Halloween is hands down my favorite holiday. Which makes living in Chicago all the more fun. Chicago is a city with history — a whole lot of history. So it’s hardly surprising that it’s also a city with ghosts — a whole lot of ghosts.

From victims of the Great Chicago Fire, to jilted lovers and murderous masterminds, here are 10 spine-chilling tales from Chicago’s haunted history.

1. Death alley behind James M. Nederlander Theatre

Oriental Theater

Today it’s known as the Nederlander Theatre. But in 1903, it was called the Iroquois Theater and became the site of an infamous fire — despite claims that the building was “fire-proof.” During the blaze, the fire doors were locked, trapping 2,000 patrons inside. When the flames subsided, 602 people were pronounced dead, 212 of them children.

It took more than five hours to retrieve the bodies, with the alley behind the theater functioning as a temporary morgue. Today, reports of faint cries, apparitions, and feelings of being touched or even pushed by invisible entities have been reported. Hence the nickname “Death Alley.”

James M. Nederlander Theatre

Ghostly tales don’t seem to keep avid theater goers away, however. The Nederlander Theatre’s stunning architecture and run of premieres and Broadway shows keep the crowds coming and the ghosts at bay.

2. H.H. Holmes’ Murder Castle

The former home of the country’s serial killer, H.H. Holmes, is located in Chicago’s Englewood neighborhood. While the building has been replaced by the local post office, the site was originally the location of Holmes’ infamous Murder Castle.

Built in 1893, Holmes hired multiple contractors for various portions of the project to ensure that no one person, aside from himself, knew the floor plan in its entirety. Incorporated into the plan were stairs and hallways that led to nowhere, oddly angled hallways and windowless rooms, designed to disorient and trap his victims, whose bodies eventually would be sold to science.

It’s hard to know definitively just how many people Homes murdered. And although he confessed to 27, most of whom were women, some historians believe the number to be in the 200s. Today, maintenance workers report odd sightings and feelings of intense anxiety while in the building’s basement, where most of the murders took place.

It’s been over 120 years since Homes terrorized the Englewood neighborhood, but his legend is very much alive. If you want to read more, Holmes’ life and experiences are the subject of the bestseller Devil in the White City.

Holmes is a popular topic on various Chicago ghost tours. Check out a sampling of tours here.

3. Chicago Water Tower

Historic Water Tower-2

This downtown landmark has a tragic history. Located along The Magnificent Mile, this striking Gothic Revival building is home to a large water pump intended to draw water from Lake Michigan.

This iconic limestone building was one of the few to survive the devastating Great Chicago Fire of 1871. Though it remained standing, it wan’t devoid of tragedy. History holds that as the flames raged, one brave worker stayed behind to tirelessly man the pumps. As the fire inched ever closer, and with no salvation in sight, he retreated to the upper floors of the tower where he hung himself. Multiple reports have claimed that the silhouette of a hanging man can be seen in the tower’s top floor windows. However, when police are called to the scene, no body can be found.

Historic Water Tower-1

Today, the tower has been transformed into The City Gallery at Historic Water Tower, a frequent venue for cool exhibitions — currently Stand Up for Landmarks! Protests, Posters & Pictures, which catalogs images, artifacts and ephemera relating to the seldom told story of public activism, outreach campaigns and governmental legislation. Take a peek Monday-Friday 10am-7pm and Saturday-Sunday 10am-5pm free of charge.

4. Congress Plaza Hotel

Congress Hotel

Named the most haunted place in Illinois by Travel & Leisure, the Congress Plaza Hotel’s history begins with the World’s Columbian Exposition, or The World’s Fair, as its better known.

Built in 1893 to help house the influx of visitors to the city, the hotel quickly became the focus of rumors. For instance, some say that mobster Al Capone and his cohorts owned the hotel and committed gruesome crimes there, although these claims have come under some scrutiny.

Cocktails and Capone-3

Mob rumors aside, if you find yourself spending the night in the South Tower, you might just run into “Peg Leg Johnny,” the spirit of a hobo who was brutally murdered in the alley behind the hotel. Who he was, and the circumstances of his death, remain a mystery.

