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Vacations from Chicago to Orlando

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5night(s)
Hotel Landy Orlando Universal Blvd Tribute
-
Chicago (ORD) To Orlando (MCO)
Flight+Hotel
from
$540 cmp-price-disclaimer
Per person based on 2-person occupancy
Updated:9 hours ago
5night(s)
Melia Orlando Suite Hotel at Celebration
-
Chicago (ORD) To Orlando (MCO)
Flight+Hotel
from
$561 cmp-price-disclaimer
Per person based on 2-person occupancy
Updated:9 hours ago
5night(s)
Sheraton Vistana Villages
-
Chicago (ORD) To Orlando (MCO)
Flight+Hotel
from
$607 cmp-price-disclaimer
Per person based on 2-person occupancy
Updated:9 hours ago
5night(s)
Hyatt Regency Grand Cypress
-
Chicago (ORD) To Orlando (MCO)
Flight+Hotel
from
$654 cmp-price-disclaimer
Per person based on 2-person occupancy
Updated:9 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 Orlando

$

  • 5 night stay

    Four Seasons at Walt Disney World

    gradegradegradegradegradegradegradegradegradegrade
    ORD - MCO
    10/29/2025 - 11/03/2025
    from
    $4,160*
    per person based on 2-person occupancy
    Updated:9hoursago

  • 5 night stay

    Hyatt Regency Orlando

    gradegradegradegradegradegradegradegradegradegrade
    ORD - MCO
    10/29/2025 - 11/03/2025
    from
    $856*
    per person based on 2-person occupancy
    Updated:9hoursago

  • 5 night stay

    Loews Portofino Bay Hotel at Universal Orlando

    gradegradegradegradegradegradegradegradegradegrade
    ORD - MCO
    10/29/2025 - 11/03/2025
    from
    $2,400*
    per person based on 2-person occupancy
    Updated:9hoursago

  • 5 night stay

    Universal Helios Grand Hotel, a Loews Hotel

    gradegradegradegradegradegradegradegradegradegrade
    ORD - MCO
    10/29/2025 - 11/03/2025
    from
    $2,437*
    per person based on 2-person occupancy
    Updated:9hoursago

  • 5 night stay

    Hotel Landy Orlando Universal Blvd Tribute

    gradegradegradegradegradegradegradegradegradegrade
    ORD - MCO
    10/29/2025 - 11/03/2025
    from
    $540*
    per person based on 2-person occupancy
    Updated:9hoursago

    • *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 Orlando

    Weather in Orlando

    Tuesday light rain
    84°F 7/01/2025
    Wednesday light rain
    91°F 7/02/2025
    Thursday moderate rain
    81°F 7/03/2025
    Friday light rain
    92°F 7/04/2025
    Saturday moderate rain
    86°F 7/05/2025
    Sunday light rain
    92°F 7/06/2025
    Monday light rain
    94°F 7/07/2025
    Powered by: OpenWeatherMap.org

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