Site of the Saint Valentine’s Day Massacre

Although the building in which the massacre happened was torn down in 1967, in an attempt to expunge Chicago’s gangster history, the grounds still remain. Curiously, the City of Chicago seems intent for the spot to always remain an unmarked, yet a strangely vacant lot. 

On the morning of Valentine's Day, February 14th 1929, in a garage and a depot for the North Side mob, seven men were gunned down by unknown henchmen for Al Capone. Pretending to be cops, the assassins lined up their victims against the brick wall of the garage and opened fire, fatally shooting them in the back.

No one noticed. But a dog tied up nearby who belonged to one of the dead men finally attracted the attention of a neighbor. When she went to investigate, the horror of looking upon such horror took hold. According to legend, people still hear her screams as well as a dog barking and the sound of phantom gunfire. 

Incidentally, you can still see the wall where the gangsters were lined up and shot, but that will require a follow-up weekend in Vegas. The infamous brick wall has been reconstructed and is on permanent exhibit at The Mob Museum in Las Vegas. However, dinner can be had by walking just next door to Riccardo Enoteca, one of Chicago’s most highly regarded Italian restaurants. The rumor is that dogs being walked in the area still act strangely while passing the site of the Saint Valentine’s Day Massacre. A window seat at Riccardo Enoteca is the perfect vantage point to test that hypothesis.

James M. Nederlander Theatre’s Death Alley

Today’s Nederlander Theater was originally the site of the Iroquois Theatre, which was the scene of a 1903 fire, which is still regarded as the worst single-building fire in American history. The Iroquois was destroyed by fire on December 30th, 1903, the day before New Year's Eve. 602 were killed, among them families on a special holiday outing to see a sold out show.

Since the time of the fire, people have reported all kinds of paranormal activity here, including apparitions of falling bodies, visions of fire erupting from the back of the current building, and the smell of smoke. Bystanders in the alley sometimes report hearing whistling and feeling that their hands have been grabbed by something unseen.

Witnesses have reported seeing the apparition of a woman in period clothing in the alley by the current theater’s stage door sign.

When Wicked played here, one stage manager confided that they had so much trouble putting on the show here. It was like everything was going wrong. When they finally got the first act on, he came out and sat down outside to have a cigarette. When he lit the cigarette, he reflexively threw his match on the ground. Then he heard a woman’s voice scolding him saying that “smoke will kill you.” He looks up and sees a woman wearing a hoop skirt and a big hat, who promptly disappears. Later after the show, after everyone including the actors had left, he turned the lights out preparing to leave, and heard the toilet flushing in the women's bathroom and little girls giggling. Of course, when he checked it out no one else was in the building.

In addition to its haunted history, Nederlander Theater is a venue for the production company Broadway In Chicago. The Nederlander hosts touring musicals and plays sure to add some theatrical flair to your haunted weekend in Chicago. Broadway In Chicago is best known for attracting pre-Broadway productions, including prestigious shows such as Wicked, The Producers, Kinky Boots, The Book of Mormon, and Hamilton.

The Congress Hotel

When seeking out adventurous lodgings for your haunted weekend in Chicago, look no further than The Congress Plaza Hotel. The consensus among locals is that this historic hotel is the most haunted in Chicago. Plus it’s colorful past complete with multiple haunting hotspots makes it the perfect place to launch your own private, after hours paranormal investigation.

Originally constructed for the World’s Columbian Exposition in 1893, the hotel, unfortunately, became a hangout of Dr. HH Holmes, America’s first serial killer. This notorious World’s Fair predator frequented the lobby luring young ladies to his torture castle just a few blocks down the street.

There are many haunted hotspots in the hotel, including the 12th or 13th floor of the north tower, where the ghost of a murdered 6-year-old boy has been heard and seen playing and running. The 4th floor of the south tower, specifically room 441, is home to an unidentified female spirit who hovers near the bed or pulls the covers off sleepers. Throughout the building, the ghost of a vagrant nicknamed Peg Leg Johnny is said to lurk. Other manifestations reported throughout the hotel include TV channels changing by themselves and shadow figures pacing in the closets. While ghostly visitations can never be a guaranteed amenity, some packages do include a full American breakfast and limited time specials include complimentary drinks.

