The 12 Most Bone-Chillingly Haunted Places Around Chicago

From serial killer lairs and ghastly hotels to curious modern-day nightclubs.

Spooky Season is filled with all your usual kitch—stoops lined with eerily carved pumpkins, plastic skeletons dangling from porches, and a ridiculous amount of brightly colored candy that seems to cover every surface. But October also comes with a less tangible hair-raising vibe… ghosts!

Teeming with creepy stories, unsolved mysteries, and urban legends, Chicago has a long history of unusual paranormal phenomena—whether you believe in that kind of thing or not, otherworldly events have been documented at sites across the city, many of which remain accessible to this day. But don't just take our word for it, find out for yourself at these 12 haunted Chicagoland destinations… if you dare.

Nederlander Theatre
Nederlander Theatre | Flickr/ajay_suresh

James M. Nederlander Theatre’s Death Alley

24 W. Randolph Street, Loop
Over on Randolph Street in the heart of Chicago lurks a pedestrian alleyway known as Couch Place, which has a far more sinister history than the name might imply. While the Nederlander Theatre, erected in 1926, now occupies the adjacent lot, the turn-of-the-century Iroquois Theatre once stood in its place. The Iroquois was built in the Renaissance-style, and was said to have cost a whopping 1 million dollars—that’s 32 million dollars today—boasting a grand opulence that surely attracted large audiences.

At the time, the newspapers claimed the theater was completely fireproof, quelling public fears leftover from the Great Chicago Fire 32 years earlier. During a sold-out show on one chilly December day, flames erupted from a stage light’s spark, and, panicking, the 1,724 patrons couldn’t find the exit doors. The hysteria led to many people jumping to their death, landing in the alley where a growing number of bodies piled up on top of one another. By the time the fire was extinguished, a total of 602 people had lost their lives.

The tragedy resulted in much-needed updates to fire safety measures both in Chicago and around the world, but at a massive cost. Today, there are documented accounts of screams, faint cries, physical pushes, cold spots, and other paranormal activity in and around Couch Place, earning itself the ghoulish nickname “Death Alley.”

The Drake Hotel
The Drake Hotel | Flickr/Stephen Hogan

140 E. Walton Place, Mag Mile
Guests of the famous Drake Hotel can expect unparalleled luxury and comfort, but that might not be all they’re in for. The iconic 1920s lodging has had its fair share of famous guests, including Bing Crosby, Queen Elizbeth II, Marylyn Monroe, Princess Diana, and Walt Disney. But lesser-known are the visitors who made a name for themselves not by checking in, but by never checking out…

Two such guests are said to be the grieving parents of Bobby Franks, the 14-year-old boy who was kidnapped and murdered by notorious criminals Leopold and Loeb, two wealthy University of Chicago students intent on committing the crime of the century. During the famous murder trial, the forlorn parents moved into the hotel to get away from the press and distance themselves from their anguish. While Franks’ father later died in his suite from “a broken heart,” his surviving mother never got over her son’s death, crying insistently in that same suite for years. Rumor has it they both live on inside that room, listlessly wandering the halls engulfed in everlasting sorrow.

The hotel is also home to another story, that of a young woman in a red dress. In 1920, she attended a New Year’s Eve Gala only to find her philandering husband with another woman. In a pit of despair, the woman in red leapt off the 10th floor balcony to her death. There have been reports of her ghost still haunting The Gold Coast Room and the Palm Court, both located on that very same 10th floor.

Marina City Towers
Marina City Towers | gg5795/Shutterstock

300 N State Street, River North
Marina City, the iconic corn cob-like structures jutting out over the Chicago River, has had dark ties from the start. Created in an attempt to keep white flight at bay, the developers envisioned a city within a city on Chicago’s downtown riverfront and left it in the hands of architect Bertrand Goldberg. Mayhem, naturally, ensued.

The east tower has long been the site of mysterious accidents and unusual deaths, with some events occurring even before the building's completion. In 1961, three workers fell to their death from the 43rd floor, and in that same year, seven men were severely injured when their elevator destabilized and plummeted. Only one year later, another worker tragically fell to his death from that same tower. Once the towers were finished, mysterious reports of apparitions and shadow people began to crop up, with residents claiming to be plagued with feelings of sadness and depression. A string of murders, strange deaths, and suicides ensued, and, to this day, the reputation of the corn cob towers remains disturbing and perplexing, leading to its super creepy appearance in Jordan Peele’s 2021 Candyman remake.

