The sky was as clear and blue as the water of Lake Michigan. A bright sun shined down through the tips of the tall buildings as I stepped out of the cab, just under the sign of The Drake Hotel. I peered up at the building.

The First Impression

It’s a famous building, built in raucous 1920, as Chicago rebuilt following the Great Chicago Fire of 1871. It’s sandy colored façade cut a low rectangle out of the sky. In the shadow of a much sleeker, much newer building with two giant spires, the hotel’s age shows.


I smiled brightly at the sun, feeling it on my face. The cab driver swung my bag out of the trunk and nearly tossed it at the car behind us. He expected it to be heavier. I was only in Chicago for a brief business trip, 36 hours and I’d be back in DC. So, I packed light. I retrieved my bag and walked through the brassy gold revolving door.

The air cooled as I spun. I stepped out onto a thick blue carpet that climbed up the stairs to the lobby. It was a chilly, eerie entryway. I hoisted my bag and ignored the shiver tickling my spine, hoping the next level would be brighter and less ominous.

Room for all at the Drake Hotel

A man in a brown service coat that looked like it would have been made in the 1940s, complete with gold buttons that trailed down the left side, greeted me at the top of the stairs. He offered to help me with my bag. When he smiled, his white teeth got lost in the shadows of the room. I said no thank you and got my key.

I went into the elevator, which had the same sinister eerie feel as the rest of the hotel – gold accents, candelabra scones that flickered with a sepia light, deep toned woods, damask wallpaper. It was as if the art deco and Victorian era styles had a baby. This place was ripe for a spirit.


When I entered my room, there was more darkness, despite a large window and a bright sun. I turned on every lamp and light switch. It didn’t help. The hotel seemed impervious to light. I rushed to change and meet my colleagues in one of the ballrooms.

When I walked out of my door, the hallway had a unsettling stillness, all quiet except for a strange buzzing sound, like a swarm of bees was stuck in the wall. “If I see two twins at the end of the hall, I’m out of here,” I mumbled to myself. (Of course, since I was traveling I brought The Travelers along for company and we had to stop to take pictures to document the eerie hotel experience.)


Ghostly Encounters

To get to our meeting room, I had to pass through a large ballroom, with shimmering crystal chandeliers and intricate patterns swirling along the walls and balcony that rimmed the top of the room.


I hurried through the room to an annex on the side. When I entered the room for our meeting, it felt slightly better to be around people.  I made a joke to my colleague that if I saw redrum written anywhere I would go back to the airport. She looked at me with terror in her eyes and said, “Don’t say things like that. You’re freaking me out.”

I was curious though, was it possible this hotel was haunted?

Our hotel contact came in to check on our meeting, we’ll call her Ann. When she’d finished her list of talking points, I asked her: “Ann, is this hotel haunted?” I expected her to laugh. She did smile, a strange sort of smile. Her eyes darted around and she fiddled with her clipboard.

“Well, I’ve never seen any,” she said. “But.”

My colleague jumped in, “But? No, you’re kidding, right?”

“I’ve been here late at night and early in the morning and I haven’t seen anything. But there are stories, other employees…” she trailed off.

“Don’t tell me any more please,” my colleague begged. Ann quietly left the room as my fingers tapped away on my keyboard looking up “Drake Hotel” and “Ghost.” The Drake popped up on all different types of ghost sites – Ghost tours, most famous haunted hotels, top 10 true ghost stories.

Here are the stories they told.

The woman in red

20170512_230514On the opening night of The Drake Hotel, New Years Eve 1920, a man and his fiancé attended the gala held in the Drake’s Gold Coast Room. The fiancé glided and waltzed in a red silk dress. At some point during the night, the man disappeared and did not return.

The fiancé searched for him, becoming panicked as she roamed the corridors. She finally found him, in the Palm Court parlor, his body draped over another woman, arms wrapped around her, kissing. Devastated, the fiancé ran to the roof of the building and jumped off to her death. Since then, guests at the Drake have reported seeing a Woman in Red ghost in the Gold Coast Room, Palm Court, and on the top floor and the roof, replaying her final night.

Other stories have her jumping out the 10th story window and say she haunts the 10th floor.

The woman in black

woman in blackApparently women and the color of clothes they wore are very important to the spirit community at The Drake. The other popular ghost story involves an unsolved murder.
In January, 1944, Mrs. Adele Born Williams, a 58 year old society mother, walked up to her apartment at the Drake Hotel with her daughter. The door was unlocked. Inside, they found a gray-haired woman in a black fur coat hiding in the bathroom. The woman pulled an antique gun from her purse and fired at the daughter, but missed. As she fled the room she fired more shots, hitting the mother in the head and killing her.

Then things got really weird. The woman in the fur coat was never found. But the murder weapon was. It was found in a stairwell, after the police searched it and found nothing there. Similarly, a spare key to Williams’ room was reported missing from the front desk at the time of the murder. Mysteriously, it appeared back on the desk at 10 o’clock that evening. Mrs. Williams had $100,000 in cash in a safety deposit box for reasons unclear. No jewelry or valuables were taken.

To this day, the mystery remains unsolved. There was never an official suspect, and though various motives were suspected, none of them really held up. The woman in black was never identified. Although it was a huge story in 1944, today, it’s largely unknown, unless you’ve seen the ghost at The Drake.

Woman in my room

As it drew close to midnight, our meeting finally ended and I headed back to my room. Feeling a little unsettled, I decided to order a glass of wine and started my second job – writer – for the night. The hotel staff member who brought my drink wore a vest with red piping and had the manners of an 18th century butler. “May I come in,” he asked. I think he might have even bowed. He looked ancient, not in his face, which was young and round. But, in his mannerisms. If he wasn’t carrying a tray I may have thought he was a ghost.


After the staff member from the hotel left I sat down to write again. I don’t generally believe in ghosts. They fall into that category for me of “I don’t think they’re real, but they could be.” I guess I believe in them enough for the weird buzzing and the sudden bang that seemed to come from nowhere make my chest flutter. And enough that when I looked back over my shoulder, the tiniest part of me worried I might see a ghost. And enough to refuse to open the closet door in my room too.

And I believed in them enough that when I finally crawled into my bed, I left the light on in the bathroom on and pulled the comforter up over my head and dreamed of a ghostly women in red.

You can check out any time you like

In the morning I dressed, packed and went back to our meeting. At 6am the halls were empty. The floors creaked, strange noises banged through the walls. The elevator felt less empty than I’d like it to feel when there was no one in there but me.

Finally, in the afternoon, I reversed out through the revolving doors, having not left the hotel for 36 hours and stepped into the sunny, abnormally warm Chicago streets. It was like coming out of a weird dream. I got in the cab, closed my eyes, rolled down the window and let the wind blow my hair against my face. By the time I reached the airport, the tingle in my spine disappeared. I felt normal again.

Would I go back to The Drake? Heck yeah, that was kind of fun!