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Vacations from Chicago to Orlando

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Change fee waiver

If you purchase an American Airlines Vacations package between March 1, 2020 at 9 a.m. CT and April 30, 2020 at 11:59 p.m. CT, you may change your trip once without paying a change fee. Changes must be made prior to the departure of your original flight. Any difference in fare or hotel rate will apply. For complete terms, click here

2-5 night deals from Chicago to Orlando

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  1. 4 night stay

    Radisson Lake Buena Vista

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    ORD - MCO
    7/18/2020 - 7/22/2020
    from
    $267*
    per person

  2. 4 night stay

    Rosen Inn Pointe Orlando

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    ORD - MCO
    7/18/2020 - 7/22/2020
    from
    $200*
    per person

  3. 4 night stay

    Cypress Pointe Resort by Diamond Resorts

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    ORD - MCO
    7/18/2020 - 7/22/2020
    from
    $264*
    per person

  4. 4 night stay

    Ramada by Wyndham Kissimmee Gateway

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    ORD - MCO
    7/18/2020 - 7/22/2020
    from
    $172*
    per person

  5. 4 night stay

    Champions World Resort

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    ORD - MCO
    7/18/2020 - 7/22/2020
    from
    $173*
    per person

*Average total price per person based on round trip flights in the Main Cabin and double occupancy hotel stays

6-10 night deals from Chicago to Orlando

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  1. 8 night stay

    Hilton Grand Vacations at Tuscany Village

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    ORD - MCO
    12/24/2020 - 1/01/2021
    from
    $792*
    per person

  2. 8 night stay

    Hyatt Regency Orlando

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    ORD - MCO
    12/24/2020 - 1/01/2021
    from
    $846*
    per person

  3. 8 night stay

    Rosen Inn Pointe Orlando

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    ORD - MCO
    12/24/2020 - 1/01/2021
    from
    $588*
    per person

  4. 8 night stay

    Rosen Centre Resort

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    ORD - MCO
    12/24/2020 - 1/01/2021
    from
    $720*
    per person

  5. 8 night stay

    Hilton Grand Vacations at SeaWorld

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    ORD - MCO
    12/24/2020 - 1/01/2021
    from
    $851*
    per person

*Average total price per person based on round trip flights in the Main Cabin and double occupancy hotel stays

Vacations from Chicago to Orlando

Weather in Orlando

Wednesday sky is clear
76°F 4/01/2020
Thursday sky is clear
78°F 4/02/2020
Friday sky is clear
82°F 4/03/2020
Saturday sky is clear
83°F 4/04/2020
Sunday light rain
77°F 4/05/2020
Monday light rain
69°F 4/06/2020
Tuesday light rain
86°F 4/07/2020
Powered by: OpenWeatherMap.org

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