Flights from Chicago to San Juan with American Airlines

Recent searches for flights from Chicago to San Juan

Apr 2025
From$387*
Updated: 17 hours ago
Round tripIEconomy
$387
$656
Displaying fares for April-2025
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range$387-$656

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

$

  • Chicago (ORD)to

    San Juan (SJU)
    05/10/25 - 05/17/25
    from
    $387*
    Updated: 23 hours ago
    Round trip
    I
    Economy

    Chicago (ORD)to

    San Juan (SJU)
    06/05/25 - 06/12/25
    from
    $387*
    Updated: 23 hours ago
    Round trip
    I
    Economy

    Chicago (ORD)to

    San Juan (SJU)
    05/04/25 - 05/09/25
    from
    $387*
    Updated: 20 hours ago
    Round trip
    I
    Economy

    Chicago (ORD)to

    San Juan (SJU)
    05/11/25 - 05/17/25
    from
    $387*
    Updated: 20 hours ago
    Round trip
    I
    Economy

  • Chicago (ORD)to

    San Juan (SJU)
    05/01/25 - 05/14/25
    from
    $387*
    Updated: 16 hours ago
    Round trip
    I
    Economy

    Chicago (ORD)to

    San Juan (SJU)
    07/24/25 - 08/08/25
    from
    $387*
    Updated: 1 hour ago
    Round trip
    I
    Economy

    Chicago (ORD)to

    San Juan (SJU)
    05/31/25 - 06/04/25
    from
    $387*
    Updated: 23 hours ago
    Round trip
    I
    Economy

    Chicago (ORD)to

    San Juan (SJU)
    05/29/25 - 06/04/25
    from
    $387*
    Updated: 4 hours ago
    Round trip
    I
    Economy

  • Chicago (ORD)to

    San Juan (SJU)
    04/28/25 - 05/05/25
    from
    $387*
    Updated: 16 hours ago
    Round trip
    I
    Economy

    Chicago (ORD)to

    San Juan (SJU)
    04/29/25 - 05/17/25
    from
    $387*
    Updated: 4 hours ago
    Round trip
    I
    Economy

    Chicago (ORD)to

    San Juan (SJU)
    04/30/25 - 05/14/25
    from
    $387*
    Updated: 1 hour ago
    Round trip
    I
    Economy

    Chicago (ORD)to

    San Juan (SJU)
    05/12/25 - 05/21/25
    from
    $387*
    Updated: 18 hours ago
    Round trip
    I
    Economy

  • Chicago (ORD)to

    San Juan (SJU)
    05/31/25 - 06/07/25
    from
    $391*
    Updated: 23 hours ago
    Round trip
    I
    Economy

    Chicago (ORD)to

    San Juan (SJU)
    05/03/25 - 05/10/25
    from
    $391*
    Updated: 23 hours ago
    Round trip
    I
    Economy

    Chicago (ORD)to

    San Juan (SJU)
    05/15/25 - 05/22/25
    from
    $391*
    Updated: 23 hours ago
    Round trip
    I
    Economy

    Chicago (ORD)to

    San Juan (SJU)
    07/08/25 - 07/16/25
    from
    $391*
    Updated: 4 hours ago
    Round trip
    I
    Economy

*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.

Flights from Chicago to San Juan with American Airlines

Find deals on Chicago to San Juan flights

$

Chicago (ORD)to

San Juan (SJU)
01/24/26 - 01/29/26

Round trip

I

Economy

from
$382
Updated: 18 hours ago

Chicago (ORD)to

San Juan (SJU)
10/01/25 - 10/07/25

Round trip

I

Economy

from
$387
Updated: 22 hours ago

Chicago (ORD)to

San Juan (SJU)
02/14/26 - 02/24/26

Round trip

I

Economy

from
$387
Updated: 18 hours ago

Chicago (ORD)to

San Juan (SJU)
12/06/25 - 12/14/25

Round trip

I

Economy

from
$391
Updated: 3 hours ago

Chicago (ORD)to

San Juan (SJU)
11/23/25 - 12/03/25

Round trip

I

Economy

from
$402
Updated: 21 hours ago

Chicago (ORD)to

San Juan (SJU)
12/12/25 - 12/20/25

Round trip

I

Economy

from
$411
Updated: 18 hours ago

Chicago (ORD)to

San Juan (SJU)
11/28/25 - 12/07/25

Round trip

I

Economy

from
$443
Updated: 20 hours ago

Chicago (ORD)to

San Juan (SJU)
10/16/25 - 10/19/25

Round trip

I

Economy

from
$473
Updated: 3 minutes ago

Chicago (ORD)to

San Juan (SJU)
10/15/25 - 10/19/25

Round trip

I

Economy

from
$478
Updated: 23 minutes ago

Chicago (ORD)to

San Juan (SJU)
11/23/25 - 11/30/25

Round trip

I

Economy

from
$522
Updated: 21 hours 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.

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