$161 Cheap American Airlines flights Chicago (ORD) to San Juan (SJU)

Apply the “Price (lowest to highest)” filter on Expedia to search for cheap American Airlines return flights from $321 from ORD to SJU. Affordable one-way options from $161 are also available.**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.

Browse for round-trip or one-way flights to San Juan in October or September. You could find cheaper fares with American Airlines during these quieter months.

Start your search for American Airlines flights from ORD to SJU about one month before you want to leave. The most affordable time to reserve an international flight is usually 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 fare class, the best day to book international airfare is usually Sunday. Friday is often the most expensive. Travelers who book 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.

You can easily fly from O’Hare Intl. Airport (ORD) to Luis Munoz Marin Intl. Airport (SJU) on any of American Airlines’s 7 weekly direct flights. Make use of our “Nonstop” and “Airline” filters to find the American Airlines flight that’ll land at SJU at your preferred time.

It takes around 4h 35m to fly nonstop from O’Hare Intl. Airport (ORD) to Luis Munoz Marin Intl. Airport (SJU) with American Airlines.

The first American Airlines flight from ORD to SJU takes off at 8:10AM UTC-6, arriving at 2:45PM UTC-4. If you want to set off later in the day, the last American Airlines flight leaves ORD at 8:10AM UTC-6 and lands at SJU at 2:45PM UTC-4. Flying earlier is often a good option as morning and mid-morning flights are 20% less likely to be 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.

Take an American Airlines flight from O’Hare Intl. Airport (ORD) to San Juan, and you’ll most likely arrive at Luis Munoz Marin Intl. Airport (SJU). This is the airline’s primary hub in this destination.

Chances are you’ll board a Boeing 737-800 for your American Airlines flight from O’Hare Intl. Airport (ORD) to Luis Munoz Marin Intl. Airport (SJU). However, you could be switched to a different aircraft if there are operational changes.

Changes are typically free within 24 hours of booking, but your airline may charge you after that. For further information about modifying your reservation, check out your “Trips,” select your flight and click on “Manage Booking.” If you want the flexibility to adjust your plans without extra charges, apply the “Changes included” and “No cancel fee” filters when planning your trip.