Chicago Vacation Packages for 2021

Chicago Flight + Hotel packages

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 2679 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 2,679 Properties in Chicago

Estimated price for 1 night/2 adults

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 ...

    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 ...

      River Hotel

      River Hotel

      75 East Wacker Drive, Chicago, IL
        4.0 out of 5.0
         
         

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

        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. ...

          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 ...

            DoubleTree by Hilton Chicago - Magnificent Mile

            DoubleTree by Hilton Chicago - Magnificent Mile

            300 E Ohio St, Chicago, IL
              3.5 out of 5.0
               
               

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

              Hilton Garden Inn Chicago Downtown/Magnificent Mile

              Hilton Garden Inn Chicago Downtown/Magnificent Mile

              10 E Grand Ave, Chicago, IL
                3.0 out of 5.0
                 
                 

                Located in River North, this hotel is within a 5-minute walk of State Street and Michigan Avenue. House of Blues Chicago and Chicago Riverwalk are also within ...

                Millennium Knickerbocker Chicago

                Millennium Knickerbocker Chicago

                163 East Walton Place, Chicago, IL
                  4.0 out of 5.0
                   
                   

                  Located in Near North Side, this hotel is within a 10-minute walk of John Hancock Center and Museum of Contemporary Art. Millennium Park and Navy Pier are also ...

                  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 ...

                    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 ...

                        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 ...

                          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 ...

                            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 ...

                              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 ...

                                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.