Graveyard Shift Creepiest Ghost Stories From Chicago  

Jacoby Bancroft
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List Rules Vote up the Windy City ghost story that freaks you out the most

Chicago is a city with its own fair share of tragedy and pain. Natural disasters, horrible accidents, and bloody massacres are deeply ingrained in the city's culture and past, creating a series of terrifying urban legends and ghost stories. The ghost stories about Chicago are some of the creepiest in the United States, but they also highlight just how much the city has been through since it was formed. Below you'll find a list of some of the most haunted places in Chicago and a few Chicago ghosts you never want to run into.

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The Eastland Disaster


The Eastland Disaster is listed (or ranked) 1 on the list Creepiest Ghost Stories From Chicago
Photo: wallyg/flickr/CC-BY-NC-ND 2.0

The capsizing of the Eastland steamer in Chicago is one of the worst boating disasters of all time. As the gigantic ship made its way toward Michigan City, a horrible accident caused the ship to tip over. Out of the estimated 3,200 people who were on board, the final death tally reached 835. The mystery of why exactly the boat tipped over was never solved. But the story was far from over

The armory building where most of the dead were taken during the disaster eventually was taken over by Oprah Winfrey and her show. A lot of the crew who worked on the show claimed that the ghosts of the dead passengers often haunted the building. They heard strange noises like children's laughter and the clinking of phantom glasses, and even saw apparitions, the most popular being one they dubbed the Gray Lady. Even the site of the actual disaster is supposedly haunted, with reports of people passing by the spot hearing bloodcurdling screams of the doomed passengers. 
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The Haunted Water Tower


The Haunted Water Tower is listed (or ranked) 2 on the list Creepiest Ghost Stories From Chicago
Photo:  Tama66/Pixabay/CC0 1.0
The Great Fire of 1871 still stands as one of the worst events to ever happen to Chicago. It left more than 300 people dead and over 100,000 people without homes. One thing that miraculously stayed standing amongst the destruction was the water tower, mostly thanks to the work of one brave worker. The man stayed behind as the fire raced toward the tower, manning the pumps instead of fleeing. Just before the fire consumed him, he hanged himself to avoid being burned to death. Now his ghost haunts the very water tower he tried to protect. Tourists and locals report seeing a shadowy figure of a hanging man from the tower's upstairs windows. 
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Resurrection Mary


Resurrection Mary is listed (or ranked) 3 on the list Creepiest Ghost Stories From Chicago
Photo: Juhana Leinonen/flickr/CC-BY 2.0

Resurrection Mary is one of Chicago's most famous ghost stories. It involves a young woman who wanders the streets around Resurrection Cemetery, scaring unsuspecting good Samaritans who stop to help her get home.

One popular legend about how she came to be states that she was a young woman in the early 1930s who really loved to dance. She liked to go out to dance halls and have a good time. One night she was hit by a passing car on her way home and was killed. She was then buried at the cemetery in her favorite dancing clothes.

Now her spirit roams the place around the cemetery and even the dance halls. Mary still likes to go to dance halls, and after she finds a boy to dance with for the night, she asks him for a ride home. She tells her date that she lives on the cemetery grounds because her father is the caretaker--then when they arrive at the cemetery, she disappears right in front of her his eyes.
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Flight 191


Flight 191 is listed (or ranked) 4 on the list Creepiest Ghost Stories From Chicago
Photo:  Hiljon/Pixabay/CC0 1.0

One of the worst airline disasters in American history happened in Chicago in 1979, when Flight 191 dropped from the sky shortly after taking off from O'Hare International. It killed everyone on board, all 271 passengers and crew. After a lengthy investigation, the crash was chalked up to a number of factors, including a stress crack in a flange that held the engine pylon. The entire community was changed forever after that fateful day. 

It wasn't long before reports of ghostly activity surrounding the crash site started to emerge. People started to claim seeing odd, bobbing white lights, but no source was ever found. The creepiest stories came from a small trailer park adjacent to the crash site, where for months after the crash, residents kept reporting frantic knocking at their doors, but no one was ever there. To this day, there are still frequent reports of weird knockings, strange sounds, and a few spirits roaming about the area.