American Airlines flights from Chicago to San Antonio

Recent searches for flights from Chicago to San Antonio

Aug 2026
From$535*
Updated: 8 hours ago
Round tripIEconomy
Sep 2026
From$297*
Updated: 1 hour ago
Round tripIEconomy
Oct 2026
From$297*
Updated: 1 hour ago
Round tripIEconomy
cmp-daily-histogram-bars-legend-min-price-aria-label $297
cmp-daily-histogram-bars-legend-max-price-aria-label $597
Displaying fares for August-2026
  • ORD–SAT, 08/27/26 – 08/29/26: From $563
    27

    Th

    AUG

  • CHI–SAT, 08/28/26 – 09/04/26: From $591
    28

    Fr

  • ORD–SAT, 08/29/26 – 09/05/26: From $535
    29

    Sa

  • ORD–SAT, 08/30/26 – 09/05/26: From $563
    30

    Su

  • CHI–SAT, 08/31/26 – 09/07/26: From $591
    31

    Mo

  • ORD–SAT, 09/01/26 – 09/08/26: From $535
    01

    Tu

    SEP

  • CHI–SAT, 09/02/26 – 09/09/26: From $535
    02

    We

  • ORD–SAT, 09/03/26 – 09/05/26: From $563
    03

    Th

  • ORD–SAT, 09/04/26 – 09/05/26: From $563
    04

    Fr

  • CHI–SAT, 09/05/26 – 09/12/26: From $485
    05

    Sa

  • ORD–SAT, 09/06/26 – 09/13/26: From $509
    06

    Su

  • ORD–SAT, 09/07/26 – 09/14/26: From $597
    07

    Mo

  • ORD–SAT, 09/08/26 – 09/15/26: From $535
    08

    Tu

  • CHI–SAT, 09/09/26 – 09/16/26: From $485
    09

    We

  • ORD–SAT, 09/10/26 – 09/17/26: From $366
    10

    Th

  • CHI–SAT, 09/11/26 – 09/18/26: From $379
    11

    Fr

  • CHI–SAT, 09/12/26 – 09/19/26: From $366
    12

    Sa

  • ORD–SAT, 09/13/26 – 09/20/26: From $565
    13

    Su

  • ORD–SAT, 09/14/26 – 09/21/26: From $440
    14

    Mo

  • CHI–SAT, 09/15/26 – 09/22/26: From $416
    15

    Tu

  • CHI–SAT, 09/16/26 – 09/23/26: From $416
    16

    We

  • CHI–SAT, 09/17/26 – 09/24/26: From $297
    17

    Th

  • ORD–SAT, 09/18/26 – 09/21/26: From $310
    18

    Fr

  • CHI–SAT, 09/19/26 – 09/26/26: From $297
    19

    Sa

  • ORD–SAT, 09/20/26 – 09/25/26: From $435
    20

    Su

  • ORD–SAT, 09/21/26 – 09/28/26: From $297
    21

    Mo

  • ORD–SAT, 09/22/26 – 09/29/26: From $297
    22

    Tu

  • ORD–SAT, 09/23/26 – 09/30/26: From $297
    23

    We

  • CHI–SAT: cmp-view-offers-disclaimer. Find Offers
    24

    Th

  • CHI–SAT: cmp-view-offers-disclaimer. Find Offers
    25

    Fr

  • ORD–SAT, 09/26/26 – 10/03/26: From $297
    26

    Sa

    • range$297-$597

    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 Antonio flights

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    Chicago (ORD)to

    San Antonio (SAT)
    11/07/26 - 11/14/26

    Round trip

    Economy

    from
    $297Fare subject to changes
    Updated: 1 hour ago

    Chicago (ORD)to

    San Antonio (SAT)
    11/09/26 - 11/16/26

    Round trip

    Economy

    from
    $297Fare subject to changes
    Updated: 1 hour ago

    Chicago (ORD)to

    San Antonio (SAT)
    11/11/26 - 11/18/26

    Round trip

    Economy

    from
    $297Fare subject to changes
    Updated: 1 hour ago

    Chicago (ORD)to

    San Antonio (SAT)
    11/14/26 - 11/21/26

    Round trip

    Economy

    from
    $297Fare subject to changes
    Updated: 1 hour ago

    Chicago (ORD)to

    San Antonio (SAT)
    11/16/26 - 11/23/26

    Round trip

    Economy

    from
    $297Fare subject to changes
    Updated: 1 hour ago

    Chicago (ORD)to

    San Antonio (SAT)
    10/07/26 - 10/14/26

    Round trip

    Economy

    from
    $297Fare subject to changes
    Updated: 1 hour ago

    Chicago (ORD)to

    San Antonio (SAT)
    10/10/26 - 10/17/26

    Round trip

    Economy

    from
    $297Fare subject to changes
    Updated: 1 hour ago

    Chicago (ORD)to

    San Antonio (SAT)
    10/15/26 - 10/22/26

    Round trip

    Economy

    from
    $297Fare subject to changes
    Updated: 1 hour 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 Antonio

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