Historic Hotels in Chicago

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Movie star residents, haunted hotel rooms, presidential guests, and more -- Oyster knows what to look for when it comes to fun, historic hotels. We travel through time to give you the scoop on the world's historical and culturally relevant hotels. Take a look at our top historic picks in Chicago and get inspired!

  • Opened in late 2010, this upscale hotel is housed in a historic neoclassical-style building with crystal chandeliers and a grand staircase in the lobby. But sophisticated rooms are thoroughly modern, and big, elegant bathrooms have separate showers and soaking tubs. The Loop location is convenient for business travelers, and the 24-four fitness center is top-notch.

  • The original historic Palmer House Hotel 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. The dramatic lobby, with glittering chandeliers and a painted ceiling, evokes the hotel's grand past. Numerous famous guests have passed through here, including Charles Dickens and Frank Sinatra.

  • The Knickerbocker has gone through several incarnations 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, US Armed Forces officers would fill the property's hallways and 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 has reinvented itself once again. However, the elegant two-storied lobby still honors the hotel's historic past, with marble ornaments and wood moldings.

  • Originally built in 1929 to house the exclusive Medinah Athletics Club, the building sank into oblivion after closing its doors in 1934 due to the stock-market crash. Decades later, in 1988, InterContinental Hotels bought the property and invested several million dollars to turn it into what it is today: one of the most luxurious hotels in Chicago. The four-story lobby, with a huge staircase and Spanish-inspired fountains and chandeliers, reminds the hotel’s guests of the building’s grand past. Natural light pours through huge windows into the wonderful junior Olympic indoor swimming pool located on the eighth floor. Several rows of seating and a terra-cotta fountain with Spanish tiles remain from the building’s golden days, when young elite athletes would fill the hallways of the majestic club.

  • The 535-room Drake Hotel is a historic property on upscale Magnificent Mile and one of Chicago’s grande dames, with an impressive lobby full of chandeliers and a beautiful classic decor. Despite its historic status, modern amenities abound: There is a large, modern fitness center; wonderful dining options on-site, including the Palm Court, where a harp player entertains the guests during the afternoon tea; and even a shopping arcade with designer names like Chanel. But while the rooms are adequate and have some modern perks (like flat-screen TVs and MP3 players), the bathrooms are sub-par and could use an upgrade. The golden days of this luxurious property might be slowly fading, but it is still a great pick for its history and high-class notoriety.

  • Devised in 1895 by prominent architects Daniel Burnham, John Root and Charles Atwood as the Reliance Building, the 14-story structure soon became a landmark in Chicago. With a steel-and-glass design that had yet to be accepted, it would soon set the precedent for the modern skyscrapers that nowadays surround the property. In 1999, after having been forgotten for decades despite its designation as a National Historic Landmark in 1976, Kimpton Hotels restored it as the Burnham. The mosaic floors and the metal elevators are only two of the multiple features that were rebuilt to match the original design.

  • Built in 1927 as the world's largest hotel, the Hilton Chicago still keeps part of its old-world charm. And though the recent renovations have given the hotel a more modern look and upgraded amenities, what’s really interesting about the property is its past: In the 1940s, the property served as the army’s barracks, while in 1968, the hotel was again in the spotlight after angry policemen tossed rioters gathered during the Democratic National Convention through the hotel’s windows. More recently, there has been a more discreet (and probably unnoticed) appearance of the historic hotel in the TV: ER used to film helicopter landings on the hotel’s rooftop deck.

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