Flights from Chicago to San Juan with American Airlines

Recent searches for flights from Chicago to San Juan

DisclaimerFares displayed have been collected within the last 24hrs and may no longer be available at time of booking. Modifying this information may result in a different fare. To find the most updated fare, please visit aa.com. Fares listed may be Basic Economy, which class is subject to additional terms and conditions. Additional baggage fees and charges for optional products and services may apply.

Popular flights with American Airlines

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*Fares displayed have been collected within the last 24hrs and may no longer be available at time of booking. Some fares listed may include one or more connections that are Basic Economy, which class is subject to additional terms and conditions. Modifying this information may result in a different fare. To find the most updated fare, please visit aa.com. Additional baggage fees and charges for optional products and services may apply.

Earn up to a $200 statement credit + 40,000 bonus miles. Plus, first checked bag is free on domestic American Airlines itineraries. Terms apply. Opens in a new browser. 

Flights from Chicago to San Juan with American Airlines

Find deals on Chicago to San Juan flights

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Chicago (ORD)to

San Juan (SJU)
01/25/26 - 03/10/26

Round trip

Economy

from
$362Fare subject to changes
Updated: 8 hours ago

Chicago (ORD)to

San Juan (SJU)
02/02/26 - 03/16/26

Round trip

Economy

from
$382Fare subject to changes
Updated: 8 hours ago

Chicago (ORD)to

San Juan (SJU)
04/22/26 - 04/27/26

Round trip

Economy

from
$382Fare subject to changes
Updated: 4 hours ago

Chicago (ORD)to

San Juan (SJU)
02/07/26 - 02/19/26

Round trip

Economy

from
$382Fare subject to changes
Updated: 23 hours ago

Chicago (ORD)to

San Juan (SJU)
02/15/26 - 04/01/26

Round trip

Economy

from
$382Fare subject to changes
Updated: 8 hours ago

Chicago (ORD)to

San Juan (SJU)
03/05/26 - 03/16/26

Round trip

Economy

from
$382Fare subject to changes
Updated: 7 hours ago

Chicago (ORD)to

San Juan (SJU)
03/04/26 - 03/18/26

Round trip

Economy

from
$382Fare subject to changes
Updated: 6 hours ago

Chicago (ORD)to

San Juan (SJU)
01/31/26 - 02/07/26

Round trip

Economy

from
$387Fare subject to changes
Updated: 2 hours ago

Chicago (ORD)to

San Juan (SJU)
01/26/26 - 03/09/26

Round trip

Economy

from
$409Fare subject to changes
Updated: 8 hours ago

Chicago (ORD)to

San Juan (SJU)
04/11/26 - 04/19/26

Round trip

Economy

from
$438Fare subject to changes
Updated: 6 minutes ago

*Fares displayed have been collected within the last 24hrs and may no longer be available at time of booking. Some fares listed may include one or more connections that are Basic Economy, which class is subject to additional terms and conditions. Modifying this information may result in a different fare. To find the most updated fare, please visit aa.com. Additional baggage fees and charges for optional products and services may apply.