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Vacations from Chicago to St. Maarten

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7night(s)
Hilton Vacation Club Flamingo Beach St. Maarten
-
Chicago (ORD) To St. Maarten (SXM)
Flight+Hotel
from
$1,222 cmp-price-disclaimer
Per person based on 2-person occupancy
Updated:20 hours ago
7night(s)
Port de Plaisance Resort, Trademark Collection by
-
Chicago (ORD) To St. Maarten (SXM)
Flight+Hotel
from
$1,305 cmp-price-disclaimer
Per person based on 2-person occupancy
Updated:20 hours ago
7night(s)
Hilton Vacation Club Royal Palm St. Maarten
-
Chicago (ORD) To St. Maarten (SXM)
Flight+Hotel
from
$1,408 cmp-price-disclaimer
Per person based on 2-person occupancy
Updated:20 hours ago
7night(s)
Royal Islander Resort La Terrasse
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Chicago (ORD) To St. Maarten (SXM)
Flight+Hotel
from
$1,471 cmp-price-disclaimer
Per person based on 2-person occupancy
Updated:20 hours ago
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*Average total price per person based on round trip flights in the Main Cabin and double occupancy hotel stays. Prices displayed have been collected within the last 24 hrs and may no longer be available at time of booking. Modifying this information may result in a different price. To find the most updated price, please visit aavacations.com.
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Discover our best deals from Chicago to St. Maarten

$

  • 4 night stay

    Sonesta Ocean Point Resort Adults Only

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    ORD - SXM
    1/15/2026 - 1/19/2026
    from
    $1,794*
    per person based on 2-person occupancy
    Updated:12hoursago

  • 4 night stay

    Jw Marriott St. Maarten Beach Resort & Spa

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    ORD - SXM
    1/15/2026 - 1/19/2026
    from
    $2,141*
    per person based on 2-person occupancy
    Updated:12hoursago

  • 4 night stay

    Palm Court

    gradegradegradegradegradegradegradegradegradegrade
    ORD - SXM
    1/15/2026 - 1/19/2026
    from
    $1,222*
    per person based on 2-person occupancy
    Updated:12hoursago

  • 4 night stay

    Esmeralda Resort

    gradegradegradegradegradegradegradegradegradegrade
    ORD - SXM
    1/15/2026 - 1/19/2026
    from
    $1,304*
    per person based on 2-person occupancy
    Updated:12hoursago

  • 4 night stay

    Royal Islander Resort La Terrasse

    gradegradegradegradegradegradegradegradegradegrade
    ORD - SXM
    1/15/2026 - 1/19/2026
    from
    $1,332*
    per person based on 2-person occupancy
    Updated:12hoursago

    • *Average total price per person based on round trip flights in the Main Cabin and double occupancy hotel stays. Prices displayed have been collected within the last 24 hrs and may no longer be available at time of booking. Modifying this information may result in a different price. To find the most updated price, please visit aavacations.com.

    Vacations from Chicago to St. Maarten

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