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Live the high life at these luxury properties


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Featured Chicago Luxury Hotels

See all 1,472 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 (2,247 reviews)
$260/ night for 2 guests

The property was clean and sparkling. The room was beautiful. The service really stood out - every single service person that we came across (valet, bell, front desk, restaurant wait-staff, even phone staff...) was helpful, cheerful and extremely mannerly. We enjoyed our brunch and view of the city ...

Reviewed on Feb 19, 2019
LuxuryConciergeRoomservice
The Langham, Chicago
The Langham, Chicago
5.0 out of 5.0 330 North Wabash Avenue, Chicago
Free Cancellation
4.9/5 (1,124 reviews)
$278/ night for 2 guests

Great location and close to shopping and restaurants. Hotel very clean and the staff very friendly.

Reviewed on Feb 21, 2019
LuxurySpaDining
The Peninsula Chicago
The Peninsula Chicago
5.0 out of 5.0 108 East Superior Street, Chicago
Free Cancellation
4.9/5 (1,056 reviews)
$380/ night for 2 guests

Excepcional hotel and staff I was so happy with the hotel with the amenities and the city

Reviewed on Feb 19, 2019
LuxurySpaFitness Center
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 (1,937 reviews)
$125/ night for 2 guests

Hotel was the complete package. Check in was quick and easy. The rooms are clean and the bed is very comfortable. The lounge area was great to hang out after exploring the city.

Reviewed on Feb 12, 2019
LuxuryBarConcierge
Sofitel Chicago Magnificent Mile
Sofitel Chicago Magnificent Mile
4.5 out of 5.0 20 E Chestnut St, Chicago
Free Cancellation
4.6/5 (2,338 reviews)
$104/ night for 2 guests

Hotel rooms were very clean and modern. Bathroom shower was awesome and bed was super comfortable.

Reviewed on Feb 20, 2019
LuxuryConciergeDining
Thompson Chicago
Thompson Chicago
4.5 out of 5.0 21 East Bellevue, Chicago
Free Cancellation
4.7/5 (2,223 reviews)
$159/ night for 2 guests

We were in town for a short visit and this hotel was perfect for us! Staff is friendly, hotel is clean, and amenities are great. Restaurant in the hotel has a great breakfast and the bar is perfect for late night cocktails. Within walking distance to great shopping and huge variety of restaurants. ...

Reviewed on Feb 15, 2019
LuxuryBarDining
Waldorf Astoria Chicago
Waldorf Astoria Chicago
5.0 out of 5.0 11 E. Walton Street, Chicago
Free Cancellation
4.8/5 (872 reviews)
$274/ night for 2 guests

The fireplace in the room was so nice! I loved staying at this property!

Reviewed on Feb 10, 2019
LuxuryDiningConcierge
Radisson Blu Aqua Hotel Chicago
Radisson Blu Aqua Hotel Chicago
4.5 out of 5.0 221 N Columbus Dr, Chicago
4.5/5 (1,916 reviews)
$161/ night for 2 guests

The views were terrific. We had a corner room, so our views were 270 degrees, and we had a wrap-around balcony. The bed and sheets were very comfortable. The shower was very good, and our bathroom also had a separate bathtub.

Reviewed on Feb 20, 2019
LuxuryFitness CenterSports
Palmer House a Hilton Hotel
Palmer House a Hilton Hotel
4.0 out of 5.0 17 E Monroe St, Chicago
4.2/5 (11,526 reviews)
$95/ night for 2 guests

I LOVE this hotel, especially the lobby. The lobby is such a nice place to relax and have a drink.

Reviewed on Feb 22, 2019
LuxuryHistoricalConcierge
Chicago Athletic Association
Chicago Athletic Association
4.5 out of 5.0 12 South Michigan Avenue, Chicago
Free Cancellation
4.6/5 (1,446 reviews)
$123/ night for 2 guests

Excellent room and Restaurants. I would definitely stay here again.

Reviewed on Feb 19, 2019
LuxuryDiningFree Wifi
Loews Chicago Hotel
Loews Chicago Hotel
4.5 out of 5.0 455 North Park Drive, Chicago
Free Cancellation
4.7/5 (1,516 reviews)
$129/ night for 2 guests

Everything about this place was nice. Staff was extremely friendly and courteous. If I need to stay downtown again, I'm definitely staying there.

Reviewed on Feb 21, 2019
LuxuryConciergeDining
Hotel Arista
Hotel Arista
4.5 out of 5.0 2139 City Gate Ln, Naperville
Free Cancellation
4.7/5 (1,242 reviews)
$129/ night for 2 guests

Great hotel. I arrived here later in the evening after a flight. I ordered room service since the restaurant was closed and it was quick and delicious. The room was spacious with all the bells and whistles. The bed was comfortable and I had a good sleep. I wish I stayed longer to enjoy the hotel ...

Reviewed on Feb 21, 2019
LuxuryRoomserviceBusiness
The Ritz-Carlton, Chicago
The Ritz-Carlton, Chicago
5.0 out of 5.0 160 E Pearson Street, Chicago
Free Cancellation
4.6/5 (1,287 reviews)
$224/ night for 2 guests

Beautiful building and wonderful staff. The warmth and generosity of the staff was amazing and the rooms and facilities were sublime.

Reviewed on Feb 3, 2019
LuxuryConciergeFitness Center
The James Chicago-Magnificent Mile
The James Chicago-Magnificent Mile
4.5 out of 5.0 55 East Ontario Street, Chicago
4.5/5 (2,305 reviews)

We love this hotel. Have stayed before and would stay again. Our only complaint is that we have to call downstairs for ice.

Reviewed on Dec 3, 2018
LuxuryConciergeFitness Center
Fairmont Chicago at Millennium Park
Fairmont Chicago at Millennium Park
4.5 out of 5.0 200 North Columbus Drive, Chicago
4.3/5 (2,360 reviews)
$161/ night for 2 guests

Lovely room and the bed could not have been more comfortable. From a design point of view the room could use a touch of warmth through judicious use of color. Black, white, beige and gray in a Chicago winter doesn't speak the same "Welcome!" that the front desk staff does.

Reviewed on Feb 18, 2019
LuxuryConciergeWifi
Four Seasons Hotel Chicago
Four Seasons Hotel Chicago
5.0 out of 5.0 120 East Delaware Place, Chicago
Free Cancellation
4.7/5 (643 reviews)
$298/ night for 2 guests

Location - good. Staff - good. Food good but - not as healthy as I would like...

Reviewed on Feb 17, 2019
LuxuryConciergeRecreation
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 (3,286 reviews)
$144/ night for 2 guests

First, the staff are the kindest, most friendly and eager to please staff I have ever encountered. Seriously-better than Disney World-just genuinely happy people both over the phone and in person. The environmental staff were so efficient and the entire building is so clean. I loved the accommodations-the ...

Reviewed on Feb 19, 2019
LuxuryDiningRoomservice
Virgin Hotels Chicago
Virgin Hotels Chicago
4.5 out of 5.0 203 N Wabash Ave, Chicago
Free Cancellation
4.7/5 (2,083 reviews)
$136/ night for 2 guests

Lovely room, good service, overall enjoyed my one-night stay.

Reviewed on Feb 20, 2019
LuxuryBarNature
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Luxury Hotels: Our travelers loved these

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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.