Skip to main content

Vacations from Chicago to St. Thomas

cmp-clean-button-action-description-origin
cmp-clean-button-action-description-destination
Disclaimer
Advanced search
Bag and optional fees
Changes to checked bag fees and allowances

Choose 2 or more:

Please check if you want to include it in the search.

Enter to select travel class and passengers


Changes to checked bag fees and allowances Opens external site in a new window

Discover our best deals from Chicago to St. Thomas

$

  • 4 night stay

    The Westin Beach Resort & Spa at Frenchman's Reef

    gradegradegradegradegradegradegradegradegradegrade
    ORD - STT
    7/23/2025 - 7/27/2025
    from
    $1,538*
    per person based on 2-person occupancy
    Updated:11hoursago

  • 4 night stay

    The Ritz-Carlton, St. Thomas

    gradegradegradegradegradegradegradegradegradegrade
    ORD - STT
    7/23/2025 - 7/27/2025
    from
    $2,178*
    per person based on 2-person occupancy
    Updated:11hoursago

  • 4 night stay

    Morningstar Buoy Haus Beach Resort At Frenchman's Reef, Autograph Collection

    gradegradegradegradegradegradegradegradegradegrade
    ORD - STT
    7/23/2025 - 7/27/2025
    from
    $2,166*
    per person based on 2-person occupancy
    Updated:11hoursago

  • 4 night stay

    The Westin St. John Resort Villas

    gradegradegradegradegradegradegradegradegradegrade
    ORD - STT
    7/23/2025 - 7/27/2025
    from
    $2,171*
    per person based on 2-person occupancy
    Updated:11hoursago

  • 4 night stay

    Marriott's Frenchman's Cove

    gradegradegradegradegradegradegradegradegradegrade
    ORD - STT
    7/23/2025 - 7/27/2025
    from
    $2,311*
    per person based on 2-person occupancy
    Updated:11hoursago

    • *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. Thomas

    Weather in St. Thomas

    Friday light rain
    80°F 1/17/2025
    Saturday light rain
    79°F 1/18/2025
    Sunday light rain
    80°F 1/19/2025
    Monday light rain
    80°F 1/20/2025
    Tuesday light rain
    80°F 1/21/2025
    Wednesday light rain
    80°F 1/22/2025
    Thursday light rain
    80°F 1/23/2025
    Powered by: OpenWeatherMap.org

    You may also like...