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Where to Stay in Chicago: Historic Hotels

By Elisabeth Blair on January 30, 2014


Often on our architectural walking tours, locals and tourists alike will ask me about the best Chicago hotels. Being a Chicago native, I cannot recommend from experience. Instead, I recommend from history. Here are some of the best historic hotels in Chicago. There where I would stay if given the excuse.

Photo Credit: Chicago Postcard Museum
Photo Credit: Chicago Postcard Museum

Maybe the Most Legendary of the Best Historic Hotels

At Chicago Detours, we try to promote the more positive and cultural aspects of Chicago history. But for those desiring the gangster fix, I’d recommend staying at the Renaissance Blackstone Hotel. The historic barber shop, which was eliminated during recent renovations (what were they thinking?), can be seen in the film “The Untouchables.” All sorts of politicians, from mob bosses, to senators, to presidents, are known for staying at this historic hotel and for dealings in its smoke-filled rooms. We credit the Blackstone Hotel for this term as the legendary location of the first “smoke-filled room” where Warren Harding was nominated to run for president.

Hotel architects Marshall & Fox designed the Blackstone for the Drake brothers, who were powerful figures in the American hotel industry. It opened in 1908 and got its name for Timothy B. Blackstone, the head of the Union Stockyards and several railroads. Our tour guests can find it just a few blocks south of where our 1893 World’s Fair Tour begins on Michigan Avenue.

Hollywood on the Mag Mile

The Drake brothers had Marshall & Fox build another one of the best historic hotels in Chicago – their namesake. The Drake Hotel opened on New Year’s Eve in 1920 as a high-society palace in the posh Gold Coast neighborhood. At the opposite end of Michigan Avenue from the Blackstone Hotel, one can get a taste of Hollywood glamour in the Cape Cod Room. You can still see where Marilyn Monroe and Joe DiMaggio came as giggling lovers and carved their initials into the wooden bar. I often recommend a visit by guests intrigued by the glamour of the Intercontinental at the end of our Historic Chicago Walking Bar Tour.

Many know the 20-foot tall, neon-pink letters as a fixture of the Chicago Lakeshore Drive skyline, but just recently they have been brought into 2014 with light purple LED lights. Today the Drake Hotel leads in green initiatives around the city and continues to host all manner of celebrities and dignitaries.

Photo Credit: Palmer House Hilton Hotel
Photo Credit: Palmer House Hilton Hotel

The Best Historic Hotel in Chicago

For the architecture and the art, on a staycation in Chicago I would go to the Palmer House Hilton Hotel. It’s my favorite of the best historic hotels in downtown. Often, I have had the pleasure of meeting friends and private tour guests in their opulent lobby. With Beaux-Arts frescoes on its ceiling, from which hang 24-karat gold chandeliers by Tiffany, the lobby speaks for a gentle era of leisure and luxury. On the mezzanine are cozy nooks to drink and watch the crowd gather and the stars line up to play. In the Empire Room, where the chandelier pictured here hangs, performers such as Frank Sinatra, Ella Fitzgerald and Liberace graced the stage.

The Great Chicago Fire destroyed Potter Palmer’s first hotel was destroyed in t. He’d built it as a wedding gift from Potter to his wife. The history of the hotel and a collection of its art and artifacts are on view at the Hotel Museum. I’d also recommend the Lockwood. There you can grab a drink before exploring the hotel or experience it from the aforementioned cozy nooks.

Even without the excuse of needing to stay the night, locals and tourist alike can enjoy these historic hotels. Simply remember to step inside and enjoy the interior architecture.

— Elizabeth Tieri, Chicago Detours Tour Guide


Chicago Detours offers guided walking and bus tours of architecture, history and culture to public and private groups. We are a passionate team of educators, historians, artists and storytellers, and are proud to be one of very few tour companies in Chicago that is rated five stars on both Google and TripAdvisor.


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