The 15 Most Chilling Ghost Stories From Chicago

Like all major cities, Chicago has a lot of interesting history surrounding it. The city's location on the banks of Lake Michigan and along the Chicago River made it an invaluable fort and transportat

Like all major cities, Chicago has a lot of interesting history surrounding it. The city's location on the banks of Lake Michigan and along the Chicago River made it an invaluable fort and transportation hub in the nineteenth century. Chicago would become a destination for many immigrants in the nineteenth and twentieth centuries. The city would also become home to one of the world's most notorious gangsters--public enemy #1 Al Capone. Chicago has hosted the World's Fair more than once, which is why we have the Ferris wheel at Navy Pier today.

Though often seen as a hotspot of art, entertainment, and industry, Chicago is also a hotspot for other, more sordid things that many people don't know about: its ghost stories.

Established as Fort Dearborn in 1803, Chicago has seen countless mass murders. From the Great Chicago Fire to Dr. H. H. Holmes, from the Iroquois Theater to the St. Valentine's Day Massacre, it's hard to go anywhere in the city and not set foot over bloodied ground. But it isn't just the ghosts of these mass killings who haunt the city- who hasn't heard the story of the devil baby of Hull House, or Resurrection Mary in her white dress? There are ghosts everywhere, and if you've got the right guide, there is no shortage of ghost stories. But in case you don't have the money to throw at a ghost tour or one of the many books about Chicago's ghost stories, we've compiled a list for you. Here they are, from bone-chilling to keep-you-up-at-night-scary, fifteen of Chicago's scariest ghost stories.

15 The Fort Dearborn Massacre


It's no surprise that Chicago is as haunted as it is when you look at the city's establishment. Occupied by Native Americans, the territory was considered ideal for a military outpost. In 1803, Captain John Whistler's troops constructed a fort and named it after Secretary of War Henry Dearborn. During the War of 1812, General William Hull ordered the evacuation of Fort Dearborn, which contained not only soldiers but also their families. As the 148 men, women, and children evacuated, they were ambushed by 500 Potawatomi warriors. 86 of the evacuees were killed.

There was no paranormal activity reported around the area--until the 1980s, when construction unearthed human bones. At first believed to be the bones of cholera victims from the 1840s, specialists determined that the bones were from the early 1800s and almost certainly the bones of the Fort Dearborn Massacre victims. Ever since their discovery, people have reported seeing figures in pioneer and military clothing running around and screaming in a field north of 16th Street. Many believe that this is because their bones were disturbed and there is no memorial for the victims. Makes you wonder...

14 The St. Valentine's Day Massacre


Everyone, even non-Chicagoans, has some level of familiarity with the St. Valentine's Day Massacre. On the morning of February 14th, 1929, five members of the North Side gang and two hangers-on were killed by Al Capone's men, two of whom were dressed as police officers. The seven men were lined up against the wall of a garage on North Clark Street, where they were awaiting a delivery, shot with Tommy guns, and killed. The only survivor was a dog named Highball, who barked loudly until one of the victim's landlady came to the scene.

The massacre stunned and fascinated the nation. The public at the time was obsessed with gruesome souvenirs--reports say that passerby dipped their handkerchiefs in John Dillinger's bloody wounds after he was shot, and one person supposedly tried to cut off Clyde's ear after he and his partner Bonnie were killed in a police ambush. This gang-related death was no different; when the garage was torn down in 1967, a Vancouver businessman bought the brick wall against which the men had been shot and took it on tour. The wall has also been kept in a crime museum (where the bullet holes were painted red to resemble blood) and a nightclub. Currently, it can be found in the Mob Museum in Las Vegas. Why has it moved around so much? The superstitious believe that ill fortune befalls whoever owns the brick wall. Additionally, when the garage still stood, people often reported hearing a dog barking and a woman screaming, even when there was no dog or woman in the vicinity.

