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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 1825 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.

Top Hotel Deals

See all 1,825 Properties in Chicago

Estimated price for 1 night/2 adults

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 ...

    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 steps from Lakefront Trail and Grant Park. State Street and Columbia College Chicago are also within 5 minutes. Harrison Station ...

      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 ...

        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 ...

          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. Chicago Water Tower and Michigan ...

            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. ...

              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 ...

                Sofitel Chicago Magnificent Mile

                Sofitel Chicago Magnificent Mile

                20 E Chestnut St, Chicago, IL
                  4.5 out of 5.0
                   
                   

                  Located in Near North Side, this luxury hotel is within a 5-minute walk of State Street, John Hancock Center, and Water Tower Place. Chicago Water Tower and ...

                  Hotel Julian

                  Hotel Julian

                  168 N Michigan Avenue, Chicago, IL
                    4.0 out of 5.0
                     
                     

                    Located in The Loop, this hotel is steps from Chicago Theatre, Grant Park, and State Street. Chicago Cultural Center and Ford Center for the Performing Arts ...

                    Renaissance Chicago O'Hare Suites Hotel

                    Renaissance Chicago O'Hare Suites Hotel

                    8500 West Bryn Mawr Avenue, Chicago, IL
                      4.0 out of 5.0
                       
                       

                      Located in O'Hare, this hotel is within 3 mi (5 km) of Rivers Casino, Donald E. Stephens Convention Center, and Rosemont Theatre. Fashion Outlets of Chicago ...

                      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 1825 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.