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5 stars Hotels in Chicago, Illinois

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Featured Chicago 5 stars Hotels

See all 801 Hotels in Chicago
The Ritz-Carlton, Chicago
The Ritz-Carlton, Chicago
160 E Pearson Street, Chicago
5.0 out of 5.0
4.6 out of 5 (411 reviews)
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Wonderful experience! Great room, great bed! Perfect location! The service was wonderful. Great room, great bed, great pillows. This was the perfect place to stay in Chicago. Look forward to to seeing your remodel.
  19 May 2017

C$346

C$346
The Peninsula Chicago
The Peninsula Chicago
108 East Superior Street, Chicago
5.0 out of 5.0
4.9 out of 5 (237 reviews)
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perfect Chicago getaway Incredible friendly and helpful service, first-class room, beautiful pool and ideal location
  20 May 2017

C$543

C$543
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 (751 reviews)
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The staff was very friendly and upgraded my room when I arrived at the hotel. I had planned on just dropping my bags but was allowed to check in at 9:00am because my room was available. The hotel is high quality; everything one would expect from a Trump location. The rooms are spotless, quiet and ...
  22 May 2017

C$454

C$454
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)
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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$495

C$495
The Langham, Chicago
The Langham, Chicago
330 North Wabash Avenue, Chicago
5.0 out of 5.0
4.9 out of 5 (250 reviews)
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Not impressed at all I stayed last year in The Langham NYC and it was superb but The Langham Chicago wasn´t the same story for me, the street was VERY NOISY almost all the time, ambulances, fire trucks, horns, you name it, the room is not "noise proof" at all. Besides I stayed in a Junior Suite and it was very little ...
  17 May 2017

C$425

C$425
Park Hyatt - Chicago
Park Hyatt - Chicago
800 N Michigan Ave, Chicago
5.0 out of 5.0
4.8 out of 5 (124 reviews)
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Great experience, fantastic location, friendly and acccomadating staff.
  11 May 2017

C$360

C$360
Waldorf Astoria Chicago
Waldorf Astoria Chicago
11 E. Walton Street, Chicago
5.0 out of 5.0
4.7 out of 5 (219 reviews)
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Best Hotel in Chicago What can I say? This place is phenomenal! From the rooms (spacious and comfortable) to the service (always top-notch), the Waldorf is simply the best hotel I have ever stayed in during numerous visits to the Windy City.
  11 May 2017

C$483

C$483
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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 801 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.