8 Historic Chicago Hotels Worth Revisiting For Your Wedding

The Drake opened its doors on New Year’s Eve back in 1920 and it hasn’t skipped a beat since. Throughout the roaring twenties, the Gold Coast gem was the go-to spot for high-society socialites, eventually giving birth to its very popular high tea, a service still enjoyed by groups (including bridal showers) today. Unaffected by the crash of 1929, the illustrious urban resort continued to draw an elite crowd, including Bing Crosby, Walt Disney, George Gershwin and Charles Lindbergh — all of whom could be found sipping a libation while listening to Herbie Kay in The Gold Coast Room.

Over the years, that same 6,838 square-foot space (nearly the same size as the ballroom at Buckingham Palace) has hosted countless galas, weddings and other celebrations. The Grand Ballroom was originally built in the roaring twenties for The Charleston craze, but that’s not the only fun fact: the floor is literally equipped to put a spring in your step! And you can’t leave this historic property without stopping by the Cape Cod Room to see where newlyweds Marilyn Monroe and Joe Dimaggio carved their initials into the wooden counter.

Originally built in 1929 as the exclusive Medinah Athletics Club, the building closed its doors in 1934 due to the stock-market crash. Decades later, in 1988, InterContinental Hotels bought the property and turned it into a luxurious hotel without losing an ounce of historic charm. The four-story lobby, with a huge staircase and Spanish-inspired fountains and chandeliers, reminds guests of the building’s grand past.

When it comes to event space, one room is more impressive than the next. The Spanish Tea Court was created to celebrate the era of King Ferdinand and Queen Isabella, while the Louis XVI-inspired Renaissance Room is paneled in rare, imported Carpathian Elm Burl wood. The crown jewel is the Grand Ballroom, complete with 37 hand-painted murals (restored by the artist who consulted on the restoration of the Sistine Chapel ceiling) and a 12,000-pound Baccarat crystal chandelier — the largest in North America.

Since its opening on April 16, 1910, the Blackstone has attracted a bevy of celebrities, socialites, political powerhouses and infamous icons. Aptly named “The Hotel of Presidents,” the Blackstone has hosted a dozen chief executives, from Teddy Roosevelt to Jimmy Carter. Along with the Astors, Rockefellers and Vanderbilts, the hotel hosted such notable talent as Lena Horne, Nat King Cole and Rudolph Valentino. Legendary mob bosses “Lucky” Luciano and Al Capone put the Blackstone on the map in Chicago’s crime world.

Several years later — and after a failed attempt at becoming a condo building at the hands of the Maharishi Yogi, personal guru to the Beatles — the hotel was shuttered in the 1990s, not to reopen until 2008. Luckily, despite the passing of time, the Renaissance Blackstone has managed to retain its classic charm everywhere from unique venue spaces like its stately Crystal Ballroom to smaller details like the luxurious woodwork seen throughout the property.

Back in 1895, prominent architects Daniel Burnham, John Root and Charles Atwood designed the 14-story Reliance Building, which quickly became known as a landmark in Chicago. The steel-and-glass design was the first of its kind, setting the precedent for the modern skyscraper. In 1999, Kimpton Hotels restored the property as the Burnham. The mosaic floors and the metal elevators are only two examples of features that were rebuilt to match the original design.

To say the Palmer House is rich in history is a bit of an understatement. The grandiose property was built by businessman Potter Palmer as a gift for his bride Bertha in 1871. Just thirteen days after opening, the Great Chicago Fire ravaged the city, but the hotel was rebuilt with a $1.7 million signature loan (the largest individual loan at the time) and reopened in 1873.  It was also the first building to ever employ the use of the elevator and the light bulb. To top it all off, the brownie was created in its kitchen.

By the turn of the century, the Palmer House had become a social hotspot and host to a laundry list of prominent figures ranging from U.S. presidents to Charles Dickens to Oscar Wilde. In 1933, the Golden Empire Dining Room of Palmer House was converted into an entertainment epicenter. The venue hosted several legendary entertainers, including Frank Sinatra, Judy Garland, Ella Fitzgerald, Harry Belafonte, Louis Armstrong and Liberace. Today, the dramatic lobby — with glittering chandeliers and a painted ceiling — four ballrooms and Empire Room transport guests to another time and place.

The Knickerbocker has gone through many changes since it opened in 1927. Legend has it that in the 1930s, the hotel housed a casino frequented by Al Capone. During World War II and the Korean War, U.S. Armed Forces officers would play cards in the Officer’s Club. In 1952, Richard Nixon was nominated Vice President during the Republican National Convention held in the hotel. Finally, in the 1970s it became the Playboy Hotel, owned by Hugh Hefner. After completing a multi-million dollar renovation in 2008, the hotel reinvented itself once again while still honoring the past. The Crystal Ballroom — home to Chicago’s only built-in, illuminated dance floor — has been a popular venue for events of all types throughout its history.

Built in 1927 as the world’s largest hotel, this massive Mag Mile institution still keeps part of its old-world charm despite going through a multitude of circumstances and owners — three before becoming the Hilton Chicago. In the 1940s, the property served as the army’s barracks, while in 1968, the hotel was in the news after cantankerous policemen tossed rioters (gathered during the Democratic National Convention) through the hotel’s windows. On the positive side, the hotel was home to over 150 Olympians scheduled to appear on the “Oprah Winfrey Show” after the 2008 Summer Olympics (Michael Phelps stayed in the Imperial Suite!).  

This swanky hotel reopened on its 125th year anniversary in the summer of 2015 with so much buzz, there were long lines to get into its restaurants and bars. The “Club” was originally formed in 1890 “To provide a setting for athletic, business and social activities” by AG Spalding (Spalding Sporting Goods), Cyrus McCormick (McCormick Harvesting Machine Co. ne International Harvester) and Marshall Field. Like most architectural stories of this period, part of the structure was destroyed by the Chicago Fire, but it still managed to be completed in time for the end of the Columbia Exposition in 1893.

The Chicago Athletic Association hotel was the only athletic club to survive the depression by working through their waiting list. During the depression, their wait list diminished from 12-15 years to 4-5 years. It remained a club for the City’s elite until its closure in 2007.  Today, The Chicago Athletic Association hotel is home to some of the most stunning historic special event and meeting spaces in the city, ranging from the sprawling Madison Ballroom to the intricately designed White City Ballroom to the athletic-inspired Stagg Court — quite possibly one of the coolest meeting spaces in Chicago.