Southwest® flights from Portland, OR to Fort Myers/Naples from $239

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Low fares from Portland, OR to Fort Myers/Naples

$

Portland, OR (PDX)to

Fort Myers/Naples (RSW)
Depart: 10/07/2026

One-way

Basic

From
$239
Seen: 10 hrs ago

Portland, OR (PDX)to

Fort Myers/Naples (RSW)
Depart: 09/15/2026

One-way

Basic

From
$283
Seen: 16 hrs ago

Portland, OR (PDX)to

Fort Myers/Naples (RSW)
Depart: 09/19/2026

One-way

Basic

From
$283
Seen: 1 hour ago

Portland, OR (PDX)to

Fort Myers/Naples (RSW)
Depart: 10/07/2026

One-way

Choice

From
$294
Seen: 10 hrs ago

Portland, OR (PDX)to

Fort Myers/Naples (RSW)
Depart: 09/23/2026

One-way

Basic

From
$298
Seen: 10 hrs ago

Portland, OR (PDX)to

Fort Myers/Naples (RSW)
Depart: 09/11/2026

One-way

Basic

From
$332
Seen: 12 hrs ago

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Explore flights from Portland, OR to Fort Myers/Naples

Sep 2026
From$283*
Seen: 1 hour ago
One Way/Basic
Oct 2026
From$239*
Seen: 10 hrs ago
One Way/Basic
Nov 2026
No result for this month.
cmp-daily-histogram-bars-legend-min-price-aria-label $239
Displaying fares for September-2026
  • PDX–RSW: cmp-view-offers-disclaimer. Find Offers
    10

    Thu

    SEP

  • PDX–RSW, 09/11/2026: From $332
    11

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    12

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    13

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    Mon

  • PDX–RSW, 09/15/2026: From $283
    15

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    16

    Wed

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    17

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    18

    Fri

  • PDX–RSW, 09/19/2026: From $283
    19

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    20

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    21

    Mon

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    22

    Tue

  • PDX–RSW, 09/23/2026: From $298
    23

    Wed

  • PDX–RSW, 09/24/2026: From $332
    24

    Thu

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    25

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    27

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    28

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    29

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    30

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    01

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    OCT

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    03

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    05

    Mon

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    06

    Tue

  • PDX–RSW, 10/07/2026: From $239
    07

    Wed

  • PDX–RSW, 10/08/2026: From $352
    08

    Thu

  • PDX–RSW, 10/09/2026: From $357
    09

    Fri

    • Range$239-$357

    *Fares displayed have been collected within the last 24 hours and may no longer be available at time of booking. Additional fees and charges for optional products and services may apply. Modifying this information may result in a different fare. To find the most updated fare, please visit Southwest.com. Fares listed are Basic, which are subject to additional terms and conditions.

    Flight Details

    Departing from:
    Portland International Airport
    Arriving at:
    Southwest Florida Regional Airport
    Distance:
    2598 miles

    Route Information

    55† Weekly flights

    † Weekly flights based on DOT published scheduled average flights Monday through Sunday between 9/1/2025 and 9/30/2025. Note: route may not operate every day of the week.

    ‡ Nonstop flights based on DOT published scheduled average flights Monday through Sunday between 9/1/2025 and 9/30/2025.

    Questions we hear the most

    There are 55 weekly flights from Portland, OR to Fort Myers/Naples on Southwest Airlines.
    To find the lowest fares by day and time to fly Portland, OR to Fort Myers/Naples with Southwest, check out our Low Fare Calendar.
    You can rent a car at Southwest Florida Regional Airport book yours with your flight.
    Yes! Flights from Portland, OR to Fort Myers/Naples—or from here or there to anywhere—can be changed with no change fees. Fare difference may apply.
    Check the status of your upcoming Southwest flight.
    Check out the Southwest Airlines® Help Center for answers about everything Southwest.

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