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1 Hilton Head Island to Caribbean. 2  Hilton Head Island to United States. 3  Hilton Head Island to Mexico. 4  US Airways. 5  Delta Air Lines.  Charlotte.
Hilton Head Island Weather in October. The weather cools down during October at Hilton Head Island in South Carolina. This means that most days this month are pleasantly warm. This page gives detailed information on the typical October weather for Hilton Head Island.