But that isn't the only spooky thing about the massacre. Al Capone claimed that he was haunted by the ghost of James Clark, one of the massacre's victims. While many argue that Clark's "ghost" was more likely a result of Capone's syphilis-induced hallucinations, others have pointed out that Clark appeared to Capone before his Alcatraz days, before his syphilis had impaired his lucidity. So, was it really a ghost? Or just a manifestation of guilt and disease? We leave that to you.

13 The Wynekoop Family


While it seems doubtful that the Wynekoop mansion was truly haunted when it stood, the house was host to one of the eeriest murders in the city, if not the country, and because of its similarity to Guillermo del Toro's ghost-ridden Crimson Peak, we can't help but include it as a ghost story.

The Wynekoop mansion was one of the most prominent in Chicago. Built in 1903 by Frank and Dr. Alice Wynekoop, the house witnessed some strange things. First, the death of Frank and Alice's daughter, Mary Louise; second, Frank's brother attempted to strangle his estranged wife during their divorce settlement. Strangest of all, though, was the death of Frank and Alice's daughter-in-law, Rheta. Rheta was an heiress with aspirations of being a professional violin-player, and when the dashing Earle Wynekoop asked her to marry him, Rheta thought her dreams were coming true. Unfortunately, as she was quick to discover, Earle had only been interested in her inheritance. While Earle was on one of his many trips out of town, a coroner was summoned to the Wynekoop home, where he found Rheta lying completely naked on an operating table, partially nude, a bullet wound in her back. When asked why she hadn't summoned the police, Alice said that she didn't want to create a scandal. The coroner reportedly said, "Well madam, this is murder," and went upstairs to call the police.

The investigation that followed would prove to be one of the strangest in United States history. While detectives believed the womanizing Earle had murdered his wife, Alice insisted that he could not have as he was out of town. She changed her story numerous times and eventually claimed that she had accidentally killed Rheta during a routine procedure (possibly an abortion) and shot her in a panic. Friends, family members, neighbors, and boarders of Alice vehemently denied that she could have murdered her daughter-in-law. To further confuse matters, Earle returned from his trip and insisted that he had killed Rheta, not his mother.

Love letters between Earle and Alice led police to believe that Alice had murdered Rheta out of jealousy and to make her precious little boy happy. Public opinion was heavily divided over who was the real killer, causing the case to drag on for weeks. Finally, Alice was given 25 years in prison; she was released early in 1949 (sixteen years after Rheta's death) and died two years later at the age of 79. No one is entirely certain what became of Earle.

Romantics like to say that they could hear the sounds of Rheta's violin in the house before it was torn down, but this is one of the less-substantiated ghost stories. Either way, you have to admit that it's pretty creepy!

12 The Water Tower Hanging Man

Like the St. Valentine's Day Massacre, everyone in and outside of Chicago has heard of the Great Chicago Fire. In case you haven't, here's a little bit of background: in 1871, a fire started in Mrs. O'Leary's barn. Some say it was because her cow kicked over a lantern, but the more likely reason is that her son Jim and his mates got rowdy after some drinks and accidentally knocked over a lantern. Whatever the case, Chicago was going through a dry season, most of the houses were made of wood, and it isn't called the Windy City for nothing. The fire raged for two days, destroying over three miles of homes and businesses, leaving 100,000 people homeless, and killing roughly 300 people.

One of the fire's victims was, strangely enough, not killed directly by the fire. The famous water tower still standing in the downtown area was only two years old when the fire tore through Chicago. Though most of the men evacuated, one lone hero stayed behind to pump water and put out as much of the fire as possible. When the fire reached the water tower, however, he knew that it was the end; rather than be burned alive, legend has it that he hanged himself in the water tower. Many people have reported seeing the shadow of a hanging man in the water tower; even police have seen the apparition! Luckily, this doesn't seem to be a malevolent ghost; just a chilling reminder of the selflessness of one man.

