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 994 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 (1,950 reviews)
    Trump Great room, great staff, great service, & great location. Could not have been better.
    Apr 23, 2018

    Trump International Hotel & Tower Chicago$256

    Trump International Hotel & Tower Chicago$256
    The Langham, Chicago

    The Langham, Chicago

    330 North Wabash Avenue, Chicago
      5.0 out of 5.0
       
       
      4.9 out of 5 (797 reviews)
      Chicago at its bestThe Langham - Chicago is simply superb. The location is magnificent, the property is uniquely sophisticated yet unpretentious, the rooms are spacious and the attention to detail and comfort is evident. The staff is gracious, courteous and informed, eager to help and provide excellent recommendations; ...
      Apr 20, 2018

      The Langham, Chicago$298

      The Langham, Chicago$298
      The Peninsula Chicago

      The Peninsula Chicago

      108 East Superior Street, Chicago
        5.0 out of 5.0
         
         
        4.9 out of 5 (811 reviews)
        Outstanding service and locationIt’s been a couple of years since I stayed at The Peninsula and this visit reminded me why it’s such a wonderful hotel....service, room comfort, location. The rooms have been renovated to include great tech features since my last stay. Loved it!
        Apr 16, 2018

        The Peninsula Chicago$319

        The Peninsula Chicago$319
        The Ritz-Carlton, Chicago

        The Ritz-Carlton, Chicago

        160 E Pearson Street, Chicago
          5.0 out of 5.0
           
           
          4.6 out of 5 (1,123 reviews)
          Everything was very good for 2 exceptions. We were celebrating my daughter's birthday and I called ahead few days before and asked for complimentary birthday cake. Unfortunately, they forgot about it in the day of check in. Next, shower heads needs to be replaced. The water pressure was horrible. ...
          Apr 23, 2018

          The Ritz-Carlton, Chicago$223

          The Ritz-Carlton, Chicago$223
          Four Seasons Hotel Chicago

          Four Seasons Hotel Chicago

          120 East Delaware Place, Chicago
            5.0 out of 5.0
             
             
            4.7 out of 5 (573 reviews)
            Birthday celebration Excellent rooms and service. Housekeeping always prompt when we request some necessity.
            Apr 22, 2018

            Four Seasons Hotel Chicago$320

            Four Seasons Hotel Chicago$320
            Park Hyatt - Chicago

            Park Hyatt - Chicago

            800 N Michigan Ave, Chicago
              5.0 out of 5.0
               
               
              4.7 out of 5 (425 reviews)
              Would definitely go there again!This was one of my best experiences staying at hotel. Truth to be told I am not much of good lodging spender but both times I stayed at Hyatt it was unforgettable experience! The pool was excellent, Jacuzzi and steam room, the restaurant and bar are top level. Stuff is friendly and nice.
              Mar 26, 2018

              Park Hyatt - Chicago$309

              Park Hyatt - Chicago$309
              Waldorf Astoria Chicago

              Waldorf Astoria Chicago

              11 E. Walton Street, Chicago
                5.0 out of 5.0
                 
                 
                4.8 out of 5 (722 reviews)
                Beautiful hotelAmazing hotel. Beautiful finishings. The staff is we’re so kind. The bed was very comfortable. Can’t wait to go back
                Apr 22, 2018

                Waldorf Astoria Chicago$284

                Waldorf Astoria Chicago$284

                Featured Chicago 4 Star Hotels

                See all 994 Hotels in Chicago
                The Whitehall Hotel

                The Whitehall Hotel

                105 E Delaware Pl, Chicago
                  4.0 out of 5.0
                   
                   
                  4.1 out of 5 (7,574 reviews)
                  Nice hotel and friendly staff. Rooms need some upgrading.
                  Apr 20, 2018

                  The Whitehall Hotel$110

                  The Whitehall Hotel$110
                  Wyndham Grand Chicago Riverfront

                  Wyndham Grand Chicago Riverfront

                  71 E Wacker Dr, Chicago
                    4.0 out of 5.0
                     
                     
                    4.4 out of 5 (6,531 reviews)
                    Great hotel with a great location. We enjoyed a great stay at the Wyndham Grand. In for a few days. Great location to see everything.
                    Apr 23, 2018

