The Stories Behind Chicago's Most Haunted Places

By Emma G. Gallegos in Arts & Entertainment on Oct 30, 2015 5:39PM

Chicago's history is littered spooky and tragic tales from the prolific serial killer H.H. Holmes to the Great Chicago Fire to whatever lies beneath the surface of the Chicago River or Lake Michigan. Even our local Hooters might have a history. With Halloween approaching, it's the perfect chance to revisit a few of city's most haunted places. As always leave your own favorite ghost stories in the comments.

blue-star.jpg
The former site of Cullerton Hotel (Photo by Chicago Crime Scenes via the Creative Commons on Flickr)

The Cullerton Hotel

Part of Al Capone's legacy in Chicago may be the trail of unhappy spirits left in his wake. There are the supposedly cursed bricks at the site of the St. Valentine's Day Massacre that are believed to have brought bad luck to their owners. But in recent years, paranormal enthusiasts have honed in on the site of what was once known as the Cullerton Hotel, a bordello run by Capone. The hotel was in The Levee, which was Chicago's red-light district. Until the whole district on the near South Side was shut down by the vice commission, the hotel was the site of gambling, child prostitution, gambling, saloons and peep shows.

Anna Aaron of Extreme Vision Paranormal described it as a "quite a place of energy and activity." In particular, psychics and other ghost hunters said the back rooms where the women were kept made them uneasy and they felt "a strong female presence." They also felt the presence of an angry "blue demon" who kept saying "azul" (the Spanish word for "blue") in a low, growly voice. After the ghost hunters' visit, David, then the owner of Blue Star Auto Store that took over the space, later told CBS Chicago that though there is some weird stuff at the site, he's never had any encounters from beyond. Right now there are plans in the works to transform that site into apartments. DNA Info reported last year that developers don't plan on tearing down the building but instead replacing all of the exterior bricks. Joshua Rubenstein, a principal with the developer Windy City RE, told DNAinfo, "We find that for us there's greater value in keeping the existing building. ... In this case there's also a bit of a historical angle."

The Cullerton Hotel was located at 2001 S. State St. on the near South Side

hh-holmes-murder-castle.jpg
It didn't look so scary then! (Wikipedia)

The Site of H. H. Holmes' "Murder Castle"

H.H. Holmes, one of the most terrifying serial killers of all time who will soon be played by Leonardo DiCaprio, set up shop in Englewood before the Columbian Exposition. The former site of his "Murder Castle" is currently a post office that gives no hint of its past:

hh-holmes-po.jpg
Here is where the "murder castle" once stood (Google Maps)

The first floor had shops, and the third had his personal apartments. The nasty stuff—killing, experimenting on or getting rid of the bodies—reportedly happened on the second floor and cellar. The house was like a real-life haunted house with 100 rooms, stairs and passageways that led nowhere, doorless rooms, trap doors, padded rooms, a shaft to the cell for easy disposal of bodies and a gas chamber. Holmes oversaw the construction. He was constantly hiring and firing workers so none of them would know the full design of what was actually being built.

Ghosts of Chicago author Adam Selzer visited the site to see what was leftover from the bad old days. He found a tunnel that might have been an escape hatch and he heard some very eerie voices.

The Murder Castle was once located at W. 63rd St. and S. Wallace Ave. in Englewood

eastland-disaster.jpg
The Eastland Disaster (Bain News Service via the Library of Congress)

The Former Second Regiment Armory

There are all sorts of hauntings rumored to have come out of the horrific Eastland disaster on the Chicago River on July 24, 1915. When the Eastland tipped over into the Chicago, 844 people were killed. Some people say they can hear moans and screams near the Clark Street Bridge where the tragedy happened. But a lot of the haunting is centered around the makeshift morgue set up in what was then known as the Second Regiment Armory. The building was about 1.5 miles away from the tragedy itself, but it was an awful scene between the victims and their grieving, hysterical families who came to identify them.

