Southwest® flights from Milwaukee to Portland, OR from $205

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Low fares from Milwaukee to Portland, OR

$

Milwaukee (MKE)to

Portland, OR (PDX)
Depart: 12/09/2026

One-way

Basic

From
$205
Seen: 21 hrs ago

Milwaukee (MKE)to

Portland, OR (PDX)
Depart: 12/05/2026

One-way

Basic

From
$205
Seen: 18 hrs ago

Milwaukee (MKE)to

Portland, OR (PDX)
Depart: 12/08/2026

One-way

Basic

From
$205
Seen: 20 hrs ago

Milwaukee (MKE)to

Portland, OR (PDX)
Depart: 01/05/2027

One-way

Basic

From
$205
Seen: 11 hrs ago

Milwaukee (MKE)to

Portland, OR (PDX)
Depart: 12/17/2026

One-way

Basic

From
$225
Seen: 20 hrs ago

Milwaukee (MKE)to

Portland, OR (PDX)
Depart: 12/10/2026

One-way

Basic

From
$225
Seen: 21 hrs ago

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Explore flights from Milwaukee to Portland, OR

Nov 2026
From$329*
Seen: 9 hrs ago
One Way/Basic
Dec 2026
From$205*
Seen: 20 hrs ago
One Way/Basic
Jan 2027
From$205*
Seen: 11 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $205
cmp-daily-histogram-bars-legend-max-price-aria-label $545
Displaying fares for November-2026
  • MKE–PDX, 11/12/2026: From $452
    12

    Thu

    NOV

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

    Fri

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

    Sat

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

    Sun

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

    Mon

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

    Tue

  • MKE–PDX, 11/18/2026: From $452
    18

    Wed

  • MKE–PDX, 11/19/2026: From $452
    19

    Thu

  • MKE–PDX, 11/20/2026: From $452
    20

    Fri

  • MKE–PDX, 11/21/2026: From $452
    21

    Sat

  • MKE–PDX, 11/22/2026: From $452
    22

    Sun

  • MKE–PDX, 11/23/2026: From $452
    23

    Mon

  • MKE–PDX, 11/24/2026: From $452
    24

    Tue

  • MKE–PDX, 11/25/2026: From $329
    25

    Wed

  • MKE–PDX, 11/26/2026: From $329
    26

    Thu

  • MKE–PDX, 11/27/2026: From $369
    27

    Fri

  • MKE–PDX, 11/28/2026: From $480
    28

    Sat

  • MKE–PDX, 11/29/2026: From $545
    29

    Sun

  • MKE–PDX, 11/30/2026: From $359
    30

    Mon

  • MKE–PDX, 12/01/2026: From $329
    01

    Tue

    DEC

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

    Wed

  • MKE–PDX: cmp-view-offers-disclaimer. Find Offers
    03

    Thu

  • MKE–PDX: cmp-view-offers-disclaimer. Find Offers
    04

    Fri

  • MKE–PDX, 12/05/2026: From $205
    05

    Sat

  • MKE–PDX, 12/06/2026: From $289
    06

    Sun

  • MKE–PDX, 12/07/2026: From $225
    07

    Mon

  • MKE–PDX, 12/08/2026: From $205
    08

    Tue

  • MKE–PDX, 12/09/2026: From $205
    09

    Wed

  • MKE–PDX, 12/10/2026: From $225
    10

    Thu

  • MKE–PDX, 12/11/2026: From $240
    11

    Fri

    • Range$205-$545

    *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:
    General Mitchell Airport
    Arriving at:
    Portland International Airport
    Distance:
    1718 miles

    Questions we hear the most

    There are 122 weekly flights from Milwaukee to Portland, OR on Southwest Airlines.
    To find the lowest fares by day and time to fly Milwaukee to Portland, OR with Southwest, check out our Low Fare Calendar.
    You can rent a car at Portland International Airport book yours with your flight.
    Yes! Flights from Milwaukee to Portland, OR—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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