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Lowest round trip fares by airline from Dallas and Chicago

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

Cheap flights from Dallas to Chicago

Cheap flights from Dallas to Chicago

If you’ll be arriving at Chicago O’Hare International Airport (ORD) from Dallas Fort Worth Airport (DFW), then upon your arrival, you’ll be a mere 20 minutes from downtown Chicago. After a short drive, you can see the Western Hemisphere’s tallest building, the Willis Tower, eat Chicago-style pizza at Lou Malnati’s Pizzeria, or take an architectural boat tour on Lake Michigan.

Key Facts

Chicago’s street design is visitor-friendly, so you’ll find it’s a convenient option to rent a car once you arrive. The city features several diagonal roadways, such as Lincoln Avenue, Milwaukee Avenue and Clark Street, which make traversing the city even easier. If you want to take the scenic route, search for Lake Shore Drive on your car’s GPS system. The roadway will allow you to drive the length of the city while remaining close to the lake.

Hints and Tips

The flight time from Dallas to Chicago is one hour and 48 minutes. Consider reserving your car rental at the airport since it's the most convenient pick-up spot. Budget in parking fees for your visit to Chicago. If you park on the street, then set a timer because you can only park on the city’s streets for two hours.

Once you have your rental car, you can use it to tour nearby places of interest like Amish Country, and the historical town of Galena.

Packages from Dallas to Chicago

Hotels in Chicago

See all 1,635 Properties in Chicago

Estimated price for 1 night/2 adults

Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue, Chicago, IL
    3.5 out of 5.0
     
     
    3.8 out of 5 (20 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$109

    Aug 18 - Aug 19

    Congress Plaza Hotel$109
    Hyatt Regency Chicago

    Hyatt Regency Chicago

    151 East Wacker Dr, Chicago, IL
      4.0 out of 5.0
       
       
      4.2 out of 5 (89 reviews)

      Located in The Loop, this eco-friendly hotel is steps from Chicago Riverwalk and Michigan Avenue Bridge. Chicago Theatre and Millennium Park are also within ...

      Hyatt Regency Chicago$199

      Jul 21 - Jul 22

      Hyatt Regency Chicago$199
      Travelodge by Wyndham Downtown Chicago

      Travelodge by Wyndham Downtown Chicago

      65 E Harrison St, Chicago, IL
        2.0 out of 5.0
         
         
        3.0 out of 5 (39 reviews)

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

        Travelodge by Wyndham Downtown Chicago$95

        Jul 28 - Jul 29

        Travelodge by Wyndham Downtown Chicago$95
        Hotel Essex Chicago

        Hotel Essex Chicago

        800 S Michigan Ave, Chicago, IL
          4.0 out of 5.0
           
           
          4.0 out of 5 (1 reviews)

          Located in The Loop, this hotel is within a 5-minute walk of Lakefront Trail, State Street, and Columbia College Chicago. Grant Park and Buckingham Fountain ...

          Hotel Essex Chicago$113

          Aug 11 - Aug 12

          Hotel Essex Chicago$113
          Central Loop Hotel

          Central Loop Hotel

          111 West Adams Street, Chicago, IL
            4.0 out of 5.0
             
             
            4.2 out of 5 (47 reviews)

            Located in The Loop, this boutique hotel is within a 5-minute walk of Chicago Board of Trade Building and State Street. Willis Tower and Skydeck Ledge are also ...

            Central Loop Hotel$116

            Jul 28 - Jul 29

            Central Loop Hotel$116
            Warwick Allerton - Chicago

            Warwick Allerton - Chicago

            701 North Michigan Avenue, Chicago, IL
              4.0 out of 5.0
               
               
              3.9 out of 5 (115 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$112

              Jul 21 - Jul 22

              Warwick Allerton - Chicago$112
              Kinzie Hotel

              Kinzie Hotel

              20 W Kinzie St, Chicago, IL
                4.0 out of 5.0
                 
                 
                4.5 out of 5 (59 reviews)

                Located in River North, this hotel is steps from House of Blues Chicago and State Street. Tribune Tower and Wrigley Building are also within 10 minutes. Grand ...

                Kinzie Hotel$138

                Aug 11 - Aug 12

                Kinzie Hotel$138
                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 Navy Pier, Millennium Park, and Art Institute of Chicago. Cloud Gate and Grant Park are also ...

                  The St. Clair Hotel – Magnificent Mile$130

                  Aug 18 - Aug 19

                  The St. Clair Hotel – Magnificent Mile$130
                  Hilton Chicago- Michigan Ave Cultural Mile

                  Hilton Chicago- Michigan Ave Cultural Mile

                  720 S Michigan Ave, Chicago, IL
                    4.0 out of 5.0
                     
                     
                    4.3 out of 5 (26 reviews)

                    Located in The Loop, this historic hotel is within a 5-minute walk of Columbia College Chicago and Grant Park. Art Institute of Chicago and Millennium Park are ...

                    Hilton Chicago- Michigan Ave Cultural Mile$162

                    Jul 25 - Jul 26

                    Hilton Chicago- Michigan Ave Cultural Mile$162
                    The Whitehall Hotel

                    The Whitehall Hotel

                    105 E Delaware Pl, Chicago, IL
                      4.0 out of 5.0
                       
                       
                      3.8 out of 5 (141 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$119

                      Jul 28 - Jul 29

                      The Whitehall Hotel$119
                      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.