American Airlines flights from Chicago to Grand Cayman

Recent searches for flights from Chicago to Grand Cayman

Sep 2026
From$821*
Updated: 9 hours ago
Round tripIEconomy
Oct 2026
From$597*
Updated: 9 hours ago
Round tripIEconomy
Nov 2026
From$597*
Updated: 9 hours ago
Round tripIEconomy
cmp-daily-histogram-bars-legend-min-price-aria-label $637
cmp-daily-histogram-bars-legend-max-price-aria-label $2.3K
Displaying fares for September-2026
  • ORD–GCM: cmp-view-offers-disclaimer. Find Offers
    16

    We

    SEP

  • ORD–GCM, 09/17/26 – 09/24/26: From $1,023
    17

    Th

  • ORD–GCM, 09/18/26 – 09/25/26: From $1,023
    18

    Fr

  • ORD–GCM, 09/19/26 – 09/26/26: From $1,023
    19

    Sa

  • ORD–GCM, 09/20/26 – 09/27/26: From $988
    20

    Su

  • ORD–GCM, 09/21/26 – 09/28/26: From $983
    21

    Mo

  • ORD–GCM, 09/22/26 – 09/29/26: From $1,063
    22

    Tu

  • ORD–GCM, 09/23/26 – 09/30/26: From $911
    23

    We

  • ORD–GCM, 09/24/26 – 10/01/26: From $906
    24

    Th

  • ORD–GCM, 09/25/26 – 10/02/26: From $906
    25

    Fr

  • ORD–GCM, 09/26/26 – 10/03/26: From $906
    26

    Sa

  • ORD–GCM, 09/27/26 – 10/04/26: From $911
    27

    Su

  • ORD–GCM, 09/28/26 – 10/05/26: From $906
    28

    Mo

  • ORD–GCM, 09/29/26 – 10/06/26: From $906
    29

    Tu

  • ORD–GCM, 09/30/26 – 10/07/26: From $821
    30

    We

  • ORD–GCM, 10/01/26 – 10/08/26: From $816
    01

    Th

    OCT

  • ORD–GCM, 10/02/26 – 10/09/26: From $816
    02

    Fr

  • ORD–GCM, 10/03/26 – 10/10/26: From $816
    03

    Sa

  • ORD–GCM, 10/04/26 – 10/11/26: From $821
    04

    Su

  • ORD–GCM, 10/05/26 – 10/12/26: From $816
    05

    Mo

  • ORD–GCM, 10/06/26 – 10/13/26: From $816
    06

    Tu

  • ORD–GCM, 10/07/26 – 10/14/26: From $689
    07

    We

  • ORD–GCM, 10/08/26 – 10/15/26: From $684
    08

    Th

  • ORD–GCM, 10/09/26 – 10/16/26: From $914
    09

    Fr

  • ORD–GCM, 10/10/26 – 10/17/26: From $2,280
    10

    Sa

  • ORD–GCM, 10/11/26 – 10/18/26: From $772
    11

    Su

  • ORD–GCM, 10/12/26 – 10/19/26: From $724
    12

    Mo

  • ORD–GCM, 10/13/26 – 10/20/26: From $684
    13

    Tu

  • ORD–GCM, 10/14/26 – 10/21/26: From $642
    14

    We

  • ORD–GCM, 10/15/26 – 10/22/26: From $637
    15

    Th

    • range$637-$2,280

    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

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    Chicago (ORD)to

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

    Round trip

    Economy

    from
    $587Fare subject to changes
    Updated: 9 hours ago

    Chicago (ORD)to

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

    Round trip

    Economy

    from
    $592Fare subject to changes
    Updated: 9 hours ago

    Chicago (ORD)to

    Grand Cayman (GCM)
    01/05/27 - 01/12/27

    Round trip

    Economy

    from
    $593Fare subject to changes
    Updated: 9 hours ago

    Chicago (ORD)to

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

    Round trip

    Economy

    from
    $597Fare subject to changes
    Updated: 9 hours ago

    Chicago (ORD)to

    Grand Cayman (GCM)
    11/17/26 - 11/24/26

    Round trip

    Economy

    from
    $597Fare subject to changes
    Updated: 9 hours ago

    Chicago (ORD)to

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

    Round trip

    Economy

    from
    $597Fare subject to changes
    Updated: 9 hours ago

    Chicago (ORD)to

    Grand Cayman (GCM)
    11/03/26 - 11/10/26

    Round trip

    Economy

    from
    $597Fare subject to changes
    Updated: 9 hours ago

    Chicago (ORD)to

    Grand Cayman (GCM)
    11/10/26 - 11/17/26

    Round trip

    Economy

    from
    $597Fare subject to changes
    Updated: 9 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.

    Citi / AAdvantage credit card offer.