$100 Cheap American Airlines flights Portland (PWM) to Chicago (ORD)

Landing cheap one-way American Airlines flights from PWM to ORD from $100 on Expedia is easy — just filter by "Price (lowest to highest)." Alternatively, check out our affordable return fares from $199 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.

Search for affordable American Airlines flights from Portland Intl. Jetport Airport (PWM) to O'Hare Intl. Airport (ORD) one to three months ahead of your departure. 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. No matter the fare type and journey, the best day to book a domestic flight is usually Sunday and the most expensive 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 find the earliest departures from PWM to ORD with American Airlines, filter your search by "Morning" and "Early 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.