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Lowest round trip fares by airline from Portland and Chicago

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

Cheap flights from Portland to Chicago

Cheap flights from Portland to Chicago

Whether traveling for a business meeting or vacation, as you arrive in Chicago from Portland, get ready to experience the day-and-night action of this busy city. Chicago's O'Hare International Airport is active 24 hours a day, so you'll want to have your rental car reserved and waiting for you. After you collect your luggage, you could stretch your legs at Woodfield Mall, or head over to the shores of Lake Michigan for a leisurely stroll.

Key Facts

Sports fans could pay a visit to the Wrigleyville if the Cubs are playing. You'll find plenty of Chicago-style hot dogs and pizza from street vendors to fill you up. From there, take one of the local streets east to connect to Lake Shore Drive. Drive south until you reach Museum Campus, which features attractions including the Field Museum of Natural History, the Shedd Aquarium and the Addler Planetarium.

Hints and Tips

Your trip from Portland International Airport (PDX) to O'Hare International Airport (ORD) should take about three hours. From ORD, it's a short drive to the downtown area where you can catch a game of the Bulls or Blackhawks. Afterward, visit the iconic Buckingham Fountain, which is located in Grant Park. There is plenty of space at the park to take a jog or have a picnic, between visiting Chicago's attractions.

Packages from Portland to Chicago

Hotels in Chicago

See all 1,732 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 (23 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$116

    Congress Plaza 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 (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$101

      Warwick Allerton - Chicago$101
      Millennium Knickerbocker Chicago

      Millennium Knickerbocker Chicago

      163 East Walton Place, Chicago, IL
        4.0 out of 5.0
         
         
        4.2 out of 5 (34 reviews)

        Located in Near North Side, this hotel is within a 10-minute walk of John Hancock Center and Museum of Contemporary Art. Navy Pier and Millennium Park are also ...

        Millennium Knickerbocker Chicago$95

        Millennium Knickerbocker Chicago$95
        Hotel Essex Chicago

        Hotel Essex Chicago

        800 S Michigan Ave, Chicago, IL
          4.0 out of 5.0
           
           
          3.8 out of 5 (4 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$86

          Hotel Essex Chicago$86
          The Whitehall Hotel

          The Whitehall Hotel

          105 E Delaware Pl, Chicago, IL
            4.0 out of 5.0
             
             
            3.8 out of 5 (142 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$94

            The Whitehall Hotel$94
            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

              Travelodge by Wyndham Downtown Chicago$95
              Palmer House a Hilton Hotel

              Palmer House a Hilton Hotel

              17 E Monroe St, Chicago, IL
                4.0 out of 5.0
                 
                 
                3.9 out of 5 (53 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$139

                Palmer House a Hilton Hotel$139
                Hilton Chicago O'Hare Airport

                Hilton Chicago O'Hare Airport

                Ohare International Airport, Chicago, IL
                  4.0 out of 5.0
                   
                   
                  4.0 out of 5 (20 reviews)

                  Located in O'Hare, this hotel is within 6 mi (10 km) of Fashion Outlets of Chicago, Donald E. Stephens Convention Center, and Rosemont Theatre. Allstate Arena ...

                  Hilton Chicago O'Hare Airport$110

                  Hilton Chicago O'Hare Airport$110
                  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$103

                    Kinzie Hotel$103
                    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$127

                      Hyatt Regency Chicago$127
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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.