Flights from Chicago to San Juan with American Airlines

Recent searches for flights from Chicago to San Juan

Jul 2025
From$391*
Updated: 22 hours ago
Round tripIEconomy
$391
$610
Displaying fares for July-2025
  • 03

    Th

    JUL

  • 04

    Fr

  • 05

    Sa

  • 06

    Su

  • 07

    Mo

  • 08

    Tu

  • 09

    We

  • 10

    Th

  • 11

    Fr

  • 12

    Sa

  • 13

    Su

  • 14

    Mo

  • 15

    Tu

  • 16

    We

  • 17

    Th

  • 18

    Fr

  • 19

    Sa

  • 20

    Su

  • 21

    Mo

  • 22

    Tu

  • 23

    We

  • 24

    Th

  • 25

    Fr

  • 26

    Sa

  • 27

    Su

  • 28

    Mo

  • 29

    Tu

  • 30

    We

  • 31

    Th

  • 01

    Fr

    AUG

  • 02

    Sa

    • range$391-$610

    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

    *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

    $
    keyboard_arrow_down

    Chicago (ORD)to

    San Juan (SJU)
    01/23/26 - 02/02/26

    Round trip

    Economy

    from
    $382Fare subject to changes
    Updated: 21 hours ago

    Chicago (ORD)to

    San Juan (SJU)
    02/04/26 - 02/14/26

    Round trip

    Economy

    from
    $382Fare subject to changes
    Updated: 21 hours ago

    Chicago (ORD)to

    San Juan (SJU)
    03/11/26 - 03/16/26

    Round trip

    Economy

    from
    $382Fare subject to changes
    Updated: 14 hours ago

    Chicago (ORD)to

    San Juan (SJU)
    03/15/26 - 03/18/26

    Round trip

    Economy

    from
    $382Fare subject to changes
    Updated: 20 hours ago

    Chicago (ORD)to

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

    Round trip

    Economy

    from
    $387Fare subject to changes
    Updated: 17 hours ago

    Chicago (ORD)to

    San Juan (SJU)
    01/16/26 - 01/28/26

    Round trip

    Economy

    from
    $387Fare subject to changes
    Updated: 11 hours ago

    Chicago (ORD)to

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

    Round trip

    Economy

    from
    $387Fare subject to changes
    Updated: 59 minutes ago

    Chicago (ORD)to

    San Juan (SJU)
    02/16/26 - 02/27/26

    Round trip

    Economy

    from
    $407Fare subject to changes
    Updated: 11 hours ago

    Chicago (ORD)to

    San Juan (SJU)
    02/15/26 - 02/21/26

    Round trip

    Economy

    from
    $412Fare subject to changes
    Updated: 11 hours ago

    Chicago (ORD)to

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

    Round trip

    Economy

    from
    $427Fare subject to changes
    Updated: 22 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.