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5 stars Hotels in Chicago, Illinois

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Featured Chicago 5 stars Hotels

See all 961 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 (422 reviews)
Girls WeekendWe had the most spectacular time at the Ritz. Myself and my 2 oldest friends (40 years +) splurged for the weekend. The Ritz could not have been more accommodating. We had the most beautiful room that had both the lake and city view. The staff was wonderful - handling our luggage and the car. We ...
  21 Aug 2017

C$298

C$298
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 (787 reviews)
Very nice hotel. Gorgeous views.I loved staying at this hotel. It was beautiful and had first rate amenities. Would love to stay here again.
  22 Aug 2017

C$347

C$347
The Peninsula Chicago

The Peninsula Chicago

108 East Superior Street, Chicago
5.0 out of 5.0
4.9 out of 5 (249 reviews)
Very classy.It was wonderful!!. My wife and I were in Chicago for our anniversary - our experience was fantastic. We would definitely recommend this hotel to anyone.
  8 Aug 2017

C$501

C$501
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

120 East Delaware Place, Chicago
5.0 out of 5.0
4.7 out of 5 (174 reviews)
Excellent Hotel in a perfect location in ChicagoWe were in Chicago for the weekend to celebrate our anniversary. We had originally reserved a "city view King" room, but when we checked in we were upgraded to a gorgeous corner suite on the 37th floor with a view of both the Lake and the city ... the person who checked us in asked if we were celebrating ...
  17 Aug 2017

C$503

C$503
Park Hyatt - Chicago

Park Hyatt - Chicago

800 N Michigan Ave, Chicago
5.0 out of 5.0
4.8 out of 5 (137 reviews)
Great Location in the Middle of the MileWonderful location and Great Staff and service. This hotel is right on the Mile but adjacent to a small park which is a great place to sit and relax. All the amenities you need for a great getaway.
  17 Aug 2017

C$333

C$333
Waldorf Astoria Chicago

Waldorf Astoria Chicago

11 E. Walton Street, Chicago
5.0 out of 5.0
4.7 out of 5 (231 reviews)
Beautiful hotel. Amazing hotel. Great location. Staff is a bit overworked. Front desk didn't always answer the phone.
  19 Aug 2017

C$390

C$390
The Langham, Chicago

The Langham, Chicago

330 North Wabash Avenue, Chicago
5.0 out of 5.0
4.9 out of 5 (267 reviews)
Lived up to the hypeTwo night, weekend stay to commence four week US holiday. Due to our flights being standby we could only book accommodation day of arrival so price was reasonable and thankfully available. Front desk service was exemplary, as you'd expect with this chain. We were upgraded to higher floor being Expedia ...
  19 Aug 2017

C$419

C$419
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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 961 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.