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Top Hotel Deals

See all 1,619 Properties in Chicago

Estimated price for 1 night/2 adults

Hotel Essex Chicago

Hotel Essex Chicago

800 S Michigan Ave, Chicago, IL
    4.0 out of 5.0
     
     

    Located in The Loop, this hotel is within a 5-minute walk of Lakefront Trail, State Street, and Columbia College Chicago. Grant Park and Buckingham Fountain ...

    Hotel Essex Chicago$90

    May 27 - May 28

    Hotel Essex Chicago$90
    Palmer House a Hilton Hotel

    Palmer House a Hilton Hotel

    17 E Monroe St, Chicago, IL
      4.0 out of 5.0
       
       

      This 1925 Beaux Arts-style Chicago hotel is steps from Millennium Park, 2 blocks from Macy's and the Art Institute, and 1 mile from Lake Michigan, Magnificent ...

      Palmer House a Hilton Hotel$125

      May 26 - May 27

      Palmer House a Hilton Hotel$125
      Hyatt Regency Chicago

      Hyatt Regency Chicago

      151 East Wacker Dr, Chicago, IL
        4.0 out of 5.0
         
         

        Located in The Loop, this eco-friendly hotel is steps from Chicago Riverwalk and Michigan Avenue Bridge. Chicago Theatre and Millennium Park are also within ...

        Hyatt Regency Chicago$175

        Jun 20 - Jun 21

        Hyatt Regency Chicago$175
        Embassy Suites Chicago Downtown Magnificent Mile

        Embassy Suites Chicago Downtown Magnificent Mile

        511 North Columbus Drive, Chicago, IL
          4.0 out of 5.0
           
           

          Located in Near North Side, this hotel is within a 10-minute walk of Chicago Riverwalk, Michigan Avenue, and Northwestern Memorial Hospital. Navy Pier and Water ...

          Embassy Suites Chicago Downtown Magnificent Mile$147

          May 28 - May 29

          Embassy Suites Chicago Downtown Magnificent Mile$147
          Hyatt Centric Chicago Magnificent Mile

          Hyatt Centric Chicago Magnificent Mile

          633 N Saint Clair St, Chicago, IL
            4.0 out of 5.0
             
             

            Located in Near North Side, this romantic hotel is steps from Northwestern Memorial Hospital and Michigan Avenue. Water Tower Place and John Hancock Center are ...

            Hyatt Centric Chicago Magnificent Mile$236

            Jun 14 - Jun 15

            Hyatt Centric Chicago Magnificent Mile$236
            Omni Chicago Suites - Magnificent Mile

            Omni Chicago Suites - Magnificent Mile

            676 N Michigan Ave, Chicago, IL
              4.5 out of 5.0
               
               

              Omni Chicago Suites - Magnificent Mile is at the center of Chicago’s most prestigious neighborhood, 3 blocks from the shores of Lake Michigan and around the ...

              Omni Chicago Suites - Magnificent Mile$179

              May 27 - May 28

              Omni Chicago Suites - Magnificent Mile$179
              The St. Clair Hotel – Magnificent Mile

              The St. Clair Hotel – Magnificent Mile

              162 East Ontario Street, Chicago, IL
                2.5 out of 5.0
                 
                 

                Located in Near North Side, this hotel is within 1 mi (2 km) of Navy Pier, Millennium Park, and Cloud Gate. Art Institute of Chicago and Grant Park are also ...

                The St. Clair Hotel – Magnificent Mile$140

                May 26 - May 27

                The St. Clair Hotel – Magnificent Mile$140
                Congress Plaza Hotel

                Congress Plaza Hotel

                520 South Michigan Avenue, Chicago, IL
                  3.5 out of 5.0
                   
                   

                  Built in 1893, this downtown Chicago hotel offers a convenient location across from Grant Park and close to Lake Michigan.

                  Congress Plaza Hotel$116

                  May 28 - May 29

                  Congress Plaza Hotel$116
                  River Hotel

                  River Hotel

                  75 East Wacker Drive, Chicago, IL
                    4.0 out of 5.0
                     
                     

                    Located in The Loop, this hotel is within a 5-minute walk of Chicago Riverwalk and Chicago Theatre. Michigan Avenue and House of Blues Chicago are also within ...

                    River Hotel$94

                    May 27 - May 28

                    River Hotel$94
                    The Whitehall Hotel

                    The Whitehall Hotel

                    105 E Delaware Pl, Chicago, IL
                      4.0 out of 5.0
                       
                       

                      Located in Near North Side, this romantic hotel is steps from 900 North Michigan Shops, John Hancock Center, and Water Tower Place. Michigan Avenue and State ...

                      The Whitehall Hotel$179

                      Jun 18 - Jun 19

                      The Whitehall Hotel$179

                      Top Flight Deals

                      These prices were available within the past 7 days. Prices quoted are per person, round trip, for the period specified. Prices and availability are subject to change. Additional terms apply.

                      Chicago Vacation Packages

                      Trying to figure out a way to package your flight and hotel, while saving some money? The AARP Travel Center Powered by Expedia® can help you get everything you need, while saving you both money and some time. We're here to book everything you'll need to make your Chicago trip one to remember. In only a few clicks, you can select the best Chicago vacation package for you. We have a huge list of flights and hotels, and Chicago activities to select from.

                      Chicago Hotel Deals

                      You can choose from around 1619 hotels. Whether you want to stay in the heart of the city or pick a spot that is near all the Chicago hot spots, we have plenty of options available.

                      We have fantastic rates on everything from family-friendly resorts that meet all the vacation must-haves to inexpensive hotels perfect for those on a budget. You can look through our vast catalog of options and pick the hotel that is perfect for you and your family. With AARP Travel Center's Chicago hotel packages, you not only get a great rate on your flight, but also a wonderful place to stay.

                      Things to do in Chicago

                      People from all over make this city their vacation destination, and with good reason. A little curiosity and asking the right people, like your hotel's concierge, goes a long way into having a unique experience.

                      If you need more suggestions, then make sure to click on AARP's "Things to Do" tab.

                      Book Together and Save

                      As an AARP Member, you get to take advantage of all the great deals. You'll save on select hotels worldwide, flights, and also car rentals. No matter what Chicago vacation package you pick, your membership savings helps you get a great deal. The hardest packing you'll have to do is for your suitcase. Bundle now and get ready for your Chicago vacation.