American Airlines flights from Chicago to Grand Cayman

Recent searches for flights from Chicago to Grand Cayman

Aug 2026
From$926*
Updated: 2 hours ago
Round tripIEconomy
Sep 2026
From$601*
Updated: 2 hours ago
Round tripIEconomy
Oct 2026
From$601*
Updated: 2 hours ago
Round tripIEconomy
cmp-daily-histogram-bars-legend-min-price-aria-label $601
cmp-daily-histogram-bars-legend-max-price-aria-label $2.7K
Displaying fares for August-2026
  • ORD–GCM: cmp-view-offers-disclaimer. Find Offers
    27

    Th

    AUG

  • ORD–GCM, 08/28/26 – 09/04/26: From $1,121
    28

    Fr

  • ORD–GCM, 08/29/26 – 09/05/26: From $1,121
    29

    Sa

  • ORD–GCM, 08/30/26 – 09/06/26: From $926
    30

    Su

  • ORD–GCM, 08/31/26 – 09/07/26: From $1,539
    31

    Mo

  • ORD–GCM, 09/01/26 – 09/08/26: From $921
    01

    Tu

    SEP

  • ORD–GCM, 09/02/26 – 09/09/26: From $2,678
    02

    We

  • ORD–GCM, 09/03/26 – 09/10/26: From $826
    03

    Th

  • ORD–GCM, 09/04/26 – 09/11/26: From $866
    04

    Fr

  • ORD–GCM, 09/05/26 – 09/12/26: From $826
    05

    Sa

  • ORD–GCM, 09/06/26 – 09/13/26: From $831
    06

    Su

  • ORD–GCM, 09/07/26 – 09/14/26: From $826
    07

    Mo

  • ORD–GCM, 09/08/26 – 09/15/26: From $826
    08

    Tu

  • ORD–GCM, 09/09/26 – 09/16/26: From $831
    09

    We

  • ORD–GCM, 09/10/26 – 09/17/26: From $736
    10

    Th

  • ORD–GCM, 09/11/26 – 09/18/26: From $736
    11

    Fr

  • ORD–GCM, 09/12/26 – 09/19/26: From $727
    12

    Sa

  • ORD–GCM, 09/13/26 – 09/20/26: From $741
    13

    Su

  • ORD–GCM, 09/14/26 – 09/21/26: From $736
    14

    Mo

  • ORD–GCM, 09/15/26 – 09/22/26: From $736
    15

    Tu

  • ORD–GCM, 09/16/26 – 09/23/26: From $741
    16

    We

  • ORD–GCM, 09/17/26 – 09/24/26: From $646
    17

    Th

  • ORD–GCM, 09/18/26 – 09/25/26: From $646
    18

    Fr

  • ORD–GCM, 09/19/26 – 09/26/26: From $686
    19

    Sa

  • ORD–GCM, 09/20/26 – 09/27/26: From $651
    20

    Su

  • ORD–GCM, 09/21/26 – 09/28/26: From $646
    21

    Mo

  • ORD–GCM, 09/22/26 – 09/29/26: From $686
    22

    Tu

  • ORD–GCM, 09/23/26 – 09/30/26: From $651
    23

    We

  • ORD–GCM, 09/24/26 – 10/01/26: From $601
    24

    Th

  • ORD–GCM, 09/25/26 – 10/02/26: From $601
    25

    Fr

  • ORD–GCM, 09/26/26 – 10/03/26: From $601
    26

    Sa

    • range$601-$2,678

    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 Chicago to Grand Cayman flights

    $
    keyboard_arrow_down

    Chicago (ORD)to

    Grand Cayman (GCM)
    12/15/26 - 12/22/26

    Round trip

    Economy

    from
    $541Fare subject to changes
    Updated: 2 hours ago

    Chicago (ORD)to

    Grand Cayman (GCM)
    12/16/26 - 12/23/26

    Round trip

    Economy

    from
    $546Fare subject to changes
    Updated: 2 hours ago

    Chicago (ORD)to

    Grand Cayman (GCM)
    12/01/26 - 12/08/26

    Round trip

    Economy

    from
    $551Fare subject to changes
    Updated: 2 hours ago

    Chicago (ORD)to

    Grand Cayman (GCM)
    12/08/26 - 12/15/26

    Round trip

    Economy

    from
    $551Fare subject to changes
    Updated: 2 hours ago

    Chicago (ORD)to

    Grand Cayman (GCM)
    12/02/26 - 12/09/26

    Round trip

    Economy

    from
    $556Fare subject to changes
    Updated: 2 hours ago

    Chicago (ORD)to

    Grand Cayman (GCM)
    12/09/26 - 12/16/26

    Round trip

    Economy

    from
    $556Fare subject to changes
    Updated: 2 hours ago

    Chicago (ORD)to

    Grand Cayman (GCM)
    12/17/26 - 12/24/26

    Round trip

    Economy

    from
    $562Fare subject to changes
    Updated: 2 hours ago

    Chicago (ORD)to

    Grand Cayman (GCM)
    12/14/26 - 12/21/26

    Round trip

    Economy

    from
    $566Fare subject to changes
    Updated: 2 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 Chicago to Grand Cayman

    Looking for lower fares on your trip from Chicago to Grand Cayman? 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 Chicago to Grand Cayman