American Airlines flights from Chicago to San Juan

Recent searches for flights from Chicago to San Juan

Aug 2026
From$247*
Updated: 6 hours ago
Round tripIEconomy
Sep 2026
From$252*
Updated: 2 hours ago
Round tripIEconomy
Oct 2026
From$456*
Updated: 4 hours ago
Round tripIEconomy
cmp-daily-histogram-bars-legend-min-price-aria-label $247
cmp-daily-histogram-bars-legend-max-price-aria-label $496
Displaying fares for August-2026
  • ORD–SJU, 08/04/26 – 08/09/26: From $496
    04

    Tu

    AUG

  • CHI–SJU, 08/05/26 – 08/12/26: From $396
    05

    We

  • ORD–SJU, 08/06/26 – 08/13/26: From $431
    06

    Th

  • CHI–SJU, 08/07/26 – 08/14/26: From $395
    07

    Fr

  • ORD–SJU, 08/08/26 – 08/15/26: From $395
    08

    Sa

  • CHI–SJU, 08/09/26 – 08/16/26: From $395
    09

    Su

  • ORD–SJU, 08/10/26 – 08/14/26: From $406
    10

    Mo

  • ORD–SJU, 08/11/26 – 08/18/26: From $322
    11

    Tu

  • ORD–SJU, 08/12/26 – 08/19/26: From $331
    12

    We

  • CHI–SJU, 08/13/26 – 08/20/26: From $326
    13

    Th

  • ORD–SJU, 08/14/26 – 08/21/26: From $322
    14

    Fr

  • ORD–SJU, 08/15/26 – 08/25/26: From $322
    15

    Sa

  • CHI–SJU, 08/16/26 – 08/23/26: From $322
    16

    Su

  • ORD–SJU, 08/17/26 – 08/24/26: From $322
    17

    Mo

  • CHI–SJU, 08/18/26 – 08/25/26: From $252
    18

    Tu

  • CHI–SJU, 08/19/26 – 08/26/26: From $257
    19

    We

  • ORD–SJU, 08/20/26 – 08/27/26: From $252
    20

    Th

  • ORD–SJU, 08/21/26 – 08/28/26: From $247
    21

    Fr

  • CHI–SJU, 08/22/26 – 08/29/26: From $282
    22

    Sa

  • ORD–SJU, 08/23/26 – 08/30/26: From $252
    23

    Su

  • CHI–SJU, 08/24/26 – 08/31/26: From $252
    24

    Mo

  • ORD–SJU, 08/25/26 – 09/01/26: From $252
    25

    Tu

  • ORD–SJU, 08/26/26 – 09/02/26: From $252
    26

    We

  • CHI–SJU, 08/27/26 – 09/03/26: From $272
    27

    Th

  • CHI–SJU, 08/28/26 – 09/04/26: From $272
    28

    Fr

  • CHI–SJU, 08/29/26 – 09/05/26: From $307
    29

    Sa

  • ORD–SJU, 08/30/26 – 09/06/26: From $252
    30

    Su

  • ORD–SJU, 08/31/26 – 09/07/26: From $252
    31

    Mo

  • CHI–SJU: cmp-view-offers-disclaimer. Find Offers
    01

    Tu

    SEP

  • CHI–SJU, 09/02/26 – 09/09/26: From $257
    02

    We

  • CHI–SJU: cmp-view-offers-disclaimer. Find Offers
    03

    Th

    • range$247-$496

    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.

    Find deals on Chicago to San Juan flights

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    Chicago (ORD)to

    San Juan (SJU)
    08/21/26 - 08/28/26

    Round trip

    Economy

    from
    $247Fare subject to changes
    Updated: 6 hours ago

    Chicago (ORD)to

    San Juan (SJU)
    08/21/26 - 08/28/26

    Round trip

    Economy

    from
    $252Fare subject to changes
    Updated: 2 hours ago

    Chicago (ORD)to

    San Juan (SJU)
    08/23/26 - 08/30/26

    Round trip

    Economy

    from
    $252Fare subject to changes
    Updated: 2 hours ago

    Chicago (ORD)to

    San Juan (SJU)
    08/31/26 - 09/07/26

    Round trip

    Economy

    from
    $252Fare subject to changes
    Updated: 2 hours ago

    Chicago (ORD)to

    San Juan (SJU)
    08/18/26 - 08/25/26

    Round trip

    Economy

    from
    $252Fare subject to changes
    Updated: 2 hours ago

    Chicago (ORD)to

    San Juan (SJU)
    08/24/26 - 08/31/26

    Round trip

    Economy

    from
    $252Fare subject to changes
    Updated: 2 hours ago

    Chicago (ORD)to

    San Juan (SJU)
    08/25/26 - 09/01/26

    Round trip

    Economy

    from
    $252Fare subject to changes
    Updated: 2 hours ago

    Chicago (ORD)to

    San Juan (SJU)
    08/30/26 - 09/06/26

    Round trip

    Economy

    from
    $252Fare subject to changes
    Updated: 2 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.

    Finding cheap flights from Chicago to San Juan

    Looking for lower fares on your trip from Chicago to San Juan? Here are a few ways to save.

    • Book early: Booking 1 to 3 months ahead can help you find lower fares
    • Be flexible with dates: Midweek travel, like Tuesdays and Wednesdays, can be more affordable
    • Travel during less busy periods: Flying outside peak travel times can help find lower fares and avoid crowds

    Earn up to $500 back on your next American Airlines flight plus, 30,000 bonus miles. Offers vary elsewhere. Opens another site in a new window that may not meet accessibility guidelines.

    Upgrade your flight with Main Cabin Extra

    Make your trip more comfortable with Main Cabin Extra. Enjoy benefits like:

    • Extra legroom: More space with seats at the front of the Main Cabin or in exit rows.
    • Early boarding: Preferred Group 5 boarding allows easier access to overhead bins.
    • Complimentary drinks: Enjoy beer, wine and spirits on flights with full beverage service.

    Discover how Main Cabin Extra can enhance your trip.

    American Airlines flights from Chicago to San Juan