11 The Irish Castle


If you decide to go looking for the Irish Castle, you can't miss it because it boasts it's the only castle in Chicago. Completed in 1887, the Irish Castle, sometimes known as the Givins Castle, was built by a wealthy businessman named Robert Givins, who wanted the castle to resemble those of his homeland. Supposedly he built it for his bride-to-be, who was still living in Ireland. Rumor has it that she died before she could come to Chicago, however, casting a dark shadow over the castle.

After Robert Givins, the castle housed a manufacturer and a doctor before becoming a girls' school. One of the school's students died of influenza in the 1930s. Some thirty years later, after the castle had been sold to the Unitarian Church, a custodian was cleaning when she encountered a girl in a long dress. She and the girl had a pleasant conversation, during which time the girl said that things looked different from when she had lived there. After leaving the room, it occurred to the custodian that the church had owned the castle for more than twenty years; the girl couldn't have lived there. She ran back to the room but the girl, as you've probably guessed right now, was not there. The doors and windows were locked, and there were no footprints in the snow outside. There was no way this was a human girl.

Another thirty or so years later, one of the pastors recalled seeing a pair of small arms hug her husband from behind; her husband claimed he felt nothing. Some have even said that when passing by the castle, they can see a candle passing by windows and going up and down stairs even when no one is in the building. Some believe that the girl's spirit lingers because of the nature of her death; because she was delirious with fever by the time she passed away, paranormal experts believe she died in a confused state and does not realize she is dead.

10 The Red Lion Pub


The Red Lion Pub does not house one ghost; it houses several. Unfortunately, who these people are and where they came from is something of a mystery.

Built in 1882, the Red Lion Pub is right across the street from the Biograph Theater, the same theater where John Dillinger saw his last movie before federal agents ambushed him in the alley of the same building. While Dillinger's ghost doesn't haunt the premises (if you believe it was Dillinger indeed who was shot), owner John Cordwell has felt the spirit of his deceased father many times. Other ghosts include those of a woman who was known to wear an excessive amount of lavender perfume and who died in the pub; rather than a visual appearance, you can often tell she's in the room because of an overwhelming lavender scent. Another woman who died in the pub was killed by a jealous boyfriend in the 1920s, and her ghost still lingers. Some speculate that this may be the same spirit who locks women in the bathroom for fifteen to twenty minutes at a time. She doesn't do anything, as far as we can tell. Perhaps she only wants some company. Additionally, the ghost of what many believe to be a former owner likes to go up and down the stairs as if he's going about his business; old habits die hard.

Not all of the spirits are so friendly. A cowboy has been sighted stomping around the bar, which is especially confusing as the bar was established around the same time barbed wire was developed, putting most cowboys out of the job. Perhaps this particular cowboy is angry his job was taken? Other spirits include a woman who died of an epileptic seizure and often appears by restricting patrons' breathing, as well as a blond and a black-haired man who paranormal experts believe killed each other in a bar fight. These last two spirits have been known to throw things across the room, so if you ever pay this building a visit, look out!

9 The Excalibur Club


Known for years as the Excalibur Club, the now-closed Castle Chicago is one of the more questionably haunted buildings. Though employees of the Excalibur Club claimed frequent and violent paranormal interactions, visitors to the establishment rarely experienced encounters of the paranormal variety. Still, if what employees say is true, Castle Chicago is home to a poltergeist.

Established as the Chicago Historical Society in 1896, the building would go on to serve as a morgue for the Eastland disaster, which we'll get into a bit later. If you know anything about ghost stories, you'll know that this alone would make the building a paranormal hotspot. Poltergeists often materialize at the sites of violent deaths or where victims of a violent death were buried--the morgue of one of the country's greatest disasters is a perfect location for just such an entity. Employees of the Excalibur Club have claimed to be pushed down stairs and over railings. One waitress in particular was dragged by the wrist, and while there was no visible hand holding her, the red marks on her arm suggests something was definitely pulling her.

