American Airlines flights from Chicago to Santiago, DR

Recent searches for flights from Chicago to Santiago, DR

Aug 2026
From$587*
Updated: 1 hour ago
Round tripIEconomy
Sep 2026
From$428*
Updated: 2 hours ago
Round tripIEconomy
Oct 2026
From$428*
Updated: 2 hours ago
Round tripIEconomy
cmp-daily-histogram-bars-legend-min-price-aria-label $428
cmp-daily-histogram-bars-legend-max-price-aria-label $972
Displaying fares for August-2026
  • CHI–STI, 08/12/26 – 08/19/26: From $972
    12

    We

    AUG

  • CHI–STI, 08/13/26 – 08/20/26: From $967
    13

    Th

  • ORD–STI, 08/14/26 – 08/21/26: From $967
    14

    Fr

  • ORD–STI, 08/15/26 – 08/22/26: From $942
    15

    Sa

  • ORD–STI, 08/16/26 – 08/23/26: From $947
    16

    Su

  • CHI–STI, 08/17/26 – 08/24/26: From $917
    17

    Mo

  • CHI–STI, 08/18/26 – 08/25/26: From $917
    18

    Tu

  • CHI–STI, 08/19/26 – 08/26/26: From $815
    19

    We

  • CHI–STI, 08/20/26 – 08/27/26: From $810
    20

    Th

  • CHI–STI, 08/21/26 – 08/28/26: From $810
    21

    Fr

  • ORD–STI, 08/22/26 – 08/29/26: From $810
    22

    Sa

  • ORD–STI, 08/23/26 – 08/30/26: From $815
    23

    Su

  • CHI–STI, 08/24/26 – 08/31/26: From $828
    24

    Mo

  • ORD–STI, 08/25/26 – 09/01/26: From $810
    25

    Tu

  • CHI–STI, 08/26/26 – 09/02/26: From $592
    26

    We

  • ORD–STI, 08/27/26 – 09/03/26: From $587
    27

    Th

  • CHI–STI, 08/28/26 – 09/04/26: From $587
    28

    Fr

  • ORD–STI, 08/29/26 – 09/05/26: From $644
    29

    Sa

  • ORD–STI, 08/30/26 – 09/06/26: From $699
    30

    Su

  • ORD–STI, 08/31/26 – 09/07/26: From $694
    31

    Mo

  • CHI–STI, 09/01/26 – 09/08/26: From $638
    01

    Tu

    SEP

  • ORD–STI, 09/02/26 – 09/09/26: From $433
    02

    We

  • ORD–STI, 09/03/26 – 09/10/26: From $514
    03

    Th

  • ORD–STI, 09/04/26 – 09/11/26: From $565
    04

    Fr

  • ORD–STI, 09/05/26 – 09/12/26: From $592
    05

    Sa

  • ORD–STI, 09/06/26 – 09/13/26: From $632
    06

    Su

  • ORD–STI, 09/07/26 – 09/14/26: From $496
    07

    Mo

  • ORD–STI, 09/08/26 – 09/15/26: From $428
    08

    Tu

  • CHI–STI, 09/09/26 – 09/16/26: From $469
    09

    We

  • CHI–STI, 09/10/26 – 09/17/26: From $433
    10

    Th

  • CHI–STI, 09/11/26 – 09/18/26: From $428
    11

    Fr

    • range$428-$972

    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 Santiago, DR flights

    $
    keyboard_arrow_down

    Chicago (ORD)to

    Santiago, DR (STI)
    11/03/26 - 11/10/26

    Round trip

    Economy

    from
    $428Fare subject to changes
    Updated: 2 hours ago

    Chicago (ORD)to

    Santiago, DR (STI)
    11/06/26 - 11/13/26

    Round trip

    Economy

    from
    $428Fare subject to changes
    Updated: 2 hours ago

    Chicago (ORD)to

    Santiago, DR (STI)
    11/07/26 - 11/14/26

    Round trip

    Economy

    from
    $428Fare subject to changes
    Updated: 2 hours ago

    Chicago (ORD)to

    Santiago, DR (STI)
    11/10/26 - 11/17/26

    Round trip

    Economy

    from
    $428Fare subject to changes
    Updated: 2 hours ago

    Chicago (ORD)to

    Santiago, DR (STI)
    11/12/26 - 11/19/26

    Round trip

    Economy

    from
    $428Fare subject to changes
    Updated: 2 hours ago

    Chicago (ORD)to

    Santiago, DR (STI)
    10/19/26 - 10/26/26

    Round trip

    Economy

    from
    $428Fare subject to changes
    Updated: 2 hours ago

    Chicago (ORD)to

    Santiago, DR (STI)
    10/20/26 - 10/27/26

    Round trip

    Economy

    from
    $428Fare subject to changes
    Updated: 2 hours ago

    Chicago (ORD)to

    Santiago, DR (STI)
    10/23/26 - 10/30/26

    Round trip

    Economy

    from
    $428Fare 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 Santiago, DR

    Looking for lower fares on your trip from Chicago to Santiago, DR? 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 Santiago, DR