Luxury in Chicago

Chicago Luxury Hotels

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Featured Chicago Luxury Hotels

Trump International Hotel & Tower Chicago
5 out of 5
401 N Wabash Ave, Chicago, IL
Free CancellationReserve now, pay when you stay
CA $361
per night
Nov 17 - Nov 18
4.8/5Exceptional! (2,064 reviews)

"Excellent and attentive staff. Beautiful suite! Check in was expeditious. Room service was timely. The stay would have been almost perfect, however, I was erroneously charged for using the room’s minibar when I never used a single item. Yes I was able to call (twice) and have the charge removed, ..."…"

Reviewed on Oct. 21, 2019

Trump International Hotel & Tower Chicago
The Langham, Chicago
5 out of 5
330 North Wabash Avenue, Chicago, IL
CA $368
per night
Nov 17 - Nov 18
4.9/5Exceptional! (1,598 reviews)

"Super location with great views of the river. Easy to enjoy the city from this location. Staff were super helpful and we loved our stay here. Would definitely come back and re-enjoy all the benefits of a Club Room. The hotel managed to tick all our holiday boxes- except for the weather. Better next ..."…"

Reviewed on Oct. 21, 2019

The Langham, Chicago
The Peninsula Chicago
5 out of 5
108 East Superior Street, Chicago, IL
Free CancellationReserve now, pay when you stay
CA $522
per night
Nov 3 - Nov 4
4.9/5Exceptional! (1,276 reviews)

"WOW!!! Our stay at the Peninsula was PERFECT. From the beginning Bradley at check in made us feel so welcome!! The location of the Hotel is excellent, rooms are spotless and GORGEOUS, service could not have been any better from the guys outside like Hector and Floyd to the housekeeping, restaurants, ..."…"

Reviewed on Oct. 22, 2019

The Peninsula Chicago
The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago
4.5 out of 5
521 North Rush Street, Chicago, IL
Free CancellationReserve now, pay when you stay
CA $211
per night
Nov 17 - Nov 18
4.6/5Wonderful! (1,956 reviews)

"Perfect location in downtown Chicago! We had a great time, hotel was quiet, bed and pillows comfortable!"…"

Reviewed on Aug. 24, 2019

The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago
Sofitel Chicago Magnificent Mile
4.5 out of 5
20 E Chestnut St, Chicago, IL
Free CancellationReserve now, pay when you stay
CA $186
per night
Nov 3 - Nov 4
4.6/5Exceptional! (2,279 reviews)

"I loved this hotel. Booked the cheapest room which is supposed to be from the the 6-10th floor. Ended up on the 9th. The room felt very quite and had a great view of the Hancock Tower. Nice bed, nice big window, large T.V. and great bathtub. Felt upscale without being the most expensive in town."…"

Reviewed on Oct. 21, 2019

Sofitel Chicago Magnificent Mile
Thompson Chicago
4.5 out of 5
21 East Bellevue, Chicago, IL
Free Cancellation
CA $234
per night
Oct 27 - Oct 28
4.7/5Exceptional! (2,073 reviews)

"Inner city view was beautiful night time was perfect."…"

Reviewed on Oct. 13, 2019

Thompson Chicago
Waldorf Astoria Chicago
5 out of 5
11 E. Walton Street, Chicago, IL
Free CancellationReserve now, pay when you stay
CA $340
per night
Oct 31 - Nov 1
4.7/5Exceptional! (972 reviews)

"Exceptional hotel. The Waldorf Astoria is as good as it gets."…"

Reviewed on Sep. 29, 2019

Waldorf Astoria Chicago
Radisson Blu Aqua Hotel Chicago
4.5 out of 5
221 N Columbus Dr, Chicago, IL
Free CancellationReserve now, pay when you stay
CA $199
per night
Nov 22 - Nov 23
4.5/5Wonderful! (2,020 reviews)

"Had wonderful customer service, great location. Only thing I wish they had was furniture on the balconies of the room. We loved being able to be outside enjoying the views but would have enjoyed chairs."…"

Reviewed on Oct. 21, 2019

Radisson Blu Aqua Hotel Chicago
Palmer House a Hilton Hotel
4 out of 5
17 E Monroe St, Chicago, IL
Free CancellationReserve now, pay when you stay
CA $178
per night
Nov 15 - Nov 16
4.2/5Excellent! (12,681 reviews)

"Spectacular dining room--vaulted ceilings, gorgeous Beaux Arts decor. My floor had photo portraits of old singers, actors and musicians lining the corridor. The staff was excellent. It was just a wonderful little city-unto-itself."…"

Reviewed on Oct. 21, 2019

Palmer House a Hilton Hotel
Chicago Athletic Association
4.5 out of 5
12 South Michigan Avenue, Chicago, IL
Free Cancellation
CA $233
per night
Nov 17 - Nov 18
4.6/5Wonderful! (1,604 reviews)

"The property was great, very historical and wonderful staff. The location to Millennium Park is perfect and feels very safe. Unfortunately the homeless people are everywhere in Chicago and like to beg outside of this area."…"

