$142 Cheap American Airlines flights Key West (EYW) to Portland (PWM)

Finding cheap one-way American Airlines flights from EYW to PWM from $142 on Expedia is a breeze — just filter by "Price (lowest to highest)." Or check out our affordable return fares from $269 for your next exciting vacation.**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.

Look for affordable American Airlines flights from Key West Intl. Airport (EYW) to Portland Intl. Jetport Airport (PWM) one to three months prior to your day of 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 itinerary, 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 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.

Search American Airlines's earliest flights from EYW to PWM by using our "Morning" and "Early Morning" filters. Not only will you get to your destination sooner, early departures also have a 20% less chance of being canceled.**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.