                    Wyndham Grand Chicago Riverfront$134

                    Wyndham Grand Chicago Riverfront$134
                    Hilton Chicago O'Hare Airport

                    Hilton Chicago O'Hare Airport

                    Ohare International Airport, Chicago
                      4.0 out of 5.0
                       
                       
                      4.0 out of 5 (3,280 reviews)
                      Very pleasantly surprisedI reserved a room with a twin bed and didn’t know what to expect. Checking in they warned me that these lower rate rooms are by the elevator (ugh) and offered to upgrade me to a king bed room for $40 more. I passed and the room was near the elevator but it was surprisingly quiet! The bed was plenty ...
                      Apr 23, 2018

                      Hilton Chicago O'Hare Airport$93

                      Hilton Chicago O'Hare Airport$93
                      Palmer House a Hilton Hotel

                      Palmer House a Hilton Hotel

                      17 E Monroe St, Chicago
                        4.0 out of 5.0
                         
                         
                        4.2 out of 5 (10,147 reviews)
                        Nice stay!Enjoyed the Magic Parlor and breakfast brunch! Nice room
                        Apr 22, 2018

                        Palmer House a Hilton Hotel$118

                        Palmer House a Hilton Hotel$118
                        Central Loop Hotel

                        Central Loop Hotel

                        111 West Adams Street, Chicago
                          4.0 out of 5.0
                           
                           
                          4.2 out of 5 (4,033 reviews)
                          Very clean but not upscale. no lamp on the desk made reading difficult. the toilet flush was loose, NBD but should have been fixed.
                          Apr 23, 2018

                          Central Loop Hotel$125

                          Central Loop Hotel$125
                          The Godfrey Hotel Chicago

                          The Godfrey Hotel Chicago

                          127 West Huron, at LaSalle, Chicago
                            4.5 out of 5.0
                             
                             
                            4.4 out of 5 (2,460 reviews)
                            Great Downtown Hotel Great staff, location and rooms. Perfect spot for anything downtown.
                            Apr 19, 2018

                            The Godfrey Hotel Chicago$119

                            The Godfrey Hotel Chicago$119
                            River Hotel

                            River Hotel

                            75 East Wacker Drive, Chicago
                              4.0 out of 5.0
                               
                               
                              4.2 out of 5 (4,190 reviews)
                              It was very nice and convenient to everything. Beautiful views.
                              Apr 21, 2018

                              River Hotel$141

                              River Hotel$141
                              Warwick Allerton - Chicago

                              Warwick Allerton - Chicago

                              701 North Michigan Avenue, Chicago
                                4.0 out of 5.0
                                 
                                 
                                4.1 out of 5 (8,679 reviews)
                                Vintage hotel in the middle of downtownWhen we checked in they asked if we were first time visitors, which we were, so they gave us a complimentary room upgrade. Great views of the city and staff was friendly and helpful.
                                Apr 23, 2018

                                Warwick Allerton - Chicago$78

                                Warwick Allerton - Chicago$78
                                Millennium Knickerbocker Chicago

                                Millennium Knickerbocker Chicago

                                163 East Walton Place, Chicago
                                  4.0 out of 5.0
                                   
                                   
                                  4.3 out of 5 (5,662 reviews)
                                  The expierenceIt was a good experience the fridge was stocked but the prices are ridiculous. But other than thst it was nice.
                                  Apr 22, 2018

                                  Millennium Knickerbocker Chicago$101

                                  Millennium Knickerbocker Chicago$101
                                  Hyatt Regency Chicago

                                  Hyatt Regency Chicago

                                  151 East Wacker Dr, Chicago
                                    4.0 out of 5.0
                                     
                                     
                                    4.4 out of 5 (9,212 reviews)
                                    The view was incredible (14th floor, partial view of the lake) and the room was unbelievable! So clean and comfortable. One of the nicest stays I've had!
                                    Apr 23, 2018

                                    Hyatt Regency Chicago$112

                                    Hyatt Regency Chicago$112

                                    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.