$90 Cheap United flights Chicago (ORD) to Portland (PDX)

Use the “Price (lowest to highest)” filter on Expedia to search for cheap United Airlines round-trip flights from $188 from ORD to PDX. Affordable one-way options from $90 are available as well.**These prices were available on Expedia within the past 7 days, for flights departing within the next year. Prices and availability are subject to change. Additional terms apply.

Look for return or one-way flights to Portland in January or December. You could find an affordable fare with United Airlines during these off-peak times.

Begin your search one to three months ahead of your departure date to get cheap fares on United Airlines flights from O’Hare Intl. Airport (ORD) to Portland Intl. Airport (PDX). You can save 25% by booking your domestic flight 34 to 86 days in advance compared to last-minute reservations made 6 to 12 days out. You could also cut costs by buying your fare on a Sunday, as it’s 6% cheaper on average than a Monday, the most expensive day to book.* Get the timing right, and you can enjoy significant savings on domestic trips.*Ideal booking window recommendation is based on average round-trip ticket prices for January through November for 2024. Best day of the week to book recommendation is based on average round-trip ticket prices for January through October 2024. All data sourced from ARC’s global airline sales database.

United Airlines offers direct flights from O’Hare Intl. Airport (ORD) to Portland Intl. Airport (PDX), with 17 weekly departures. Simply select the “Nonstop” and “Airline” filters while searching on Expedia to find all direct United Airlines flights to PDX.

Depart O’Hare Intl. Airport (ORD) for Portland Intl. Airport (PDX) on a direct United Airlines flight, and you’ll be in the skies for around 4h 42m.

Sunday has the most United Airlines flights from O’Hare Intl. Airport (ORD) to Portland Intl. Airport (PDX). With 3 daily departures, this is the best day of the week to find something that will suit your schedule.

The first flight from ORD to PDX with United Airlines departs at 8:56AM UTC-6. You’ll land at 11:39AM UTC-8. The final United Airlines flight of the day leaves at 8:15PM UTC-6 and arrives at 10:57PM UTC-8. With 20% fewer cancellations for morning departures, setting off early is generally the best way to go.**Most reliable time of the day recommendation is based on January through August 2024 flight status data sourced from OAG’s global flight data platform.

Portland Intl. Airport (PDX) is the primary Portland gateway for United Airlines flights from O’Hare Intl. Airport (ORD).

A rewarding loyalty program and the opportunity to collect points through United Mileage Plus are the start of the reasons to depart from ORD to PDX with United Airlines. Plus, when you sign up to Expedia’s free One Key™ program, you can receive OneKeyCash™* alongside United Airlines’s loyalty program earnings. It’s yours to spend on your next adventure.*OneKeyCash™ disclaimer - OneKeyCash™ is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.

United Airlines generally flies Boeing 737-900 planes for flights from O’Hare Intl. Airport (ORD) to Portland Intl. Airport (PDX). This airline also operates the Boeing 737-800 on this route. Keep in mind that aircraft type can change depending on operational needs, so the plane you board could be different when you leave.

Depending on the type of fare you purchased, a fee generally applies if you cancel or change your booking more than 24 hours after it has been confirmed. To find flexible fares, select our “Changes included” or “No cancel fee” filter while searching for flights. For more details on canceling or modifying your reservation, visit “Trips,” select your flight and click on “Manage Booking.”