The Drake, A Hilton Hotel: A Chicago-Style Icon with Gangsters, Ghosts, and Glamour

Strictly speaking, for something to be iconic it should be representative of something larger. So that when you look at it, it’s a symbol for something greater than itself. Like the Eifel Tower is to Paris, the Empire State Building to New York City, or the Opera House to Sydney. More so than any other building, The Drake, a Hilton Hotel has become iconic of Chicago. The building’s history practically mirrors that of its home. It’s rich with glamour, gangsters, Hollywood stars, politicians, royalty, and even some good old-fashioned ghosts. It’s pink gothic neon (well, now LED) letters hovering over the Lake Michigan skyline has become the “Hollywood” sign for Chicago. Like those white capital letters in the Hollywood Hills, you know you’ve made it to the White City when you see their pink glow. Now you just have to buckle up and enjoy the ride. Because it’s only natural that Chicago’s icon has a dark side…a side that The Drake just begs you to explore.

A New Year and a New Beginning…for Some

Of course a hotel that was to become a city’s icon would open its doors for the very first time on New Years Eve. On the last day of 1920, 2,000 guests welcomed the New Year and a new luxury hotel in The Drake. It was only one year prior that the Drake Brothers, their hotelier father’s wealthy friends, and noted Chicago architects Marshall and Fox were able to finance their plans for a grand hotel and the financing itself was years in the making. Tracy and John Drake were no strangers to the world of luxury hotels. Their father, John, had been one of Chicago’s first hotel magnates and it was his connections to another Chicago hotelier and businessman, Potter Palmer, that got the Drake brothers this enviable piece of land when they bought it from Palmer’s estate in 1916. This perfect spot between Chicago’s residential Gold Coast, replete with mansions, and the Magnificent Mile, the city’s burgeoning high class shopping mecca, also boasted unobstructed views of Lake Michigan, being only one block away from Oak Street Beach.

 Marshall and Fox designed the hotel in the Beaux-Arts design that was becoming synonymous with Chicago following the World’s Fair. The exterior of the hotel would feature all of this school’s emphasis on symmetry, arches, and use of stone in its construction while the interior would be the height of luxury with a grand arrival hall, distinct formal entertaining spaces, and marble staircases and columns. By the time the countdown to 1921 had begun the hotel had cost $10 million to build. Just to keep this level of opulence in perspective, in today’s money that would be $120 million.

Yet, on this New Years Eve opening night where confetti fell and revelers shared midnight kisses, one partygoer breathed her last. According to Drake legend, a “Woman in Red” was in attendance that night but left the celebration in tears when she discovered her fiancé in the arms of another woman. The Woman in Red ran to the elevator and, while accounts vary as to where she got off (some say the roof, others the 10th floor), she threw herself off the building to her death. The fact that no newspaper reports exist of this occurrence only add to the mystery, with claims that the Drake brothers and their wealthy friends hid it from the press to avoid bad publicity. But ghosts don’t lie…for decades guests have reported seeing a morose woman in red wandering the Gold Coast Ballroom, the Palm Court, and the 10th floor.

Good Times, Famous Faces, and Murder

The twenties did indeed roar at The Drake. The hotel’s first decade was booked with opulent parties thrown by Chicago high society, as well as daily high teas in The Fountain Court. Winston Churchill himself had high tea here during his visit in 1929. Meanwhile, the hotel’s Gold Coast Ballroom with white and gold carved marble columns and seating for 1,000 hosted concerts by George Gershwin and, in the 1930’s, big band leader Herbie Kay with audience members such as Charles Lindbergh and Amelia Earhart. Even when the good times came to an end for many Americans during the Great Depression of the 1930s and World War II in the early ‘40s, the Drake Hotel kept busy with performances by Frank Sinatra and Dean Martin and visits from almost every political dignitary from Eleanor Roosevelt to Herbert Hoover.

