American Airlines flights from Chicago to St. Maarten/St. Martin

Recent searches for flights from Chicago to St. Maarten/St. Martin

Sep 2026
From$659*
Updated: 6 hours ago
Round tripIEconomy
Oct 2026
From$559*
Updated: 6 hours ago
Round tripIEconomy
Nov 2026
From$559*
Updated: 6 hours ago
Round tripIEconomy
cmp-daily-histogram-bars-legend-min-price-aria-label $559
cmp-daily-histogram-bars-legend-max-price-aria-label $2.2K
Displaying fares for September-2026
  • ORD–SXM: cmp-view-offers-disclaimer. Find Offers
    12

    Sa

    SEP

  • ORD–SXM, 09/13/26 – 09/20/26: From $986
    13

    Su

  • ORD–SXM, 09/14/26 – 09/21/26: From $1,013
    14

    Mo

  • ORD–SXM, 09/15/26 – 09/22/26: From $2,240
    15

    Tu

  • ORD–SXM, 09/16/26 – 09/23/26: From $784
    16

    We

  • ORD–SXM, 09/17/26 – 09/24/26: From $871
    17

    Th

  • ORD–SXM, 09/18/26 – 09/25/26: From $871
    18

    Fr

  • ORD–SXM, 09/19/26 – 09/26/26: From $821
    19

    Sa

  • ORD–SXM, 09/20/26 – 09/27/26: From $826
    20

    Su

  • ORD–SXM, 09/21/26 – 09/28/26: From $821
    21

    Mo

  • ORD–SXM, 09/22/26 – 09/29/26: From $1,131
    22

    Tu

  • ORD–SXM, 09/23/26 – 09/30/26: From $1,063
    23

    We

  • ORD–SXM, 09/24/26 – 10/01/26: From $762
    24

    Th

  • ORD–SXM, 09/25/26 – 10/02/26: From $762
    25

    Fr

  • ORD–SXM, 09/26/26 – 10/03/26: From $667
    26

    Sa

  • ORD–SXM, 09/27/26 – 10/04/26: From $672
    27

    Su

  • ORD–SXM, 09/28/26 – 10/05/26: From $667
    28

    Mo

  • ORD–SXM, 09/29/26 – 10/06/26: From $659
    29

    Tu

  • ORD–SXM, 09/30/26 – 10/07/26: From $985
    30

    We

  • ORD–SXM, 10/01/26 – 10/08/26: From $712
    01

    Th

    OCT

  • ORD–SXM, 10/02/26 – 10/09/26: From $712
    02

    Fr

  • ORD–SXM, 10/03/26 – 10/10/26: From $604
    03

    Sa

  • ORD–SXM, 10/04/26 – 10/11/26: From $609
    04

    Su

  • ORD–SXM, 10/05/26 – 10/12/26: From $604
    05

    Mo

  • ORD–SXM, 10/06/26 – 10/13/26: From $559
    06

    Tu

  • ORD–SXM, 10/07/26 – 10/14/26: From $564
    07

    We

  • ORD–SXM, 10/08/26 – 10/15/26: From $667
    08

    Th

  • ORD–SXM, 10/09/26 – 10/16/26: From $684
    09

    Fr

  • ORD–SXM, 10/10/26 – 10/17/26: From $604
    10

    Sa

  • ORD–SXM, 10/11/26 – 10/16/26: From $559
    11

    Su

    • range$559-$2,240

    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 St. Maarten/St. Martin flights

    $
    keyboard_arrow_down

    Chicago (ORD)to

    St. Maarten/St. Martin (SXM)
    10/27/26 - 11/03/26

    Round trip

    Economy

    from
    $559Fare subject to changes
    Updated: 6 hours ago

    Chicago (ORD)to

    St. Maarten/St. Martin (SXM)
    11/10/26 - 11/17/26

    Round trip

    Economy

    from
    $559Fare subject to changes
    Updated: 6 hours ago

    Chicago (ORD)to

    St. Maarten/St. Martin (SXM)
    10/06/26 - 10/13/26

    Round trip

    Economy

    from
    $559Fare subject to changes
    Updated: 6 hours ago

    Chicago (ORD)to

    St. Maarten/St. Martin (SXM)
    10/13/26 - 10/20/26

    Round trip

    Economy

    from
    $559Fare subject to changes
    Updated: 6 hours ago

    Chicago (ORD)to

    St. Maarten/St. Martin (SXM)
    10/20/26 - 10/27/26

    Round trip

    Economy

    from
    $559Fare subject to changes
    Updated: 6 hours ago

    Chicago (ORD)to

    St. Maarten/St. Martin (SXM)
    11/03/26 - 11/10/26

    Round trip

    Economy

    from
    $559Fare subject to changes
    Updated: 6 hours ago

    Chicago (ORD)to

    St. Maarten/St. Martin (SXM)
    10/18/26 - 10/23/26

    Round trip

    Economy

    from
    $559Fare subject to changes
    Updated: 20 hours ago

    Chicago (ORD)to

    St. Maarten/St. Martin (SXM)
    11/11/26 - 11/18/26

    Round trip

    Economy

    from
    $564Fare subject to changes
    Updated: 6 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 St. Maarten/St. Martin

    Looking for lower fares on your trip from Chicago to St. Maarten/St. Martin? 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

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    • 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 St. Maarten/St. Martin