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Vacations from Chicago to Hilton Head Island

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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 15, 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 Hilton Head Island

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  1. 3 night stay

    Marriott's SurfWatch

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    ORD - HHH
    9/24/2020 - 9/27/2020
    from
    $939*
    per person

  2. 3 night stay

    Bluewater Resort & Marina by Spinnaker Resorts

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    ORD - HHH
    9/24/2020 - 9/27/2020
    from
    $560*
    per person

  3. 3 night stay

    Omni Hilton Head Oceanfront Resort

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    ORD - HHH
    9/24/2020 - 9/27/2020
    from
    $647*
    per person

  4. 3 night stay

    Marriott's Harbour Point and Sunset Pointe at Shelter Cove

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    ORD - HHH
    9/24/2020 - 9/27/2020
    from
    $694*
    per person

  5. 3 night stay

    Ocean Oak Resort By Hilton Grand Vacations

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    ORD - HHH
    9/24/2020 - 9/27/2020
    from
    $734*
    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 Hilton Head Island

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  1. 7 night stay

    Bluewater Resort & Marina by Spinnaker Resorts

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    ORD - HHH
    7/05/2020 - 7/12/2020
    from
    $1,404*
    per person

  2. 7 night stay

    Omni Hilton Head Oceanfront Resort

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    ORD - HHH
    7/05/2020 - 7/12/2020
    from
    $1,540*
    per person

  3. 7 night stay

    Sonesta Resort Hilton Head Island

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    ORD - HHH
    7/05/2020 - 7/12/2020
    from
    $1,723*
    per person

  4. 7 night stay

    Marriott's Harbour Point and Sunset Pointe at Shelter Cove

    gradegradegradegradegradegradegradegradegradegrade
    ORD - HHH
    7/05/2020 - 7/12/2020
    from
    $2,387*
    per person

  5. 7 night stay

    Ocean Oak Resort By Hilton Grand Vacations

    gradegradegradegradegradegradegradegradegradegrade
    ORD - HHH
    7/05/2020 - 7/12/2020
    from
    $2,926*
    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 Hilton Head Island

Weather in Hilton Head Island

Monday scattered clouds
79°F 3/30/2020
Tuesday moderate rain
71°F 3/31/2020
Wednesday broken clouds
62°F 4/01/2020
Thursday overcast clouds
67°F 4/02/2020
Friday sky is clear
71°F 4/03/2020
Saturday overcast clouds
71°F 4/04/2020
Sunday light rain
73°F 4/05/2020
Powered by: OpenWeatherMap.org

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