The Woman in Red and the Haunted Drake Hotel Christmas Bride

Few places in Chicago feel as timeless during the holiday season as The Drake Hotel. When December arrives and Michigan Avenue glows with winter lights, the hotel’s grand silhouette takes on a nostalgic charm that fits perfectly with Chicago ghost hotel legends. The history of the Drake Hotel in Chicago begins with architect Benjamin Marshall and financiers John and Tracy Drake, who opened the hotel on New Year's Eve in 1920. Standing tall at 140 E. Walton Place, its Jazz Age style and enduring elegance make it one of the most recognizable landmarks on the Magnificent Mile. Generations of celebrities, royalty, and travelers have passed through its halls, adding layers to the Drake Hotel Chicago history and deepening the mystery surrounding one of the most haunted hotels in Chicago.

A Pink Neon Beacon on Michigan Avenue

The glowing pink Drake sign feels especially striking during the December nights when holiday decorations line the street. While warm lights surround it, the building also carries whispers of a tragic Christmas story tied to the haunted Drake Hotel Chicago. This is the tale behind the ghost lady in red, a story that has helped cement the Drake as one of the most haunted hotels in Illinois.

The Fateful New Year's Eve of 1920

During the hotel’s New Year’s Eve gala in 1920, the Woman in Red arrived full of joy. She had accepted a Christmas Eve proposal only a week before. The holiday celebrations, the festive dinner menus, and the excitement of the grand opening created a magical atmosphere. But the night turned dark when she discovered her fiancé with another woman. Heartbroken, she fled toward the rooftop. Some versions say she jumped from the tenth floor. Either way, her tragic end became a lasting thread in haunted Chicago hotel lore. People still ask if the Drake Hotel Chicago is haunted, and her story is the reason many believe it is one of the most haunted hotels in the Chicago area.

Haunting Sightings of the Woman in Red

Since that night, sightings of the Woman in Red have been reported throughout this haunted Chicago hotel. Guests and staff claim to see her near the Gold Coast Room where the gala took place, in the Palm Court where tea at The Drake Hotel Chicago remains a beloved tradition, along the top floor, and near the rooftop. Others insist the tenth floor holds the strongest energy. Her presence adds to the Drake Hotel haunted Chicago identity and keeps visitors wondering if the Drake Hotel in Chicago is haunted or if it is simply the most haunted hotel in Chicago by reputation.

One eerie photograph taken by a guest named Becky during a ghost hunt with our guide Tony Szabelski appears to show a woman’s silhouette seated quietly in a ballroom. The black and white image has become part of the Drake Hotel haunted story and fuels ongoing debates about haunted hotels in Chicago Illinois. Many guests visit hoping to see something for themselves, especially during winter when the halls feel quieter and the atmosphere seems to hold more history.

The Drake Hotel: More Than Just a Landmark

The tragic story of the Woman in Red has become woven into the Drake Hotel history. It has transformed the hotel from an architectural masterpiece into a symbol of love, loss, betrayal, and lingering spirits. As December nights grow colder and the city prepares for Christmas and New Year celebrations, the hotel’s reputation as a haunted Chicago hotel becomes even more captivating. Visitors come not only for its elegance but also to learn whether the Drake Hotel is haunted or if these tales belong only to folklore.

Ready to explore Chicago’s most haunted hotel stories for yourself

Join us on the Original Chicago Hauntings Ghost Bus tour. We visit some of the city’s most iconic haunted locations, including the Congress Plaza, another site often listed as a contender for the most haunted hotel in Illinois. Tours run every Saturday at 7pm, offering the perfect chance to step into Chicago’s ghostly past during the holiday season.

See why guests rate this as a must-experience Chicago ghost tour by checking our reviews on Google.

For more chilling stories, explore our paranormal investigations and ghost encounter guides in “Ghosts of Lincoln Park: A Chicago Hauntings Companion” and “The Original Chicago Hauntings Companion” by Ursula Bielski, written by our American Ghost Walks team.

If you love haunted hotels in Chicago or want to uncover more stories behind the most haunted hotels in the Chicago area, browse our full American Ghost Books collection and find your next late night read.

Find Your Next Paranormal Experience