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

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

Aug 2026
From$580*
Updated: 5 hours ago
Round tripIEconomy
Sep 2026
From$580*
Updated: 5 hours ago
Round tripIEconomy
Oct 2026
From$580*
Updated: 5 hours ago
Round tripIEconomy
cmp-daily-histogram-bars-legend-min-price-aria-label $580
cmp-daily-histogram-bars-legend-max-price-aria-label $913
Displaying fares for August-2026
  • ORD–POS, 08/05/26 – 08/12/26: From $793
    05

    We

    AUG

  • ORD–POS, 08/06/26 – 08/13/26: From $772
    06

    Th

  • ORD–POS, 08/07/26 – 08/14/26: From $913
    07

    Fr

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

    Sa

  • ORD–POS, 08/09/26 – 08/16/26: From $831
    09

    Su

  • ORD–POS, 08/10/26 – 08/17/26: From $799
    10

    Mo

  • ORD–POS, 08/11/26 – 08/18/26: From $816
    11

    Tu

  • ORD–POS, 08/12/26 – 08/19/26: From $777
    12

    We

  • ORD–POS, 08/13/26 – 08/20/26: From $772
    13

    Th

  • ORD–POS, 08/14/26 – 08/21/26: From $772
    14

    Fr

  • ORD–POS, 08/15/26 – 08/22/26: From $826
    15

    Sa

  • ORD–POS, 08/16/26 – 08/23/26: From $831
    16

    Su

  • ORD–POS, 08/17/26 – 08/24/26: From $799
    17

    Mo

  • ORD–POS, 08/18/26 – 08/25/26: From $772
    18

    Tu

  • ORD–POS, 08/19/26 – 08/26/26: From $681
    19

    We

  • ORD–POS, 08/20/26 – 08/27/26: From $676
    20

    Th

  • ORD–POS, 08/21/26 – 08/28/26: From $676
    21

    Fr

  • ORD–POS, 08/22/26 – 08/29/26: From $703
    22

    Sa

  • ORD–POS, 08/23/26 – 08/30/26: From $708
    23

    Su

  • ORD–POS, 08/24/26 – 08/31/26: From $676
    24

    Mo

  • ORD–POS, 08/25/26 – 09/01/26: From $676
    25

    Tu

  • ORD–POS, 08/26/26 – 09/02/26: From $585
    26

    We

  • ORD–POS, 08/27/26 – 09/03/26: From $580
    27

    Th

  • ORD–POS, 08/28/26 – 09/04/26: From $584
    28

    Fr

  • ORD–POS, 08/29/26 – 09/05/26: From $584
    29

    Sa

  • ORD–POS, 08/30/26 – 09/06/26: From $708
    30

    Su

  • ORD–POS, 08/31/26 – 09/07/26: From $700
    31

    Mo

  • ORD–POS, 09/01/26 – 09/08/26: From $580
    01

    Tu

    SEP

  • ORD–POS, 09/02/26 – 09/09/26: From $585
    02

    We

  • ORD–POS, 09/03/26 – 09/10/26: From $630
    03

    Th

  • ORD–POS, 09/04/26 – 09/11/26: From $630
    04

    Fr

    • range$580-$913

    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

    $
    keyboard_arrow_down

    Chicago (ORD)to

    Port-of-Spain, Trinidad (POS)
    10/03/26 - 10/10/26

    Round trip

    Economy

    from
    $580Fare subject to changes
    Updated: 5 hours ago

    Chicago (ORD)to

    Port-of-Spain, Trinidad (POS)
    10/05/26 - 10/12/26

    Round trip

    Economy

    from
    $580Fare subject to changes
    Updated: 5 hours ago

    Chicago (ORD)to

    Port-of-Spain, Trinidad (POS)
    10/06/26 - 10/13/26

    Round trip

    Economy

    from
    $580Fare subject to changes
    Updated: 5 hours ago

    Chicago (ORD)to

    Port-of-Spain, Trinidad (POS)
    10/10/26 - 10/17/26

    Round trip

    Economy

    from
    $580Fare subject to changes
    Updated: 5 hours ago

    Chicago (ORD)to

    Port-of-Spain, Trinidad (POS)
    10/13/26 - 10/20/26

    Round trip

    Economy

    from
    $580Fare subject to changes
    Updated: 5 hours ago

    Chicago (ORD)to

    Port-of-Spain, Trinidad (POS)
    10/15/26 - 10/22/26

    Round trip

    Economy

    from
    $580Fare subject to changes
    Updated: 5 hours ago

    Chicago (ORD)to

    Port-of-Spain, Trinidad (POS)
    10/16/26 - 10/23/26

    Round trip

    Economy

    from
    $580Fare subject to changes
    Updated: 5 hours ago

    Chicago (ORD)to

    Port-of-Spain, Trinidad (POS)
    09/07/26 - 09/14/26

    Round trip

    Economy

    from
    $580Fare subject to changes
    Updated: 5 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 Port-of-Spain, Trinidad

    Looking for lower fares on your trip from Chicago to Port-of-Spain, Trinidad? 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 Port-of-Spain, Trinidad