American Airlines flights from San Jose to Chicago

Recent searches for flights from San Jose to Chicago

Mar 2026
From$687*
Updated: 22 hours ago
Round tripIEconomy
Apr 2026
From$282*
Updated: 22 hours ago
Round tripIEconomy
May 2026
From$342*
Updated: 5 hours ago
Round tripIEconomy
$282
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    • range$282-$1,121

    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 San Jose to Chicago flights

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    San Jose (SJC)to

    Chicago (ORD)
    04/08/26 - 04/11/26

    Round trip

    Economy

    from
    $282Fare subject to changes
    Updated: 22 hours ago

    San Jose (SJC)to

    Chicago (ORD)
    05/26/26 - 05/30/26

    Round trip

    Economy

    from
    $342Fare subject to changes
    Updated: 5 hours ago

    San Jose (SJC)to

    Chicago (ORD)
    07/28/26 - 08/04/26

    Round trip

    Economy

    from
    $427Fare subject to changes
    Updated: 4 hours ago

    San Jose (SJC)to

    Chicago (ORD)
    05/14/26 - 05/18/26

    Round trip

    Economy

    from
    $477Fare subject to changes
    Updated: 3 hours ago

    San Jose (SJC)to

    Chicago (ORD)
    06/19/26 - 06/23/26

    Round trip

    Economy

    from
    $482Fare subject to changes
    Updated: 5 hours ago

    San Jose (SJC)to

    Chicago (ORD)
    08/30/26 - 09/04/26

    Round trip

    Economy

    from
    $502Fare subject to changes
    Updated: 4 hours ago

    San Jose (SJC)to

    Chicago (ORD)
    06/05/26 - 06/08/26

    Round trip

    Economy

    from
    $545Fare subject to changes
    Updated: 4 hours ago

    San Jose (SJC)to

    Chicago (ORD)
    03/20/26 - 03/23/26

    Round trip

    Economy

    from
    $687Fare 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.

    American Airlines flights from San Jose to Chicago

    Earn up to $400 back on your next American Airlines flight plus, 30,000 bonus miles. Terms apply. Opens another site in a new window that may not meet accessibility guidelines.