Southwest® flights from Portland, OR to Boston from $224

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Low fares from Portland, OR to Boston

$

Portland, OR (PDX)to

Boston (BOS)
Depart: 12/03/2026

One-way

Basic

From
$224
Seen: 20 hrs ago

Portland, OR (PDX)to

Boston (BOS)
Depart: 12/04/2026

One-way

Basic

From
$224
Seen: 19 hrs ago

Portland, OR (PDX)to

Boston (BOS)
Depart: 02/12/2027

One-way

Basic

From
$254
Seen: 3 hrs ago

Portland, OR (PDX)to

Boston (BOS)
Depart: 12/22/2026

One-way

Basic

From
$259
Seen: 6 hrs ago

Portland, OR (PDX)to

Boston (BOS)
Depart: 12/03/2026

One-way

Choice

From
$279
Seen: 20 hrs ago

Portland, OR (PDX)to

Boston (BOS)
Depart: 12/01/2026

One-way

Basic

From
$279
Seen: 3 hrs ago

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Explore flights from Portland, OR to Boston

Nov 2026
From$359*
Seen: 17 hrs ago
One Way/Basic
Dec 2026
From$224*
Seen: 20 hrs ago
One Way/Basic
Jan 2027
No result for this month.
cmp-daily-histogram-bars-legend-min-price-aria-label $224
cmp-daily-histogram-bars-legend-max-price-aria-label $489
Displaying fares for November-2026
  • PDX–BOS, 11/11/2026: From $387
    11

    Wed

    NOV

  • PDX–BOS, 11/12/2026: From $427
    12

    Thu

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

    Fri

  • PDX–BOS, 11/14/2026: From $393
    14

    Sat

  • PDX–BOS: cmp-view-offers-disclaimer. Find Offers
    15

    Sun

  • PDX–BOS, 11/16/2026: From $414
    16

    Mon

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

    Tue

  • PDX–BOS, 11/18/2026: From $359
    18

    Wed

  • PDX–BOS, 11/19/2026: From $359
    19

    Thu

  • PDX–BOS, 11/20/2026: From $359
    20

    Fri

  • PDX–BOS, 11/21/2026: From $359
    21

    Sat

  • PDX–BOS, 11/22/2026: From $359
    22

    Sun

  • PDX–BOS, 11/23/2026: From $359
    23

    Mon

  • PDX–BOS: cmp-view-offers-disclaimer. Find Offers
    24

    Tue

  • PDX–BOS, 11/25/2026: From $359
    25

    Wed

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

    Thu

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

    Fri

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

    Sat

  • PDX–BOS, 11/29/2026: From $489
    29

    Sun

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

    Mon

  • PDX–BOS, 12/01/2026: From $279
    01

    Tue

    DEC

  • PDX–BOS: cmp-view-offers-disclaimer. Find Offers
    02

    Wed

  • PDX–BOS, 12/03/2026: From $224
    03

    Thu

  • PDX–BOS, 12/04/2026: From $224
    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: cmp-view-offers-disclaimer. Find Offers
    08

    Tue

  • PDX–BOS: cmp-view-offers-disclaimer. Find Offers
    09

    Wed

  • PDX–BOS: cmp-view-offers-disclaimer. Find Offers
    10

    Thu

    • Range$224-$489

    *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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