American Airlines flights from Chicago to Port-of-Spain, Trinidad

Recent searches for flights from Chicago to Port-of-Spain, Trinidad

Sep 2026
From$759*
Updated: 8 hours ago
Round tripIEconomy
Oct 2026
From$650*
Updated: 8 hours ago
Round tripIEconomy
Nov 2026
From$650*
Updated: 8 hours ago
Round tripIEconomy
cmp-daily-histogram-bars-legend-min-price-aria-label $650
cmp-daily-histogram-bars-legend-max-price-aria-label $816
Displaying fares for September-2026
  • ORD–POS, 09/16/26 – 09/23/26: From $782
    16

    We

    SEP

  • ORD–POS, 09/17/26 – 09/24/26: From $816
    17

    Th

  • ORD–POS, 09/18/26 – 09/25/26: From $777
    18

    Fr

  • ORD–POS, 09/19/26 – 09/26/26: From $777
    19

    Sa

  • ORD–POS, 09/20/26 – 09/27/26: From $782
    20

    Su

  • ORD–POS, 09/21/26 – 09/28/26: From $777
    21

    Mo

  • ORD–POS, 09/22/26 – 09/29/26: From $777
    22

    Tu

  • ORD–POS, 09/23/26 – 09/30/26: From $782
    23

    We

  • ORD–POS, 09/24/26 – 10/01/26: From $777
    24

    Th

  • ORD–POS, 09/25/26 – 10/02/26: From $777
    25

    Fr

  • ORD–POS, 09/26/26 – 10/03/26: From $777
    26

    Sa

  • ORD–POS, 09/27/26 – 10/04/26: From $782
    27

    Su

  • ORD–POS, 09/28/26 – 10/05/26: From $777
    28

    Mo

  • ORD–POS, 09/29/26 – 10/06/26: From $759
    29

    Tu

  • ORD–POS, 09/30/26 – 10/07/26: From $764
    30

    We

  • ORD–POS, 10/01/26 – 10/08/26: From $759
    01

    Th

    OCT

  • ORD–POS, 10/02/26 – 10/09/26: From $759
    02

    Fr

  • ORD–POS, 10/03/26 – 10/10/26: From $761
    03

    Sa

  • ORD–POS, 10/04/26 – 10/11/26: From $766
    04

    Su

  • ORD–POS, 10/05/26 – 10/12/26: From $761
    05

    Mo

  • ORD–POS, 10/06/26 – 10/13/26: From $695
    06

    Tu

  • ORD–POS, 10/07/26 – 10/14/26: From $700
    07

    We

  • ORD–POS, 10/08/26 – 10/15/26: From $695
    08

    Th

  • ORD–POS, 10/09/26 – 10/16/26: From $698
    09

    Fr

  • ORD–POS, 10/10/26 – 10/17/26: From $698
    10

    Sa

  • ORD–POS, 10/11/26 – 10/18/26: From $703
    11

    Su

  • ORD–POS, 10/12/26 – 10/19/26: From $695
    12

    Mo

  • ORD–POS, 10/13/26 – 10/20/26: From $650
    13

    Tu

  • ORD–POS, 10/14/26 – 10/21/26: From $691
    14

    We

  • ORD–POS, 10/15/26 – 10/22/26: From $654
    15

    Th

    • range$650-$816

    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 Port-of-Spain, Trinidad flights

    $
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    Chicago (ORD)to

    Port-of-Spain, Trinidad (POS)
    12/05/26 - 12/12/26

    Round trip

    Economy

    from
    $650Fare subject to changes
    Updated: 8 hours ago

    Chicago (ORD)to

    Port-of-Spain, Trinidad (POS)
    12/07/26 - 12/14/26

    Round trip

    Economy

    from
    $650Fare subject to changes
    Updated: 8 hours ago

    Chicago (ORD)to

    Port-of-Spain, Trinidad (POS)
    11/07/26 - 11/14/26

    Round trip

    Economy

    from
    $650Fare subject to changes
    Updated: 8 hours ago

    Chicago (ORD)to

    Port-of-Spain, Trinidad (POS)
    10/19/26 - 10/26/26

    Round trip

    Economy

    from
    $650Fare subject to changes
    Updated: 8 hours ago

    Chicago (ORD)to

    Port-of-Spain, Trinidad (POS)
    01/08/27 - 01/15/27

    Round trip

    Economy

    from
    $650Fare subject to changes
    Updated: 8 hours ago

    Chicago (ORD)to

    Port-of-Spain, Trinidad (POS)
    01/12/27 - 01/19/27

    Round trip

    Economy

    from
    $650Fare subject to changes
    Updated: 8 hours ago

    Chicago (ORD)to

    Port-of-Spain, Trinidad (POS)
    12/04/26 - 12/11/26

    Round trip

    Economy

    from
    $650Fare subject to changes
    Updated: 8 hours ago

    Chicago (ORD)to

    Port-of-Spain, Trinidad (POS)
    12/08/26 - 12/15/26

    Round trip

    Economy

    from
    $650Fare subject to changes
    Updated: 8 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.

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