American Airlines flights from San Antonio to Chicago

Recent searches for flights from San Antonio to Chicago

Aug 2026
From$310*
Updated: 1 hour ago
Round tripIEconomy
Sep 2026
From$310*
Updated: 1 hour ago
Round tripIEconomy
Oct 2026
From$323*
Updated: 1 hour ago
Round tripIEconomy
cmp-daily-histogram-bars-legend-min-price-aria-label $310
cmp-daily-histogram-bars-legend-max-price-aria-label $571
Displaying fares for August-2026
  • SAT–ORD, 08/04/26 – 08/05/26: From $515
    04

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    AUG

  • SAT–CHI, 08/05/26 – 08/12/26: From $515
    05

    We

  • SAT–ORD, 08/06/26 – 08/13/26: From $571
    06

    Th

  • SAT–ORD, 08/07/26 – 08/08/26: From $543
    07

    Fr

  • SAT–ORD, 08/08/26 – 08/15/26: From $515
    08

    Sa

  • SAT–CHI, 08/09/26 – 08/16/26: From $571
    09

    Su

  • SAT–ORD, 08/10/26 – 08/17/26: From $567
    10

    Mo

  • SAT–CHI, 08/11/26 – 08/18/26: From $515
    11

    Tu

  • SAT–CHI, 08/12/26 – 08/19/26: From $515
    12

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  • SAT–ORD, 08/13/26 – 08/20/26: From $567
    13

    Th

  • SAT–ORD, 08/14/26 – 08/18/26: From $543
    14

    Fr

  • SAT–CHI, 08/15/26 – 08/22/26: From $515
    15

    Sa

  • SAT–ORD, 08/16/26 – 08/23/26: From $567
    16

    Su

  • SAT–CHI, 08/17/26 – 08/24/26: From $567
    17

    Mo

  • SAT–ORD, 08/18/26 – 08/25/26: From $419
    18

    Tu

  • SAT–CHI, 08/19/26 – 08/26/26: From $419
    19

    We

  • SAT–CHI, 08/20/26 – 08/27/26: From $443
    20

    Th

  • SAT–CHI, 08/21/26 – 08/28/26: From $477
    21

    Fr

  • SAT–ORD, 08/22/26 – 08/29/26: From $419
    22

    Sa

  • SAT–CHI, 08/23/26 – 08/30/26: From $545
    23

    Su

  • SAT–ORD, 08/24/26 – 08/31/26: From $443
    24

    Mo

  • SAT–CHI, 08/25/26 – 09/01/26: From $323
    25

    Tu

  • SAT–CHI, 08/26/26 – 09/02/26: From $323
    26

    We

  • SAT–ORD, 08/27/26 – 09/03/26: From $323
    27

    Th

  • SAT–CHI, 08/28/26 – 09/04/26: From $391
    28

    Fr

  • SAT–ORD, 08/29/26 – 09/05/26: From $310
    29

    Sa

  • SAT–ORD, 08/30/26 – 09/06/26: From $412
    30

    Su

  • SAT–ORD, 08/31/26 – 09/07/26: From $323
    31

    Mo

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

    Tu

    SEP

  • SAT–CHI: cmp-view-offers-disclaimer. Find Offers
    02

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  • SAT–CHI, 09/03/26 – 09/06/26: From $310
    03

    Th

    • range$310-$571

    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 Antonio to Chicago flights

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    San Antonio (SAT)to

    Chicago (ORD)
    09/03/26 - 09/06/26

    Round trip

    Economy

    from
    $310Fare subject to changes
    Updated: 7 hours ago

    San Antonio (SAT)to

    Chicago (ORD)
    09/05/26 - 09/12/26

    Round trip

    Economy

    from
    $310Fare subject to changes
    Updated: 12 hours ago

    San Antonio (SAT)to

    Chicago (ORD)
    08/29/26 - 09/05/26

    Round trip

    Economy

    from
    $310Fare subject to changes
    Updated: 12 hours ago

    San Antonio (SAT)to

    Chicago (ORD)
    11/19/26 - 11/26/26

    Round trip

    Economy

    from
    $310Fare subject to changes
    Updated: 19 hours ago

    San Antonio (SAT)to

    Chicago (ORD)
    09/07/26 - 09/14/26

    Round trip

    Economy

    from
    $323Fare subject to changes
    Updated: 12 hours ago

    San Antonio (SAT)to

    Chicago (ORD)
    09/14/26 - 09/21/26

    Round trip

    Economy

    from
    $323Fare subject to changes
    Updated: 12 hours ago

    San Antonio (SAT)to

    Chicago (ORD)
    09/15/26 - 09/22/26

    Round trip

    Economy

    from
    $323Fare subject to changes
    Updated: 12 hours ago

    San Antonio (SAT)to

    Chicago (ORD)
    09/21/26 - 09/28/26

    Round trip

    Economy

    from
    $323Fare subject to changes
    Updated: 12 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 San Antonio to Chicago

    Looking for lower fares on your trip from San Antonio to Chicago? 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 San Antonio to Chicago