American Airlines flights from Grand Cayman to Chicago

Recent searches for flights from Grand Cayman to Chicago

Sep 2026
FromUSD827*
Updated: 21 minutes ago
Round tripIEconomy
Oct 2026
FromUSD684*
Updated: 21 minutes ago
Round tripIEconomy
Nov 2026
FromUSD684*
Updated: 21 minutes ago
Round tripIEconomy
cmp-daily-histogram-bars-legend-min-price-aria-label USD684
cmp-daily-histogram-bars-legend-max-price-aria-label USD1.2K
Displaying fares for September-2026
  • GCM–ORD, 14/09/2026 – 21/09/2026: From USD1,024
    14

    Mo

    SEP

  • GCM–ORD, 15/09/2026 – 22/09/2026: From USD1,215
    15

    Tu

  • GCM–ORD, 16/09/2026 – 23/09/2026: From USD989
    16

    We

  • GCM–ORD, 17/09/2026 – 24/09/2026: From USD984
    17

    Th

  • GCM–ORD, 18/09/2026 – 25/09/2026: From USD1,024
    18

    Fr

  • GCM–ORD, 19/09/2026 – 26/09/2026: From USD1,024
    19

    Sa

  • GCM–ORD, 20/09/2026 – 27/09/2026: From USD1,029
    20

    Su

  • GCM–ORD, 21/09/2026 – 28/09/2026: From USD917
    21

    Mo

  • GCM–ORD, 22/09/2026 – 29/09/2026: From USD917
    22

    Tu

  • GCM–ORD, 23/09/2026 – 30/09/2026: From USD922
    23

    We

  • GCM–ORD, 24/09/2026 – 01/10/2026: From USD917
    24

    Th

  • GCM–ORD, 25/09/2026 – 02/10/2026: From USD917
    25

    Fr

  • GCM–ORD, 26/09/2026 – 03/10/2026: From USD917
    26

    Sa

  • GCM–ORD, 27/09/2026 – 04/10/2026: From USD922
    27

    Su

  • GCM–ORD, 28/09/2026 – 05/10/2026: From USD827
    28

    Mo

  • GCM–ORD, 29/09/2026 – 06/10/2026: From USD827
    29

    Tu

  • GCM–ORD, 30/09/2026 – 07/10/2026: From USD832
    30

    We

  • GCM–ORD, 01/10/2026 – 08/10/2026: From USD827
    01

    Th

    OCT

  • GCM–ORD, 02/10/2026 – 09/10/2026: From USD827
    02

    Fr

  • GCM–ORD, 03/10/2026 – 10/10/2026: From USD827
    03

    Sa

  • GCM–ORD, 04/10/2026 – 11/10/2026: From USD832
    04

    Su

  • GCM–ORD, 05/10/2026 – 12/10/2026: From USD733
    05

    Mo

  • GCM–ORD, 06/10/2026 – 13/10/2026: From USD733
    06

    Tu

  • GCM–ORD, 07/10/2026 – 14/10/2026: From USD738
    07

    We

  • GCM–ORD, 08/10/2026 – 15/10/2026: From USD773
    08

    Th

  • GCM–ORD, 09/10/2026 – 16/10/2026: From USD773
    09

    Fr

  • GCM–ORD, 10/10/2026 – 17/10/2026: From USD773
    10

    Sa

  • GCM–ORD, 11/10/2026 – 18/10/2026: From USD738
    11

    Su

  • GCM–ORD, 12/10/2026 – 19/10/2026: From USD724
    12

    Mo

  • GCM–ORD, 13/10/2026 – 20/10/2026: From USD684
    13

    Tu

    • rangeUSD684-USD1,215

    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.

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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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