Again, we're a little skeptical about whether or not this place is haunted, but if it is, we suggest you keep away lest you incur the wrath of a malevolent spirit!

8 Rosehill Cemetery


Like other historic cemeteries, there are a lot of ghost stories surrounding Rosehill. Established in 1859, the cemetery became a replacement for the cemetery in Lincoln Park, causing many graves to be moved--never a good thing to do if you want to avoid disgruntled spirits. The cemetery is home to over 1,500 graves, many of which are Confederate and Union soldiers and Chicago celebrities. One of these celebrities, Richard Warren Sears, is one of the cemetery's most prominent ghosts. Buried in the same mausoleum as his business rival, Aaron Montgomery Ward, Sears can sometimes be seen walking up and down the hallways of the mausoleum, from his tomb to that of Ward's. It appears their rivalry in life extends to the afterlife!

A woman was once spotted in the cemetery after closing, standing next to a grave; when a groundskeeper approached the woman, he saw that she was floating. She disappeared without a word. The next day, a woman called and asked if a marker could be put on her aunt's grave. She said that her aunt had come to her in a dream and asked her to put a marker on the grave. The groundskeeper went to the grave and found that it was the same grave over which the woman had been floating.

Visitors to the cemetery will notice a monument in a glass case, inside of which is a woman reclining on a bed with her infant daughter. The woman is Frances Pearce. Frances died at the age of 20, and her newborn daughter followed her to the grave only a few months later. Frances's husband, Horatio, built the monument for his beloved wife and daughter. It is said that on the anniversary of Frances's death, a white haze fills the glass case.

7 The Murder Castle of H.H. Holmes


The first serial killer in the United States--if not the world--was a man known as Dr. Henry Howard Holmes. Though he confessed to 27 murders, only nine of which could be confirmed, it is estimated that he killed upwards of 200 people. Most of these victims were killed in Chicago--right in Holmes's murder castle.

Holmes bought a drugstore, and when visitors asked the whereabouts of the owner, Holmes told them that she had moved to California--more likely, she was one of Holmes's first victims. Across the street from the drugstore, Holmes built a three story hotel that took up an entire block. He constantly changed construction teams because he didn't want anyone to know the full layout of what would become a major crime scene. The castle opened as a hostel for World's Fair visitors. Many of these visitors were women. He put gas lines through some of the rooms to asphyxiate his guests; other rooms were soundproof. While Holmes let most of his victims suffocate or starve to death, he also had a chamber specifically designated for hanging. Perhaps the most gruesome part of all? Holmes would sell the skeletons and organs for a profit.

Because of the number of missing people, it did not take long for police to zero in on Holmes. He was tried for murder, found guilty, and hanged.

The murder castle never got the chance to be haunted; it was torn down, left as an empty lot, and turned into a post office in 1938. The really spooky part of the story is the "curse" left by Holmes.

6 The Eastland Disaster


The Eastland is one of the lesser known disasters in U.S. history, which is surprising given that it claimed more lives than the Great Chicago Fire and was the worst shipwreck to happen in the Great Lakes. The SS Eastland was one of several steamships that had been chartered to take employees of Western Electric Company and their families to a picnic in Michigan City, Indiana. Passengers began boarding on the south bank of the Chicago River between Clark and LaSalle around 6:30 am. In less than an hour, the ship had reached its capacity of 2,572 passengers. Many passengers were on the upper decks, which made the ship top-heavy and not very stable. The crew let water into the ballast tanks in an effort to stabilize the ship, but this would prove to be a fatal mistake. Something caught the attention of the passengers on the decks and they crowded on the port side. The ship, already unstable, rolled completely onto its side and rested on the river bottom, which was twenty feet below the surface. Despite the fact that the water was only twenty feet deep, the wharf was twenty feet away, and a nearby ship rushed to help. 848 people died. Many of these were passengers who had been below decks and were trapped under water; many of the passengers who perished above decks were women who were weighed down by their heavy dresses. The bodies were taken to the 2nd Regiment Armory; you may know it today as Oprah Winfrey's Harpo Studios.

