American Airlines flights from Key West to Portland, OR

Recent searches for flights from Key West to Portland, OR

Aug 2026
From$473*
Updated: 4 hours ago
Round tripIEconomy
Sep 2026
From$524*
Updated: 4 hours ago
Round tripIEconomy
Oct 2026
From$427*
Updated: 4 hours ago
Round tripIEconomy
cmp-daily-histogram-bars-legend-min-price-aria-label $473
cmp-daily-histogram-bars-legend-max-price-aria-label $1.3K
Displaying fares for August-2026
  • EYW–PDX, 08/10/26 – 08/17/26: From $666
    10

    Mo

    AUG

  • EYW–PDX, 08/11/26 – 08/18/26: From $555
    11

    Tu

  • EYW–PDX, 08/12/26 – 08/19/26: From $619
    12

    We

  • EYW–PDX, 08/13/26 – 08/20/26: From $636
    13

    Th

  • EYW–PDX, 08/14/26 – 08/21/26: From $701
    14

    Fr

  • EYW–PDX, 08/15/26 – 08/22/26: From $619
    15

    Sa

  • EYW–PDX, 08/16/26 – 08/23/26: From $1,255
    16

    Su

  • EYW–PDX, 08/17/26 – 08/24/26: From $499
    17

    Mo

  • EYW–PDX, 08/18/26 – 08/25/26: From $555
    18

    Tu

  • EYW–PDX, 08/19/26 – 08/26/26: From $619
    19

    We

  • EYW–PDX, 08/20/26 – 08/27/26: From $576
    20

    Th

  • EYW–PDX, 08/21/26 – 08/28/26: From $576
    21

    Fr

  • EYW–PDX, 08/22/26 – 08/29/26: From $683
    22

    Sa

  • EYW–PDX, 08/23/26 – 08/30/26: From $896
    23

    Su

  • EYW–PDX, 08/24/26 – 08/31/26: From $473
    24

    Mo

  • EYW–PDX, 08/25/26 – 09/01/26: From $601
    25

    Tu

  • EYW–PDX, 08/26/26 – 09/02/26: From $601
    26

    We

  • EYW–PDX, 08/27/26 – 09/03/26: From $672
    27

    Th

  • EYW–PDX, 08/28/26 – 09/04/26: From $606
    28

    Fr

  • EYW–PDX, 08/29/26 – 09/05/26: From $473
    29

    Sa

  • EYW–PDX, 08/30/26 – 09/06/26: From $473
    30

    Su

  • EYW–PDX, 08/31/26 – 09/07/26: From $560
    31

    Mo

  • EYW–PDX, 09/01/26 – 09/08/26: From $650
    01

    Tu

    SEP

  • EYW–PDX, 09/02/26 – 09/09/26: From $555
    02

    We

  • EYW–PDX, 09/03/26 – 09/10/26: From $560
    03

    Th

  • EYW–PDX, 09/04/26 – 09/11/26: From $582
    04

    Fr

  • EYW–PDX, 09/05/26 – 09/12/26: From $524
    05

    Sa

  • EYW–PDX, 09/06/26 – 09/13/26: From $626
    06

    Su

  • EYW–PDX: cmp-view-offers-disclaimer. Find Offers
    07

    Mo

  • EYW–PDX: cmp-view-offers-disclaimer. Find Offers
    08

    Tu

  • EYW–PDX, 09/09/26 – 09/16/26: From $678
    09

    We

    • range$473-$1,255

    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, OR flights

    $
    keyboard_arrow_down

    Key West (EYW)to

    Portland, OR (PDX)
    10/06/26 - 10/13/26

    Round trip

    Economy

    from
    $427Fare subject to changes
    Updated: 4 hours ago

    Key West (EYW)to

    Portland, OR (PDX)
    10/28/26 - 11/04/26

    Round trip

    Economy

    from
    $427Fare subject to changes
    Updated: 4 hours ago

    Key West (EYW)to

    Portland, OR (PDX)
    11/01/26 - 11/08/26

    Round trip

    Economy

    from
    $427Fare subject to changes
    Updated: 4 hours ago

    Key West (EYW)to

    Portland, OR (PDX)
    10/20/26 - 10/27/26

    Round trip

    Economy

    from
    $427Fare subject to changes
    Updated: 4 hours ago

    Key West (EYW)to

    Portland, OR (PDX)
    10/23/26 - 10/30/26

    Round trip

    Economy

    from
    $427Fare subject to changes
    Updated: 4 hours ago

    Key West (EYW)to

    Portland, OR (PDX)
    11/05/26 - 11/12/26

    Round trip

    Economy

    from
    $427Fare subject to changes
    Updated: 4 hours ago

    Key West (EYW)to

    Portland, OR (PDX)
    10/16/26 - 10/23/26

    Round trip

    Economy

    from
    $427Fare subject to changes
    Updated: 4 hours ago

    Key West (EYW)to

    Portland, OR (PDX)
    10/21/26 - 10/28/26

    Round trip

    Economy

    from
    $427Fare subject to changes
    Updated: 4 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 Key West to Portland, OR

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