And why wouldn’t everyone want to flock here? The Drake opened America’s first themed restaurant in 1932 with the Cape Cod Room featuring New England-themed seafood cuisine. In 1933, the hotel’s brand new restaurant, the Coq d’Or, was the city’s first to obtain a liquor license at the end of Prohibition. In 1940, the hotel’s signature neon sign was lit and The Fountain Room began changing its décor according to the season with a massive fountain and open ceiling for lake breezes in the summer, replaced by a massive stone fireplace in the fall and winter.

Now don’t forget for a minute that we’re talking about Chicago in the 1930s and 40s. There’s not an old hotel in the city that doesn’t boast a gangster connection and The Drake is no exception. Frank “The Enforcer” Nitti was head of the Chicago Outfit during this time and had a suite of rooms at the hotel. When President Barak Obama’s Secret Service was sweeping the property for his 2010 visit, a secret tunnel that would enable Nitti to flee rivals or the police was discovered from these rooms to the Grand Ballroom. But only in Chicago would a gangster’s stay be trumped by murder and mystery. In 1944, a mysterious “Lady in Black” shot and killed a wealthy hotel guest by the name of Adele Born Williams in her room on the 8th floor. Though Ms. William’s daughter witnessed the crime, provided details as to the woman’s black coat, gray hair, and middle-aged appearance, and the gun used in the crime was found in a stairwell several days later, the mysterious “Lady in Black” was never found.

The Times Change But an Icon Remains

The 1950s were still part of a long heyday for the hotel. In 1954 newlyweds Joe Dimaggio and Marilyn Monroe visited and, over dinner in the Cape Cod Room, carved their initials into the bar like childhood lovers. Cary Grant and Grace Kelly sipped martinis at the Coq d’Or. Queen Elizabeth II stayed at The Drake for her first and only visit to Chicago in 1959 and had high tea in the Fountain Room. But the late 60’s and early 70’s saw a decline for so many of the city’s old buildings. Money for restoration and upkeep were hard to come by and new and modern was thought to be more appealing than old and historical. Though the Drake brothers lost ownership of the hotel during The Depression, the Brashears family had owned it through their family partnership since that time with great success. But by 1979, the hotel had become too costly and the Brashears were looking for a buyer. In 1980, the hotel was placed on the National Register of Historic Places and was sold to a local Chicago realty group. But the next decade continued to be lackluster for The Drake until 1996, when hotel conglomerate Hilton International purchased it for just under $40 million and began a five-year renovation, costing $45 million. This included brightening the guest rooms with lighter draperies and bed linens, refreshing all the bathrooms, and sprucing up the lobby with brighter lighting, as well as a marketing campaign that appealed to lovers of “real Chicago.” Princess Diana’s visit in 1996 only added to the hotel’s new prestige. By all reports the Princess loved her stay and the suite where she stayed, just a year before she died, is now called the Princess Diana Suite. It’s a favorite spot for brides to stay the night before their wedding in the ballroom below.

The Drake has undergone several renovations over the past twenty years, with the Hilton Corporation acquiring Hilton International in 2005 and renaming the hotel The Drake, A Hilton Hotel. It’s 553 guest rooms and 74 suites have all the latest 21st century amenities like flat screen HD TVs and free WiFi. The lobby is alive with vibrant blue and gold carpeting, brightening the rich mahogany and marble that have anchored it for almost a century. The Fountain Court is now the Palm Court and its décor doesn’t change seasonally any more but the fountain and is still the perfect background noise to the clinking of china and silver during high tea. The Cape Cod Room was replaced in 2016 with the elegant Café on Oak, but the initials MM and JD are still etched into its bar and the ever-present Coq d’Or remains with deep red banquets, wood paneling, and cocktails reminiscent of the end of Prohibition.

We use the word icon so frequently these days, often to describe people and things that simply don’t measure up. Perhaps its because we’re always searching for something that truly is iconic, something that really does conjure up an image that is grand. The Drake is one of the few places that truly is an icon of the city in which it was born. For only Chicago can birth an icon with gangsters, ghosts, murder, and grandeur.

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