$145 Cheap JetBlue Airways flights San Juan (SJU) to Chicago (ORD)

Scoring cheap one-way JetBlue Airways flights from SJU to ORD from $145 on Expedia is a cinch — just filter by "Price (lowest to highest)." Or check out our budget-friendly round-trip fares from $284 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.

Getting the best JetBlue Airways deals from SJU to ORD often comes down to booking at the right moment. You can save 17% on international flights when you book 18 to 29 days before takeoff instead of four to five months ahead. As an added bonus, you can pocket 17% on average by buying your fare on a Sunday compared to a Friday, which is usually the most expensive day to book.* It's a good idea to start checking out flights about one month before you want to travel.*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.

Find JetBlue Airways's earliest flights from SJU to ORD by checking the "Morning" and "Early Morning" filters. Not only will you get to where you're going sooner, early departures also experience 20% 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.