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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 2444 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 2,444 Properties in Chicago

Estimated price for 1 night/2 adults

The Godfrey Hotel Chicago

The Godfrey Hotel Chicago

127 West Huron, at LaSalle, Chicago, IL
    4.5 out of 5.0
     
     

    Located in River North, this luxury hotel is within a 10-minute walk of State Street, Michigan Avenue, and Northwestern Memorial Hospital. Chicago Riverwalk ...

    LondonHouse Chicago, Curio Collection by Hilton

    LondonHouse Chicago, Curio Collection by Hilton

    85 East Wacker Drive, Chicago, IL
      4.5 out of 5.0
       
       

      Located in The Loop, this luxury hotel is steps from Chicago Riverwalk and Michigan Avenue. Grant Park and Chicago Theatre are also within 10 minutes. Clark-Lake ...

      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 romantic hotel is steps from Chinese Consulate and State Street. Water Tower Place and Michigan Avenue are also within 10 minutes. ...

        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, Water Tower Place, and Michigan Avenue. John Hancock Center and State ...

          Royal Sonesta Chicago Riverfront

          Royal Sonesta Chicago Riverfront

          71 E Wacker Dr, Chicago, IL
            4.0 out of 5.0
             
             

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

            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 Grant Park, Millennium Park, and Art Institute of Chicago. Navy Pier and Cloud Gate are also ...

              Best Western Grant Park Hotel

              Best Western Grant Park Hotel

              1100 S Michigan Ave, Chicago, IL
                2.5 out of 5.0
                 
                 

                Located in The Loop, this hotel is within a 10-minute walk of Grant Park and Columbia College Chicago. Field Museum of Natural History and John G. Shedd Aquarium ...

                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 Aon Center are also within 10 minutes. ...

                  Aloft Chicago O'Hare

                  Aloft Chicago O'Hare

                  9700 Balmoral Ave, Rosemont, IL
                    3.0 out of 5.0
                     
                     

                    Situated in Rosemont, this hotel is within a 5-minute walk of Parkway Bank Park Entertainment District and Fashion Outlets of Chicago. Donald E. Stephens Convention ...

                    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 Millennium Park are also ...

                      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.