Beginning of main content

Chicago Flight + Hotel packages

Top Hotel Deals

See all 1,527 Properties in Chicago
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 ...

    Hyatt Regency Chicago

    Hyatt Regency Chicago

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

      This Magnificent Mile hotel is located among Chicago's world-class shopping, restaurants and attractions. The Navy Pier, Millennium Park and Art Institute are ...

      Embassy Suites Chicago Downtown Magnificent Mile

      Embassy Suites Chicago Downtown Magnificent Mile

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

        The Embassy Suites Chicago Downtown Magnificent Mile offers a newly renovated fresh look and is located two blocks from Navy Pier, Magnificent Mile shopping, ...

        Freehand Chicago

        Freehand Chicago

        19 East Ohio Street, Chicago, IL
          3.5 out of 5.0
           
           

          Located in River North, this hotel is within a 10-minute walk of Chinese Consulate, Holy Name Cathedral, and Northwestern Memorial Hospital. Museum of Contemporary ...

          The St. Clair Hotel – Magnificent Mile

          The St. Clair Hotel – Magnificent Mile

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

            The hotel is a half-block from the Magnificent Mile and an 8-minute walk from Grand/State Metro Station. Many attractions are within a 15-minute walk, including ...

            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.

              Hyatt Centric Chicago Magnificent Mile

              Hyatt Centric Chicago Magnificent Mile

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

                This smoke-free 17-story hotel is 1 block from North Michigan Avenue's boutique and specialty stores, 3 blocks from Lake Michigan, 6 blocks from the State & ...

                River Hotel

                River Hotel

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

                  Located in The Loop, this hotel is 0.1 mi (0.1 km) from Chicago Riverwalk.

                  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 ...

                    Warwick Allerton - Chicago

                    Warwick Allerton - Chicago

                    701 North Michigan Avenue, Chicago, IL
                      4.0 out of 5.0
                       
                       

                      Located on Michigan Avenue in the middle of Chicago's Magnificent Mile, this 1920s Italian Renaissance hotel is surrounded by fashionable shops, 1 mile from ...

                      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 1527 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.