Spirits of the Windy City: Is Chicago Haunted?

Published on January 11, 2024

Even if you, as Ray Parker Jr. sang, “ain’t ‘fraid of no ghost,” you’ll still want to take eATLAS’ Spirits of the Windy City Adventure, which visits several of the places described below and others, and pairs them with nearby drinks for a fun and spooky night out. The pub crawl was created by Concierge Preferred, a curated guide through some of the best activities Chicago has to offer.

By Dave Lifton (@daveeatschicago)

Built for the 1893 World’s Columbian Exposition, the Congress Plaza Hotel is believed to haunted by four spirits. The most famous is the apparition of a woman kicking sleeping guests awake in Room 441, and is reportedly the inspiration for Stephen King’s short story “1408.” People have also described having lights and appliances turned on by Peg Leg Johnny, a man who lived, and was killed, in the alley behind the hotel prior to its construction. Other guests have seen the ghost of a young boy whose mother killed herself in the Congress Plaza during World War II. Lastly, there is Al Capone, who is said to roam the building, but there is little historical evidence connecting him to the hotel.

Although the tales of H.H. Holmes preying on and murdering women at the fair were likely exaggerated, his exploits have nonetheless entered the lore of American true crime. A post office now sits on a part of the land in the South Side neighborhood of Englewood where his notorious “Murder Castle” once stood, and employees have described seeing and/or hearing numerous unexplained phenomena in the basement.

On Dec. 20, 1903, a fire broke out during a performance at the Iriquois Theatre in the Loop that caused more than 600 deaths due to inefficient safety features. Many of the deaths were the result of people jumping from the uncompleted fire escapes above Couch Place, the alley behind the theater’s entrance on Randolph St., which was then used as an impromptu morgue. Couch Place has since earned the nickname, “The Alley of Death,” and paranormal experts have claimed the alley has cold winds even on warm days, and is visited by those who perished on that day.

The Chicago Water Tower on Michigan Ave. is one of the few structures in town that survived the Great Chicago Fire of 1871, and serves as a symbol of the city’s strength and resilience. But that doesn’t mean it was unaffected by the destruction. One story is that a man decided to keep working as the fire spread and, as the flames began to engulf the tower, he climbed to the top and hanged himself. People looking up at the top windows of the tower have seen the ghostly figure of a man.

A few blocks north of the Water Tower is the Drake Hotel. During its opening night celebration on New Year’s Eve, 1920, a red-clad woman caught her fiancé with another woman. Distraught, she threw herself out of the 10th floor window, giving rise to the legend of the Lady In Red who haunts that floor and the ballroom.

Another wide-scale tragedy where spirits are said to roam is the site of the S.S. Eastland disaster on the south bank of the Chicago River at Clark St. On July 24, 1915, an outing to a picnic in Michigan City, Ind., for employees of the Western Electric Company turned deadly when the Eastland likely exceeded its capacity of 2,300 passengers. The top-heavy ship capsized into the river, and 844 people drowned. Bodies have been reported floating in the river at the site, and there have been stories of unexplained noises and figures in the Reid Murdoch building across the water, which was used as a morgue during the disaster.

In Graceland Cemetery, there is a statue of six-year-old Inez Clarke, who was killed by lightning in 1880, enclosed in glass. According to the legend, the statue disappears during thunderstorms.

Chicago’s Southwest Side is considered to be the domain of Resurrection Mary, who was killed while walking home after attending a dance at the Oh Henry Ballroom in nearby Willow Springs. For decades, she’s been spotted hitchhiking on Archer Ave. in the white dress she wore that fateful night, and she exits the car once it reaches Resurrection Cemetery in Justice, where she is buried. A bar across the street from the graveyard, Chet’s Melody Lounge, leaves a Bloody Mary at a corner barstool for her every Sunday.

One doesn’t get to be a major city without having some skeletons in the closet, and Chicago, a city rooted in tragedy, certainly has plenty. But do these spirits haunt Chicago? Paranormal experts say yes, and we’ll leave it up to you to determine if they’re correct.

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