American Airlines flights from Hilton Head Island to Chicago

Recent searches for flights from Hilton Head Island to Chicago

Aug 2026
From$462*
Updated: 4 hours ago
Round tripIEconomy
Sep 2026
From$319*
Updated: 4 hours ago
Round tripIEconomy
Oct 2026
From$309*
Updated: 4 hours ago
Round tripIEconomy
cmp-daily-histogram-bars-legend-min-price-aria-label $319
cmp-daily-histogram-bars-legend-max-price-aria-label $669
Displaying fares for August-2026
  • HHH–ORD: cmp-view-offers-disclaimer. Find Offers
    30

    Su

    AUG

  • HHH–ORD, 08/31/26 – 09/07/26: From $462
    31

    Mo

  • HHH–ORD, 09/01/26 – 09/08/26: From $424
    01

    Tu

    SEP

  • HHH–ORD, 09/02/26 – 09/09/26: From $434
    02

    We

  • HHH–ORD, 09/03/26 – 09/10/26: From $525
    03

    Th

  • HHH–ORD, 09/04/26 – 09/11/26: From $620
    04

    Fr

  • HHH–ORD, 09/05/26 – 09/12/26: From $359
    05

    Sa

  • HHH–ORD, 09/06/26 – 09/13/26: From $369
    06

    Su

  • HHH–ORD, 09/07/26 – 09/14/26: From $669
    07

    Mo

  • HHH–ORD, 09/08/26 – 09/15/26: From $409
    08

    Tu

  • HHH–ORD, 09/09/26 – 09/16/26: From $379
    09

    We

  • HHH–ORD, 09/10/26 – 09/17/26: From $486
    10

    Th

  • HHH–ORD, 09/11/26 – 09/18/26: From $454
    11

    Fr

  • HHH–ORD, 09/12/26 – 09/19/26: From $409
    12

    Sa

  • HHH–ORD, 09/13/26 – 09/20/26: From $576
    13

    Su

  • HHH–ORD, 09/14/26 – 09/21/26: From $414
    14

    Mo

  • HHH–ORD, 09/15/26 – 09/22/26: From $339
    15

    Tu

  • HHH–ORD, 09/16/26 – 09/23/26: From $339
    16

    We

  • HHH–ORD, 09/17/26 – 09/24/26: From $466
    17

    Th

  • HHH–ORD, 09/18/26 – 09/25/26: From $509
    18

    Fr

  • HHH–ORD, 09/19/26 – 09/26/26: From $389
    19

    Sa

  • HHH–ORD, 09/20/26 – 09/27/26: From $414
    20

    Su

  • HHH–ORD, 09/21/26 – 09/28/26: From $339
    21

    Mo

  • HHH–ORD, 09/22/26 – 09/29/26: From $319
    22

    Tu

  • HHH–ORD, 09/23/26 – 09/30/26: From $339
    23

    We

  • HHH–ORD, 09/24/26 – 10/01/26: From $512
    24

    Th

  • HHH–ORD, 09/25/26 – 10/02/26: From $319
    25

    Fr

  • HHH–ORD, 09/26/26 – 10/03/26: From $419
    26

    Sa

  • HHH–ORD: cmp-view-offers-disclaimer. Find Offers
    27

    Su

  • HHH–ORD: cmp-view-offers-disclaimer. Find Offers
    28

    Mo

  • HHH–ORD: cmp-view-offers-disclaimer. Find Offers
    29

    Tu

    • range$319-$669

    DisclaimerFares displayed have been collected within the last 24hrs and may no longer be available at time of booking. Modifying this information may result in a different fare. To find the most updated fare, please visit aa.com. Fares listed may be Basic Economy, which class is subject to additional terms and conditions. Additional baggage fees and charges for optional products and services may apply.

    Find deals on Hilton Head Island to Chicago flights

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    Hilton Head Island (HHH)to

    Chicago (ORD)
    11/07/26 - 11/14/26

    Round trip

    Economy

    from
    $299Fare subject to changes
    Updated: 4 hours ago

    Hilton Head Island (HHH)to

    Chicago (ORD)
    10/31/26 - 11/07/26

    Round trip

    Economy

    from
    $309Fare subject to changes
    Updated: 4 hours ago

    Hilton Head Island (HHH)to

    Chicago (ORD)
    10/14/26 - 10/21/26

    Round trip

    Economy

    from
    $319Fare subject to changes
    Updated: 4 hours ago

    Hilton Head Island (HHH)to

    Chicago (ORD)
    10/23/26 - 10/30/26

    Round trip

    Economy

    from
    $319Fare subject to changes
    Updated: 4 hours ago

    Hilton Head Island (HHH)to

    Chicago (ORD)
    10/26/26 - 11/02/26

    Round trip

    Economy

    from
    $319Fare subject to changes
    Updated: 4 hours ago

    Hilton Head Island (HHH)to

    Chicago (ORD)
    10/30/26 - 11/06/26

    Round trip

    Economy

    from
    $319Fare subject to changes
    Updated: 4 hours ago

    Hilton Head Island (HHH)to

    Chicago (ORD)
    11/01/26 - 11/08/26

    Round trip

    Economy

    from
    $319Fare subject to changes
    Updated: 4 hours ago

    Hilton Head Island (HHH)to

    Chicago (ORD)
    11/06/26 - 11/13/26

    Round trip

    Economy

    from
    $319Fare subject to changes
    Updated: 4 hours ago

    *Fares displayed have been collected within the last 24hrs and may no longer be available at time of booking. Some fares listed may include one or more connections that are Basic Economy, which class is subject to additional terms and conditions. Modifying this information may result in a different fare. To find the most updated fare, please visit aa.com. Additional baggage fees and charges for optional products and services may apply.

    Finding cheap flights from Hilton Head Island to Chicago

    Looking for lower fares on your trip from Hilton Head Island to Chicago? Here are a few ways to save.

    • Book early: Booking 1 to 3 months ahead can help you find lower fares
    • Be flexible with dates: Midweek travel, like Tuesdays and Wednesdays, can be more affordable
    • Travel during less busy periods: Flying outside peak travel times can help find lower fares and avoid crowds

    Earn up to $500 back on your next American Airlines flight plus, 30,000 bonus miles. Offers vary elsewhere. Opens another site in a new window that may not meet accessibility guidelines.

    Upgrade your flight with Main Cabin Extra

    Make your trip more comfortable with Main Cabin Extra. Enjoy benefits like:

    • Extra legroom: More space with seats at the front of the Main Cabin or in exit rows.
    • Early boarding: Preferred Group 5 boarding allows easier access to overhead bins.
    • Complimentary drinks: Enjoy beer, wine and spirits on flights with full beverage service.

    Discover how Main Cabin Extra can enhance your trip.

    American Airlines flights from Hilton Head Island to Chicago