$114 Cheap American Airlines flights Portland (PDX) to Chicago (ORD)

Landing cheap one-way American Airlines flights from PDX to ORD from $114 on Expedia is easy — just filter by “Price (lowest to highest).” Or check out our affordable return fares from $199 for your next exciting adventure.**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 jet away to Chicago with American Airlines. You could also find great prices on one-way and return tickets in February.

Search for cheap American Airlines flights from Portland Intl. Airport (PDX) to O’Hare Intl. Airport (ORD) one to three months ahead of your departure date. Travelers who book domestic flights 34 to 86 days in advance can save 25% compared to those who book just 6 to 12 days ahead. Regardless of fare class and journey, the best day of the week to book a domestic flight is generally Sunday and the most expensive day is typically Monday. Passengers who book on a Sunday can save 6% on average compared to those who book their travel on a Monday.**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 figure out if there’s a direct route from PDX to ORD with American Airlines or another carrier, check the “Nonstop” box when searching for flights.

To find the earliest departures from PDX to ORD with American Airlines, filter your search by “Early Morning” and “Morning.” Booking an early flight generally means you’re less likely to experience 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.

American Airlines flights from Portland Intl. Airport (PDX) to Chicago come in to land at O’Hare Intl. Airport (ORD). This is the main gateway here.

Depending on your ticket type, a fee will generally apply if you cancel or reschedule your flight more than 24 hours after it’s confirmed. To find flexible fares, select our “Changes included” and “No cancel fee” boxes while searching for flights. For more details on changing or canceling your reservation, head to “Trips,” select your flight and tick “Manage Booking.”