Southwest® flights from Portland, OR to Boston from $141

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Low fares from Portland, OR to Boston

$

Portland, OR (PDX)to

Boston (BOS)
Depart: 11/09/2026

One-way

Basic

From
$141
Seen: 7 hrs ago

Portland, OR (PDX)to

Boston (BOS)
Depart: 01/19/2027

One-way

Basic

From
$141
Seen: 19 hrs ago

Portland, OR (PDX)to

Boston (BOS)
Depart: 11/09/2026

One-way

Choice

From
$196
Seen: 7 hrs ago

Portland, OR (PDX)to

Boston (BOS)
Depart: 01/19/2027

One-way

Choice

From
$197
Seen: 19 hrs ago

Portland, OR (PDX)to

Boston (BOS)
Depart: 01/05/2027

One-way

Basic

From
$219
Seen: 4 hrs ago

Portland, OR (PDX)to

Boston (BOS)
Depart: 12/20/2026

One-way

Basic

From
$219
Seen: 9 hrs ago

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Explore flights from Portland, OR to Boston

Oct 2026
From$354*
Seen: 7 hrs ago
One Way/Basic
Nov 2026
From$141*
Seen: 7 hrs ago
One Way/Basic
Dec 2026
From$219*
Seen: 9 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $141
Displaying fares for October-2026
  • PDX–BOS, 10/21/2026: From $382
    21

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    OCT

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    22

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  • PDX–BOS, 10/24/2026: From $388
    24

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  • PDX–BOS, 10/28/2026: From $354
    28

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  • PDX–BOS, 10/29/2026: From $354
    29

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  • PDX–BOS, 10/31/2026: From $354
    31

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  • PDX–BOS, 11/01/2026: From $354
    01

    Sun

    NOV

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  • PDX–BOS, 11/08/2026: From $249
    08

    Sun

  • PDX–BOS, 11/09/2026: From $141
    09

    Mon

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    10

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    11

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    12

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    14

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    15

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    16

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    18

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    19

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    20

    Fri

    • Range$141-$388

    *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:
    Logan International Airport
    Distance:
    2537 miles

    Questions we hear the most

    There are 70 weekly flights from Portland, OR to Boston on Southwest Airlines.
    To find the lowest fares by day and time to fly Portland, OR to Boston with Southwest, check out our Low Fare Calendar.
    You can rent a car at Logan International Airport book yours with your flight.
    Yes! Flights from Portland, OR to Boston—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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