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Lowest round trip fares by airline from San Diego and Chicago

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

Cheap flights from San Diego to Chicago

Cheap flights from San Diego to Chicago

Leave coastal California and explore the Windy City for business or leisure, by flying from San Diego to Chicago O'Hare International Airport (ORD). Begin your tour through this Midwest cultural mecca by visiting the Museum Campus, where you can discover marine life at the Shedd Aquarium, or study dinosaur fossils at the Field Museum. This museum complex is part of the waterfront Grant Park, which boasts an array of other attractions like the Buckingham Fountain and the Petrillo Music Shell.

Key Facts

You can explore downtown Chicago by riding CTA trains, or driving along Interstate-90 in a rental car. This highway will also lead you to Chicago's suburbs such as Elgin and Park Ridge. Head to the U.S. Cellular Field to cheer on the Chicago White Sox, or visit Wrigley Field to root for the Chicago Cubs.

Book a room along Magnificent Mile to enjoy great views of Chicago's iconic skyline, and then do some shopping in upscale designer stores. Visit the Chicago History Museum and discover the heritage of Chi-Town. Take an elevator to the top of the Willis Tower and enjoy sweeping views of downtown Chicago and Lake Michigan.

Hints and Tips

The flight from San Diego International Airport (SAN) to Chicago takes about four hours to complete. Once you land at ORD, check out the historic military airplanes on display in Terminal 2.

Hotels in Chicago

See all 1,399 Properties in Chicago
Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue, Chicago, IL
    3.5 out of 5.0
     
     
    3.9 out of 5 (29 reviews)

    Located in The Loop, this hotel is steps from Columbia College Chicago, Museum of Contemporary Photography, and Auditorium Building and Theatre. Fine Arts Building ...

    Congress Plaza Hotel$98

    Congress Plaza Hotel$98
    Hotel Essex Chicago

    Hotel Essex Chicago

    800 S Michigan Ave, Chicago, IL
      4.0 out of 5.0
       
       
      4.0 out of 5 (5 reviews)

      Located in The Loop, this hotel is steps from Lakefront Trail and Grant Park. State Street and Columbia College Chicago are also within 5 minutes. Harrison Station ...

      Hotel Essex Chicago$86

      Hotel Essex Chicago$86
      Eurostars Magnificent Mile, previously Dana Hotel

      Eurostars Magnificent Mile, previously Dana Hotel

      660 North State Street, Chicago, IL
        4.0 out of 5.0
         
         
        4.5 out of 5 (28 reviews)

        Located in River North, this spa hotel is steps from Chinese Consulate and State Street. Chicago Water Tower and Tribune Tower are also within 10 minutes. Chicago ...

        Eurostars Magnificent Mile, previously Dana Hotel$117

        Eurostars Magnificent Mile, previously Dana Hotel$117
        The St. Clair Hotel – Magnificent Mile

        The St. Clair Hotel – Magnificent Mile

        162 East Ontario Street, Chicago, IL
          2.5 out of 5.0
           
           
          4.0 out of 5 (5 reviews)

          Located in Near North Side, this hotel is within 1 mi (2 km) of Grant Park, Navy Pier, and Millennium Park. Art Institute of Chicago and Cloud Gate are also ...

          The St. Clair Hotel – Magnificent Mile$100

          The St. Clair Hotel – Magnificent Mile$100
          Inn of Chicago

          Inn of Chicago

          162 E Ohio St, Chicago, IL
            3.0 out of 5.0
             
             
            3.5 out of 5 (35 reviews)

            Located in Near North Side, this beach hotel is within a 5-minute walk of Michigan Avenue, Tribune Tower, and Northwestern Memorial Hospital. Chicago Water Tower ...

            Inn of Chicago$74

            Inn of Chicago$74
            Warwick Allerton - Chicago

            Warwick Allerton - Chicago

            701 North Michigan Avenue, Chicago, IL
              4.0 out of 5.0
               
               
              3.9 out of 5 (117 reviews)

              This family-friendly Chicago hotel is located in the entertainment district, just steps from Northwestern Memorial Hospital and Michigan Avenue. Chicago Water ...

              Warwick Allerton - Chicago$94

              Warwick Allerton - Chicago$94
              DoubleTree by Hilton Chicago - Magnificent Mile

              DoubleTree by Hilton Chicago - Magnificent Mile

              300 E Ohio St, Chicago, IL
                3.5 out of 5.0
                 
                 
                4.2 out of 5 (30 reviews)

                Located in Near North Side, this hotel is within a 10-minute walk of Michigan Avenue, Chicago Riverwalk, and Tribune Tower. Chicago Water Tower and Northwestern ...

                DoubleTree by Hilton Chicago - Magnificent Mile$104

                DoubleTree by Hilton Chicago - Magnificent Mile$104
                Wyndham Grand Chicago Riverfront

                Wyndham Grand Chicago Riverfront

                71 E Wacker Dr, Chicago, IL
                  4.0 out of 5.0
                   
                   
                  4.4 out of 5 (30 reviews)

                  Located in The Loop, this romantic hotel is within a 5-minute walk of Michigan Avenue and Chicago Theatre. Tribune Tower and Grant Park are also within 10 minutes. ...

                  Wyndham Grand Chicago Riverfront$135

                  Wyndham Grand Chicago Riverfront$135
                  The Whitehall Hotel

                  The Whitehall Hotel

                  105 E Delaware Pl, Chicago, IL
                    4.0 out of 5.0
                     
                     
                    3.8 out of 5 (146 reviews)

                    Located in Near North Side, this romantic hotel is steps from 900 North Michigan Shops, John Hancock Center, and Water Tower Place. Chicago Water Tower and Michigan ...

                    The Whitehall Hotel$111

                    The Whitehall Hotel$111
                    Palmer House a Hilton Hotel

                    Palmer House a Hilton Hotel

                    17 E Monroe St, Chicago, IL
                      4.0 out of 5.0
                       
                       
                      4.0 out of 5 (54 reviews)

                      Located in The Loop, this spa hotel is within a 5-minute walk of Art Institute of Chicago and Millennium Park. Chicago Theatre and Willis Tower are also within ...

                      Palmer House a Hilton Hotel$136

                      Palmer House a Hilton Hotel$136
                      Map

                      *Savings based on all holiday package bookings with Flight + Hotel on CheapTickets.com from January through December 2017, as compared to the price of the same components booked separately. Savings will vary based on origin/destination, length of trip, stay dates and selected travel supplier(s). Savings not available on all packages. For Free Flight or 100% Off Flight deals, package savings is greater than or equal to the current cost of one component, when both are priced separately.

                      *Price based on the lowest price found within past 24 hours and based upon one night stay for two adults over the next thirty days. Prices and availability subject to change. Additional terms may apply.