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Flights from Portland to Chicago

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

Plan Your Trip from Portland to Chicago

Portland International Airport

Flights from Portland depart from the Portland International Airport, located at 7000 NE Airport Way. The airport is approximately 22 miles south of downtown Portland and is serviced by 13 airlines, including Delta, Air Canada, Frontier and United. Orbitz.com makes it easy to book domestic and international flights from Portland. You don't have to scour the Internet to find cheap airline tickets. Orbitz.com searches all of the flights available to get you a ticket with a low fare.

Parking and Transportation

The Portland International Airport offers long-term parking for $19 per day. If you plan to leave your car at the airport for more than 90 days, you need to make prior arrangements with the airport's parking office. You can take a taxi from downtown Portland to the airport for approximately $32, so if you plan to leave your vehicle for more than two days, taking a taxi to the airport is a cheaper option. Streetcars also run from the downtown area to the airport, and streetcar tickets cost $2.40. If you need transportation when you arrive at your destination, Orbitz.com can reserve a rental car for you.

Dining at the Airport

If you want to grab a quick meal before your flight, the Portland International Airport has a variety of restaurant choices. You can stop in Starbucks or Coffee People for a quick snack. If you want a meal, you can eat at Wendy's, Sandoval's or Pizza Schmizza. Orbitz.com does more than book flights from Portland. The website has all of the tools you need to make sure your trip goes smoothly, giving you plenty of time to eat before your flight.

Airports in Chicago

Chicago O'Hare International Airport is located on West O'Hare, approximately 18 miles from downtown Chicago. It has hubs for every major airline that offers flights to Chicago, including American Airlines, British Airways and JetBlue. The Chicago Midway International Airport is located on South Cicero Avenue, approximately 12 miles from downtown Chicago. Seven airlines service Midway airport, including Air Tran, Delta and Southwest Airlines. Orbitz.com searches flights arriving at both airports so you get the best prices.

Transportation from the Airport

Both airports offer public transportation via Chicago's elevated train system. The tickets cost $2.25, or you can purchase an all-day pass for $5.75. Taxi services are also available from both airports. Cab fares to downtown Chicago range from $35 to $45. If you want to rent a car for the duration of your stay, Orbitz.com can reserve a vehicle for you. Both airports have onsite rental car facilities.

Weather in Chicago

Summer temperatures in Chicago range from 66 to 84 degrees Fahrenheit, and the temperatures during the winter months range from 18 to 35 degrees Fahrenheit. Chicago is prone to heavy snowfall during the winter months, so most vacationers travel to Chicago during the summer. However, if you use Orbitz.com and schedule your trip during the off-peak travel season, it's easy to find cheap flights to Chicago.

Highlights and Attractions

Orbitz.com not only helps you find cheap flights to Chicago, but can also help you purchase tickets to the Sears Tower or make reservations for guided city tours.

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Fare, taxes & fees: Fares include all taxes and fees, except baggage fees. Rates shown reflect fares found by other Orbitz 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 $30 service fee charged by Orbitz. Additional airline charges may apply.

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.