Flights from Chicago to San Juan with American Airlines

Recent searches for flights from Chicago to San Juan

May 2025
From$464*
Updated: 3 hours ago
Round tripIEconomy
$391
$600
Displaying fares for May-2025
21

We

MAY

22

Th

23

Fr

24

Sa

25

Su

26

Mo

27

Tu

28

We

29

Th

30

Fr

31

Sa

01

Su

JUN

02

Mo

03

Tu

04

We

05

Th

06

Fr

07

Sa

08

Su

09

Mo

10

Tu

11

We

12

Th

13

Fr

14

Sa

15

Su

16

Mo

17

Tu

18

We

19

Th

20

Fr

range$391-$600

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

$
keyboard_arrow_down

  • Chicago (ORD)to

    San Juan (SJU)
    08/08/25 - 08/15/25
    from
    $391Fare subject to changes
    Updated: 4 hours ago
    Round trip
    I
    Economy

    Chicago (ORD)to

    San Juan (SJU)
    08/14/25 - 08/21/25
    from
    $391Fare subject to changes
    Updated: 4 hours ago
    Round trip
    I
    Economy

    Chicago (ORD)to

    San Juan (SJU)
    07/05/25 - 07/12/25
    from
    $391Fare subject to changes
    Updated: 4 hours ago
    Round trip
    I
    Economy

    Chicago (ORD)to

    San Juan (SJU)
    06/10/25 - 06/17/25
    from
    $391Fare subject to changes
    Updated: 4 hours ago
    Round trip
    I
    Economy

  • Chicago (ORD)to

    San Juan (SJU)
    09/22/25 - 09/26/25
    from
    $391Fare subject to changes
    Updated: 9 hours ago
    Round trip
    I
    Economy

    Chicago (ORD)to

    San Juan (SJU)
    07/09/25 - 07/30/25
    from
    $391Fare subject to changes
    Updated: 13 hours ago
    Round trip
    I
    Economy

    Chicago (ORD)to

    San Juan (SJU)
    07/02/25 - 07/09/25
    from
    $391Fare subject to changes
    Updated: 4 hours ago
    Round trip
    I
    Economy

    Chicago (ORD)to

    San Juan (SJU)
    07/13/25 - 07/19/25
    from
    $391Fare subject to changes
    Updated: 7 hours ago
    Round trip
    I
    Economy

  • Chicago (ORD)to

    San Juan (SJU)
    07/16/25 - 07/30/25
    from
    $391Fare subject to changes
    Updated: 13 hours ago
    Round trip
    I
    Economy

    Chicago (ORD)to

    San Juan (SJU)
    07/26/25 - 08/02/25
    from
    $391Fare subject to changes
    Updated: 4 hours ago
    Round trip
    I
    Economy

    Chicago (ORD)to

    San Juan (SJU)
    10/10/25 - 10/12/25
    from
    $392Fare subject to changes
    Updated: 7 hours ago
    Round trip
    I
    Economy

    Chicago (ORD)to

    San Juan (SJU)
    08/15/25 - 08/22/25
    from
    $402Fare subject to changes
    Updated: 4 hours ago
    Round trip
    I
    Economy

  • Chicago (ORD)to

    San Juan (SJU)
    08/13/25 - 08/20/25
    from
    $406Fare subject to changes
    Updated: 4 hours ago
    Round trip
    I
    Economy

    Chicago (ORD)to

    San Juan (SJU)
    07/10/25 - 07/17/25
    from
    $407Fare subject to changes
    Updated: 4 hours ago
    Round trip
    I
    Economy

    Chicago (ORD)to

    San Juan (SJU)
    06/19/25 - 06/24/25
    from
    $411Fare subject to changes
    Updated: 9 hours ago
    Round trip
    I
    Economy

    Chicago (ORD)to

    San Juan (SJU)
    06/14/25 - 06/21/25
    from
    $411Fare subject to changes
    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

$
keyboard_arrow_down

Chicago (ORD)to

San Juan (SJU)
02/15/26 - 02/27/26

Round trip

I

Economy

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

Chicago (ORD)to

San Juan (SJU)
03/11/26 - 03/21/26

Round trip

I

Economy

from
$387Fare subject to changes
Updated: 10 hours ago

Chicago (ORD)to

San Juan (SJU)
01/16/26 - 01/24/26

Round trip

I

Economy

from
$387Fare subject to changes
Updated: 12 hours ago

Chicago (ORD)to

San Juan (SJU)
01/31/26 - 02/08/26

Round trip

I

Economy

from
$387Fare subject to changes
Updated: 20 minutes ago

Chicago (ORD)to

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

Round trip

I

Economy

from
$387Fare subject to changes
Updated: 8 hours ago

Chicago (ORD)to

San Juan (SJU)
01/02/26 - 01/11/26

Round trip

I

Economy

from
$391Fare subject to changes
Updated: 5 hours ago

Chicago (ORD)to

San Juan (SJU)
01/15/26 - 01/25/26

Round trip

I

Economy

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

Chicago (ORD)to

San Juan (SJU)
12/04/25 - 12/14/25

Round trip

I

Economy

from
$391Fare subject to changes
Updated: 7 hours ago

Chicago (ORD)to

San Juan (SJU)
04/07/26 - 04/13/26

Round trip

I

Economy

from
$407Fare subject to changes
Updated: 5 hours ago

Chicago (ORD)to

San Juan (SJU)
03/13/26 - 03/22/26

Round trip

I

Economy

from
$454Fare subject to changes
Updated: 23 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