Over 800 people can't die in one fell swoop and not leave some phantoms behind. Employees at Harpo Studios claim that they have heard laughing and sobbing, clinking glasses and old-timey music. Many staff members have even reported hearing a large group of footsteps on the stairs or in the lobby without any kind of explanation. There is even a ghost who wanders the studio who has been dubbed the Gray Lady.

But it isn't just the studio that's haunted; strange noises have been reported coming from the river, and if you look closely enough, rumor has it that you can see faces in the water. Next time you're walking by the river at Clark and LaSalle, look closely at the water--what you see might surprise you!

5 The Woman In The Red Dress

via drakehotelnewyearsparty

One of Chicago's more infamous ghost stories is set in the Drake Hotel. There are two variations of this story, and both are equally chilling. Both begin in the Drake Hotel at its opening party on New Year's Eve, 1920. The first version says that while a party raged on the tenth floor, a woman in a red dress had too much fun and fell out of a window. The second version says that the woman in the red dress was attending the New Year's Eve party with either her husband or her fiance. Her gentleman escort went to get her a drink, but after he had been gone for a long time, the woman went in search of him. She found him flirting with another woman. The woman was so overcome with jealousy that she threw herself out of a tenth-story window.

Whatever the case, the woman in red is the Drake's most prominent ghost. Visitors see her often, usually hanging around the tenth floor. Some have even seen her jump out of the window, reliving the moment when she took her life.

4 The Congress Plaza Hotel


Widely regarded as the most haunted hotel in Chicago and one of the most haunted in the world, there is no end to the oddities at the Congress Plaza Hotel. Like Dr. H. H. Holmes's murder castle, the hotel was built for the 1893 World's Fair. The connection to Holmes doesn't end there; Holmes confessed to meeting women in the lobby of the hotel and taking them back to his hostel, where he tortured and murdered them before harvesting their skeletons and organs.

The Congress has its share of spooks. A Polish woman in the 1930s came to America with her two sons. Her husband promised to join them later, but the woman later discovered that he'd taken up with another woman. Maddened by grief, the woman grabbed her two sons and jumped out of a sixth floor window. All three died from the fall, but only two of the bodies made it to the morgue. The spirit of the boy who didn't go is said to wander the halls of the sixth floor and play pranks on guests.

When the Gold Room banquet hall was built, a worker got trapped in the wall he was plastering and suffocated. Sometimes, it is said, you can see his hand reach out from the wall. The Florentine Room, a second banquet hall, is host to a female ghost who will whisper in guests' ears. At night, the security staff frequently hears chairs move around, mysterious knocking, and people talking, even though no one is in the room.


3 The Iroquois Theater Fire


Like the Eastland disaster, the Iroquois Theater Fire is a little-known disaster in Chicago history that ended up killing more people than the Great Chicago Fire. Known today as the Ford Oriental Theater, the Iroquois opened in November 1903. Because there had been several delays in opening the theater, the syndicate of owners decided against fireproofing the building because that would only further delay the opening. Despite the lack of sprinklers, air shaft, asbestos curtain, and telephone, the theater was advertised as "absolutely fireproof." Little did anyone know how quickly that claim would be challenged.

On December 30th, 1903, over 2,000 people packed into the Iroquois Theater for a matinee performance of Mr. Bluebeard, starring Eddie Foy. Interestingly enough, the show had had disappointing attendance up until December 30th; not only was it full for that performance, but hundreds of people had bought standing room only tickets. Some were even sitting in the aisles, blocking the entrances and exits. Sometime during the second half of the play, a stage light short-circuited and ignited sparks, which quickly caught on the muslin curtain. Eddie Foy reportedly ran out onto the stage and pleaded for the audience to remain calm while they took care of the fire. As you've probably guessed by now, the fire was impossible to control. In an already flammable wood building with velvet seats the audience was largely trapped inside. People were blocking the aisles and hallways, and the locks on the doors were a new model and therefore unfamiliar to most of the patrons. The few doors that were opened let in a rush of wind that only fanned the flames. It did not take long for the theater to be consumed in flames. This was also during a time when the fire department was usually summoned by someone knocking on the front door, so it would be too late by the time Engine 13 arrived.

