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Lowest round trip fares by airline from Washington and Chicago

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

Cheap flights from Washington to Chicago

Cheap flights from Washington DC to Chicago

Washington Dulles International Airport (IAD) is located about 26 miles outside of Washington, D.C. in Chantilly, Virginia. The airport has its own 16-mile access freeway, which can be reached from I-95 and I-66. Public transit services also have routes stopping at IAD.

Flights from IAD to Chicago O’Hare International Airport (ORD) take two hours with no stops. ORD is accessible to the Metra, the “L” train and suburban bus services. O’Hare is located northwest of Chicago between I-294 and I-90, which both connect to the city.

Attractions and tips

Chicago is a huge city, offering professional baseball, Grant Park, the Museum of Contemporary Art and more. Visitors must try the city’s pizza at the top places like Marie’s, Vito & Nick’s, or Coalfire.

The Lincoln Park Zoo is great for families and those seeking outdoor fun. Visitors must stop by Millennium Park to see the famed Bean, a giant mirrored bean sculpture that was the most popular tourist attraction in the entire city of Chicago 2007.

Chicago is known as the Windy City, so a jacket might be nice unless it’s summer. The city’s climate varies significantly, so it is best to check the weather before your trip. Visitors to Chicago can stay in the many upscale Airport Hotels or downtown.

Packages from Washington to Chicago

Hotels in Chicago

See all 1,649 Properties in Chicago

Estimated price for 1 night/2 adults

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$99

    Jun 30 - Jul 1

    Hotel Essex Chicago$99
    Congress Plaza Hotel

    Congress Plaza Hotel

    520 South Michigan Avenue, Chicago, IL
      3.5 out of 5.0
       
       
      3.9 out of 5 (17 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$89

      Jul 1 - Jul 2

      Congress Plaza Hotel$89
      Hyatt Regency Chicago

      Hyatt Regency Chicago

      151 East Wacker Dr, Chicago, IL
        4.0 out of 5.0
         
         
        4.2 out of 5 (88 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$108

        Jul 3 - Jul 4

        Hyatt Regency Chicago$108
        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$76

          Jul 1 - Jul 2

          Central Loop Hotel$76
          Travelodge by Wyndham Downtown Chicago

          Travelodge by Wyndham Downtown Chicago

          65 E Harrison St, Chicago, IL
            2.0 out of 5.0
             
             
            2.9 out of 5 (38 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 3 - Jul 4

            Travelodge by Wyndham Downtown Chicago$95
            Hyatt Regency McCormick Place

            Hyatt Regency McCormick Place

            2233 S Martin Luther King Dr, Chicago, IL
              4.0 out of 5.0
               
               
              3.6 out of 5 (21 reviews)

              Located in South Loop, this eco-friendly hotel is within a 5-minute walk of McCormick Place and Wintrust Arena. Lakefront Trail and Soldier Field are also within ...

              Hyatt Regency McCormick Place$108

              Jul 3 - Jul 4

              Hyatt Regency McCormick Place$108
              The Whitehall Hotel

              The Whitehall Hotel

              105 E Delaware Pl, Chicago, IL
                4.0 out of 5.0
                 
                 
                3.8 out of 5 (140 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$84

                Jun 30 - Jul 1

                The Whitehall Hotel$84
                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 (52 reviews)

                  Located in The Loop, this spa hotel is within a 5-minute walk of State Street, Art Institute of Chicago, and Millennium Park. Chicago Cultural Center and Ford ...

                  Palmer House a Hilton Hotel$110

                  Jul 3 - Jul 4

                  Palmer House a Hilton Hotel$110
                  Hilton Chicago- Michigan Ave Cultural Mile

                  Hilton Chicago- Michigan Ave Cultural Mile

                  720 S Michigan Ave, Chicago, IL
                    4.0 out of 5.0
                     
                     
                    4.5 out of 5 (24 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$106

                    Jul 3 - Jul 4

                    Hilton Chicago- Michigan Ave Cultural Mile$106
                    River Hotel

                    River Hotel

                    75 East Wacker Drive, Chicago, IL
                      4.0 out of 5.0
                       
                       
                      4.2 out of 5 (39 reviews)

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

                      River Hotel$80

                      Jul 1 - Jul 2

                      River Hotel$80
                      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.

                      Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other CheapTickets users over the past 7 days. Due to rapidly changing airline prices & seat availability, these fares may no longer be available.

                      Refunds/changes/cancellations: Itinerary changes, if permitted for the fare, will have a $75 service fee charged by CheapTickets.

                      Other conditions: Schedules, fares and rules are subject to change without notice. Seats are limited and may not be available on all flights/dates or in all markets. Lower fares may be available. Fares will not be honored retroactively or in exchange for any wholly/partially unused ticket. Tickets are non-transferable and non-refundable. Fare rules are provided for the selected itinerary before booking.