Beginning of main content
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5

Search 590,000 properties worldwide.

Search over a million flights, hotels, packages, and more

No Expedia cancellation fee to change or cancel almost any hotel reservation.


Featured Chicago 5 Star Hotels

See all 992 Hotels in Chicago
The Godfrey Hotel Chicago

The Godfrey Hotel Chicago

127 West Huron, at LaSalle, Chicago
5.0 out of 5.0
4.4 out of 5 (2,373 reviews)
Great modern hotel in downtown coreFantastic hotel. Boutique design, modern, clean, excellent staff, great bathrooms and large room with nice amenities. Definitely will stay here again.
  Feb 20, 2018

$94

$94
Omni Chicago Suites - Magnificent Mile

Omni Chicago Suites - Magnificent Mile

676 N Michigan Ave, Chicago
5.0 out of 5.0
4.4 out of 5 (2,879 reviews)
All good. It was very pleasant, easy, great location and incredibly friendly and helpful staff. Only comments was that the living area in my suite was not well lit and the TV connection did not work. I was not there long enough to complain. I would return as it was clean, affordable and well located.
  Feb 21, 2018

$134

$134
Loews Chicago Hotel

Loews Chicago Hotel

455 North Park Drive, Chicago
5.0 out of 5.0
4.7 out of 5 (1,038 reviews)
My entire stay was very pleasant. The employees were very courteous.
  Feb 20, 2018

$139

$139
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 (1,938 reviews)
Windy City WeekendOutstanding service at a beautiful hotel. Great location. Walked all over town, and a few cab rides. Highly recommend. Concierge service was top notch.
  Feb 19, 2018

$236

$236
The Langham, Chicago

The Langham, Chicago

330 North Wabash Avenue, Chicago
5.0 out of 5.0
4.9 out of 5 (735 reviews)
From check in to check out we were treated like royalty...Thank you
  Feb 19, 2018

$278

$278
Loews Chicago O'Hare Hotel

Loews Chicago O'Hare Hotel

5300 N River Rd, Rosemont
5.0 out of 5.0
4.5 out of 5 (1,827 reviews)
Nice location close to everything Great staff from check in to check out. Two problemsthe beds and pillows not very comfortable mattress need to be replace for softer mattress and pillows and pillows either too low or too high with two pillows
  Feb 20, 2018

$129

$129
Thompson Chicago

Thompson Chicago

21 East Bellevue, Chicago
5.0 out of 5.0
4.7 out of 5 (2,047 reviews)
Thompson HotelOur favorite hotel to stay while in Chicago. Great, friendly staff. Great location. Pet friendly.
  Feb 21, 2018

$195

$195
LondonHouse Chicago, Curio Collection by Hilton

LondonHouse Chicago, Curio Collection by Hilton

85 East Wacker Drive, Chicago
5.0 out of 5.0
4.6 out of 5 (871 reviews)
Good stayEverything was as good as u walk in and walk out. Great service and good views!! Definitely coming back.
  Feb 20, 2018

$99

$99
Fairmont Chicago at Millennium Park

Fairmont Chicago at Millennium Park

200 North Columbus Drive, Chicago
5.0 out of 5.0
4.4 out of 5 (3,408 reviews)
Nice hotel in downtown ChicagoI traveled to Chicago for a week long conference from St. Louis. Check-in was nice, the front desk person was friendly and professional. When I requested a fridge for my leftover Giordano's, it was delivered within minutes which was very nice. They cleaned the rooms no matter where I left my linens. ...
  Feb 20, 2018

$152

$152
Virgin Hotels Chicago

Virgin Hotels Chicago

203 N Wabash Ave, Chicago
5.0 out of 5.0
4.8 out of 5 (1,524 reviews)
Nice hotel and great locationWe had a great time staying at the Virgin Hotels!
  Feb 19, 2018

Ready for an incredible adventure? Add even more pleasure on your next trip to Chicago by treating yourself to the best of the best when it comes to accommodation. It's an ideal fusion. After all, you love the finer things in life, both at home and when you book a getaway. You'll join the multitudes of vacationers who have made Chicago so popular in the last year. Come see what all the fuss is about. Furthermore, you'll find that these hotels are kept in fantastic condition and provide a fine place to lay your head at night. Book one of Expedia's luxurious 5-star hotels in Chicago and get ready to be pampered like never before. Don't wait any longer!

5-Star Hotels in Chicago

Don't be afraid to be pampered during your trip, along with the best conditions. Spa treatments, delicious meals, and one-on-one attention are all at your fingertips. We have a tremendous number of hotels in the region, and all of them provide awesome amenities. Besides that, you'll find that these hotels are kept in fantastic condition and provide a fine place to lay your head at night. How do you want to relax? A reflexology treatment that will leave you feeling great? 24-hour room service, so you can order that chocolate soufflé© in the wee hours of the morning? A full-body massage to help your cares fall away? Don't want to take our word for it? Then explore the 12,572 reviews various guests have left on Expedia and get to know these places.

Can't wait to get outside? You're in luck. You'll find all kinds of activities in a sprawling city like this one, like visiting art galleries and taking in live performances. Say hi to the locals -- they'll be happy to sit down for a pint or a cuppa.

Your Getaway Starts Today

The results are in, and Chicago 5-star hotels are the place to be when you book your next vacation. Many visitors recommend a trip to this location, so don't wait any longer. Don't put off your dream vacation any longer -- this is a great time to find 5-star hotel deals in @region! Decide on one of the 5-star hotels in Chicago today and relax in luxe surroundings when you're ready.

Recently booked 5 Star Hotels in Chicago

Edward Hotel Chicago
3.5 out of 5.0
Last booking: 6 minutes ago
FieldHouse Jones
3.5 out of 5.0
Last booking: 13 minutes ago
Red Roof Inn Chicago - Downers Grove
2.5 out of 5.0
Last booking: 18 minutes ago
DoubleTree by Hilton Wood Dale-Elk Grove
4.0 out of 5.0
Last booking: 21 minutes ago
Travelodge Hotel Downtown
2.5 out of 5.0
Last booking: 26 minutes ago
DoubleTree by Hilton Chicago - North Shore Conference Center
4.0 out of 5.0
Last booking: 26 minutes ago
Motel 6 Prospect Heights, IL
2.0 out of 5.0
Last booking: 28 minutes ago
Baymont Inn & Suites Chicago/Calumet City
2.5 out of 5.0
Last booking: 31 minutes ago
The Godfrey Hotel Chicago
5.0 out of 5.0
Last booking: 35 minutes ago