Spooky Places in and Around Chicago to Explore This Halloween

Chicago isn’t just a city of skyscrapers, deep-dish pizza, and historic landmarks—it’s also a city full of ghost stories and haunted destinations. From abandoned cemeteries to historic hotels with a reputation for paranormal activity, Chicago has a spooky side that draws thrill-seekers every Halloween season. If you’re ready to dive into the city’s darker history, these 14 haunted locations will send shivers down your spine.

1. Bachelor’s Grove Cemetery – The Most Haunted Cemetery Near Chicago

Located in the southwest suburbs, Bachelor’s Grove Cemetery has been abandoned for decades but is one of the most haunted places in the Midwest. Visitors have reported ghostly apparitions, floating orbs, phantom cars, and even a mysterious farmhouse that appears and disappears. The most famous legend is the “White Lady,” said to wander the grounds carrying an infant. Paranormal investigators from across the country continue to study this chilling site.

2. Congress Plaza Hotel – Chicago’s Haunted Landmark

Right in downtown Chicago on Michigan Avenue, the Congress Plaza Hotel is as spooky as it is historic. Built in 1893 for the World’s Fair, the hotel has long been associated with ghost stories. Guests report shadowy figures, unexplained noises, and cold spots. Some say the ghost of gangster Al Capone still lingers in the halls. With its grand ballroom and historic charm, it’s no surprise that the Congress Plaza is known as one of the most haunted hotels in America.

3. Hull House – The Legend of the Devil Baby

The Jane Addams Hull House is a historic site with a chilling legend. In the early 1900s, rumors spread about a “Devil Baby” born at the house. Thousands of curious Chicagoans flocked to catch a glimpse, though no proof was ever found. Today, visitors and staff claim to hear footsteps, whispers, and see ghostly figures. Whether you believe the legend or not, Hull House remains one of Chicago’s most eerie destinations.

4. Graceland Cemetery – Resting Place of Chicago’s Spirits

Graceland Cemetery on the North Side is both beautiful and unsettling. Many of Chicago’s most influential figures are buried here, but it’s the ghost stories that keep visitors talking. The most famous involves the statue of Inez Clarke, a young girl who died tragically in the 1800s. Legend says her statue moves or disappears during storms. The cemetery is filled with Gothic architecture, making it a hauntingly beautiful stop.

5. Resurrection Cemetery – The Tale of Resurrection Mary

One of Chicago’s most famous ghost stories comes from Resurrection Cemetery in Justice, Illinois. The legend of Resurrection Mary tells of a young woman who hitches rides with strangers, only to vanish near the cemetery gates. For decades, drivers have claimed to encounter her. Whether you believe the story or not, this site remains one of the most talked-about haunted spots in the Chicago area.

6. St. Valentine’s Day Massacre Site – Chicago’s Gangster Ghosts

Chicago’s gangster history is legendary, and the St. Valentine’s Day Massacre site is a reminder of its dark past. In 1929, seven men were executed in a brutal gangland slaying linked to Al Capone. Today, visitors say they hear gunshots, screams, and even see ghostly figures at the site. Though the original garage has been demolished, the lot still carries an unsettling energy.

7. Excalibur Nightclub (Now Tao Chicago) – Spirits of River North

Before it was Tao Chicago, the Excalibur Nightclub was one of the city’s most haunted nightspots. The building was used as a makeshift morgue after the Eastland Disaster of 1915, when a capsized ship claimed more than 800 lives. Staff and visitors have long reported eerie feelings, cold drafts, and sightings of ghostly figures inside the historic building.

8. Oriental Theatre – Ghosts of the Stage

Now known as the Nederlander Theatre, this Chicago Loop landmark is said to be haunted by actors and staff from its long history. Ghostly figures have been spotted backstage, and mysterious footsteps echo in the empty halls. The theater’s dark history includes a tragic fire in the Iroquois Theatre in 1903, which claimed more than 600 lives. Paranormal enthusiasts believe some of those spirits still linger today.

9. The Drake Hotel – The Lady in Red

The Drake Hotel on the Magnificent Mile is famous for luxury—and for one of Chicago’s most enduring ghost stories. Guests and staff have reported seeing the “Lady in Red,” a woman who supposedly leapt to her death after discovering her fiancé with another woman. To this day, her spirit is said to wander the Gold Coast Room and the hallways of the historic hotel.

10. Fort Dearborn Site – Spirits of Chicago’s Early Days

Chicago’s haunted history goes back to its beginnings. The original site of Fort Dearborn, near today’s Michigan Avenue Bridge, is believed to be haunted by the spirits of soldiers and settlers who perished during a violent battle in 1812. Visitors report feelings of dread and sudden cold spots when walking the area.

11. Holy Name Cathedral – The Ghost of Hymie Weiss

Holy Name Cathedral on State Street may be a sacred place, but it’s also the site of one of Chicago’s most infamous gangster murders. Hymie Weiss, a rival of Al Capone, was gunned down outside the church in 1926. Some believe his spirit remains, lingering in the shadows of the cathedral’s walls.

12. The Fine Arts Building – Ghostly Artists of Chicago

Built in 1885, the Fine Arts Building is a hub for artists and musicians. But it’s also said to house lingering spirits from its long history. Tenants and visitors have reported seeing ghostly figures, hearing phantom music, and feeling watched in empty hallways. The building’s old architecture only adds to its eerie reputation.

13. Prairie Avenue Mansions – Haunted Homes of Chicago’s Elite

Chicago’s Prairie Avenue District is home to some of the city’s oldest mansions, many of which were once occupied by wealthy industrialists. With over a century of history, it’s no surprise that ghost stories abound. From strange noises to ghostly figures in the windows, these historic homes remain part of Chicago’s haunted lore.

14. Chicago Water Tower – Survivor of the Great Fire

The Chicago Water Tower is one of the few structures that survived the Great Chicago Fire of 1871. Legend has it that a worker trapped inside the tower during the blaze still haunts the landmark. Visitors have reported seeing shadowy figures in the windows and hearing unexplained noises.

Travel Between Haunted Destinations in Comfort

Exploring haunted Chicago is thrilling—but parking, traffic, and late-night rideshares can take away from the fun. That’s why many locals and tourists prefer booking a private car service Chicago.

With a professional chauffeur, you can relax, stay safe, and enjoy every eerie stop on your ghost tour. Whether it’s Bachelor’s Grove, the Congress Plaza Hotel, or the Drake, traveling in comfort makes your spooky adventure unforgettable.