Skip to main content
Beginning of main content

ORD (Chicago) to SJU (San Juan) Flights $275.77

Search over 321,000 hotels worldwide and 400 airlines worldwide.
Secure incredible value with Expedia's Price Guarantee.
No Expedia cancellation fee to change or cancel almost any hotel reservation.

Cheap ORD to SJU Flights

Prices found within past 7 days. Prices and availability subject to change. Additional terms may apply.

Interesting Facts About Flights from Chicago to San Juan (ORD to SJU)

Question : If traveling from ORD to SJU, how long can you expect to be in the air?
Answer : When flying from ORD to SJU, it will take four hours and 29 minutes on average.

Question : Who struggles with getting their passengers to Luis Munoz Marin International Airport (SJU) on time?
Answer : If you're flying United Airlines to San Juan from Chicago, you may be tardy as they're late 18% of the time. If you should choose this airline, be sure to track the flight status to stay on top of the departure time.

Question : Do travelers from Chicago typically stay in San Juan for very long?
Answer : Passengers from ORD to SJU stay seven days on average.

Question : How much should a trip from Chicago (ORD) to San Juan (SJU) cost?
Answer : Ranging from $293 to $1,594, prices for ORD to SJU fluctuate less than the majority of routes from the United States. Remember, the sooner you book, the more you'll be able to save.

Question : If your plans are flexible, have you considered changing your departure day?
Answer : The cheapest day to fly in August is Monday. Flexibility is paramount when booking travel plans in order to keep travel costs down.

Question : Who's offering the cheapest round-trip flight to Luis Munoz Marin International Airport (SJU) over the coming months?
Answer : JetBlue Airways is your best bet for finding that coveted low fare. They're offering fares as low as $293, while prices for other flights are as high as $1,594.

Question : In terms of overall promptness, how does ORD to SJU rank compared to the rest of the world?
Answer : The best measurement of overall promptness combines both on-time percentage and total delay minutes. ORD to SJU currently has 4 stars out of 5, earning it one of the best performances in the world. You can fly worry-free on this route.