Beginning of main content

Book Exclusive Chicago Resorts Today

Search Flights

Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5

Chicago Hotels

Search Flight + Hotel

Search 400 airlines and 321,000 hotels worldwide.

Get the guaranteed best price available for your trip.

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


Featured Chicago 5 Star Hotels

See all 962 Hotels in Chicago
The Peninsula Chicago

The Peninsula Chicago

108 East Superior Street, Chicago
5.0 out of 5.0
4.8 out of 5 (18 reviews)
Elegant downtown hotelThe Penisula Hotel was located within walking distance of most local sights, shopping and resturants. The staff was friendly and extremely accommodating. The room was spotless and comfortable. The view from our room was amazing!
  Jul 3, 2015

$399

$399
The Ritz-Carlton, Chicago

The Ritz-Carlton, Chicago

160 E Pearson Street, Chicago
5.0 out of 5.0
4.3 out of 5 (19 reviews)
Nice new club floor New club floor just opened. Staff was very responsive and helped with special dietary needs.
  Apr 16, 2017

$297

$297
Trump International Hotel & Tower Chicago

Trump International Hotel & Tower Chicago

401 N Wabash Ave, Chicago
5.0 out of 5.0
4.6 out of 5 (16 reviews)
Visited Chicago and had an amazing time.The city was wonderful. People friendly. Went to The Yankees vs Cubs baseball game on Sat, had a blast. The hotel was beautiful, staff very friendly and helpful. We will definitely stay here again.
  May 9, 2017

$276

$276
Four Seasons Hotel Chicago

Four Seasons Hotel Chicago

120 East Delaware Place, Chicago
5.0 out of 5.0
4.7 out of 5 (11 reviews)
Great, exceeded my expectationEverything was perfect, seamless and pristine. Food and bar area was well appointed. Our last visit was years ago with our daughters...but did not use the pool this time.
  Aug 1, 2016

$320

$320
Waldorf Astoria Chicago

Waldorf Astoria Chicago

11 E. Walton Street, Chicago
5.0 out of 5.0
5.0 out of 5 (6 reviews)
High quality everything!The Waldorf is high class and quality from the minute you step in and are greeted, to the beautiful, comfortable, spacious rooms with all the amenities, including a Nespresso machine. We loved our stay there, and the staff were first class!
  May 17, 2017

$319

$319
The Langham, Chicago

The Langham, Chicago

330 North Wabash Avenue, Chicago
5.0 out of 5.0
4.8 out of 5 (4 reviews)
Luxury HotelWe loved our stay at the Langham-very clean, staff is excellent. Was a 5 star experience.
  Jul 5, 2017

$344

$344
Park Hyatt - Chicago

Park Hyatt - Chicago

800 N Michigan Ave, Chicago
5.0 out of 5.0
5.0 out of 5 (2 reviews)
Beautiful hotel!!!The hotel is beautiful, the service was excellent, the room huge and very nice, the food wonderful!!!
 DrC2013 May 31, 2013

$262

$262
Map

About Chicago 5 stars Star Hotels

Book your travels from the selection of 5 stars star hotels in Chicago, Illinois.