$64 Cheap JetBlue Airways flights Boston (BOS) to Chicago (ORD)

Use the "Price (lowest to highest)" filter on Expedia to find cheap JetBlue Airways return flights from $127 from BOS to ORD. Affordable one-way options from $64 are also on offer.**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.

Start searching one to three months ahead of your travel date to get cheaper fares on JetBlue Airways flights from Logan Intl. Airport (BOS) to O'Hare Intl. Airport (ORD). 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 spot on, and you can enjoy significant savings on domestic journeys.*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.

The earliest JetBlue Airways flight from BOS to ORD takes off at 3:52PM UTC-5, landing at 5:55PM UTC-6. If you want to head off later in the day, the last JetBlue Airways flight leaves BOS at 3:52PM UTC-5 and touches down at ORD at 5:55PM UTC-6. Flying earlier is generally a wise choice as morning and mid-morning flights are 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.