American Airlines flights from Chicago to Santiago, DR

Recent searches for flights from Chicago to Santiago, DR

Sep 2026
From$436*
Updated: 2 hours ago
Round tripIEconomy
Oct 2026
From$436*
Updated: 1 hour ago
Round tripIEconomy
Nov 2026
From$436*
Updated: 1 hour ago
Round tripIEconomy
cmp-daily-histogram-bars-legend-min-price-aria-label $436
cmp-daily-histogram-bars-legend-max-price-aria-label $1.5K
Displaying fares for September-2026
  • CHI–STI, 09/02/26 – 09/09/26: From $814
    02

    We

    SEP

  • ORD–STI, 09/03/26 – 09/10/26: From $869
    03

    Th

  • ORD–STI, 09/04/26 – 09/11/26: From $859
    04

    Fr

  • ORD–STI, 09/05/26 – 09/12/26: From $974
    05

    Sa

  • ORD–STI, 09/06/26 – 09/13/26: From $1,512
    06

    Su

  • ORD–STI, 09/07/26 – 09/14/26: From $889
    07

    Mo

  • CHI–STI, 09/08/26 – 09/15/26: From $715
    08

    Tu

  • ORD–STI, 09/09/26 – 09/16/26: From $720
    09

    We

  • CHI–STI, 09/10/26 – 09/17/26: From $710
    10

    Th

  • CHI–STI, 09/11/26 – 09/18/26: From $710
    11

    Fr

  • ORD–STI, 09/12/26 – 09/19/26: From $924
    12

    Sa

  • ORD–STI, 09/13/26 – 09/20/26: From $929
    13

    Su

  • ORD–STI, 09/14/26 – 09/21/26: From $844
    14

    Mo

  • ORD–STI, 09/15/26 – 09/22/26: From $666
    15

    Tu

  • ORD–STI, 09/16/26 – 09/23/26: From $671
    16

    We

  • ORD–STI, 09/17/26 – 09/24/26: From $671
    17

    Th

  • CHI–STI, 09/18/26 – 09/25/26: From $710
    18

    Fr

  • ORD–STI, 09/19/26 – 09/26/26: From $850
    19

    Sa

  • ORD–STI, 09/20/26 – 09/27/26: From $855
    20

    Su

  • ORD–STI, 09/21/26 – 09/25/26: From $661
    21

    Mo

  • CHI–STI, 09/22/26 – 09/29/26: From $595
    22

    Tu

  • ORD–STI, 09/23/26 – 09/30/26: From $600
    23

    We

  • CHI–STI, 09/24/26 – 10/01/26: From $556
    24

    Th

  • CHI–STI, 09/25/26 – 10/02/26: From $639
    25

    Fr

  • CHI–STI, 09/26/26 – 10/03/26: From $781
    26

    Sa

  • ORD–STI, 09/27/26 – 10/04/26: From $781
    27

    Su

  • ORD–STI, 09/28/26 – 10/05/26: From $726
    28

    Mo

  • ORD–STI, 09/29/26 – 10/06/26: From $436
    29

    Tu

  • CHI–STI, 09/30/26 – 10/07/26: From $441
    30

    We

  • ORD–STI, 10/01/26 – 10/08/26: From $493
    01

    Th

    OCT

    • range$436-$1,512

    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)
    10/20/26 - 10/27/26

    Round trip

    Economy

    from
    $436Fare subject to changes
    Updated: 2 hours ago

    Chicago (ORD)to

    Santiago, DR (STI)
    12/01/26 - 12/08/26

    Round trip

    Economy

    from
    $436Fare subject to changes
    Updated: 2 hours ago

    Chicago (ORD)to

    Santiago, DR (STI)
    12/03/26 - 12/10/26

    Round trip

    Economy

    from
    $436Fare subject to changes
    Updated: 2 hours ago

    Chicago (ORD)to

    Santiago, DR (STI)
    09/29/26 - 10/06/26

    Round trip

    Economy

    from
    $436Fare subject to changes
    Updated: 2 hours ago

    Chicago (ORD)to

    Santiago, DR (STI)
    11/17/26 - 11/24/26

    Round trip

    Economy

    from
    $436Fare subject to changes
    Updated: 2 hours ago

    Chicago (ORD)to

    Santiago, DR (STI)
    11/24/26 - 12/01/26

    Round trip

    Economy

    from
    $436Fare subject to changes
    Updated: 2 hours ago

    Chicago (ORD)to

    Santiago, DR (STI)
    10/06/26 - 10/13/26

    Round trip

    Economy

    from
    $436Fare subject to changes
    Updated: 2 hours ago

    Chicago (ORD)to

    Santiago, DR (STI)
    10/29/26 - 11/05/26

    Round trip

    Economy

    from
    $436Fare 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