoln Park, and last approximately 2.5 hours.

Haunted history tours by Lincoln Park Zoo

Join Adam Selzer, author and host of Mysterious Chicago Tours, leads spine-tingling virtual tours that dig into the zoo’s spooky history. Learn all about the area’s beginnings as a cemetery and alleged hauntings over the years. In-person tours may be available during the week of Halloween, pending city and state guidelines. Check back for updates.

Leopold and Loeb tour by Chicago History Museum

Nathan Leopold and Richard Loeb thought they could commit the perfect murder — but their gruesome crimes would make them into two of Chicago’s most infamous killers. This virtual true crime tour, hosted by author and historian Paul Durica and the Chicago History Museum, explores the Kenwood neighborhood and society’s fascination with true crime.

Entrance to Bohemian National Cemetery in ChicagoBohemian National Cemetery © Adam Alexander

Chicago Haunted Tours with Absolutely Segway Chicago

Glide around the city on this nighttime Segway tour to discover Chicago’s true ghost stories and view the site of some of Chicago’s most infamous events. Among the many stops on the tour, you’ll experience places such as “Death Alley” and Buckingham Fountain, and hear stories of Al Capone’s haunted yacht, and the famous gangster’s affiliation with a notorious Michigan Avenue hotel — allegedly the most haunted hotel in the city.

Ghost Hunt tour by Chicago Hauntings

This walking tour of the old City Cemetery grounds might just convert even the most convinced skeptics. You’ll learn the spooky history of the cemetery on this ghost hunt tour and stop at other paranormal sites, like the Suicide Bridge, the haunted zoo, and the site of the St. Valentine’s Day Massacre.

Haunted History Tours with Weird Chicago

Choose from walking tours or a private bus with Weird Chicago. Their Haunted History tour of the downtown area offers tons of fascinating info behind Chicago’s creepiest landmarks, from true stories to ghostly tales. The two-hour experience will cover both both famous and little-known spots, revealing some of the city’s creepiest history and urban legends/