American Airlines flights from Grand Cayman to Chicago

Recent searches for flights from Grand Cayman to Chicago

Aug 2026
FromUSD992*
Updated: 7 hours ago
Round tripIEconomy
Sep 2026
FromUSD672*
Updated: 7 hours ago
Round tripIEconomy
Oct 2026
FromUSD672*
Updated: 7 hours ago
Round tripIEconomy
cmp-daily-histogram-bars-legend-min-price-aria-label USD672
cmp-daily-histogram-bars-legend-max-price-aria-label USD1.7K
Displaying fares for August-2026
  • GCM–ORD: cmp-view-offers-disclaimer. Find Offers
    25

    Tu

    AUG

  • GCM–ORD, 26/08/2026 – 02/09/2026: From USD1,197
    26

    We

  • GCM–ORD, 27/08/2026 – 03/09/2026: From USD1,192
    27

    Th

  • GCM–ORD, 28/08/2026 – 04/09/2026: From USD992
    28

    Fr

  • GCM–ORD, 29/08/2026 – 05/09/2026: From USD992
    29

    Sa

  • GCM–ORD, 30/08/2026 – 06/09/2026: From USD997
    30

    Su

  • GCM–ORD, 31/08/2026 – 07/09/2026: From USD992
    31

    Mo

  • GCM–ORD, 01/09/2026 – 08/09/2026: From USD897
    01

    Tu

    SEP

  • GCM–ORD, 02/09/2026 – 09/09/2026: From USD902
    02

    We

  • GCM–ORD, 03/09/2026 – 10/09/2026: From USD897
    03

    Th

  • GCM–ORD, 04/09/2026 – 11/09/2026: From USD897
    04

    Fr

  • GCM–ORD, 05/09/2026 – 12/09/2026: From USD897
    05

    Sa

  • GCM–ORD, 06/09/2026 – 13/09/2026: From USD902
    06

    Su

  • GCM–ORD, 07/09/2026 – 14/09/2026: From USD1,490
    07

    Mo

  • GCM–ORD, 08/09/2026 – 15/09/2026: From USD807
    08

    Tu

  • GCM–ORD, 09/09/2026 – 16/09/2026: From USD1,723
    09

    We

  • GCM–ORD, 10/09/2026 – 17/09/2026: From USD807
    10

    Th

  • GCM–ORD, 11/09/2026 – 18/09/2026: From USD807
    11

    Fr

  • GCM–ORD, 12/09/2026 – 19/09/2026: From USD807
    12

    Sa

  • GCM–ORD, 13/09/2026 – 20/09/2026: From USD812
    13

    Su

  • GCM–ORD, 14/09/2026 – 21/09/2026: From USD807
    14

    Mo

  • GCM–ORD, 15/09/2026 – 22/09/2026: From USD717
    15

    Tu

  • GCM–ORD, 16/09/2026 – 23/09/2026: From USD722
    16

    We

  • GCM–ORD, 17/09/2026 – 24/09/2026: From USD717
    17

    Th

  • GCM–ORD, 18/09/2026 – 25/09/2026: From USD717
    18

    Fr

  • GCM–ORD, 19/09/2026 – 26/09/2026: From USD717
    19

    Sa

  • GCM–ORD, 20/09/2026 – 27/09/2026: From USD722
    20

    Su

  • GCM–ORD, 21/09/2026 – 28/09/2026: From USD717
    21

    Mo

  • GCM–ORD, 22/09/2026 – 29/09/2026: From USD672
    22

    Tu

  • GCM–ORD, 23/09/2026 – 30/09/2026: From USD677
    23

    We

  • GCM–ORD, 24/09/2026 – 01/10/2026: From USD672
    24

    Th

    • rangeUSD672-USD1,723

    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 Grand Cayman to Chicago flights

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    *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.

    American Airlines flights from Grand Cayman to Chicago

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