The North Tower doesn’t fare much better. Security guards have reported seeing the apparition of a playful young boy on the 12thfloor. He is believed to be the spirit of a child who, along with his sibling, was thrown from the North Tower by his panicked immigrant mother, who feared deportation. She, too, jumped to her death.

The oddest haunting, however, takes place in Room 441. Visitors have often reported seeing the silhouette of a woman as well as objects in the room move, or lights turning on and off at random. Room 441 to this date still receives the most security calls.

Feeling brave? Make your reservation here.

5. Site of Eastland River Disaster, Chicago River

Photo courtesy Eastland Disaster Historical Society

Chicago suffered one of its most devastating tragedies on July 25, 1915, when the SS Eastland steamship capsized, trapping 2,572 passengers on board. Occurring shortly after the Titanic sinking, when the lack of life boats came under scrutiny, a new regulation titled The Seamen’s Act was put into place to ensure enough safety vessels for passengers. Unfortunately, though, the addition of these life boats in the Eastland’s case caused the already top-heavy ship to rollover in the waters of the Chicago River between Clark and LaSalle Streets. Many of the passengers and crew were crushed by heavy furniture and otherwise trapped. In total, 844 passengers and crew members died that day.

Restaurant Retail space and outdoor public seating

Various Chicago establishments were used as makeshift morgues to house the recovered bodies, including Oprah Winfrey’s former production base, Harpo Studios. Various buildings have experienced ghostly sightings, and are said to elicit feelings of general unease among visitors. Reports of apparitions and unusual wave patterns also extend to the stretch of river where the Eastland disaster occurred. Today, the Chicago River is home to the award-winning Riverwalk, one of the city’s most visited sights.

6. The Drake Hotel

Drake Hotel

The Congress Plaza isn’t the only hotel with a ghostly history. Built in 1920, The Drake has long epitomized elegance and opulence, with illustrious visitors such as Bing Crosby, Frank Sinatra, Dean Martin, Marilyn Monroe, Queen Elizabeth II, Winston Churchill, Princess Diana — and, well, a few forlorn ghosts.

There are stories of Bobby Franks’ mourning parents (he’s the 15-year old who was kidnapped and murdered by rich University of Chicago students Leopold and Loeb), and the Woman in Black, the shootist in the unsolved murder of Chicago socialite, Adele Born Williams. But the Woman in Red, without a doubt, is perhaps the most famous specter of all.

Picture it: A New Year’s Eve opening gala in 1920, populated with the city’s most noteworthy residents. One of the party goers, a woman dressed in red, discovers her philandering husband (or fiancé, depending on who’s telling the story). In a frenzy of anger, jealousy and hurt, she takes an elevator to the 10th floor, and swiftly jumps to her death. The oldest of the Drake’s ghost stories, her ghostly apparition can be seen haunting the Gold Coast Room, the Palm Court, and the 10th floor.

See if you’re attune with the spirits and book a sumptuous high tea at the Palm Court. Or better still, book a stay at this historic, luxurious hotel.

7. Graceland Cemetery

Graceland Cemetery Chicago

Built in 1860, Graceland Cemetery is the final resting place of some of Chicago’s most notable individuals, not least David Adler, John Kinzie, Potter Palmer, George Pullman, and Marshall Field. However, it isn’t an illustrious personage that causes a stir at the cemetery. Rather, it’s a 6-year-old girl by the name of Inez Clarke.

Inez was struck by lightning in 1880 while playing in the rain, her grave memorialized with a stone likeness commissioned by her parents. They added a glass box to symbolically protect their daughter from the elements that had so tragically taken her.

Graceland Cemetery

On lightening struck days, cemetery workers and visitors have reported the statue entirely missing. As soon as the storm subsides, however, the statue of Inez Clarke returns to its glass box. Many surmise that she leaves to once again play in the showering rain.

Graceland Cemetery is included on a number of ghost tour itineraries. Check them out here.