Golden Dagger
Golden Dagger

2447 N Halsted Street, Lincoln Park
The Golden Dagger is a modern music venue on Halsted, but the building itself holds a much more dark and curious past. In the early 1900s, the building was said to house a brothel and, in the basement, a gathering place for the Golden Dawn, a secret society that would regularly practice rituals devoted to the supernatural. In 1930, one woman even claimed she witnessed a ritual murder while attendning a society meeting there. As the building traded hands many times throughout the decades, the stories of its past lingered, albeit faintly. When the current owners began their renovations, they reportedly uncovered Egyptian symbols on the basement ceiling as well as a pentagram displayed on the floor. Previously, a large knife was also found lodged in the building's wall, emblazoned with a skull-shaped grip. It’s no surprise, then, that rumors of ghost sightings and strange ambient noises drifting from the basement have cropped up over the years. Whatever did happen down there, the current nightly live music lineup may very well drown out the voices of those unsettled souls.

Biograph Theater
Biograph Theater | Carlos Yudica/Shutterstock

2433 N Lincoln Avenue, Lincoln Park
This historic landmark theatre in Lincoln Park, now called Victory Gardens Theatre, was built in 1914, and has survived through many erras. In 1934, notorious bank robber, auto thief, and fugitive John Dillinger, was shot and killed by the FBI just below the glitzy marquee after leaving a movie screening. Dillinger had been on the run, disguising his identity by undergoing numerous plastic surgeries to avoid being identified. Yet on July 22, he was betrayed by a woman named Ana Cumpănaș, a Romanian sex worker and brothel owner dubbed the “Lady In Red” by newspapers at the time. There has always been speculation, however, that Dillinger was not the one that was killed that night, but a friend who had gone to the theater in his place, adding to the mystery. It’s said that visions of Dillinger—or perhaps his sacrificial doppelganger—can still be seen running through the alleyway near the theatre late at night.

Site of the St. Valentine’s Day Massacre

2122 North Clark Street, Lincoln Park
It doesn’t take a historian to assume that Chicago’s famed Mob Era might be responsible for at least one or two local ghost stories. Throughout the 1920s and 1930s, notorious gangster Al Capone ran most of the northside’s illicit underground activities, from drug peddling and bootlegging to sex trafficking and other nefarious trades. On one cold Valentine's Day in 1929, rival gang members disguised as cops entered a nondescript garage on North Clark Street—which also happened to be prominent mob boss George “Bugs” Moran’s headquarters. The ambush was a success and the phony cops shot all seven of his men execution-style, while Moran narrowly escaped.

While it’s never been confirmed that Capone personally ordered this hit, Moran was his known enemy. The only witness to the bloody night was a dog named Highball, who belonged to Moran’s mechanic. Highball was the one who alerted the authorities, howling loudly into the morning. You might have passed this seemingly innocuous Clark Street lot before without feeling the slightest chill, but stroll by with your four-legged friend in tow and see what happens—dogs in the area have been known to become quite distressed, triggered by the chilling events poor Highball saw go down that fateful day.

Site Of H. H. Holmes' Murder Castle
Site Of H. H. Holmes' Murder Castle | Flickr/Stephen Hogan

Site of H.H. Holmes’ Murder Castle
611 W. 63rd Street, Englewood
One of Chicago’s most horrifying locations is a former torture hotel in Englwood belonging to notoriously prolific serial killer H.H. Holmes, the shadowy figure that inspired Erik Larson’s fictional adaptation in Devil in the White City. Before building his South Side dream house, the real Holmes graduated from medical school where he had engaged in a particularly disturbing form of insurance fraud, stealing and tampering with cadavers from the school and subsequently taking out policies on them. In 1892, Holmes completed the 70-room lodging house, complete with a peculiar and circuitous design only he was privy to as well as frightening features like soundproof rooms with no windows or door knobs, stairs that led to nowhere, and more than a few trap doors.

With the 1893 World’s Fair bringing many tourists to Chicago, Holmes advertised rooms for rent hoping to lure young women into his house of horrors. Needless to say, the plan worked, and a string of innocent souls found themselves at the mercy of this murderous madman. The building was demolished in 1938, and a post office now stands next to the house’s original plot. The workers there claim to have spotted apparitions moving about the space, noticed items mysteriously stacked and moved, and, at night, heard female voices softly singing and talking from down below.

