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

You’ll discover affordable round-trip American Airlines flights from $321 from SJU to ORD by organizing your results from “Price (lowest to highest)” on Expedia. Or look for bargains from $161 for a one-way journey.**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.

January is one of the most affordable months to travel to Chicago with American Airlines. You could also find great prices on one-way and round-trip tickets in February.

Check for American Airlines flights from SJU to ORD about one month before you want to leave. The cheapest time to reserve an international flight is usually 18 to 29 days ahead of your departure 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 can be the most expensive. Passengers 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.

American Airlines has direct flights from Luis Munoz Marin Intl. Airport (SJU) to O’Hare Intl. Airport (ORD), with 7 weekly departures. Simply apply the “Nonstop” and “Airline” filters while searching on Expedia to see all direct American Airlines flights to ORD.

From wheels-up to touchdown, a direct American Airlines flight from Luis Munoz Marin Intl. Airport (SJU) to O’Hare Intl. Airport (ORD) takes around 5h 30m.

The earliest flight from SJU to ORD with American Airlines departs at 3:36PM UTC-4. You’ll land at 7:06PM UTC-6. The last American Airlines flight of the day takes off at 3:36PM UTC-4 and arrives at 7:06PM UTC-6. With around 20% fewer cancellations for departures before midday, beginning your travel day early is generally the wisest option.**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.

Many American Airlines flights from Luis Munoz Marin Intl. Airport (SJU) to Chicago arrive at O’Hare Intl. Airport (ORD). This is the airline’s main entry point here. It’s worth exploring Expedia for flights to nearby airports like Midway Intl. Airport (MDW), as fares may be cheaper.

Set off on an American Airlines flight from Luis Munoz Marin Intl. Airport (SJU) to O’Hare Intl. Airport (ORD), and you’ll likely be flying on a Boeing 737-800. Bear in mind though, that the aircraft type can change due to operational requirements.

Changes are generally free within 24 hours of making your booking, but your airline may charge you after that. For further information about altering your flights, go to your “Trips,” select your flight and click on “Manage Booking.” If you’d like the freedom to change your plans without additional costs, apply the “Changes included” or “No cancel fee” filter when planning your next getaway.