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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 1635 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 1,635 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 ...

    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 ...

      Travelodge by Wyndham Downtown Chicago

      Travelodge by Wyndham Downtown Chicago

      65 E Harrison St, Chicago, IL
        2.0 out of 5.0
         
         

        Located in The Loop, this hotel is steps from Lakefront Trail, Columbia College Chicago, and State Street. Buckingham Fountain and Grant Park are also within ...

        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 ...

          Central Loop Hotel

          Central Loop Hotel

          111 West Adams Street, Chicago, IL
            4.0 out of 5.0
             
             

            Located in The Loop, this boutique hotel is within a 5-minute walk of Chicago Board of Trade Building and State Street. Willis Tower and Skydeck Ledge are also ...

            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 ...

              Kinzie Hotel

              Kinzie Hotel

              20 W Kinzie St, Chicago, IL
                4.0 out of 5.0
                 
                 

                Located in River North, this hotel is steps from House of Blues Chicago and State Street. Tribune Tower and Wrigley Building are also within 10 minutes. Grand ...

                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 Art Institute of Chicago. Cloud Gate and Grant Park are also ...

                  Hilton Chicago- Michigan Ave Cultural Mile

                  Hilton Chicago- Michigan Ave Cultural Mile

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

                    Located in The Loop, this historic hotel is within a 5-minute walk of Columbia College Chicago and Grant Park. Art Institute of Chicago and Millennium Park are ...

                    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 ...

                      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 1635 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.