Cheap Alaska Airlines flights Portland (PDX) to Chicago (ORD)

Use the “Price (lowest to highest)” filter on Expedia to search for cheap Alaska Airlines round-trip flights from PDX to ORD. Affordable one-way tickets are also on offer.**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.

January is one of the cheapest months to get away to Chicago with Alaska Airlines. You could also find great prices on return and one-way fares in February.

To find cheap Alaska Airlines fares from Portland Intl. Airport (PDX) to O’Hare Intl. Airport (ORD), start searching one to three months before your intended departure. Securing domestic flights 34 to 86 days in advance could save you 25% compared to booking just 6 to 12 days ahead. The day you book can also influence what you pay. Sunday tends to be the most affordable, while Monday is often the most expensive for domestic flights. You can save 6% on average by booking your flight on a Sunday.**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.

Alaska Airlines has direct flights from Portland Intl. Airport (PDX) to O’Hare Intl. Airport (ORD), with 5 weekly departures. Simply choose the “Nonstop” and “Airline” filters during your search on Expedia to show all direct Alaska Airlines flights to ORD.

From takeoff to arrival, a direct Alaska Airlines flight from Portland Intl. Airport (PDX) to O’Hare Intl. Airport (ORD) takes approximately 4h 7m.

The earliest Alaska Airlines flight from PDX to ORD departs at 7:00AM UTC-8, landing at 1:07PM UTC-6. If you’d like to jet off later in the day, the last Alaska Airlines flight leaves PDX at 7:00AM UTC-8 and lands at ORD at 1:07PM UTC-6. Flying before noon is often a wise choice as morning flights are least likely to face cancellations.**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.

O’Hare Intl. Airport (ORD) is the main gateway for Alaska Airlines flights from Portland Intl. Airport (PDX) to Chicago. But this carrier also flies to Midway Intl. Airport (MDW). Be sure to check the “All Airports” option for your destination to see exactly what’s available for your break in Chicago.

Alaska Airlines makes flying from PDX to ORD more enjoyable with a rewarding loyalty program and top-tier customer service. You could even start earning points with Mileage Plan. Be sure to join our free One Key™ rewards program to earn OneKeyCash™*, which can be redeemed on future trips.*OneKeyCash™ disclaimer - OneKeyCash™ is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.

For the Portland Intl. Airport (PDX) to O’Hare Intl. Airport (ORD) route, Alaska Airlines typically flies Boeing 737-900 and Boeing 737 MAX 9 planes. Keep in mind that last-minute changes are possible for operational demands, meaning your flight may be on a different aircraft.

You can usually change or cancel your flight, although there may be a charge if you made your booking more than 24 hours ago. Prefer to keep your options open? Make use of our “No cancel fee” and “Changes included” filters to find flights that won’t charge you extra if you need to alter your plans. To make changes, go to “Trips,” select your flight and click on “Manage Booking” for further information.