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

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

Aug 2026
From$890*
Updated: 6 hours ago
Round tripIEconomy
Sep 2026
From$665*
Updated: 4 hours ago
Round tripIEconomy
Oct 2026
From$665*
Updated: 6 hours ago
Round tripIEconomy
cmp-daily-histogram-bars-legend-min-price-aria-label $665
cmp-daily-histogram-bars-legend-max-price-aria-label $3.1K
Displaying fares for August-2026
  • CHI–SXM: cmp-view-offers-disclaimer. Find Offers
    23

    Su

    AUG

  • ORD–SXM, 08/24/26 – 08/31/26: From $3,101
    24

    Mo

  • CHI–SXM, 08/25/26 – 09/01/26: From $1,185
    25

    Tu

  • ORD–SXM, 08/26/26 – 09/02/26: From $990
    26

    We

  • ORD–SXM, 08/27/26 – 09/03/26: From $985
    27

    Th

  • CHI–SXM, 08/28/26 – 09/04/26: From $985
    28

    Fr

  • ORD–SXM, 08/29/26 – 09/05/26: From $985
    29

    Sa

  • ORD–SXM, 08/30/26 – 09/06/26: From $895
    30

    Su

  • ORD–SXM, 08/31/26 – 09/07/26: From $890
    31

    Mo

  • CHI–SXM, 09/01/26 – 09/08/26: From $890
    01

    Tu

    SEP

  • ORD–SXM, 09/02/26 – 09/09/26: From $1,494
    02

    We

  • CHI–SXM, 09/03/26 – 09/10/26: From $890
    03

    Th

  • ORD–SXM, 09/04/26 – 09/11/26: From $890
    04

    Fr

  • CHI–SXM, 09/05/26 – 09/12/26: From $890
    05

    Sa

  • ORD–SXM, 09/06/26 – 09/13/26: From $805
    06

    Su

  • ORD–SXM, 09/07/26 – 09/14/26: From $800
    07

    Mo

  • ORD–SXM, 09/08/26 – 09/15/26: From $800
    08

    Tu

  • ORD–SXM, 09/09/26 – 09/16/26: From $805
    09

    We

  • ORD–SXM, 09/10/26 – 09/17/26: From $800
    10

    Th

  • CHI–SXM, 09/11/26 – 09/18/26: From $800
    11

    Fr

  • CHI–SXM, 09/12/26 – 09/19/26: From $800
    12

    Sa

  • ORD–SXM, 09/13/26 – 09/20/26: From $800
    13

    Su

  • CHI–SXM, 09/14/26 – 09/21/26: From $710
    14

    Mo

  • ORD–SXM, 09/15/26 – 09/22/26: From $750
    15

    Tu

  • CHI–SXM, 09/16/26 – 09/23/26: From $715
    16

    We

  • CHI–SXM, 09/17/26 – 09/24/26: From $710
    17

    Th

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

    Fr

  • ORD–SXM, 09/19/26 – 09/26/26: From $710
    19

    Sa

  • ORD–SXM, 09/20/26 – 09/27/26: From $670
    20

    Su

  • CHI–SXM, 09/21/26 – 09/28/26: From $705
    21

    Mo

  • ORD–SXM, 09/22/26 – 09/29/26: From $665
    22

    Tu

    • range$665-$3,101

    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)
    12/12/26 - 12/19/26

    Round trip

    Economy

    from
    $650Fare subject to changes
    Updated: 6 hours ago

    Chicago (ORD)to

    St. Maarten/St. Martin (SXM)
    11/28/26 - 12/05/26

    Round trip

    Economy

    from
    $655Fare subject to changes
    Updated: 6 hours ago

    Chicago (ORD)to

    St. Maarten/St. Martin (SXM)
    10/31/26 - 11/07/26

    Round trip

    Economy

    from
    $665Fare subject to changes
    Updated: 6 hours ago

    Chicago (ORD)to

    St. Maarten/St. Martin (SXM)
    10/01/26 - 10/08/26

    Round trip

    Economy

    from
    $665Fare subject to changes
    Updated: 6 hours ago

    Chicago (ORD)to

    St. Maarten/St. Martin (SXM)
    10/02/26 - 10/09/26

    Round trip

    Economy

    from
    $665Fare subject to changes
    Updated: 6 hours ago

    Chicago (ORD)to

    St. Maarten/St. Martin (SXM)
    10/09/26 - 10/16/26

    Round trip

    Economy

    from
    $665Fare subject to changes
    Updated: 6 hours ago

    Chicago (ORD)to

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

    Round trip

    Economy

    from
    $665Fare subject to changes
    Updated: 6 hours ago

    Chicago (ORD)to

    St. Maarten/St. Martin (SXM)
    10/16/26 - 10/23/26

    Round trip

    Economy

    from
    $665Fare 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

    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 St. Maarten/St. Martin