Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5
Start by selecting your hotel
Due to coronavirus (COVID-19) travel advisories, some destinations may be unavailable for certain dates. Find out more.
Start by selecting your hotel

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 2464 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 2,464 Properties in Chicago

Estimated price for 1 night/2 adults

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. ...

    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 ...

      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 ...

        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 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 ...

            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. ...

              Loews Chicago Hotel

              Loews Chicago Hotel

              455 North Park Drive, Chicago, IL
                4.5 out of 5.0
                 
                 

                Located in Near North Side, this luxury hotel is within a 10-minute walk of Chicago Riverwalk, Michigan Avenue, and Northwestern Memorial Hospital. Grant Park ...

                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 ...

                  Hyatt Place Chicago/O'Hare Airport

                  Hyatt Place Chicago/O'Hare Airport

                  6810 Mannheim Rd, Rosemont, IL
                    3.0 out of 5.0
                     
                     

                    Situated near the airport, this hotel is within 3 mi (5 km) of Allstate Arena, Donald E. Stephens Convention Center, and Rosemont Theatre. Rivers Casino is 1.6 ...

                    Aloft Chicago Mag Mile

                    Aloft Chicago Mag Mile

                    243 E. Ontario, Chicago, IL
                      3.0 out of 5.0
                       
                       

                      Located in Near North Side, this hotel is within 1 mi (2 km) of Northwestern Memorial Hospital, Navy Pier, and Millennium Park. Art Institute of Chicago and ...

                      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.