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Lowest round trip fares by airline from New York and Chicago

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

Cheap flights from New York to Chicago

Cheap flights from New York to Chicago

If you are a sports fan traveling from John F. Kennedy International Airport (JFK) to O'Hare International Airport (ORD), you are not going to be disappointed upon arrival. Rooting for the White Sox, Cubs or Bulls is fun in itself, and the Cubs home turf, Wrigley Field, has become a national landmark. If you love architecture, you will be dazzled as you see some of the country’s most iconic buildings, like the Civic Opera Building, or the Tribune Tower.

Key Facts

Chicago Transit Authority trains make traveling to and from the airport and around the city, quick and inexpensive. You can take the train from the Blue Line station, located at the airport, directly into the heart of Chicago.

While traveling around Chicago, either by rental car or on the train, you will not want to miss visiting Navy Pier where you can enjoy a ride on the famous Ferris wheel, while admiring Lake Michigan and the city skyline. To reach Lake Michigan and the museum district from O'Hare, hop on I-90, also known as the Kennedy Expressway.

Hints and Tips

After a three hour flight from New York to Chicago, stretch your legs by walking around the Chicago Cultural Center. The massive building takes up an entire city block, stretching from Washington to Randolph Streets, and from Michigan Avenue to Garland Court.

Hotels in Chicago

See all 1,472 Properties in Chicago
Palmer House a Hilton Hotel

Palmer House a Hilton Hotel

17 E Monroe St, Chicago
    4.0 out of 5.0
     
     
    3.9 out of 5 (51 reviews)

    This 1925 Beaux Arts-style Chicago hotel is steps from Millennium Park, 2 blocks from Macy's and the Art Institute, and 1 mile from Lake Michigan, Magnificent ...

    Palmer House a Hilton Hotel$95

    Palmer House a Hilton Hotel$95
    Hyatt Regency Chicago

    Hyatt Regency Chicago

    151 East Wacker Dr, Chicago
      4.0 out of 5.0
       
       
      4.2 out of 5 (80 reviews)

      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$119

      Hyatt Regency Chicago$119
      Embassy Suites Chicago Downtown Magnificent Mile

      Embassy Suites Chicago Downtown Magnificent Mile

      511 North Columbus Drive, Chicago
        4.0 out of 5.0
         
         
        4.3 out of 5 (34 reviews)

        The Embassy Suites Chicago Downtown Magnificent Mile offers a newly renovated fresh look and is located two blocks from Navy Pier, Magnificent Mile shopping, ...

        Embassy Suites Chicago Downtown Magnificent Mile$98

        Embassy Suites Chicago Downtown Magnificent Mile$98
        Freehand Chicago

        Freehand Chicago

        19 East Ohio Street, Chicago
          3.5 out of 5.0
           
           
          4.2 out of 5 (11 reviews)

          Located in River North, this hotel is within 6 mi (10 km) of Chinese Consulate, Holy Name Cathedral, and Museum of Contemporary Art. Water Tower Place and Ann ...

          Freehand Chicago$69

          Freehand Chicago$69
          The St. Clair Hotel – Magnificent Mile

          The St. Clair Hotel – Magnificent Mile

          162 East Ontario Street, Chicago
            2.5 out of 5.0
             
             
            5.0 out of 5 (1 reviews)

            The hotel is a half-block from the Magnificent Mile and an 8-minute walk from Grand/State Metro Station. Many attractions are within a 15-minute walk, including ...

            The St. Clair Hotel – Magnificent Mile$65

            The St. Clair Hotel – Magnificent Mile$65
            Congress Plaza Hotel

            Congress Plaza Hotel

            520 South Michigan Avenue, Chicago
              3.5 out of 5.0
               
               
              4.0 out of 5 (12 reviews)

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

              Congress Plaza Hotel$71

              Congress Plaza Hotel$71
              Hyatt Centric Chicago Magnificent Mile

              Hyatt Centric Chicago Magnificent Mile

              633 N Saint Clair St, Chicago
                4.0 out of 5.0
                 
                 
                4.1 out of 5 (32 reviews)

                This smoke-free 17-story hotel is 1 block from North Michigan Avenue's boutique and specialty stores, 3 blocks from Lake Michigan, 6 blocks from the State & ...

                Hyatt Centric Chicago Magnificent Mile$100

                Hyatt Centric Chicago Magnificent Mile$100
                River Hotel

                River Hotel

                75 East Wacker Drive, Chicago
                  4.0 out of 5.0
                   
                   
                  4.2 out of 5 (36 reviews)

                  Located in The Loop, this hotel is within a 5-minute walk of Chicago Riverwalk and Chicago Theatre. Michigan Avenue and House of Blues Chicago are also within ...

                  River Hotel$67

                  River Hotel$67
                  Omni Chicago Suites - Magnificent Mile

                  Omni Chicago Suites - Magnificent Mile

                  676 N Michigan Ave, Chicago
                    4.5 out of 5.0
                     
                     
                    5.0 out of 5 (2 reviews)

                    Omni Chicago Suites - Magnificent Mile is at the center of Chicago’s most prestigious neighborhood, 3 blocks from the shores of Lake Michigan and around the ...

                    Omni Chicago Suites - Magnificent Mile$144

                    Omni Chicago Suites - Magnificent Mile$144
                    Warwick Allerton - Chicago

                    Warwick Allerton - Chicago

                    701 North Michigan Avenue, Chicago
                      4.0 out of 5.0
                       
                       
                      3.9 out of 5 (111 reviews)

                      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$68

                      Warwick Allerton - Chicago$68
                      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.