$101 Cheap American Airlines flights Chicago (ORD) to Portland (PDX)

Finding cheap one-way American Airlines flights from ORD to PDX from $101 on Expedia is a breeze — just filter by “Price (lowest to highest).” Alternatively, check out our affordable return fares from $179 for your next exciting getaway.**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 most affordable months to travel to Portland with American Airlines. You could also find great deals on return and one-way tickets in December.

For cheap American Airlines fares from O’Hare Intl. Airport (ORD) to Portland Intl. Airport (PDX), 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 affect the overall cost. Sunday tends to be the most affordable, while Monday is often the most expensive for domestic flights. You can save 6% on average by choosing to book 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.

To see if there’s a direct journey from ORD to PDX with American Airlines or other carriers, check the “Nonstop” filter when browsing for flights.

To find the earliest departure from ORD to PDX with American Airlines, filter your results by “Early Morning” and “Morning.” Booking an early flight generally means cancellations are less likely.**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 main Portland gateway for American Airlines flights from O’Hare Intl. Airport (ORD).

In most cases, you can modify or cancel your flight, although additional charges may apply if you made your booking more than 24 hours ago. Prefer to keep your options open? Apply the “No cancel fee” and “Changes included” filters to find flights that won’t charge you extra if you need to alter your plans. To modify your booking, visit “Trips,” select your flight and click on “Manage Booking” for more details.