Welcome to the wild and woolly Windy City, where the town takes a nickname for all the blustering windbags and conveniently happens to have that lake effect wind.

We’ll be taking a brief tour through some of the creepiest, weirdest, and most haunted places of the city, as we pull that pea coat closer and huddle as we walk.

First off, let’s pause at the Chicago River and get a bit colder as we talk through three events and locations.

The Eastland Disaster

The Western Electric Company was doing a good thing: a giant family picnic for the whole of the company. Unfortunately, they weren’t so great at selecting a company for their excursion to Michigan City, Indiana however, because the Eastland was hired.

This boat was already notorious for not being in the best of shape, but the crew upped the ante by removing the ballast so that they could cram in even more passengers on that fateful morning of July 24, 1915.

The ship began to list within a couple of minutes of loading. And by the time they were between the LaSalle and Clark Street bridges – less than 10 minutes after departure – disaster was upon them.

Nearly 850 people, including 21 entire families, perished that day.

So, of course, the river banks and many of the temporary morgues are haunted. The home of Harpo Studios, for example, has had tons of reports of creepy happenings. Old -imey music playing in hallways, children screaming, hundreds of footsteps marching the empty halls. Just an average day there.

Marina City


Next, let’s look at these corncob looking buildings side-by-side at the river. The idea behind these buildings was to create a city within the two buildings, to appeal to and keep folks from moving out to the suburbs. They’ve got stores, restaurants, groceries, and more in these two buildings, to keep everything self-contained.

But when construction on these buildings began in 1961, a ton of weird and terrifying things started happening.

  • 1961 – Three workers were killed when scaffold plummeted 43 stories
  • 1961 – Seven men were injured when a workers’ elevator dropped suddenly
  • 1962 – William Jones, working on the 40th floor had a dizzy spell and plunged to State Street Bridge
  • 1966 – The body of Roy Holland was found in his apartment after 3 weeks and 3 suicide notes
  • 1967 – June Fleck leaped from her fiancé’s 50th-floor apartment shortly before the wedding
  • 1969 – A retired government worker shot his 88-year-old mother and then himself
  • 1972 – Gloria Kirkpatrick – manager at the Marina City Theater – was stabbed to death outside the building
  • 1973 – Sandra Easton leaped to her death from the 52nd floor and crashed through the canvas on the now Smith & Wollensky restaurant
  • 1976 – Kenneth Parvin fell from the 57th floor and landed between the two towers

And the craziest part? Every single one of these incidents is associated with the East Tower, and not the West.

So, what’s our lesson here, folks? If you move to Marina City, go West!

The Chicago House of Blues

Our third point of interest is just next door at the Chicago House of Blues, formerly the home of the Marina City Theater. There’s a tale here of a little girl who haunts the joint. It’s said that she “died of an illness,” but we don’t know anything else about her.

Once, it was reported that a little boy was present, playing with his toys. When he wouldn’t share with a little girl, she screamed and cried, and vanished into thin air.

The Old Cook County Courthouse

Next, let’s move on to some chilling places nearby on Dearborn Street where some horrifying figures have been haunting the place. First up, the Old Cook County Courthouse.

The alley behind the building is a great place to take in the full ghouls of the night. It used to be the site of the gallows where some notorious figures in Chicago history were removed from society.

Some of these nasty folks include four members of the Haymarket Bomb throng who chucked a bomb into the police ranks at the famous labor rally.

Some other folks who’ve been on trial here include mobsters like Frank Nitti, Al Capone’s “Enforcer,” the crooked White Sox players who fixed the 1919 World Series, and the infamous Leopold and Loeb who committed the “Crime of the Century” when they kidnapped and killed 15-year-old Bobby Franks because they thought they were too smart to get caught.

And if you love musicals, you’ll love knowing that the trials of Belva Gaertner and Beulah Annan who inspired the lead roles in the musical Chicago were put on trial here, too.

The Haunted Chicago Fire Department

Right next door here, you see this firehouse. Well, that used to be the location of the jail that was attached to the courthouse. Something like 100 convicts were hanged here in this alley, and tons of unsavory things happened inside the jail walls.

It’s no wonder numerous firefighters report unsettling happenings and an unwillingness to stay overnight on shift in the firehouse.

The Castle

Our final stop along this brief tour of the most haunted places in Chicago is currently called Tao, but formerly has been known as Excalibur, the Castle – not to be confused with the H.H. Holmes Murder Castle, the Limelight, and formerly the Chicago Historical Society.

By Goldnpuppy – Own work, CC BY-SA 3.0

There are three main theories on who’s haunting the place.

1. Eastland Disaster Victims

The folks placed here when it was a temporary morgue seem to be haunting the Dome Room where they take liberties with flying rags, breaking glasses, and eerily speaking the names of employees when no one else is around.

2. The Lady in Red

One of the three women seen fleeing the Great Chicago Fire of 1871 ran into the then wooden structure on the site. She’s seen regularly going about the building in her bright red Victorian gown.

3. The Man in Gray

Before all of this, probably not long after the Fort Dearborn days, there was a land dispute over the spot. One man claimed to own the land while a squatter refused to leave, saying he had the right to live there.

The “landowner” however wasn’t keen on squatter’s rights, so he sent a hitman to take him out. The squatter’s body was left to rot on the land, and so it seems kind of likely he’d have a reason to haunt the place.

Thanks for Coming Folks

I appreciate you joining me for this windy walk through some of the most haunted spots in Chicago. Be sure to keep your ears open by the River where you might hear some old-timey music playing, or by the Holy Name Cathedral where two mobsters supposedly haunt after being murdered nearby. You might see the weird floating orbs of light and have your own haunted tale to tell.