Skip to main content
  1. Home keyboard_arrow_right
  2. American Airlines Vacations packages keyboard_arrow_right
  3. United States vacations keyboard_arrow_right
  4. Chicago - Orlando vacations keyboard_arrow_right

Vacations from Chicago to Orlando

Choose 2 or more:

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

Enter to select travel class and passengers

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

2-5 night deals from Chicago to Orlando

em-cmp-fare-cards-see-allemail

  1. 3 night stay

    Cypress Pointe Resort by Diamond Resorts

    gradegradegradegradegradegradegradegradegradegrade
    ORD - MCO
    10/22/2020 - 10/25/2020
    from
    $231*
    per person based on 2-person occupancy

  2. 3 night stay

    Crowne Plaza Orlando - Universal Blvd

    gradegradegradegradegradegradegradegradegradegrade
    ORD - MCO
    10/22/2020 - 10/25/2020
    from
    $233*
    per person based on 2-person occupancy

  3. 3 night stay

    Maingate Lakeside Resort

    gradegradegradegradegradegradegradegradegradegrade
    ORD - MCO
    10/22/2020 - 10/25/2020
    from
    $173*
    per person based on 2-person occupancy

  4. 3 night stay

    Monumental Movieland

    gradegradegradegradegradegradegradegradegradegrade
    ORD - MCO
    10/22/2020 - 10/25/2020
    from
    $175*
    per person based on 2-person occupancy

  5. 3 night stay

    Monumental Hotel Orlando

    gradegradegradegradegradegradegradegradegradegrade
    ORD - MCO
    10/22/2020 - 10/25/2020
    from
    $179*
    per person based on 2-person occupancy

*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.

6-10 night deals from Chicago to Orlando

em-cmp-fare-cards-see-allemail

  1. 7 night stay

    Cypress Pointe Resort by Diamond Resorts

    gradegradegradegradegradegradegradegradegradegrade
    ORD - MCO
    10/24/2020 - 10/31/2020
    from
    $380*
    per person based on 2-person occupancy

  2. 7 night stay

    Crowne Plaza Orlando - Universal Blvd

    gradegradegradegradegradegradegradegradegradegrade
    ORD - MCO
    10/24/2020 - 10/31/2020
    from
    $398*
    per person based on 2-person occupancy

  3. 7 night stay

    Grande Villas Resort by Diamond Resorts

    gradegradegradegradegradegradegradegradegradegrade
    ORD - MCO
    10/24/2020 - 10/31/2020
    from
    $425*
    per person based on 2-person occupancy

  4. 7 night stay

    Castle Hotel, Autograph Collection

    gradegradegradegradegradegradegradegradegradegrade
    ORD - MCO
    10/24/2020 - 10/31/2020
    from
    $452*
    per person based on 2-person occupancy

  5. 7 night stay

    Maingate Lakeside Resort

    gradegradegradegradegradegradegradegradegradegrade
    ORD - MCO
    10/24/2020 - 10/31/2020
    from
    $251*
    per person based on 2-person occupancy

*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

Wednesday overcast clouds
79°F 9/30/2020
Thursday few clouds
85°F 10/01/2020
Friday overcast clouds
83°F 10/02/2020
Saturday overcast clouds
77°F 10/03/2020
Sunday moderate rain
74°F 10/04/2020
Monday light rain
79°F 10/05/2020
Tuesday light rain
88°F 10/06/2020
Powered by: OpenWeatherMap.org

You may also like...