8. Site of the St. Valentine’s Day Massacre

Al Capone

Although February 14, 1929 should have been reserved for lovers, it was bullets rather than love that showered Chicago that day. It is said that Al Capone ordered a hit on Irish mobster George “Bugs” Moran. As Moran’s men entered the garage at 2122 N. Clark St. in Lincoln Park, Bugs held back, while his second in command and brother in law, James Clark, as well as fellow members of the gang, were mercilessly gunned down.

And so was born one of the bloodiest days in Chicago mob history.

Today, at the same location, it is believed that the ghost of a German Sheppard who belonged to a murdered Irish mob member still mourns its owner’s death. Most astonishingly, however, Al Capone was allegedly haunted by the spirit of James Clarke, or Jimmy as he called him. Shortly after the attack, Capone was sentenced to eight months in Eastern State Penitentiary in Pennsylvania for an illegal arms charge. While incarcerated, he repeatedly begged “Jimmy” to leave him alone. He even hired a medium, Alice Britt, to rid him of the specter, but the haunting continued till the end of his days.

Check out gangster and other unique tours here.

9. Jane Addams Hull House

Black and white picture of Hull House at night

The famed Hull House was a settlement residence on Chicago’s west side, run by Jane Addams, aka “the mother of social work,” to assist recently arriving European immigrants. It was Addams, in fact, who first spoke of the property’s paranormal nature when she claimed footsteps could be heard in the room in which she slept. Addams surmised this to be the wife of Charles Hull, the original owner of the building, who had passed away in that room.

The real urban legend of Hull House, however, is the tale of the “Devil Baby.” If it sounds like the title of a 70s B-horror flick, you’re not too far wrong. It is said that a mother-to-be and devout catholic hung a picture of the Virgin Mary in her home in order to bless her impending motherhood. Her husband, however, was just as devout an atheist, and angrily ripped the picture from the wall declaring, “I’d rather have the Devil in the house!” Well, some wishes do come true.

Jane Addams Hull House Museum

The child was reportedly born with scaly skin, hooves, and horns, and summarily abandoned at Hull House. Accounts claim that Addams tried to baptize the baby, but could not, eventually locking him in the attic until his most likely longed for death.

Although this story is a folk tale and has no basis in fact, it still captivates all those who visit Hull House. And honestly, devil babies aside, there are so many reasons to visit this lovely, free museum. Check out current special exhibitions and permanent collections hereIt’s open Tuesday-Friday 10am-4pm and Sunday Noon-4pm (closed Mondays and Saturdays).

10. Site of Fort Dearborn

Michigan and Wacker in 1920s

The oldest reported Chicago haunting begins before the city ever came into being. During the War of 1812, Fort Dearborn stood towards the intersection of Wacker Drive and Michigan Avenue in the Loop. Its American inhabitants were in the process of evacuating the fort when the Potawotamie descended. Of the fort inhabitants, 148 people died, 12 of whom were children.

Ghostly images are repeatedly reported in snapshots taken around the former site – the souls of the slain, perhaps? Look out for the numerous plaques that mark where the fort once stood. And be sure to take an extra close look at those selfies, because you may just have captured a ghost!

Bonus! Couch mausoleum in Lincoln Park

Couch Tomb
Photo courtesy Chicago Park District

The southern edge of picture postcard-worthy Lincoln Park once served as the city cemetery, which may seem somewhat incongruous given the park’s steady flow of cyclists, joggers and picnickers today. In the 1800s, however, Chicagoans were routinely interred here, while Potter’s Field, located where the park’s baseball diamond is today, became a burial ground for indigent individuals. Only one tomb survived the Great Fire of 1871, the limestone Couch Memorial crypt, located at the south end of Lincoln Park, near the Chicago History Museum. Or so it was thought! In 1998, workers digging the site for the adjacent Chicago History Museum’s parking garage discovered the remains of more than 80 people, including one perfectly preserved body sealed in a 19th-century iron coffin. Who knows what else lies buried in Lincoln Park!