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Live the high life at these luxury properties


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Featured Chicago Luxury Hotels

See all 1,283 Properties in Chicago
Trump International Hotel & Tower Chicago
Trump International Hotel & Tower Chicago
5.0 out of 5.0 401 N Wabash Ave, Chicago
Free Cancellation
4.8/5 (2,102 reviews)
$260/ nightfor 2 guests

all staff are very attentive and polite. Spa amenities is below average with high fee they charged.

Reviewed on Nov 18, 2018
The Langham, Chicago
The Langham, Chicago
5.0 out of 5.0 330 North Wabash Avenue, Chicago
Free Cancellation
4.9/5 (1,016 reviews)
$305/ nightfor 2 guests

Amazing service and amazing staff. This is the nicest hotel I have ever stayed in!

Reviewed on Nov 13, 2018
The Peninsula Chicago
The Peninsula Chicago
5.0 out of 5.0 108 East Superior Street, Chicago
Free Cancellation
4.9/5 (951 reviews)
$380/ nightfor 2 guests

Wonderful! Busy weekend due to the lighting festival. The hotel still managed to pay attention to the small details!

Reviewed on Nov 18, 2018
The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago
The Gwen, a Luxury Collection Hotel, Michigan Avenue Chicago
4.5 out of 5.0 521 North Rush Street, Chicago
Free Cancellation
4.6/5 (1,899 reviews)
$119/ nightfor 2 guests

Very comfortable beds & pillows and linens. Would be nice to have a coffee maker in the room.

Reviewed on Nov 15, 2018
Sofitel Chicago Magnificent Mile
Sofitel Chicago Magnificent Mile
4.5 out of 5.0 20 E Chestnut St, Chicago
Free Cancellation
4.6/5 (2,182 reviews)
$143/ nightfor 2 guests

Very accommodating. I love the view of the Hancock Building too!

Reviewed on Nov 13, 2018
Thompson Chicago
Thompson Chicago
4.5 out of 5.0 21 East Bellevue, Chicago
Free Cancellation
4.7/5 (2,113 reviews)
$152/ nightfor 2 guests

Like the interesting art work. Nice atmosphere as well

Reviewed on Nov 14, 2018
Waldorf Astoria Chicago
Waldorf Astoria Chicago
5.0 out of 5.0 11 E. Walton Street, Chicago
Free Cancellation
4.8/5 (834 reviews)
$256/ nightfor 2 guests

One of the very best hotel experiences I have ever had!

Reviewed on Oct 26, 2018
Radisson Blu Aqua Hotel Chicago
Radisson Blu Aqua Hotel Chicago
4.5 out of 5.0 221 N Columbus Dr, Chicago
Free Cancellation
4.5/5 (1,745 reviews)
$125/ nightfor 2 guests

Wonderful hotel but be aware not to get a room that is above the local fire Dept station. Sirens through the night making connected sleep impossible. Opt for south facing rooms.

Reviewed on Nov 18, 2018
Palmer House a Hilton Hotel
Palmer House a Hilton Hotel
4.0 out of 5.0 17 E Monroe St, Chicago
Free Cancellation
4.2/5 (11,028 reviews)
$94/ nightfor 2 guests

I enjoyed my stay here and it's a lovely property, however I was traveling on business and it was very difficult to work because the Wifi continually cut out.

Reviewed on Nov 16, 2018
Chicago Athletic Association
Chicago Athletic Association
4.5 out of 5.0 12 South Michigan Avenue, Chicago
Free Cancellation
4.6/5 (1,328 reviews)
$132/ nightfor 2 guests

Great property and location. Right across from Millennium Park. Staff friendly and helpful. Definitely recommend. Two suggested areas of improvement: 1) elevator maintenance as one was always down and waited 15 minutes to get to room. 2) no coffee maker in room. Provided upon request but maid service ...

Reviewed on Nov 18, 2018
Loews Chicago Hotel
Loews Chicago Hotel
4.5 out of 5.0 455 North Park Drive, Chicago
Free Cancellation
4.7/5 (1,377 reviews)
$116/ nightfor 2 guests

Very clean , great location, excellent shower. Loved our stay!!

Reviewed on Nov 17, 2018
Hotel Arista
Hotel Arista
4.5 out of 5.0 2139 City Gate Ln, Naperville
Free Cancellation
4.7/5 (1,163 reviews)
$125/ nightfor 2 guests

Very nice hotel staff. Had an issue with initial room, front desk moved us to a new room and issue was resolved. Easy to work with.

Reviewed on Nov 13, 2018
The Ritz-Carlton, Chicago
The Ritz-Carlton, Chicago
5.0 out of 5.0 160 E Pearson Street, Chicago
4.6/5 (1,243 reviews)
$224/ nightfor 2 guests

Great hotel... in a perfect location in the city.. close to everything

Reviewed on Nov 5, 2018
The James Chicago-Magnificent Mile
The James Chicago-Magnificent Mile
4.5 out of 5.0 55 East Ontario Street, Chicago
Free Cancellation
4.5/5 (2,216 reviews)
$116/ nightfor 2 guests

Great hotel we come a couple times a year! Great location to Michigan Ave and friendly staff!

Reviewed on Nov 17, 2018
Fairmont Chicago at Millennium Park
Fairmont Chicago at Millennium Park
4.5 out of 5.0 200 North Columbus Drive, Chicago
Free Cancellation
4.3/5 (2,251 reviews)
$152/ nightfor 2 guests

Comfortable stay. Great location. Highly recommend it.

Reviewed on Nov 14, 2018
Four Seasons Hotel Chicago
Four Seasons Hotel Chicago
5.0 out of 5.0 120 East Delaware Place, Chicago
Free Cancellation
4.7/5 (626 reviews)
$293/ nightfor 2 guests

Absolutely wonderful hotel and amazing room. Check in was easy and staff was great. Wish I'd stayed longer

Reviewed on Nov 16, 2018
Omni Chicago Suites - Magnificent Mile
Omni Chicago Suites - Magnificent Mile
4.5 out of 5.0 676 N Michigan Ave, Chicago
Free Cancellation
4.4/5 (3,110 reviews)
$149/ nightfor 2 guests

Staff was very friendly and professional. They even made friends with my 4 year old daughter.

Reviewed on Nov 15, 2018
Virgin Hotels Chicago
Virgin Hotels Chicago
4.5 out of 5.0 203 N Wabash Ave, Chicago
Free Cancellation
4.7/5 (1,921 reviews)
$116/ nightfor 2 guests

It was one of the most unique room layouts I have stayed at, great concept, staff was outstanding.

Reviewed on Nov 16, 2018

Travelers loved these Luxury Hotels

Recently booked Luxury Hotels in Chicago

Ramada by Wyndham Waukegan/Great Lakes
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Omni Chicago Suites - Magnificent Mile
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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.