Flights from Chicago to Hilton Head Island from $ 269*

Promotion Code

Featured daily fares for flights from Chicago (ORD) to Hilton Head Island (HHH)

$ 269
$ 873
Displaying fares for March-2026
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  • Range$ 269-$ 873

    More United deals on Chicago (ORD) to Hilton Head Island (HHH) flights

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    More United deals on Chicago (ORD) to Hilton Head Island (HHH) flights
    From
    To
    Fare Type
    Dates
    Price
    Chicago (ORD)Hilton Head Island (HHH)Roundtrip
    |
    Economy
    06/19/26 - 06/22/26

    from

    $ 269

    Viewed: 22 hours ago

    Chicago (ORD)Hilton Head Island (HHH)Roundtrip
    |
    Economy
    06/19/26 - 06/23/26

    from

    $ 269

    Viewed: 22 hours ago

    Chicago (ORD)Hilton Head Island (HHH)Roundtrip
    |
    Economy
    06/02/26 - 06/09/26

    from

    $ 269

    Viewed: 22 hours ago

    Chicago (ORD)Hilton Head Island (HHH)Roundtrip
    |
    Economy
    06/03/26 - 06/10/26

    from

    $ 269

    Viewed: 22 hours ago

    Chicago (ORD)Hilton Head Island (HHH)Roundtrip
    |
    Economy
    06/11/26 - 06/18/26

    from

    $ 269

    Viewed: 22 hours ago

    Chicago (ORD)Hilton Head Island (HHH)Roundtrip
    |
    Economy
    04/18/26 - 04/22/26

    from

    $ 269

    Viewed: 22 hours ago

    Chicago (ORD)Hilton Head Island (HHH)Roundtrip
    |
    Economy
    06/08/26 - 06/15/26

    from

    $ 269

    Viewed: 22 hours ago

    Chicago (ORD)Hilton Head Island (HHH)Roundtrip
    |
    Economy
    06/15/26 - 06/22/26

    from

    $ 269

    Viewed: 22 hours ago

    *Prices have been available for round trips within the last 48 hours and may not be currently available. For Economy class, fares listed may be Basic Economy, which is our most restrictive fare option and subject to additional restrictions. Additional baggage charges and fees for other optional service may apply. Other terms and conditions may apply. Schedules are subject to change without notice.