Southwest® flights from Chicago (Midway) to Portland, OR from $149

Promo Code

Low fares from Chicago (Midway) to Portland, OR

$

Chicago (Midway) (MDW)to

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

One-way

Basic

From
$149
Seen: 8 hrs ago

Chicago (Midway) (MDW)to

Portland, OR (PDX)
Depart: 10/28/2026

One-way

Basic

From
$149
Seen: 22 hrs ago

Chicago (Midway) (MDW)to

Portland, OR (PDX)
Depart: 09/15/2026

One-way

Basic

From
$149
Seen: 4 hrs ago

Chicago (Midway) (MDW)to

Portland, OR (PDX)
Depart: 09/16/2026

One-way

Basic

From
$149
Seen: 2 hrs ago

Chicago (Midway) (MDW)to

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

One-way

Basic

From
$149
Seen: 1 hour ago

Chicago (Midway) (MDW)to

Portland, OR (PDX)
Depart: 10/07/2026

One-way

Basic

From
$149
Seen: 17 hrs ago

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Explore flights from Chicago (Midway) to Portland, OR

Aug 2026
From$159*
Seen: 9 minutes ago
One Way/Basic
Sep 2026
From$149*
Seen: 7 hrs ago
One Way/Basic
Oct 2026
From$149*
Seen: 4 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $159
cmp-daily-histogram-bars-legend-max-price-aria-label $315
Displaying fares for August-2026
  • MDW–PDX, 08/01/2026: From $219
    01

    Sat

    AUG

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

    Sun

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    03

    Mon

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    04

    Tue

  • MDW–PDX, 08/05/2026: From $275
    05

    Wed

  • MDW–PDX, 08/06/2026: From $315
    06

    Thu

  • MDW–PDX, 08/07/2026: From $242
    07

    Fri

  • MDW–PDX, 08/08/2026: From $219
    08

    Sat

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    09

    Sun

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    10

    Mon

  • MDW–PDX, 08/11/2026: From $219
    11

    Tue

  • MDW–PDX, 08/12/2026: From $219
    12

    Wed

  • MDW–PDX, 08/13/2026: From $242
    13

    Thu

  • MDW–PDX, 08/14/2026: From $242
    14

    Fri

  • MDW–PDX, 08/15/2026: From $219
    15

    Sat

  • MDW–PDX, 08/16/2026: From $242
    16

    Sun

  • MDW–PDX, 08/17/2026: From $242
    17

    Mon

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

    Tue

  • MDW–PDX, 08/19/2026: From $219
    19

    Wed

  • MDW–PDX, 08/20/2026: From $242
    20

    Thu

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    21

    Fri

  • MDW–PDX, 08/22/2026: From $198
    22

    Sat

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    23

    Sun

  • MDW–PDX, 08/24/2026: From $243
    24

    Mon

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    25

    Tue

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

    Wed

  • MDW–PDX, 08/27/2026: From $159
    27

    Thu

  • MDW–PDX, 08/28/2026: From $159
    28

    Fri

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

    Sat

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    30

    Sun

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    31

    Mon

    • Range$159-$315

    *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:
    Chicago Midway International Airport
    Arriving at:
    Portland International Airport
    Average flight time:
    4 hours 22 minutes
    Distance:
    1751 miles

    Route Information

    152† Weekly flights
    • 2‡ Nonstop flights per day Monday through Friday
    • 1‡ Nonstop flight on Saturday
    • 1‡ Nonstop flight on Sunday

    † 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

    The average flight time from Chicago (Midway) to Portland, OR is 4 hours 22 minutes.
    There are 152 weekly flights from Chicago (Midway) to Portland, OR on Southwest Airlines.
    Yes, Southwest flies nonstop from Chicago (Midway) to Portland, OR 2 times per day from Monday through Friday.
    Yes, Southwest flies nonstop from Chicago (Midway) to Portland, OR once per day on Saturdays and Sundays.
    To find the lowest fares by day and time to fly Chicago (Midway) 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 Chicago (Midway) 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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