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Lowest round trip fares by airline from Orlando and Chicago

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

Cheap flights from Orlando to Chicago

Cheap flights from Orlando to Chicago

First-time visitors headed to Chicago from Orlando may be in for a bit of culture shock. The Windy City boasts an impressive skyline that you'll see long before you land at O'Hare International Airport (ORD). Some of the world's tallest buildings call Chicago home, including the former record holder, Willis Tower. Locals still refer to the famous skyscraper as the Sears Tower, and brave visitors can take an elevator ride to the observation deck 103 floors up from the lobby.

Key Facts

Greater Chicagoland is served by the Chicago Transit Authority, which operates buses, trains and subway lines throughout the city. Since Chicago is such a sprawling metropolis, the best way to see as many sights as possible, is to opt for a rental car. In general, navigation in Chicago is easy as the streets are set up in a grid, but you may want to opt for an in-vehicle GPS, as the city spans more than 235 square miles.

Hints and Tips

If you're on a direct flight from Orlando International Airport (MCO) to Chicago, you'll be in the air for less than three hours. O'Hare is a family-friendly facility that houses a replica airport playground in Terminal 2, where children can pretend to be pilots and unwind after a flight. For your convenience, a variety of rental car companies offer free shuttle service outside of baggage claim.

Packages from Orlando to Chicago

Chicago vacations with economy flights

Hotels in Chicago

See all 1,825 Properties in Chicago
Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue, Chicago, IL
    3.5 out of 5.0
     
     
    3.8 out of 5 (27 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$149

    Congress Plaza Hotel$149
    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$129

      Hotel Essex Chicago$129
      The Whitehall Hotel

      The Whitehall Hotel

      105 E Delaware Pl, Chicago, IL
        4.0 out of 5.0
         
         
        3.8 out of 5 (143 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$112

        The Whitehall Hotel$112
        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$98

          Inn of Chicago$98
          Warwick Allerton - Chicago

          Warwick Allerton - Chicago

          701 North Michigan Avenue, Chicago, IL
            4.0 out of 5.0
             
             
            3.9 out of 5 (116 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$119

            Warwick Allerton - Chicago$119
            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$176

              Palmer House a Hilton Hotel$176
              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$120

                The St. Clair Hotel – Magnificent Mile$120
                Hyatt Regency Chicago

                Hyatt Regency Chicago

                151 East Wacker Dr, Chicago, IL
                  4.0 out of 5.0
                   
                   
                  4.2 out of 5 (90 reviews)

                  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. ...

                  Hyatt Regency Chicago$199

                  Hyatt Regency Chicago$199
                  Sofitel Chicago Magnificent Mile

                  Sofitel Chicago Magnificent Mile

                  20 E Chestnut St, Chicago, IL
                    4.5 out of 5.0
                     
                     
                    4.7 out of 5 (18 reviews)

                    Located in Near North Side, this luxury hotel is within a 5-minute walk of State Street, John Hancock Center, and Water Tower Place. Chicago Water Tower and ...

                    Sofitel Chicago Magnificent Mile$183

                    Sofitel Chicago Magnificent Mile$183
                    Swissotel - Chicago

                    Swissotel - Chicago

                    323 E Wacker Dr, Chicago, IL
                      4.5 out of 5.0
                       
                       
                      4.4 out of 5 (36 reviews)

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

                      Swissotel - Chicago$159

                      Swissotel - Chicago$159
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                      *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.