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

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

To find cheap JetBlue Airways fares from Portland Intl. Jetport Airport (PWM) to O'Hare Intl. Airport (ORD), start searching one to three months before your planned departure. Securing 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 affect the price you pay. Sunday is generally the most affordable, while Monday is often the most expensive for domestic flights. You can save 6% on average by booking your trip 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.

Sort your results by "Morning" and "Early Morning" to find the earliest flights from PWM to ORD. Heading off early means you're 20% 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.