$102 Cheap JetBlue Airways flights Chicago (ORD) to Portland (PWM)

You'll discover affordable return JetBlue Airways flights from $183 from ORD to PWM by sorting your results from "Price (lowest to highest)" on Expedia. Or search for bargains from $102 for a one-way trip.**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.

Begin your search one to three months ahead of your departure date to score cheap fares on JetBlue Airways flights from O'Hare Intl. Airport (ORD) to Portland Intl. Jetport Airport (PWM). You can save 25% by booking your domestic flight 34 to 86 days in advance versus last-minute reservations made 6 to 12 days out. You could also reduce costs by buying your fare on a Sunday, as it's 6% cheaper on average than a Monday, the most expensive day to book.* Get your timing right, and you can enjoy significant savings on domestic flights.*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 departure from ORD to PWM with JetBlue Airways, sort your results by "Early Morning" and "Morning." Booking an early flight generally 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.