Southwest® flights from Portland, OR to Boston from $169

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Low fares from Portland, OR to Boston

$

Portland, OR (PDX)to

Boston (BOS)
Depart: 09/15/2026

One-way

Basic

From
$169
Seen: 21 hrs ago

Portland, OR (PDX)to

Boston (BOS)
Depart: 10/24/2026

One-way

Basic

From
$169
Seen: 18 hrs ago

Portland, OR (PDX)to

Boston (BOS)
Depart: 09/12/2026

One-way

Basic

From
$169
Seen: 4 hrs ago

Portland, OR (PDX)to

Boston (BOS)
Depart: 09/10/2026

One-way

Basic

From
$174
Seen: 22 hrs ago

Portland, OR (PDX)to

Boston (BOS)
Depart: 10/17/2026

One-way

Basic

From
$185
Seen: 16 hrs ago

Portland, OR (PDX)to

Boston (BOS)
Depart: 09/11/2026

One-way

Basic

From
$185
Seen: 21 hrs ago

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Explore flights from Portland, OR to Boston

Aug 2026
From$342*
Seen: 22 hrs ago
One Way/Basic
Sep 2026
From$169*
Seen: 21 hrs ago
One Way/Basic
Oct 2026
From$169*
Seen: 18 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $169
cmp-daily-histogram-bars-legend-max-price-aria-label $379
Displaying fares for August-2026
  • PDX–BOS, 08/22/2026: From $348
    22

    Sat

    AUG

  • PDX–BOS, 08/23/2026: From $379
    23

    Sun

  • PDX–BOS, 08/24/2026: From $379
    24

    Mon

  • PDX–BOS, 08/25/2026: From $342
    25

    Tue

  • PDX–BOS: cmp-view-offers-disclaimer. Find Offers
    26

    Wed

  • PDX–BOS: cmp-view-offers-disclaimer. Find Offers
    27

    Thu

  • PDX–BOS: cmp-view-offers-disclaimer. Find Offers
    28

    Fri

  • PDX–BOS: cmp-view-offers-disclaimer. Find Offers
    29

    Sat

  • PDX–BOS: cmp-view-offers-disclaimer. Find Offers
    30

    Sun

  • PDX–BOS: cmp-view-offers-disclaimer. Find Offers
    31

    Mon

  • PDX–BOS, 09/01/2026: From $249
    01

    Tue

    SEP

  • PDX–BOS, 09/02/2026: From $249
    02

    Wed

  • PDX–BOS, 09/03/2026: From $299
    03

    Thu

  • PDX–BOS, 09/04/2026: From $269
    04

    Fri

  • PDX–BOS: cmp-view-offers-disclaimer. Find Offers
    05

    Sat

  • PDX–BOS: cmp-view-offers-disclaimer. Find Offers
    06

    Sun

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

    Mon

  • PDX–BOS, 09/08/2026: From $209
    08

    Tue

  • PDX–BOS, 09/09/2026: From $219
    09

    Wed

  • PDX–BOS, 09/10/2026: From $174
    10

    Thu

  • PDX–BOS, 09/11/2026: From $185
    11

    Fri

  • PDX–BOS, 09/12/2026: From $169
    12

    Sat

  • PDX–BOS: cmp-view-offers-disclaimer. Find Offers
    13

    Sun

  • PDX–BOS: cmp-view-offers-disclaimer. Find Offers
    14

    Mon

  • PDX–BOS, 09/15/2026: From $169
    15

    Tue

  • PDX–BOS: cmp-view-offers-disclaimer. Find Offers
    16

    Wed

  • PDX–BOS: cmp-view-offers-disclaimer. Find Offers
    17

    Thu

  • PDX–BOS: cmp-view-offers-disclaimer. Find Offers
    18

    Fri

  • PDX–BOS: cmp-view-offers-disclaimer. Find Offers
    19

    Sat

  • PDX–BOS: cmp-view-offers-disclaimer. Find Offers
    20

    Sun

  • PDX–BOS: cmp-view-offers-disclaimer. Find Offers
    21

    Mon

    • Range$169-$379

    *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

    Route Information

    70† 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 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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