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

Apply the "Price (lowest to highest)" filter on Expedia to look for cheap American Airlines round-trip flights from $199 from ORD to PWM. Affordable one-way options from $100 are available too.**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.

For cheap American Airlines fares from O'Hare Intl. Airport (ORD) to Portland Intl. Jetport Airport (PWM), start searching one to three months before your planned departure. Reserving 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 the overall price. Sunday is typically the cheapest, while Monday is often the most expensive for domestic flights. You can save 6% on average by booking your journey 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 find the earliest departures from ORD to PWM with American Airlines, sort your results by "Morning" and "Early Morning." Booking an early flight usually means you'll experience fewer 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.