Excalibur
Flickr/Shutter Runner

632 N. Dearborn Street, River North
The former Chicago Historical Society building—once known as Excalibur to party-friendly Chicagoans and now operating as the Asian-inspired nightclub Tao—has long had a reputation for being one of the most haunted buildings in the city. For decades, employees of Excalibur claimed to have witnessed a wide variety of supernatural activity: dozens of candles being re-lit or extinguished, wine taps turning on by themselves, bottles suddenly breaking, and even ghastly sightings of a man in a tuxedo, a woman in red, and a little girl. Visitors, for their part, have reported hearing children crying, feeling a “heavy” energy, and difficulty breathing when in the Dome Room, the building’s paranormal hot spot.

While filming an episode of Ghost Adventures, one cast member claimed to have been pushed down the stairs by an unseen force. While there have been plenty of rumors surrounding the source of this paranormal activity—the most common being that the building was used as a temporary morgue after the Eastland Disaster over a century ago—most are either false or difficult to prove simply because they pre-date the Great Chicago Fire, the catastrophic event that burned down the original building (everyone who took shelter inside the supposedly fireproof structure is said to haunt the place, too).

Bachelor's Grove Cemetery
Flickr/neur0tica

143rd Street at the Midlothian Turnpike, Midlothian
Thanks in part to a viral photo of a ghostly woman perched on a headstone in Bachelor’s Grove cemetery, this site has become known as one of the most haunted cemeteries in America. There have been over 100 reports of paranormal experiences in and around the graveyard, including ghostly figures, apparitions of a phantom farmhouse, and unexplained balls of light. And even if you don’t believe in ghosts, the destination itself sports a pretty creepy history, reportedly used as a routine dumping ground by Chicago mobsters. In recent decades, vandals have desecrated graves, with some plots reportedly being dug up for satanic rituals.

Red Lion Pub
Flickr/Bart Heird

2446 N Lincoln Avenue, Lincoln Park
Originally built in 1882 and stashed just down the street from the Biograph Theater, Dirty Dan’s Western Saloon—now known as the Red Lion Pub—lays claim to being the most haunted bar in Chicago. When present-day owner John Cordwell and his son Colin purchased the decrepit tavern from its previous proprietor, described by the pair as “an old, alcohol-sadden, toothless gem, without one redeeming defect,” they committed to cleaning up the place without sacrificing its ghoulish charm. The 1984 gave it some polish, but according to employees and the media, the pub remains home to several otherworldly residents, including a scruffy cowboy and a mischievous female spirit who likes to play jokes on staffers.

Congress Hotel
Felix Lipov/Shutterstock

520 S Michigan Avenue, Loop
The Congress Plaza Hotel is widely thought to be one of Chicago’s most haunted hotels by both ghost hunters and unsuspecting visitors alike, judging from the abnormally high number of creeped-out reviews on TripAdvisor. Originally built in 1893 to house World’s Fair guests, the hotel has played host to dozens of tragic deaths and suicides. Visitors frequently comment on the strange sealed-off rooms—including room #666. The 12th floor (which also features a sealed-off room, of course) is said to be one of the building’s most haunted stretches, while room 1408 is rumored to have inspired Stephen King’s short story by the same name. However, room 441 may be the scariest of all: Those who dare stay there frequently report being attacked in bed by a shadow woman. In 2014, an attempted overnight in room 447 famously prompted Australian celebrity chef Pete Evans to flee from the hotel without bothering to check out.

7201 Archer Avenue, Justice
Growing up, most kids live in fear of that horrifying lady in the mirror known as “Bloody Mary.” Here in Chicago, we have a different Mary to fear: Resurrection Mary. Since the 1930s, dozens of people claim to have had bizarre encounters with a young blonde female on Archer Avenue near Resurrection Cemetery. Some have even reported picking up a young female hitchhiker near the Willowbrook Ballroom, only to see her hop out of the car at Resurrection Cemetery and vanish. In other cases, drivers have reported colliding with a young female outside the cemetery gates. However, by the time they exit their car, the young woman has disappeared. Experts have been chasing this particular ghost for years, attempting to determine both the legitimacy of these claims and Mary’s identity. However, given the high number of vanishing hitchhiker stories, many skeptics have written Resurrection Mary off as good old-fashioned folklore.

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Elanor Bock is a contributor for Thrillist.
Lisa Chatroop is a contributor for Thrillist.