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Vacations from Chicago to Sarasota

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5night(s)
Legacy Hotel At IMG Academy
-
Chicago (ORD) To Sarasota (SRQ)
Flight+Hotel
from
$1,324 cmp-price-disclaimer
Per person based on 2-person occupancy
Updated:14 hours ago
5night(s)
DoubleTree by Hilton Sarasota Bradenton Airport
-
Chicago (ORD) To Sarasota (SRQ)
Flight+Hotel
from
$1,423 cmp-price-disclaimer
Per person based on 2-person occupancy
Updated:14 hours ago
5night(s)
The Sarasota Modern, A Tribute Portfolio Hotel
-
Chicago (ORD) To Sarasota (SRQ)
Flight+Hotel
from
$1,519 cmp-price-disclaimer
Per person based on 2-person occupancy
Updated:14 hours ago
5night(s)
Compass Hotel Anna Maria Sound
-
Chicago (ORD) To Sarasota (SRQ)
Flight+Hotel
from
$1,593 cmp-price-disclaimer
Per person based on 2-person occupancy
Updated:14 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 Sarasota

$

  • 3 night stay

    The Ritz-Carlton, Sarasota

    gradegradegradegradegradegradegradegradegradegrade
    ORD - SRQ
    2/06/2025 - 2/09/2025
    from
    $1,344*
    per person based on 2-person occupancy
    Updated:15hoursago

  • 3 night stay

    DoubleTree by Hilton Sarasota Bradenton Airport

    gradegradegradegradegradegradegradegradegradegrade
    ORD - SRQ
    2/06/2025 - 2/09/2025
    from
    $682*
    per person based on 2-person occupancy
    Updated:15hoursago

  • 3 night stay

    Legacy Hotel At IMG Academy

    gradegradegradegradegradegradegradegradegradegrade
    ORD - SRQ
    2/06/2025 - 2/09/2025
    from
    $869*
    per person based on 2-person occupancy
    Updated:15hoursago

  • 3 night stay

    Hyatt Regency Clearwater Beach Resort and Spa

    gradegradegradegradegradegradegradegradegradegrade
    ORD - SRQ
    2/06/2025 - 2/09/2025
    from
    $919*
    per person based on 2-person occupancy
    Updated:15hoursago

  • 3 night stay

    The Sarasota Modern, A Tribute Portfolio Hotel

    gradegradegradegradegradegradegradegradegradegrade
    ORD - SRQ
    2/06/2025 - 2/09/2025
    from
    $997*
    per person based on 2-person occupancy
    Updated:15hoursago

    • *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 Sarasota

    Weather in Sarasota

    Friday light rain
    64°F 1/17/2025
    Saturday light rain
    73°F 1/18/2025
    Sunday moderate rain
    76°F 1/19/2025
    Monday broken clouds
    52°F 1/20/2025
    Tuesday light rain
    55°F 1/21/2025
    Wednesday light rain
    63°F 1/22/2025
    Thursday light rain
    60°F 1/23/2025
    Powered by: OpenWeatherMap.org

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