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Chicago's Most Historic, Classic, and Iconic Hotels

Updated: Jan 27, 2023

Why stay in an ordinary hotel when you can stay in a historic Chicago gem? You'll feel like you've gone back in time when you walk into the lobbies of any of these historic hotels.

The following is a selection of hotels that are ideal for architecture and history buffs. This is a good place to start whether you're a local looking for a staycation or a newcomer looking for an authentically Chicago trip.

The Robey

Location: 2018 W North Ave, Chicago, IL 60647

Phone: (872) 315-3050

Perkins, Chatten, & Hammond designed this high-rise in 1929. It is currently an 89-room hotel with dark, melancholy décor, two rooftop lounges, and a small pool, rather than an office building. All of Wicker Park's and Bucktown's shops, restaurants, and bars are just a few feet away.

The Drake Hotel

Location: 140 E Walton Pl, Chicago, IL 60611

Phone: (312) 787-2200

For more than 90 years, the Drake Hotel has welcomed tourists from its vantage point at the start of the Magnificent Mile. The magnificent urban retreat cost $10 million to construct and was inspired by Renaissance-era Italian architecture. On New Year's Eve in 1920, 2,000 of Chicago's most prominent citizens were invited to the grand opening of the hotel.

The Drake quickly established itself as a hotel for the wealthy and distinguished. It has housed prominent cultural and political people from around the world in its 537 guest rooms and 74 suites. From Herbert Hoover through Bill Clinton, many US presidents have stayed in the Presidential Suite's six rooms. The Drake has hosted Winston Churchill, Amelia Earhart, Eleanor Roosevelt, Walt Disney, Frank Sinatra, Dean Martin, Charles Lindbergh, Pope John Paul II, and Princess Diana.

The Blackstone

Location: 636 South Michigan Avenue, E Balbo Dr, Chicago, IL 6060

Phone: (312) 447-0955

You'll feel as if you've stepped back in time to turn-of-the-century Chicago when you enter The Blackstone's beautiful Beaux Arts lobby. The Blackstone, which is listed on the National Register of Historic Places, opened to great fanfare in 1910. Everyone from Rudolph Valentino to Joan Crawford, Truman Capote to Tennessee Williams has stayed in its rooms.

However, from Teddy Roosevelt to Jimmy Carter, the hotel is best known for housing 12 US presidents. When a reporter watched cigar-smoking politicians during the 1920 conference, he coined the phrase "smoke-filled room."

InterContinental Chicago Magnificent Mile

Location: 505 N Michigan Ave, Chicago, IL 60611

Phone: (312) 944-4100

The hotel currently consists of two towers: a 1961 north tower and a classic 1929 south tower. The Shriners commissioned the latter, which was previously known as the Medinah Athletic Club. Walter W. Ahlschlager, the architect, drew inspiration from a variety of architectural styles. The facade had Assyrian-style carvings and a Moorish gold-painted dome, part of which can still be seen today. The 120,000-gallon pool, which was the highest indoor pool at the time, was built on the 14th floor and was designed with blue Spanish majolica tiles and a terra-cotta Neptune fountain. While many of the hotel's original club elements have vanished, the pool has remained almost unchanged.

The Alise Chicago

Location: 1 W Washington St, Chicago, IL 60602

Phone: (312) 940-7997

In 1895, the 14-story Reliance Building was regarded as one of the city's earliest skyscrapers. The building's design, which comprised steel, glass, and white glazed terracotta, was collaborated on by architects Daniel Burnahm, John Root, and Charles Atwood. Before becoming the Alise Hotel, the building housed largely offices, including Al Capone's dentist. The structure was designated as a landmark in 1970, but it needed to be restored, and a disagreement over what to do delayed any action. In 1999, it was converted as a luxury hotel for $27.5 million.

The Palmer House

Location: 17 E Monroe St, Chicago, IL 60603

Phone: (312) 726-7500

Palmer House, a Hilton Hotel in Chicago, has been providing elegant and polite hospitality to guests for more than 140 years. The Palmer House lobby has witnessed dignitaries, celebrities, and kings come and depart since it was founded in 1871, when it was billed as the world's largest hotel.

The current Palmer House was the third version of Potter Palmer's hotel dream: the first was a wedding gift that burned down when the Great Chicago Fire swept through the city, destroying nearly 3.3 square miles of the city.

Ambassador Chicago

Location: 1301 N State Pkwy, Chicago, IL 60610

Phone: (312) 787-3700

The Ambassador Chicago, which opened in 1926, quickly became a favorite of Frank Sinatra, Marilyn Monroe, and Elizabeth Taylor. Celebrities were known to frequent the famed Pump Room, now known as Food Gallery. The hotel's most remarkable feature is its lavish Art Deco lobby, which features vaulted ceilings, original crown molding, glass door knobs, decorative wrought iron, and mail chutes from the 1920s. By staying here, you’ll be surrounded by the city’s other landmarks on like Chicago’s Water Tower.

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