Southwest® flights from Portland, OR to Milwaukee from $159

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Low fares from Portland, OR to Milwaukee

$

Portland, OR (PDX)to

Milwaukee (MKE)
Depart: 10/27/2026

One-way

Basic

From
$159
Seen: 11 hrs ago

Portland, OR (PDX)to

Milwaukee (MKE)
Depart: 09/05/2026

One-way

Basic

From
$159
Seen: 5 hrs ago

Portland, OR (PDX)to

Milwaukee (MKE)
Depart: 09/15/2026

One-way

Basic

From
$159
Seen: 47 minutes ago

Portland, OR (PDX)to

Milwaukee (MKE)
Depart: 09/09/2026

One-way

Basic

From
$159
Seen: 18 hrs ago

Portland, OR (PDX)to

Milwaukee (MKE)
Depart: 10/01/2026

One-way

Basic

From
$164
Seen: 20 hrs ago

Portland, OR (PDX)to

Milwaukee (MKE)
Depart: 09/26/2026

One-way

Basic

From
$164
Seen: 18 minutes ago

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Explore flights from Portland, OR to Milwaukee

Aug 2026
From$427*
Seen: 19 hrs ago
One Way/Basic
Sep 2026
From$159*
Seen: 5 hrs ago
One Way/Basic
Oct 2026
From$159*
Seen: 11 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $159
cmp-daily-histogram-bars-legend-max-price-aria-label $427
Displaying fares for August-2026
  • PDX–MKE, 08/23/2026: From $427
    23

    Sun

    AUG

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

    Mon

  • PDX–MKE, 08/25/2026: From $427
    25

    Tue

  • PDX–MKE, 08/26/2026: From $427
    26

    Wed

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

    Thu

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

    Fri

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

    Sat

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

    Sun

  • PDX–MKE, 08/31/2026: From $427
    31

    Mon

  • PDX–MKE: cmp-view-offers-disclaimer. Find Offers
    01

    Tue

    SEP

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

    Wed

  • PDX–MKE, 09/03/2026: From $427
    03

    Thu

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

    Fri

  • PDX–MKE, 09/05/2026: From $159
    05

    Sat

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

    Sun

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

    Mon

  • PDX–MKE: cmp-view-offers-disclaimer. Find Offers
    08

    Tue

  • PDX–MKE, 09/09/2026: From $159
    09

    Wed

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

    Thu

  • PDX–MKE, 09/11/2026: From $164
    11

    Fri

  • PDX–MKE: cmp-view-offers-disclaimer. Find Offers
    12

    Sat

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

    Sun

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

    Mon

  • PDX–MKE, 09/15/2026: From $159
    15

    Tue

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

    Wed

  • PDX–MKE, 09/17/2026: From $205
    17

    Thu

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

    Fri

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

    Sat

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

    Sun

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

    Mon

  • PDX–MKE: cmp-view-offers-disclaimer. Find Offers
    22

    Tue

    • Range$159-$427

    *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:
    General Mitchell Airport
    Distance:
    1718 miles

    Route Information

    111† 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 111 weekly flights from Portland, OR to Milwaukee on Southwest Airlines.
    To find the lowest fares by day and time to fly Portland, OR to Milwaukee with Southwest, check out our Low Fare Calendar.
    You can rent a car at General Mitchell Airport book yours with your flight.
    Yes! Flights from Portland, OR to Milwaukee—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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