Top Iconic and Boutique Hotels in Chicago

Chicago is known for its historic hotels that stand out for their well-preserved architectural features. They offer experiences that range from homey to upscale boutique. They are in various hotspots of the city ensuring there’s a convenient location regardless of which areas you are looking to explore. If you are planning a trip to the city, and are looking for hotels to stay in, or check out, this list of iconic and boutique hotels will let you know which ones you can’t miss out on.

5 of the Top Iconic and Boutique Hotels in Chicago

Here is my list of the top 5 of the most iconic hotels in our beautiful city.

The Palmer House Hilton

The Palmer House originally opened in 1871. At the time it was the highest priced hotel ever built. Sadly, it was destroyed in the Great Chicago Fire just 13 days after its grand opening. It’s owners, Chicago business magnate Potter Palmer and his wife Bertha were determined to rebuild it and it was re-erected by 1873.

The downtown hotel in the Chicago Loop holds a lot of history. It is decorated by French-inspired paintings created and donated by Bertha. It also features grand chandeliers, Tiffany designs and a ceiling fresco by Louis Pierre Rigal.

It was a popular lodging choice for famous visitors like Harry Houdini and Oscar Wilde. Its Empire Dining Room hosted shows by entertainers such as Frank Sinatra, Judy Garland, Ella Fitzgerald, Louis Armstrong, and Liberace.

The Drake Hotel

The Drake advertises itself as a timeless property in a convenient location that puts guests in the middle of all the excitement Chicago has to offer. It has been recognized by the Historic Hotels of America and Historic Hotels Worldwide for upholding its historic integrity.

The hotel opened its doors on New Year’s Eve of 1920. It became a hotspot for socialites through the roaring 20’s and hosted big-name guests like Bing Crosby, Walt Disney, and George Gershwin. Its iconic sign holds a special place in the Chicago skyline.

It is home to the Cape Cod Room where Marilyn Monroe and Joe DiMaggio dined and carved their initials into the bar counter. The Coq d’Or bar opened the day after prohibition was repealed offering 40 cent whiskeys. It remains a hangout for Chicago’s well-to-do crowds. It is located in the Gold Coast within the Near North community.

The Blackstone Hotel

The Blackstone is located in downtown Chicago and considers itself the perfect combination of past and present. It was built on the site of the Blackstone Mansion, once the home of Chicago businessman, Timothy Blackstone. It opened in 1910.

If the hotel’s walls could talk, they would have plenty of stories to tell. The building was the site of the first organized crime convention and several political meetings. It was visited by well-known names like Marilyn Monroe, John F. Kennedy, and Dwight D. Eisenhower.

The hotel is known for its superior art collection. Many of the 1600 pieces that decorate the building were part of Timothy Blackstone’s art collection. They illustrate Chicago’s culture and can be found in the guest rooms, meeting rooms, public spaces and in the Art Hall.

Congress Plaza Hotel

The Congress Plaza Hotel offers world-class amenities like an on-site Barber shop. Guests are treated to spectacular views of Lake Michigan. It stands as a ‘Landmark of Chicago Hospitality.

The hotel originally opened in 1893 as the Auditorium Annex. Back then, it featured gaslighting, cobblestone streets and horse-drawn carriages. Its Peacock Alley is an underground marble passageway that connects a more recently built annex to the hotel. The South Tower features a banquet hall which was the first ballroom in America to use air conditioning.

Congress Plaza has been nicknamed ‘Home of the Presidents’ due to the many presidents that stayed there. It has hosted Teddy Roosevelt, William McKinley, Grover Cleveland, Woodrow Wilson, and Franklin Roosevelt. It has also been the site of many historic political events.

Ambassador Chicago

Formerly the Ambassador East, the Ambassador Chicago is located in Chicago’s Gold Coast area not far from the Magnificent Mile. It offers fantastic views of Lake Michigan and is known as the area’s first boutique hotel.

The building first opened its doors in 1926. It became famous for its restaurant The Pump Room which opened in 1938 and sadly closed in 2017. Its heyday was in the 50’s and 60’s when it was frequented by celebrities like Doris Day, Helen Hays and Eunice Kennedy.

The hotel sits on a quiet Chicago street nestled between elegant historic mansions. It offers 285 spacious guestrooms, a 24-hour fitness center and two top-rated restaurants.

Although we focused on my top 5 favorites here. There are many other wonderful boutique hotels in Chicago. A few other hotels to check out include:

• Wyndham Grand Chicago Riverfront
• Fairmont Chicago
• Hotel Burnham

After staying at these hotels when visiting the area, you may just want to live in the city for good.

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