Flights from Chicago to San Juan with American Airlines

Recent searches for flights from Chicago to San Juan

May 2025
From$382*
Updated: 8 hours ago
Round tripIEconomy
$382
$539
Displaying fares for May-2025
01

Th

MAY

02

Fr

03

Sa

04

Su

05

Mo

06

Tu

07

We

08

Th

09

Fr

10

Sa

11

Su

12

Mo

13

Tu

14

We

15

Th

16

Fr

17

Sa

18

Su

19

Mo

20

Tu

21

We

22

Th

23

Fr

24

Sa

25

Su

26

Mo

27

Tu

28

We

29

Th

30

Fr

31

Sa

range$382-$539

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)
    05/14/25 - 05/21/25
    from
    $385Fare subject to changes
    Updated: 8 hours ago
    Round trip
    I
    Economy

    Chicago (ORD)to

    San Juan (SJU)
    05/15/25 - 05/22/25
    from
    $385Fare subject to changes
    Updated: 8 hours ago
    Round trip
    I
    Economy

    Chicago (ORD)to

    San Juan (SJU)
    05/28/25 - 06/03/25
    from
    $387Fare subject to changes
    Updated: 3 hours ago
    Round trip
    I
    Economy

    Chicago (ORD)to

    San Juan (SJU)
    05/29/25 - 06/04/25
    from
    $387Fare subject to changes
    Updated: 16 hours ago
    Round trip
    I
    Economy

  • Chicago (ORD)to

    San Juan (SJU)
    06/02/25 - 06/05/25
    from
    $387Fare subject to changes
    Updated: 12 hours ago
    Round trip
    I
    Economy

    Chicago (ORD)to

    San Juan (SJU)
    05/19/25 - 06/24/25
    from
    $388Fare subject to changes
    Updated: 11 hours ago
    Round trip
    I
    Economy

    Chicago (ORD)to

    San Juan (SJU)
    05/18/25 - 05/25/25
    from
    $388Fare subject to changes
    Updated: 8 hours ago
    Round trip
    I
    Economy

    Chicago (ORD)to

    San Juan (SJU)
    05/20/25 - 05/27/25
    from
    $388Fare subject to changes
    Updated: 8 hours ago
    Round trip
    I
    Economy

  • Chicago (ORD)to

    San Juan (SJU)
    05/29/25 - 06/03/25
    from
    $391Fare subject to changes
    Updated: 17 hours ago
    Round trip
    I
    Economy

    Chicago (ORD)to

    San Juan (SJU)
    07/02/25 - 07/09/25
    from
    $391Fare subject to changes
    Updated: 8 hours ago
    Round trip
    I
    Economy

    Chicago (ORD)to

    San Juan (SJU)
    06/10/25 - 06/17/25
    from
    $391Fare subject to changes
    Updated: 8 hours ago
    Round trip
    I
    Economy

    Chicago (ORD)to

    San Juan (SJU)
    05/26/25 - 06/02/25
    from
    $391Fare subject to changes
    Updated: 8 hours ago
    Round trip
    I
    Economy

  • Chicago (ORD)to

    San Juan (SJU)
    09/25/25 - 09/29/25
    from
    $391Fare subject to changes
    Updated: 3 hours ago
    Round trip
    I
    Economy

    Chicago (ORD)to

    San Juan (SJU)
    06/14/25 - 06/21/25
    from
    $391Fare subject to changes
    Updated: 8 hours ago
    Round trip
    I
    Economy

    Chicago (ORD)to

    San Juan (SJU)
    08/09/25 - 08/13/25
    from
    $391Fare subject to changes
    Updated: 5 hours ago
    Round trip
    I
    Economy

    Chicago (ORD)to

    San Juan (SJU)
    05/20/25 - 05/24/25
    from
    $393Fare subject to changes
    Updated: 5 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)
01/08/26 - 01/17/26

Round trip

I

Economy

from
$391Fare subject to changes
Updated: 16 hours ago

Chicago (ORD)to

San Juan (SJU)
01/10/26 - 01/18/26

Round trip

I

Economy

from
$391Fare subject to changes
Updated: 8 hours ago

Chicago (ORD)to

San Juan (SJU)
01/20/26 - 01/25/26

Round trip

I

Economy

from
$391Fare subject to changes
Updated: 16 hours ago

Chicago (ORD)to

San Juan (SJU)
02/06/26 - 02/14/26

Round trip

I

Economy

from
$391Fare subject to changes
Updated: 3 hours ago

Chicago (ORD)to

San Juan (SJU)
12/07/25 - 12/14/25

Round trip

I

Economy

from
$391Fare subject to changes
Updated: 9 hours ago

Chicago (ORD)to

San Juan (SJU)
01/05/26 - 01/12/26

Round trip

I

Economy

from
$407Fare subject to changes
Updated: 8 hours ago

Chicago (ORD)to

San Juan (SJU)
01/04/26 - 01/11/26

Round trip

I

Economy

from
$411Fare subject to changes
Updated: 8 hours ago

Chicago (ORD)to

San Juan (SJU)
12/01/25 - 12/08/25

Round trip

I

Economy

from
$434Fare subject to changes
Updated: 9 hours ago

Chicago (ORD)to

San Juan (SJU)
03/07/26 - 03/15/26

Round trip

I

Economy

from
$436Fare subject to changes
Updated: 3 hours ago

Chicago (ORD)to

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

Round trip

I

Economy

from
$439Fare subject to changes
Updated: 8 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.

Looking for more? See other routes.

Explore American Airlines's Top-Pick Destinations