Beginning of main content
Trip Type
Flight 1
Flight 2
Flight 3
Flight 4
Flight 5

Winnetka Flight + Hotel packages

Top Hotel Deals

See all 791 Properties in Winnetka
Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue, Chicago
    3.0 out of 5.0
     
     

    Built in 1893, this downtown Chicago hotel offers a convenient location across from Grant Park and close to Lake Michigan.

    Congress Plaza Hotel$97

    Congress Plaza Hotel$97
    Hyatt Regency McCormick Place

    Hyatt Regency McCormick Place

    2233 S Martin Luther King Dr, Chicago
      4.0 out of 5.0
       
       

      Connected via enclosed skybridge to the McCormick Place convention complex, the Hyatt Regency is adjacent to a Metro station, with easy access to Chicago's downtown ...

      Hyatt Regency McCormick Place$134

      Hyatt Regency McCormick Place$134
      Hyatt Regency Chicago

      Hyatt Regency Chicago

      151 East Wacker Dr, Chicago
        4.0 out of 5.0
         
         

        This Magnificent Mile hotel is located among Chicago's world-class shopping, restaurants and attractions. The Navy Pier, Millennium Park and Art Institute are ...

        Hyatt Regency Chicago$149

        Hyatt Regency Chicago$149
        Warwick Allerton - Chicago

        Warwick Allerton - Chicago

        701 North Michigan Avenue, Chicago
          4.0 out of 5.0
           
           

          Located on Michigan Avenue in the middle of Chicago's Magnificent Mile, this 1920s Italian Renaissance hotel is surrounded by fashionable shops, 1 mile from ...

          Warwick Allerton - Chicago$125

          Warwick Allerton - Chicago$125
          Hilton Chicago- Michigan Ave Cultural Mile

          Hilton Chicago- Michigan Ave Cultural Mile

          720 S Michigan Ave, Chicago
            4.0 out of 5.0
             
             

            Overlooking Grant Park in downtown Chicago, this landmark Hilton hotel is within walking distance of Buddy Guy's Legends, Millennium Park, the Field Museum, ...

            Hilton Chicago- Michigan Ave Cultural Mile$128

            Hilton Chicago- Michigan Ave Cultural Mile$128
            Crowne Plaza Hotel Chicago O'Hare

            Crowne Plaza Hotel Chicago O'Hare

            5440 N River Rd, Rosemont
              3.5 out of 5.0
               
               

              Situated near the airport, this hotel is within a 5-minute walk of Rosemont Theatre and Donald E. Stephens Convention Center. Fashion Outlets of Chicago and ...

              Crowne Plaza Hotel Chicago O'Hare$99

              Crowne Plaza Hotel Chicago O'Hare$99
              Loews Chicago O'Hare Hotel

              Loews Chicago O'Hare Hotel

              5300 N River Rd, Rosemont
                4.5 out of 5.0
                 
                 

                This family-friendly Rosemont hotel is located near the airport, within a 10-minute walk of Rosemont Theatre, Fashion Outlets of Chicago, and Donald E. Stephens ...

                Loews Chicago O'Hare Hotel$129

                Loews Chicago O'Hare Hotel$129
                Freehand Chicago

                Freehand Chicago

                19 East Ohio Street, Chicago
                  3.5 out of 5.0
                   
                   

                  Located in River North, this hotel is within a 10-minute walk of Chinese Consulate, Holy Name Cathedral, and Northwestern Memorial Hospital. Museum of Contemporary ...

                  Freehand Chicago$134

                  Freehand Chicago$134
                  Comfort Inn Arlington Heights - O'Hare

                  Comfort Inn Arlington Heights - O'Hare

                  2120 S Arlington Heights Rd, Arlington Heights
                    2.5 out of 5.0
                     
                     

                    Situated near the airport, this hotel is within 1 mi (2 km) of Ned Brown Forest Preserve and Heritage Park. Arlington Lakes Golf Club and Metropolis Performing ...

                    Comfort Inn Arlington Heights - O'Hare$72

                    Comfort Inn Arlington Heights - O'Hare$72
                    St. Jane Chicago

                    St. Jane Chicago

                    230 North Michigan Avenue, Chicago
                      4.0 out of 5.0
                       
                       

                      On Michigan Avenue and across from Millennium Park, this rock-inspired hotel occupies the 36-story, Art Deco-style Carbide and Carbon Building in downtown's ...

                      St. Jane Chicago$152

                      St. Jane Chicago$152

                      Top Flight Deals

                      Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.