Not all of the victims were burned, however; rather than be burned to death, many people jumped out of the windows in an attempt to survive. Not everyone survived the jump, unfortunately, and there was soon a pile of bodies heaped in the alley. It is estimated that 575 people died on the day of the fire; 30 more would die over the next few weeks from injuries they had sustained during the fire.

As you can imagine, the theater and the alley beside it are full of paranormal activity. Cast, crew, and staff at the Ford Oriental have reported strange activity, noises and encounters they can't explain. The alley is the first stop on the Haunted Chicago tour, where guides encourage you to wander and get a sense for the alley. It's definitely creepy, and some people have pictures of ghostly encounters to prove it! Even if you don't believe in ghosts, you have to admit that there's something chilling about being in that place.

2 The Hull House Devil Baby


Hull House is most well known because it was one of the first settlement houses in America. Established by social work pioneer Jane Addams, Hull House provided refuge for women with limited options and for the hungry and homeless. Today, Hull House is a museum that honors the life and work of Jane Addams.

Hull House has another, more sinister reputation: the home of the legendary devil baby. As the story goes, a pious Italian girl was married to an atheist. After the girl hung a picture of the Virgin Mary, her husband ripped it apart and declared that he would rather have the devil in his house. His wish was granted; the girl gave birth to a hideous baby with horns, hooves, and a tail. Some believed that the child was conceived by Satan himself, and this would influence the later novel and film Rosemary's Baby. Disgusted, the father left the child at Hull House (a common practice for people who could not care for their children). When Addams tried to have the child baptized, he leapt from the priest's arms and ran around the church. Addams eventually caught the baby and locked him in a room upstairs until he died some years later.

While it is doubtful that such a demonic baby existed, there may have been a basis for the rumor. Some accounts record a disfigured child being left at Hull House. Because of his disfigurement, Addams kept him upstairs away from prying visitors, who came from far and wide to see the devil baby. The boy died in childhood and, it would seem, never left- visitors have reported seeing the ghostly face of a disfigured boy peering out from the upstairs windows.

1 Resurrection Mary


Probably the most well known ghost story in Chicago is that of Resurrection Mary.

Mary was a pretty girl with blonde hair and blue eyes who loved to dance. One night, while dancing at the Oh Henry ballroom, she and her boyfriend got into a fight. Rather than spend another minute with him, Mary stormed outside into the cold, determined to walk home alone. While crossing Archer, she was struck by a drunk driver, who made a hit-and-run and fled the scene. Mary died on the spot. Grief-stricken, her parents buried her in Resurrection Cemetery in a white party dress.

Since the 1930s, there have been dozens of sightings of Resurrection Mary. Usually, it goes something like this: a man will be at or near a ballroom or going down Archer when he sees a pretty girl in a white dress. The man offers her a ride home, during which time she says very little. She will stop him suddenly at the cemetery and usually vanishes in the passenger seat, but sometimes she vanishes through the cemetery gates. Other sightings involve cars striking or nearly striking Mary on Archer, but she always disappears before the driver can ask if she's alright. Because there are so many accounts of Resurrection Mary encounters, it leads us to wonder: could Resurrection Mary be real? It certainly seems like she could be. So next time you're on Archer, look out for girls in white dresses.

Sources: prairieghosts, themobmuseum,  mysteriouschicago 

Give TheRichest a Thumbs up!

Looking for an AD FREE EXPERIENCE on TheRichest?

Get Your Free Access Now!

More in Most Shocking

The 15 Most Chilling Ghost Stories From Chicago