Southwest® flights from Boston to Portland, ME from $339

Promo Code

Low fares from Boston to Portland, ME

$

Boston (BOS)to

Portland, ME (PWM)
Depart: 04/21/2026

One-way

Choice

From
$339
Seen: 5 hrs ago

Boston (BOS)to

Portland, ME (PWM)
Depart: 04/07/2026

One-way

Choice

From
$379
Seen: 5 hrs ago

Boston (BOS)to

Portland, ME (PWM)
Depart: 04/21/2026

One-way

Choice Preferred

From
$409
Seen: 5 hrs ago

Boston (BOS)to

Portland, ME (PWM)
Depart: 04/07/2026

One-way

Choice Preferred

From
$449
Seen: 5 hrs ago

Boston (BOS)to

Portland, ME (PWM)
Depart: 04/21/2026

One-way

Choice Extra

From
$449
Seen: 5 hrs ago

Boston (BOS)to

Portland, ME (PWM)
Depart: 04/17/2026

One-way

Choice

From
$480
Seen: 5 hrs ago

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Explore flights from Boston to Portland, ME

Apr 2026
From$339*
Seen: 5 hrs ago
One Way/Basic
May 2026
No result for this month.
Jun 2026
No result for this month.
$339
Displaying fares for April-2026
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    • Range$339-$480

    *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:
    Logan International Airport
    Arriving at:
    Portland International Jetport
    Distance:
    95 miles

    Route Information

    44† 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 44 weekly flights from Boston to Portland, ME on Southwest Airlines.
    To find the lowest fares by day and time to fly Boston to Portland, ME with Southwest, check out our Low Fare Calendar.
    You can rent a car at Portland International Jetport book yours with your flight.
    Yes! Flights from Boston to Portland, ME—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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