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Chicago's Most Luxurious Stays

If your idea of indulgence runs to yellow grand pianos and personalized monogrammed pillowcases, then Chicago’s got a suite for you. Take a look inside some of the city's incredible hotel rooms.

Private butler? Check. Multiple terraces? Check. Room for 150 friends? No problem—as long as you're willing to shell out big bucks for a night in one of Chicago's most luxurious hotel rooms.

Many double as locations for wedding receptions, meetings or other group events, but you can also have them all to yourself for an overnight stay. Peek at these ultra-luxe suites:

The Conrad Hilton Suite, Hilton Chicago

Photo courtesy of Conrad Hilton

The Conrad Hilton Suite, Hilton Chicago

Helicopter parking is no longer allowed on the suite’s private helipad, but this two-level, 2,300-square-foot suite remains Chicago’s most famous, exclusive and expensive. Named for the founder of the Hilton hotel chain (his portrait hangs above the two-sided fireplace, in the billiard and cocktail lounge area), many U.S. presidents and foreign dignitaries have stayed here, dating back to Harry Truman. Relax in a space that includes a baby grand piano, a winding staircase to the second floor, three terraces, gorgeous chandeliers and three bedrooms. Or if you want to have a cocktail party for 150 people, there’s space for that, too.

Rate: $10,000 a night (http://www3.hilton.com)

The Princess Diana Suite, The Drake Hotel

Photo courtesy of The Drake Hotel

The Princess Diana Suite, The Drake Hotel

Princess Diana of Wales stayed in this 1,500-square-foot suite, now adorned with photos from her three-day 1996 Chicago visit. Decorated in a formal elegant English style, the suite features panoramic views from multiple rooms, a vanity changing room, a writing room and a private bar. Rather than a cocktail, maybe you’d prefer a spot of English tea?

Rate: Starts at $1,500 a night (thedrakehotel.com)

Founders Suite, Chicago Athletic Association Hotel

Founders Suite, Chicago Athletic Association Hotel

Photos courtesy of Thomas Hart Shelby/Chicago Athletic Association Hotel

Founders Suite, Chicago Athletic Association Hotel

Once a private athletic club for Chicago’s elite, the 1893 Venetian Gothic building was rehabbed as a luxury hotel in 2015, preserving some elements from its history but also adding modern touches. In the Founders Suite, which overlooks Millennium Park, nods to the building’s former life include a wooden gym ladder, a bench made from a pommel horse and nightstand legs wrapped with leather tennis racket grip.

Rate: Starts at $1,200 a night (chicagoathletichotel.com)

Presidential Suite, Hyatt Centric The Loop Chicago

Presidential Suite, Hyatt Centric The Loop Chicago

Photos courtesy of Hyatt Centric The Loop Chicago

Presidential Suite, Hyatt Centric The Loop Chicago

Monogrammed pillowcases, personalized with your initials, await in this 1,200-square-foot apartment-like suite. The dark wood-paneled walls date to the Art Deco building’s construction in 1927. The former office building opened as a hotel in 2015.  

Rate: Starts at $1,800 a night (theloopchicago.centric.hyatt.com)

Infinity Suite, The Langham Chicago

Infinity Suite, The Langham Chicago

Photos courtesy of The Langham Chicago

Infinity Suite, The Langham Chicago

The oversized bathtub, set in a white marble bathroom, invites long soaks in front of a window-wall overlooking the city. A 24-hour butler is happy to pour a glass of champagne, and music lovers might enjoy playing the canary-yellow grand piano in the art-filled living room, surrounded by floor-to-ceiling windows that overlook the Chicago River.

Rate: $6,000 a night (langhamhotels.com)

The Presidential Suite, Waldorf Astoria

Photo courtesy of Waldorf Astoria

The Presidential Suite, Waldorf Astoria

You’ll have panoramic views of the Gold Coast neighborhood from this 3,600-square-foot space on the 26th floor. Amenities include gaming systems, surround sound, a full kitchen and a living room with fireplace.

Rate: Starts at $6,500 a night (waldorfastoriachicagohotel.com)

Grand Deluxe Lake View Suites, Trump International Hotel & Tower

Photo courtesy of Trump International

Grand Deluxe Lake View Suites, Trump International Hotel & Tower

These one- to three-bedroom suites come with contemporary marble surround fireplaces, personal attaché service, and 65-inch TVs. You’ll also find one of the most scenic living rooms in the city, with floor-to-ceiling windows that put you eye-to-eye with the iconic Wrigley Building clock and Tribune Tower, plus a view of the Chicago River and Lake Michigan.

Rate: Starts at $756 a night (trumphotels.com/chicago/)

Serenity Suite, Kimpton Hotel Monaco

Photo courtesy of Kimpton Hotel Monaco

Serenity Suite, Kimpton Hotel Monaco

Where’s the TV? It’s hidden in the baseboard of this suite’s comfy king-sized bed. Use the remote control to raise it up. Or sit in one of the room’s huge, pillow-covered window nooks that overlook the Chicago River. This relatively affordable indulgence (compared to the other suites) was created by HGTV designer and native Chicagoan Alison Victoria. And 10 percent of the room rate is donated to PAWS Chicago, a local animal shelter.

Rate: Starts at $470 a night (monaco-chicago.com)

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