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Featured Chicago 5 stars Hotels

See all 867 Hotels in Chicago
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 (831 reviews)
Great Hotel except for a bad experience at the endWe absolutely loved this hotel, it was nice comfortable and clean. Good location with walking distance to most of what Chicago has to offer in its downtown area. One thing I did not like was the from desk staff, they were not very friendly when we were checking in and completely ignored me when we ...
  16 Oct 2017

C$374

C$374
The Peninsula Chicago

The Peninsula Chicago

108 East Superior Street, Chicago
5.0 out of 5.0
4.9 out of 5 (263 reviews)
Super helpful staffEvery one working there understands and provides excellent customer service
  17 Oct 2017

C$498

C$498
The Langham, Chicago

The Langham, Chicago

330 North Wabash Avenue, Chicago
5.0 out of 5.0
4.9 out of 5 (285 reviews)
Great hotel in the perfect location. Service and staff were great
  16 Oct 2017

C$418

C$418
The Ritz-Carlton, Chicago

The Ritz-Carlton, Chicago

160 E Pearson Street, Chicago
5.0 out of 5.0
4.6 out of 5 (426 reviews)
The Ritz does not dissapoint. Room is very comfortable, the dining is simply excellent and the staff is top notch
  29 Sep 2017

C$317

C$317
Waldorf Astoria Chicago

Waldorf Astoria Chicago

11 E. Walton Street, Chicago
5.0 out of 5.0
4.7 out of 5 (252 reviews)
Wonderful hotel in the midst of downtown Chicago. I visited for a conference and this hotel was within walking distance to shopping and restaurants. Staff was welcoming and pleasant. The Michael Mina restaurant was perfect.... great bar and food.
  14 Oct 2017

C$468

C$468
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

120 East Delaware Place, Chicago
5.0 out of 5.0
4.7 out of 5 (182 reviews)
It was very pleasant and quiet. good bathroom, very good restaurant.
  1 Oct 2017

C$424

C$424
Park Hyatt - Chicago

Park Hyatt - Chicago

800 N Michigan Ave, Chicago
5.0 out of 5.0
4.7 out of 5 (148 reviews)
Pleasure weekend. Always a treat to be s guest at the Park Hyatt!
  16 Oct 2017

C$409

C$409
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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 867 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.

Recently booked Chicago hotels

The Peninsula Chicago
5.0 out of 5.0
Last booking: 15 minutes ago