Chicago is a city built on top of itself. Literally. After the Great Fire of 1871, they just leveled the rubble and started over, which basically means the entire downtown area is a giant graveyard of memories and charred remains. It's no wonder people keep seeing things. When you check into certain haunted hotels in Chicago, you aren't just paying for a high-thread-count sheet and a view of the lake; you're stepping into a space where the past refuses to stay buried.
Honestly, some of these stories are probably just the wind whistling through old elevator shafts or the sound of a 100-year-old pipe expanding. But then you hear about the recurring sightings at the Congress Plaza Hotel, and you start to wonder.
The Congress Plaza Hotel: Chicago’s Most Active Resident
If you ask any local paranormal investigator where the "real" stuff happens, they’ll point you straight toward 520 South Michigan Avenue. The Congress Plaza Hotel is massive. It's intimidating. Since its opening for the World’s Columbian Exposition in 1893, it has hosted presidents, celebrities, and—if the rumors are true—a fair share of permanent residents who never checked out.
The most famous of these is "Peg-Leg Johnny." He’s reportedly the ghost of a hobo who was murdered in the hotel. Guests see him flickering in the shadows of the South Tower. He likes to mess with the lights.
Then there's the Gold Room.
Security guards have reported hearing the sound of a phantom piano playing when the room is completely empty. Some people think it’s connected to the "Hand of Mystery," a gloved hand that allegedly protrudes from the drywall, though that sounds a bit more like urban legend than documented fact. Still, the hotel’s reputation is so intense that the management famously kept Room 441 permanently locked for years. Why? Because guests reported a female shadow figure that would kick the bed or whisper in their ears while they slept.
It’s creepy. Really.
The Tragedy of the 12th Floor
The South Tower’s 12th floor is where things get heavy. During the 1930s, a mother named Adele Vagner stayed there with her two sons. In a moment of absolute, inexplicable despair, she threw both children out the window before jumping herself. It’s a horrific piece of Chicago history. Today, staff and guests report seeing the figures of two young boys running down the hallway. They disappear when you try to follow them. It isn't just "spooky"—it’s tragic.
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What’s Actually Happening at the Drake?
The Drake Hotel is the pinnacle of Chicago luxury. It sits right at the top of the Magnificent Mile, looking out over Oak Street Beach. You’d think ghosts would prefer somewhere a bit more... dilapidated? Not the "Woman in Red."
The story goes that back in 1920, during the hotel's opening gala, a wealthy socialite found her husband in the arms of another woman. She didn't cause a scene. She didn't scream. She simply walked up to the 10th floor (or the roof, depending on who you ask) and jumped.
- The Sighting: Guests in the 10th-floor suites often report seeing a woman in a blood-red evening gown pacing the hallways.
- The Vibe: Unlike the Congress, which feels heavy and dark, the Drake's hauntings feel more like a lingering melancholy.
- The Evidence: There are no photos. There are no recordings. But there are decades of consistent logs from night porters who refuse to go into certain service elevators alone after midnight.
Some people claim she’s looking for her husband. Others think she’s just trapped in the loop of her final night. Regardless, if you’re staying at the Drake, keep an eye out for a flash of crimson in your peripheral vision.
The Hilton Chicago and the Ghost of the Elevator
The Hilton Chicago (formerly the Stevens Hotel) is another beast entirely. This place was once the largest hotel in the world. During World War II, the Army used it as a barracks.
There’s a specific ghost here that people call "The Elevator Man." He wears a vintage uniform and is usually seen in the service elevators or the basement levels. He doesn't scare people, usually. He just stands there. He looks like he’s waiting for a floor that doesn't exist anymore.
A lot of the "activity" here is attributed to the fact that the hotel has been renovated so many times. In the world of the paranormal, construction is like a dinner bell for spirits. It stirs things up. If you're staying here, pay attention to the temperature. Sudden drops of 20 degrees in a sealed hallway are a classic sign that something is moving through the space.
Why Chicago is Different
Let's be real for a second. Every old city has "haunted" spots. Savannah has them. New Orleans is practically built on them. But Chicago’s haunts feel different because they are tied to the city’s rapid, often violent, growth. From the Eastland Disaster to the St. Valentine’s Day Massacre, this city has seen a lot of concentrated grief in a very short period of time.
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The Al Capone Connection: The Blackstone Hotel
You can’t talk about Chicago history without mentioning the mob. The Blackstone Hotel was a favorite of Al Capone. He used to get his hair cut in the windowless barbershop in the basement because he was terrified of being shot through a window.
- The Smoke: Guests in the suites once frequented by Capone often report the smell of expensive cigar smoke, even though the hotel has been strictly non-smoking for years.
- The Temperature: Certain spots in the basement feel like a meat locker, even when the heat is blasting.
- The Voice: There are sporadic reports of a gruff voice telling people to "get out" when they linger too long near the old barbershop area.
Is it Capone? Who knows. But the Blackstone has a "vibe" that is undeniably old-school Chicago—a mix of high-class elegance and back-room deals.
How to Ghost Hunt Without Looking Like a Tourist
If you're actually trying to experience haunted hotels in Chicago, don't just walk around with a camera and a flashlight. You’ll get kicked out. These are working businesses.
Instead, try grabbing a drink at the bar. The lobbies of the Congress or the Drake are public. Sit there. Observe. Talk to the bartenders—they’ve seen everything. Most of them have a "story" they’ll tell you if the tip is good and the bar isn't too crowded.
- Look for: "Cold spots" that don't align with AC vents.
- Listen for: Disembodied footsteps on carpeted floors.
- Notice: The feeling of being watched in empty corridors.
Sorting Fact from Fiction
Look, I’m a skeptic at heart. A lot of "hauntings" can be explained by infrasound—low-frequency noises that cause feelings of unease or even hallucinations. Old buildings are full of infrasound. They have massive boilers, heavy machinery, and thick walls that vibrate.
But science can't always explain why five different people, who don't know each other, describe the exact same "man in a beige suit" on the 4th floor of a hotel over a twenty-year span. That’s where the mystery lives.
Chicago’s history is messy. It’s a city of survivors, but it’s also a city of those who didn't make it. When you stay in these hotels, you’re participating in that history. You’re a temporary guest in a building that has seen more than you ever will.
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Actionable Steps for the Brave
If you're ready to book a room and see for yourself, here is how you do it right.
Book the specific floors. At the Congress, ask for the 12th floor of the South Tower or anything near Room 441. At the Drake, aim for the 10th floor. Just be prepared for the fact that you might not get much sleep.
Bring a digital voice recorder. Set it on a table in your room while you’re out for dinner. When you get back, listen to the silence. Sometimes, you’ll hear "Electronic Voice Phenomena" (EVP)—whispers or clicks that weren't there when you left.
Don't provoke. If you believe in this stuff, remember that these "spirits" were people. Being disrespectful usually just results in a bad night and a grumpy housekeeper.
Check the historical records. Before you go, look up the building on the Chicago Public Library’s digital archives. Seeing the old floor plans and photos of the people who lived there makes the experience much more grounded and, frankly, much scarier.
Chicago is a beautiful, loud, vibrant city. But when the lights go down and the lakefront wind starts howling against the glass of an old hotel window, it’s very easy to believe that the past isn't as far away as we think. Be careful which door you open. You might find someone already in the room.