Top 10 Haunted Places in Chicago

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Situated off Lake Michigan in the northern half of Illinois, Chicago is rich in culture and has a wildly devoted deep-dish pizza and sports fan base. Of course, the city served as a backdrop for some of the most notorious incidents in American history.

In the 1930s, gangsters ran rampant and made headline news for their dastardly deeds. But are some of the specters of these notorious criminals and others still haunting the streets?

Follow along as we introduce some of Chicago’s most cursed locations and learn who will never sever their ties from the city where they once owned the night. If you’re ready to see some of these locations in person, book a ghost tour with Windy City Ghosts!

10) Wrigley Field

Who would have thought that the iconic baseball stadium that is home to the Chicago Cubs could be haunted? A good number of die-hard fans who bleed “Cubbie Blue” can probably tell you a few things. Some have even said they have reported seeing some entities and felt cold spots. Needless to say, these specters may be harmless and won’t cause trouble.

If you are a fan of baseball and adventure, you may want to check out Wrigley Field for a game or even some otherworldly activity that might involve the longtime radio personality known for his thick-rimmed glasses and zany calls.

9) Red Lion Pub

A streak runs across a front view image of the Red Lion Pub in Chicago

The Red Lion has seen its share of spirits and apparitions. Some are said to be a bearded man, a woman dressed in the 1920s, and a man dressed like a Wild West outlaw. Past patrons have told stories about seeing food and drinks flying out of the server trays at random and even being locked inside bathroom stalls without being able to unlock them.

Find out who else haunts this popular bar on a spirited tour with Windy City Ghosts.

8) Site of Fort Dearborn

This is considered one of the oldest sites in Chicago, and it might even be the most haunted. Fort Dearborn was established in 1803 and was the site of an incident known as the Fort Dearborn Massacre. US soldiers battled with members of the Potawatomi tribe, resulting in the deaths of 148 people, including a dozen children. It has been said that markers are near where the fort once stood.

Rumor has it that photos taken at the former fort were said to have included spirits. Even today, you may catch a specter photobombing your photos. If you happen to be in the area and decide to take pictures of where Fort Dearborn used to be, do not be surprised if you pick up a little extra on the camera.

7) Hull House

Hull House was the home of Jane Addams, one of the most famous social workers. She was best known for counseling and helping European immigrants adjust to life in America so they could live their American Dream as they saw fit. It was Addams who would be the first to recount stories of unexplained activity occurring in the home, believing it was the spirit of the original owner, Charles Hull.

However, a curse of Satanic proportions may also be looming in the house. It was said that a pregnant woman, a known devoted Catholic, was hanging a picture of the Virgin Mary inside the home as a way of blessing her and her unborn child. Her atheist husband would later tear down the picture only to declare that he would rather have the devil himself present in the house instead of God. His declarations are believed to have conjured up the devil, and its dark energy remains to this day.

6) Chicago Water Tower

This tower was slated to be the apparatus that would pump water from Lake Michigan to the people of Chicago. However, a tragic incident resulted in a change of plans. During the Great Fire of 1871, a man tried pumping as much water as he could from the tower. After realizing it was too late to save himself, he took his own life.

The tower was one of the few structures that remained after the fire, and while the man’s body was never found, his spirit is said to have stayed with it. Reports of a ghostly figure lurking inside the tower continue to this day.

5) Congress Plaza Hotel

While it may have been no Alcatraz, it has been a place fit for a king (or a big-time guy like Capone). Aside from the hotel’s sordid past, it was a past site for the World’s Fair, featuring some of the best technological advances yet to be discovered by the general population. But if you stay at this infamous hotel, do not be surprised if you meet some suspicious characters in the halls and elevators.

4) The Drake Hotel

The Drake Hotel is another hotel with some spirits that have overstayed their welcome. Before it became a haven for hauntings, it was a hotspot for some of the world’s most famous people, including Winston Churchill, Queen Elizabeth II, and even some of The Rat Pack, specifically Frank Sinatra and Dean Martin. But it’s the stories of how this place became haunted that are what it’s most known for.

One of the spirits is only known as the “Woman in Red.” It’s said that during a New Year’s Eve party in the 1920s, a woman dressed in red witnessed her husband cheating on her with another woman. Distraught, she went to the elevator to travel up to the tenth floor, only to jump to her death moments later. Witnesses claimed to have seen her on the tenth floor and in the grand ballroom where the party took place.

Another story involves a 15-year-old boy who was murdered by two college students in the early 20th century. The parents of Bobby Frank and even the boy might haunt the hotel. Guests have witnessed shadowy figures and specters wearing period clothing. One of these specters includes a woman dressed in black who was believed to be the subject of a murder involving a wealthy Chicago socialite.

3) Graceland Cemetery

The Graceland Cemetery is the final resting place of many of Chicago’s most prominent citizens. However, a story makes this place even more haunted than any other burial place. One of the people buried here is a young girl named Inez Clarke, who died at the age of six after being struck by lightning while playing outside. Her parents requested a gravestone that bore her likeness. Once completed, they asked that her gravestone be encased in glass to protect it from the elements.

It’s said that one day, after a bad storm, one of the cemetery caretakers noticed the statue of Inez missing. When the weather improved, the statue returned to the glass case where it belonged.

2) Death Alley Near Nederlander Theatre

The alley near Nederlander Theatre was set as a makeshift morgue after a fire gutted the place in 1903, resulting in the death of dozens of people. Despite being considered “fireproof,” the fire swept through the theater; as many as 2,000 people were inside, desperately trying to get out. In the aftermath, more than 600 people were killed, including well over 200 children.

Faint cries and the feelings of being pushed around or touched by an unseen force have been reported near the place that can only be known as “Death Alley.” While the Nederlander Theatre still stands today, it will forever be known as the site of one of the most tragic events in Chicago’s history.

1) Site of The St. Valentine’s Day Massacre

The St. Valentine’s Day massacre was one of the bloodiest massacres carried out by Al Capone and his mobsters. Capone planned to attack an Irish mobster named Bugs Moran. While Moran hid, Capone’s gang gunned down his brother-in-law and members of his gang, resulting in one of the bloodiest crimes in Chicago’s history.

Though Capone would eventually go to prison in Alcatraz on a different charge, it’s believed that a spirit named “Jimmy” (or James Clarke, Bug Moran’s brother-in-law and second in command who was killed in the massacre) was antagonizing him up until the end of his life. Capone even summoned a medium to help get rid of the spirit but to no avail.

Haunted Chicago

There is no shortage of haunted hotspots in the Windy City. Check out our blog to uncover more of Chicago’s most cursed, and be sure to book a ghost tour with Windy City Ghosts to see them in person.

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