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 (1,947 reviews)
    Everything about this stay was wonderful, from the friendly check-in to the comfort of the room, the 2 Michelin star restaurant and the spa. Everyone calls you by name and so very pleasant. My husband and I enjoyed the couples experience at the spa and all the amenities such as the pool, saunas etc. ...
    Apr 16, 2018

    Trump International Hotel & Tower Chicago$228

    Trump International Hotel & Tower Chicago$228
    The Langham, Chicago

    The Langham, Chicago

    330 North Wabash Avenue, Chicago
      5.0 out of 5.0
       
       
      4.9 out of 5 (796 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 (1,121 reviews)
          Centrally LocatedCentrally located within reasonable distance to airports.
          Apr 17, 2018

          The Ritz-Carlton, Chicago$239

          The Ritz-Carlton, Chicago$239
          Four Seasons Hotel Chicago

          Four Seasons Hotel Chicago

          120 East Delaware Place, Chicago
            5.0 out of 5.0
             
             
            4.7 out of 5 (572 reviews)
            Loved it.
            Apr 16, 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$280

              Park Hyatt - Chicago$280
              Waldorf Astoria Chicago

              Waldorf Astoria Chicago

              11 E. Walton Street, Chicago
                5.0 out of 5.0
                 
                 
                4.8 out of 5 (721 reviews)
                Have stayed here before because I love it.I try to stay here as much as I can while in Chicago. Even though it’s north of the mag mile, there is still great shopping and restaurants in the area. The rooms are always clean and staff very friendly and helpful. The spa is great too.
                Apr 20, 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 (7,563 reviews)
                  Nice hotel close to everythingAmazing hotel that is within walking distance to Navy Pier, Magnificent Mile and the subway. Will stay here again.
                  Apr 20, 2018

                  The Whitehall Hotel$94

                  The Whitehall Hotel$94
                  Wyndham Grand Chicago Riverfront

                  Wyndham Grand Chicago Riverfront

                  71 E Wacker Dr, Chicago
                    4.0 out of 5.0
                     
                     
                    4.4 out of 5 (6,523 reviews)
                    Very accommodating, beautiful hotelI was in Chicago for a conference. In the middle of my trip there was a storm predicted back at my home. I made the decision to end my trip two days early so as to not get stuck in Chicago. Because I had paid in full ahead of time on Expedia, it was up to the hotel if they would reimburse me for ...
                    Apr 20, 2018

                    Wyndham Grand Chicago Riverfront$119

                    Wyndham Grand Chicago Riverfront$119
                    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 (3,279 reviews)
                      Nice hotel next to airportArrived late and in the pouring rain. Valet assisted in baggage. Great stay very convenient for early morning flight
                      Apr 20, 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 (10,135 reviews)
                        Great location, clean room, and have complimentary breakfast.
                        Apr 18, 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 (4,028 reviews)
                          great stay in the center of townPros: great central location, walking distance to a lot of places, very clean, friendly staff, attached restaurant was good, weekday happy hour and snacks, big shower Cons: bed was a bit firm, no view, weekend amenities were less than weekdays (no happy hour, no snacks), and most importantly: our ...
                          Apr 18, 2018

                          Central Loop Hotel$121

                          Central Loop Hotel$121
                          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 (2,458 reviews)
                            Great Downtown Hotel Great staff, location and rooms. Perfect spot for anything downtown.
                            Apr 19, 2018

                            The Godfrey Hotel Chicago$105

                            The Godfrey Hotel Chicago$105
                            River Hotel

                            River Hotel

                            75 East Wacker Drive, Chicago
                              4.0 out of 5.0
                               
                               
                              4.2 out of 5 (4,183 reviews)
                              Perfect for the cancer conferences. Very close to the shuttle pickup spot (Wyndham Grand, right next door), and has good temp controls in the room. The staff were great and I loved the filtered water dispensers on my floor. The beds were a bit too hard for my taste. PS: tucked sheets are a pain. Let me curl up when I go to bed. Most ...
                              Apr 18, 2018

                              River Hotel$109

                              River Hotel$109
                              Warwick Allerton - Chicago

                              Warwick Allerton - Chicago

                              701 North Michigan Avenue, Chicago
                                4.0 out of 5.0
                                 
                                 
                                4.1 out of 5 (8,674 reviews)
                                Nicely located, good staff, but parking is VERY expensive!
                                Apr 17, 2018

                                Warwick Allerton - Chicago$76

                                Warwick Allerton - Chicago$76
                                Millennium Knickerbocker Chicago

                                Millennium Knickerbocker Chicago

                                163 East Walton Place, Chicago
                                  4.0 out of 5.0
                                   
                                   
                                  4.3 out of 5 (5,660 reviews)
                                  GREAT LOCATIONEasy to get everywhere. Close to busses and not far from the Red line train. Staff helpful. Martini bar staff excellent as well as the martini's If I have a criticism. .the windows in our room were filty and we could barely see out of them. 1 towel hook in the bathroom? Strange when you have 2 people ...
                                  Apr 17, 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 (9,206 reviews)
                                    Friendly staffArrived early way before regular check in and staff were friendly, helpful and got us checked in. Very good people working there throughout the hotel and great location.
                                    Apr 19, 2018

                                    Hyatt Regency Chicago$112

                                    Hyatt Regency Chicago$112
                                    Map

                                    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.