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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 2088 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 2,088 Properties in Chicago

Estimated price for 1 night/2 adults

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 ...

    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 ...

      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, Water Tower Place, and John Hancock Center. Chicago Water Tower and ...

        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 ...

          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 ...

            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. Chicago Riverwalk and Chicago Theatre are also within 10 minutes. Grand ...

              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 ...

                La Quinta Inn & Suites by Wyndham Chicago Downtown

                La Quinta Inn & Suites by Wyndham Chicago Downtown

                1 S Franklin Street, Chicago, IL
                  3.0 out of 5.0
                   
                   

                  Located in The Loop, this hotel is within a 5-minute walk of Willis Tower and Skydeck Ledge. Chicago Riverwalk and Cadillac Palace Theatre are also within 10 ...

                  Hyatt Place Chicago/Downtown - The Loop

                  Hyatt Place Chicago/Downtown - The Loop

                  28 North Franklin Street, Chicago, IL
                    3.0 out of 5.0
                     
                     

                    Located in The Loop, this hotel is within a 10-minute walk of Cadillac Palace Theatre, Willis Tower, and Chicago Riverwalk. Skydeck Ledge and 311 S Wacker Dr ...

                    The Champagne Lodge & Luxury Suites

                    The Champagne Lodge & Luxury Suites

                    16 W 621 S. Frontage Rd, Willowbrook, IL
                      3.5 out of 5.0
                       
                       

                      Situated in Willowbrook, this spa hotel is 1.9 mi (3.1 km) from Willowbrook Community Park and 2.7 mi (4.3 km) from National Shrine of St. Therese. Burr Ridge ...

                      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.