Reviewed on Oct. 8, 2019

Chicago Athletic Association
Loews Chicago Hotel
4.5 out of 5
455 North Park Drive, Chicago, IL
Free CancellationReserve now, pay when you stay
CA $199
per night
Oct 31 - Nov 1
4.7/5Exceptional! (1,865 reviews)

"Great location. Clean and chic. Comfortable lobby."…"

Reviewed on Oct. 20, 2019

Loews Chicago Hotel
Hotel Arista
4.5 out of 5
2139 City Gate Ln, Naperville, IL
Free CancellationReserve now, pay when you stay
CA $170
per night
Nov 10 - Nov 11
4.7/5Exceptional! (1,497 reviews)

"The King that we stayed in was not your typical hotel room. The bathroom was very spacious and nice with both a shower and a soaking tub. The room was spacious, bed was comfortable, and in general it was just a really nice room."…"

Reviewed on Oct. 13, 2019

Hotel Arista
The Ritz-Carlton, Chicago
5 out of 5
160 E Pearson Street, Chicago, IL
Free CancellationReserve now, pay when you stay
CA $339
per night
Oct 27 - Oct 28
4.6/5Exceptional! (1,439 reviews)

"Customer service was excellent, nothing was too much trouble."…"

Reviewed on Oct. 19, 2019

The Ritz-Carlton, Chicago
Fairmont Chicago at Millennium Park
4.5 out of 5
200 North Columbus Drive, Chicago, IL
Free CancellationReserve now, pay when you stay
CA $246
per night
Oct 31 - Nov 1
4.3/5Excellent! (2,223 reviews)

"Fantastic location! Close to many attractions and shopping, and convenient for marathon runners and spectators."…"

Reviewed on Oct. 19, 2019

Fairmont Chicago at Millennium Park
Four Seasons Hotel Chicago
5 out of 5
120 East Delaware Place, Chicago, IL
Free CancellationReserve now, pay when you stay
CA $439
per night
Nov 16 - Nov 17
4.7/5Exceptional! (744 reviews)

"I have stayed here many times. I am consistently amazed at how high quality every aspect of the Four Hotels is. The staff here in Chicago is nothing short of spot in excellent."…"

Reviewed on Oct. 10, 2019

Four Seasons Hotel Chicago
Omni Chicago Suites - Magnificent Mile
4.5 out of 5
676 N Michigan Ave, Chicago, IL
Free CancellationReserve now, pay when you stay
CA $221
per night
Nov 22 - Nov 23
4.5/5Wonderful! (3,390 reviews)

"Lovely place to stay on the Magnificent Mile, close to everything, comfortable and clean."…"

Reviewed on Oct. 19, 2019

Omni Chicago Suites - Magnificent Mile
Virgin Hotels Chicago
4.5 out of 5
203 N Wabash Ave, Chicago, IL
Free CancellationReserve now, pay when you stay
CA $199
per night
Nov 17 - Nov 18
4.7/5Exceptional! (2,475 reviews)

"The 2 floor of this hotel has a great common area that you can use for meetings, coffee, reading and it has a fun vibe. The staff really goes above and beyond as well."…"

Reviewed on Oct. 17, 2019

Virgin Hotels Chicago
Loews Chicago O'Hare Hotel
4.5 out of 5
5300 N River Rd, Rosemont, IL
Free CancellationReserve now, pay when you stay
CA $169
per night
Nov 22 - Nov 23
4.6/5Wonderful! (2,524 reviews)

"Very friendly staff and the facility is accommodating."…"

Reviewed on Oct. 21, 2019

Loews Chicago O'Hare Hotel
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Want to find a great accommodation for your luxury trip to Chicago? Let Expedia help you arrange your flight to Chicago, IL (MDW-Midway Intl.) airport or Chicago, IL (ORD-O'Hare Intl.) airport, and then choose from some places to stay that will deliver the luxury you seek. Amenities are an important consideration when you plan a trip, so we make it easy to get what you need to make your stay special. If you want a posh hotel with fine dining, a spa, or several swimming pools, Expedia can assist you in finding the best luxury hotel experience that Chicago has to offer. Known for its great views and art, Chicago also has some interesting things to see and do including Millennium Park and Willis Tower, so you may want to take in the local sights during your visit.

When to Visit Chicago

This is what you can expect the weather to be like while you stay in Chicago:

  • Hottest months: July, June, August, and September, with an average temperature of 83°F
  • Coldest months: January, February, December, and March, with an average temperature of 20°F
  • Driest months: February, January, December, and March, with an average rainfall of 2.31 inches
  • Rainiest months: May, June, July, and August, with an average rainfall of 4.05 inches

Exploring Chicago

Take in some sights and attractions while you're in Chicago by visiting Millennium Park, Willis Tower, and Skydeck Ledge. If you have a little extra time during your trip, you might want to make a stop at John Hancock Center and McCormick Place.

A few other things that make Chicago special are the:
  • Skyscrapers
  • Theater
  • Architecture
  • Museums
  • Art
  • Monuments
  • Entertainment
  • Shopping

Getting Around Chicago

Take advantage of local transportation options that make it easy to see Chicago. Nearby metro stations include Monroe Station, Monroe Station, and Adams-Wabash Station. If you want to see more of the area, hop aboard a train from Millennium Station, Chicago Van Buren Street Station, or Chicago Union Station.

More trip options

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