$116 Cheap JetBlue Airways flights Fort Myers (RSW) to Chicago (ORD)

Scoring cheap one-way JetBlue Airways flights from RSW to ORD from $116 on Expedia is a breeze --- just filter by "Price (lowest to highest)." Or check out our affordable round-trip fares from $211 for your next adventure.**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 Southwest Florida Intl. Airport (RSW) 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.* Nail your timing, and you can enjoy significant savings on domestic trips.*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 browse the earliest departures from RSW to ORD. Jetting off early means flight cancellations are less likely.**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.