American Airlines flights from Key West to Portland, ME

Recent searches for flights from Key West to Portland, ME

Sep 2026
From$351*
Updated: 1 hour ago
Round tripIEconomy
Oct 2026
From$301*
Updated: 1 hour ago
Round tripIEconomy
Nov 2026
From$301*
Updated: 1 hour ago
Round tripIEconomy
cmp-daily-histogram-bars-legend-min-price-aria-label $351
cmp-daily-histogram-bars-legend-max-price-aria-label $988
Displaying fares for September-2026
  • EYW–PWM, 09/01/26 – 09/08/26: From $497
    01

    Tu

    SEP

  • EYW–PWM, 09/02/26 – 09/09/26: From $401
    02

    We

  • EYW–PWM, 09/03/26 – 09/10/26: From $746
    03

    Th

  • EYW–PWM, 09/04/26 – 09/11/26: From $541
    04

    Fr

  • EYW–PWM, 09/05/26 – 09/12/26: From $401
    05

    Sa

  • EYW–PWM, 09/06/26 – 09/13/26: From $497
    06

    Su

  • EYW–PWM, 09/07/26 – 09/14/26: From $972
    07

    Mo

  • EYW–PWM, 09/08/26 – 09/15/26: From $502
    08

    Tu

  • EYW–PWM, 09/09/26 – 09/16/26: From $438
    09

    We

  • EYW–PWM, 09/10/26 – 09/17/26: From $546
    10

    Th

  • EYW–PWM, 09/11/26 – 09/18/26: From $399
    11

    Fr

  • EYW–PWM, 09/12/26 – 09/19/26: From $351
    12

    Sa

  • EYW–PWM, 09/13/26 – 09/20/26: From $988
    13

    Su

  • EYW–PWM, 09/14/26 – 09/21/26: From $541
    14

    Mo

  • EYW–PWM, 09/15/26 – 09/22/26: From $470
    15

    Tu

  • EYW–PWM, 09/16/26 – 09/23/26: From $401
    16

    We

  • EYW–PWM, 09/17/26 – 09/24/26: From $625
    17

    Th

  • EYW–PWM, 09/18/26 – 09/25/26: From $541
    18

    Fr

  • EYW–PWM, 09/19/26 – 09/26/26: From $433
    19

    Sa

  • EYW–PWM, 09/20/26 – 09/27/26: From $718
    20

    Su

  • EYW–PWM, 09/21/26 – 09/28/26: From $546
    21

    Mo

  • EYW–PWM, 09/22/26 – 09/29/26: From $401
    22

    Tu

  • EYW–PWM, 09/23/26 – 09/30/26: From $470
    23

    We

  • EYW–PWM, 09/24/26 – 10/01/26: From $590
    24

    Th

  • EYW–PWM, 09/25/26 – 10/02/26: From $541
    25

    Fr

  • EYW–PWM, 09/26/26 – 10/03/26: From $505
    26

    Sa

  • EYW–PWM, 09/27/26 – 10/04/26: From $955
    27

    Su

  • EYW–PWM, 09/28/26 – 10/05/26: From $562
    28

    Mo

  • EYW–PWM: cmp-view-offers-disclaimer. Find Offers
    29

    Tu

  • EYW–PWM: cmp-view-offers-disclaimer. Find Offers
    30

    We

    • range$351-$988

    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 Key West to Portland, ME flights

    $
    keyboard_arrow_down

    Key West (EYW)to

    Portland, ME (PWM)
    10/21/26 - 10/28/26

    Round trip

    Economy

    from
    $301Fare subject to changes
    Updated: 1 hour ago

    Key West (EYW)to

    Portland, ME (PWM)
    11/04/26 - 11/11/26

    Round trip

    Economy

    from
    $301Fare subject to changes
    Updated: 1 hour ago

    Key West (EYW)to

    Portland, ME (PWM)
    11/11/26 - 11/18/26

    Round trip

    Economy

    from
    $301Fare subject to changes
    Updated: 1 hour ago

    Key West (EYW)to

    Portland, ME (PWM)
    10/20/26 - 10/27/26

    Round trip

    Economy

    from
    $301Fare subject to changes
    Updated: 1 hour ago

    Key West (EYW)to

    Portland, ME (PWM)
    10/28/26 - 11/04/26

    Round trip

    Economy

    from
    $301Fare subject to changes
    Updated: 1 hour ago

    Key West (EYW)to

    Portland, ME (PWM)
    11/03/26 - 11/10/26

    Round trip

    Economy

    from
    $301Fare subject to changes
    Updated: 1 hour ago

    Key West (EYW)to

    Portland, ME (PWM)
    11/25/26 - 12/02/26

    Round trip

    Economy

    from
    $336Fare subject to changes
    Updated: 1 hour ago

    Key West (EYW)to

    Portland, ME (PWM)
    10/27/26 - 11/03/26

    Round trip

    Economy

    from
    $351Fare subject to changes
    Updated: 1 hour 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 Key West to Portland, ME

    Looking for lower fares on your trip from Key West to Portland, ME? 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 Key West to Portland, ME