"I saw hundreds of dead laid in rows," said Harlow Eldredge Smoot, according to the Eastland Disaster Historical Society. "Mothers still holding their babies. Women with handfuls of other women’s hair! And the agony expressed on the faces of the dead. Young people dressed in white dresses and trousers, and after being thrown into that stinky, dirty water of the Chicago River they looked awful. I shall never forget [it]."

harpo-studios.jpg
Exterior views of Harpo Studios on March 17, 2014 in Chicago, Illinois. (Photo by Timothy Hiatt/Getty Images)

The Second Regiment Armory clearly wasn't cursed—up until last year, it was the home of Oprah's Harpo Studios—but employees did say it was haunted. They reported seeing an apparition called the "Gray Lady," and hearing strange sounds like sobbing, old music, footsteps sounding like they belong to a large group and even the laughter of children. Commercial real estate developer Sterling Bay Cos. now owns the property.

The Second Armory Regiment was located at 1058 W. Washington Blvd. in the West Loop

congress-hotel.jpg
Congress Plaza Hotel (Photo by Kevin Klima via the Chicagoist Featured Photos pool on Flickr)

Congress Plaza Hotel

Some of the craziest ghost stories you'll ever hear in Chicago come from the formerly elegant Congress Plaza Hotel that was built to house out-of-towners visiting the Columbian Exposition in 1893. Most recently, self-described skeptic Australian chef Pete Evans got seriously spooked when he came into town after checking out Girl & the Goat. He wrote, "The walk from the elevator to room 447 was one of the weirdest experiences ... it suddenly felt airily cold and I sensed that something just wasn’t quite right with the energy, not only in the hallway, but even more so once I was inside my room." He high-tailed it out of there, and only then did he learn about the hotel's spooky history.

Selzer has a rundown of the sightings and their historical (if any) reference. In the late 1930s, a mother jumped out the window of the hotel with her two sons—Nazi persecution in their homeland was blamed. The ghost of her son Karel is believed to haunt the 12th floor. Captain Lou Ostheim, a Spanish American War vet, shot himself on the eve of his wedding at the turn of the 20th century. Guests and employees have reported seeing a shadowy figure who seems to enjoy scaring the bejeezus out of them. But there are stories of ghosts all throughout the hotel. Disconnected kitchen appliances turning on, pianos playing themselves, whispers, gunshots and humming. A story about a specter with a peg leg pops up repeatedly. Then again, not all the mayhem at the hotel is related to the undead.

The Congress Plaza Hotel is located at 520 S. Michigan Ave.

resurrection-cemetery.jpg
The Resurrection Cemetery Mausoleum in Justice, Illinois, which is notable for its stained glass windows as well as the story of Resurrection Mary (Photo by Tom Gill via the Creative Commons on Flickr)

Resurrection Cemetery

Chicagoland's most famous ghost is Resurrection Mary, a lovely hitchhiking specter who haunts Archer Avenue in the Southwest 'burbs. It's not clear who this Mary was when she walked among the living, though there are all sorts of theories. The most popular story is that there was a young woman who went out dancing at the Oh Henry Ballroom (now Willowbrook Ballroom in Willow Springs) sometime in the 1930s. She had a fight with her boyfriend and was killed in a hit-and-run after she decided to walk home. Other versions say she was on her way to go dancing. Now she hitchhikes along Archer Avenue. Some men (and it's usually men) claim that a beautiful young blonde woman dressed in white for a night of dancing asks for a ride and then she asks to be let out—or completely vanishes!—at Resurrection Cemetery. Some say Resurrection Mary bent the gates of the cemetery in the '70s, though cemetery workers emphatically denies this. The late ghost hunter Richard T. Crowe is credited with popularizing Mary's story and turning it into an important piece of Chicago folklore. In 1985, he claimed to have substantiated three dozen sightings since 1939. Resurrection Mary lives on as the subject of a local 5K, a horror movie and at least one bar marquee.

Resurrection Cemetery is located at 7201 Archer Ave. in Justice, Illinois

water-tower.jpg
Water Tower (Photo by John Hill via the Chicagoist Featured Photos pool on Flickr)

The Chicago Water Tower

What we know for sure is that the Chicago Water Tower, built of limestone, was one of few buildings in the burned district that survived the Great Chicago Fire of 1871. The tower stands as a symbol that connects the city to its pre-fire past. But there's a legend that says a selfless worker stayed behind, manning the pumps to help firefighting efforts until the flames crept upon the tower and he hung himself. There are reports of a hanging corpse in the tower windows.

The Chicago Water Tower is located at 806 N. Michigan Ave. on the Near North Side