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Start by selecting your hotel
Start by selecting your hotel

Chicago Flight + Hotel packages

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See all 1,967 Properties in Chicago

Estimated price for 1 night/2 adults

Warwick Allerton - Chicago

Warwick Allerton - Chicago

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

    This family-friendly Chicago hotel is located in the entertainment district, just steps from Northwestern Memorial Hospital and Michigan Avenue. Chicago Water ...

    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. Grant Park and Chicago Theatre are also within 10 minutes. ...

      Swissotel - Chicago

      Swissotel - Chicago

      323 E Wacker Dr, Chicago, IL
        4.5 out of 5.0
         
         

        Located in The Loop, this luxury hotel is within a 5-minute walk of Chicago Riverwalk and Michigan Avenue. Grant Park and Tribune Tower are also within 10 minutes. ...

        Congress Plaza Hotel

        Congress Plaza Hotel

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

          Located in The Loop, this hotel is steps from Columbia College Chicago, Museum of Contemporary Photography, and Auditorium Building and Theatre. Fine Arts Building ...

          Radisson Blu Aqua Hotel Chicago

          Radisson Blu Aqua Hotel Chicago

          221 N Columbus Dr, Chicago, IL
            4.5 out of 5.0
             
             

            Located in The Loop, this luxury hotel is within a 5-minute walk of Chicago Riverwalk, Grant Park, and Aon Center. Chicago Theatre and Chicago Cultural Center ...

            Eurostars Magnificent Mile, previously Dana Hotel

            Eurostars Magnificent Mile, previously Dana Hotel

            660 North State Street, Chicago, IL
              4.0 out of 5.0
               
               

              Located in River North, this spa hotel is steps from Chinese Consulate and State Street. Chicago Water Tower and Tribune Tower are also within 10 minutes. Chicago ...

              Palmer House a Hilton Hotel

              Palmer House a Hilton Hotel

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

                Located in The Loop, this spa hotel is within a 5-minute walk of Art Institute of Chicago and Millennium Park. Chicago Theatre and Willis Tower are also within ...

                Hilton Chicago O'Hare Airport

                Hilton Chicago O'Hare Airport

                Ohare International Airport, Chicago, IL
                  4.0 out of 5.0
                   
                   

                  Located in O'Hare, this hotel is within 6 mi (10 km) of Fashion Outlets of Chicago, Donald E. Stephens Convention Center, and Rosemont Theatre. Allstate Arena ...

                  Inn of Chicago

                  Inn of Chicago

                  162 E Ohio St, Chicago, IL
                    3.0 out of 5.0
                     
                     

                    Located in Near North Side, this beach hotel is within a 5-minute walk of Michigan Avenue, Tribune Tower, and Northwestern Memorial Hospital. Chicago Water Tower ...

                    DoubleTree by Hilton Chicago - Magnificent Mile

                    DoubleTree by Hilton Chicago - Magnificent Mile

                    300 E Ohio St, Chicago, IL
                      3.5 out of 5.0
                       
                       

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

                      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 1967 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.