$164 Cheap Delta flights Chicago (ORD) to San Juan (SJU)

Finding cheap one-way Delta Air Lines flights from ORD to SJU from $164 on Expedia couldn't be easier --- just filter by "Price (lowest to highest)." Or check out our affordable return fares from $327 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.

Look for Delta Air Lines flights from ORD to SJU about one month before you want to leave. The most affordable time to book an international flight is generally 18 to 29 days ahead of your travel date when you can save 17% versus booking four to five months in advance. Regardless of itinerary or ticket type, the best day to book international airfare is usually Sunday. Friday is often the most expensive. Passengers booking on a Sunday can save an average of 17% compared to those who book on a Friday.**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.

Browse Delta Air Lines's earliest flights from ORD to SJU by checking the "Early Morning" and "Morning" filters. Not only will you get to your destination sooner, early departures also have a 20% less chance of being canceled.**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.

Heading from ORD to SJU with Delta Air Lines comes with a host of benefits, including a rewarding loyalty program and an excellent in-flight experience. Plus, when you book through Expedia, One Key™ members can collect OneKeyCash™* to redeem on select future travel purchases. That's on top of the Delta SkyMiles points you can earn with Delta Air Lines.*OneKeyCash™ disclaimer - OneKeyCash™ is not redeemable for cash and can only be used on Expedia, Hotels.com and Vrbo.