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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.

Choose the best New York - Chicago flight for the price, thanks to our customer reviews

Oct 4, 2018

Crew was helpful with my awkward-shaped carry on of some antique art.

Sep 10, 2018

The captain was engaging and had a great personality while on this flight. It was smooth sailing.

Jul 27, 2018

Keep up the good work.

Jul 26, 2018

Pilot on 377 was great

Jun 24, 2018

WiFi did not work!

Jun 15, 2018

please don’t charge for baggage ~ we all need to bring clothes, etc ~ Airpines around the world have cleaner planes & modern facilities. Please upgrade the planes Flight was smooth & safe Thank you

Jun 8, 2018

Don’t like basic economy because I couldn’t choose my seat.

May 19, 2018

Broken seat caused delay. Loved the duct tape repair.

May 12, 2018

The woman who helped us at self check-in was extremely helpful and got our bags on after we were delayed in horrible traffic at LaGuardia due to construction there.

Apr 30, 2018

After recent negative publicity about United Airlines, I was nervous but didn't have any problem

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.

Packages from New York to Chicago

Hotels in Chicago

See all 1,384 Properties in Chicago
Congress Plaza Hotel

Congress Plaza Hotel

520 South Michigan Avenue, Chicago
    3.5 out of 5.0
     
     
    4.0 out of 5 (11 reviews)

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

    Congress Plaza Hotel$79

    Congress Plaza Hotel$79
    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$92

      Palmer House a Hilton Hotel$92
      Freehand Chicago

      Freehand Chicago

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

        Located in River North, this hotel is within a 10-minute walk of Chinese Consulate, Holy Name Cathedral, and Northwestern Memorial Hospital. Museum of Contemporary ...

        Freehand Chicago$69

        Freehand Chicago$69
        Comfort Inn Arlington Heights - O'Hare

        Comfort Inn Arlington Heights - O'Hare

        2120 S Arlington Heights Rd, Arlington Heights
          2.5 out of 5.0
           
           
          4.2 out of 5 (12 reviews)

          Situated near the airport, this hotel is within 1 mi (2 km) of Ned Brown Forest Preserve and Heritage Park. Arlington Lakes Golf Club and Metropolis Performing ...

          Comfort Inn Arlington Heights - O'Hare$64

          Comfort Inn Arlington Heights - O'Hare$64
          Warwick Allerton - Chicago

          Warwick Allerton - Chicago

          701 North Michigan Avenue, Chicago
            4.0 out of 5.0
             
             
            3.9 out of 5 (110 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$73

            Warwick Allerton - Chicago$73
            Hyatt Regency Chicago

            Hyatt Regency Chicago

            151 East Wacker Dr, Chicago
              4.0 out of 5.0
               
               
              4.2 out of 5 (79 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
              The Godfrey Hotel Chicago

              The Godfrey Hotel Chicago

              127 West Huron, at LaSalle, Chicago
                4.5 out of 5.0
                 
                 
                4.4 out of 5 (16 reviews)

                Located in River North, this luxury hotel is within a 15-minute walk of Magnificent Mile, John Hancock Center, and Chicago Water Tower. Merchandise Mart and ...

                The Godfrey Hotel Chicago$90

                The Godfrey Hotel Chicago$90
                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$134

                  Omni Chicago Suites - Magnificent Mile$134
                  Hilton Chicago O'Hare Airport

                  Hilton Chicago O'Hare Airport

                  Ohare International Airport, Chicago
                    4.0 out of 5.0
                     
                     
                    3.9 out of 5 (17 reviews)

                    The only hotel on airport property, the Hilton Chicago O'Hare Airport is located 2 miles from the Donald E. Stephens Convention Center and the Rosemont Theatre, ...

                    Hilton Chicago O'Hare Airport$101

                    Hilton Chicago O'Hare Airport$101
                    Edward Hotel Chicago

                    Edward Hotel Chicago

                    6600 N. Mannheim Rd, Rosemont
                      3.0 out of 5.0
                       
                       
                      3.9 out of 5 (22 reviews)

                      Situated near the airport, this spa hotel is 0.4 mi (0.6 km) from Allstate Arena and within 3 mi (5 km) of Rivers Casino and Donald E. Stephens Convention Center. ...

                      Edward Hotel Chicago$68

                      Edward Hotel 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.