The Signature Room at the 95th

Although this magical, mystery weekend is a definite departure from the Valentine’s Day norm, you can still go out for a fancy dinner. Atop what is still colloquially known as the John Hancock Center, now officially renamed 875 North Michigan Avenue, is a fine dining establishment called The Signature Room at the 95th. If you’re afraid of heights this might not be the place for you, as it's on the 95th floor of one of the tallest buildings in Chicago. It’s the extreme height that afford this line tablecloth affair its breath-taking views of the city. The building’s vertical limit has also been the cause of mysterious deaths and suicides. And that’s not even the worst of it, the unusual trapezoidal shape of the building, if local lore is any indication, might actually open a portal to hell.

After seeing the plans for the building's construction, Chicagoan Anton LaVey, founder of the Church of Satan famously warned the City Council of Chicago that the John Hancock Building would be cursed by paranormal forces. He suggested that within the trapezoid shape, the triangle with the top lopped off, is an ancient arcane symbol, which opens up a gateway for otherworldly forces. LaVey claimed the building would serve as a doorway for supernatural forces, allowing them to overtake Chicago.

John Belushi lived in this building when Dan Aykroyd and Harold Ramis were working on the script for the film Ghostbusters. Although Ramis and Aykroyd knew that they wanted to make this film about a team of rag-tag ghostbusters in New York City, they didn't have a plot. While they were visiting Belushi one weekend, he was telling them about all of the strange freak accidents and suicides that had gone on there. When they returned home to finish the script for Ghostbusters, which perhaps not coincidentally features a high-rise building that serves as a portal for paranormal forces.

In reality, since the building was completed, there have been many unexplained deaths here, including the most famous one of all, the death of a woman named Lorraine Kowalski in 1971. Kowalski was a 29-year-old socialite, who somehow crashed through a double-plated glass window and was found 85 floors below on Michigan Avenue. 

Frank Heidenreich, building’s engineer, maintained that there was no possible physical way that this diminutive woman could have crashed through the window, even if she had been pushed. It had been built to withstand over 200 pounds of force per square foot. He said during construction workmen inside the building fell off scaffolds onto single panes of the same glass without breaking it. A coroner’s jury eventually ruled Kowalski’s death accidental. These kinds of strange deaths and so-called "suicides" have continued throughout the years. There have now been 11 such unexplained events, but don’t let that spoil an excellent dinner.

The Great Escape

The Great Escape’s haunted history began in 1889. The banquet room was once a general store, milk depot, and gas station. The original bar once served railroad workers. Later the building served as a speakeasy through Prohibition. Although technically outside the city of Chicago, the Schiller Park speakeasy allegedly attracted Al Capone, who supplied their booze. 

Cold spots, doors opening and closing on their own, and sightings of multiple apparitions even that of a little girl ostensibly caught on-camera have led to myriad paranormal investigations by many different teams.

Hearing ghostly music from a defunct antique radio was the owner’s first indication of something otherworldly. Watch for the black-suited man with a clipboard that has been spotted multiple times by different witnesses. Take pictures in the banquet room and see if the orbs or silhouetted figures are captured in your photos as they have been over the years when patrons documenting their family parties have taken pictures.

Cap off the weekend with a guided bus tour where you can explore Chicago’s haunted past like the Original Chicago Hauntings Ghost Tour. Then hide yourself away at a place that happens to hold Chicago’s best kept secrets like Harry Caray’s Steakhouse for your own chance to glance inside mob enforcer Frank Nitti’s Vault. If you like hidden passages, this is mafia cloak-and-dagger at its most authentic.

Whether rekindling that old flame or sparking chemistry on a first date, these unique haunted date night ideas are different enough that they might prove memorable, one might say even haunting. Besides the positive benefits of doing something new, such opportunities as those above examine the mistakes of the past and offer a glimpse into the unknown. Explorations such as these, which touch on primal questions of life and death and good and evil, may even trigger meaningful conversations between you and your loved one for years to come.