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5 stars Hotels in Chicago, Illinois

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Featured Chicago 5 stars Hotels

See all 908 Hotels in Chicago
Waldorf Astoria Chicago

Waldorf Astoria Chicago

11 E. Walton Street, Chicago
5.0 out of 5.0
4.7 out of 5 (221 reviews)
Shopping and all restaurants very nice and clean Everyone went above and beyond.. very helpful and overall great
  23 Jun 2017

C$446

C$446
The Langham, Chicago

The Langham, Chicago

330 North Wabash Avenue, Chicago
5.0 out of 5.0
4.9 out of 5 (252 reviews)
Awesome hotel! Awesome location. Great location, great restaurant, close to the action.
  7 Jun 2017

C$449

C$449
Park Hyatt - Chicago

Park Hyatt - Chicago

800 N Michigan Ave, Chicago
5.0 out of 5.0
4.8 out of 5 (126 reviews)
Very nice hotel perfect location Close to shopping, water view from room, room was comfortable, staff friendly!
  24 Jun 2017

C$346

C$346
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

401 N Wabash Ave, Chicago
5.0 out of 5.0
4.8 out of 5 (760 reviews)
Great room. Great view. Great experience. I make a trip to Chicago once a year, I will stay at Trump from now on.
  26 Jun 2017

C$427

C$427
The Peninsula Chicago

The Peninsula Chicago

108 East Superior Street, Chicago
5.0 out of 5.0
4.9 out of 5 (242 reviews)
Best Hotel EveryThis is the best hotel I ever stayed in. The staff was very professional and the attentiveness was far beyond expectation!
  26 Jun 2017

C$537

C$537
The Ritz-Carlton, Chicago

The Ritz-Carlton, Chicago

160 E Pearson Street, Chicago
5.0 out of 5.0
4.6 out of 5 (415 reviews)
We were a little disappointed that the grand lobby was going through a renovation and we didn't know about it before we arrived, but the staff was great and we enjoyed our stay.
  31 May 2017

C$371

C$371
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

120 East Delaware Place, Chicago
5.0 out of 5.0
4.7 out of 5 (168 reviews)
Excellent hotel on the Mag-mile.Staff is extremely helpful. Special requests were addressed prior to my arrival. My suite was very spacious and well-equipped.
  5 Apr 2017

C$427

C$427
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Fine wine, delicious cheeses, and river cruises…yes, you’ve finally arrived in Chicago for a five-star vacation.

  • Search over 908 five-star hotels in Chicago
  • Stay near attractions like the symphony and The Magnificent Mile®
  • Read verified reviews to pick the best hotel for you

You’ll find everything your heart desires and more when you visit the Windy City.

Start out at The Magnificent Mile®. The “Mag Mile,” as locals call it, is a sprawling district loaded with high-end shops, restaurants, and museums. You can pick up just about anything you can imagine here, from designer threads to the perfect accent lamp for your living room. After an afternoon wandering around the Mag Mile, head to nearby Rush Street to take advantage of its hopping nightlife. Begin your evening at a high-class steakhouse, or dance the night away at one of the many posh clubs lining the street. For something a little more relaxing, attend a performance of the Chicago Symphony Orchestra to cap the night.

Return to your 5-star hotel in Chicago to relax and recharge for the evening. These accommodations offer you nothing less than the highest luxury; pretty much anything you want, you’ll get. Book a massage at the on-site spa—or better yet, have the service performed in your room or suite. Do you want a hot-stone massage, or would you prefer a soothing body wrap? Enjoy meals prepared by internationally renowned chefs, go for a relaxing swim in the crystal clear pool, and have a drink on the rooftop terrace overlooking the city skyline.

Trust Expedia.ca to help you make all your travel plans. Whether you’re visiting the city to shop until you drop or are taking in some of the many theatrical performances around town, we’ll help you find the perfect Chicago hotel to call home.