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

Promo Code

Low fares from Portland, OR to Chicago (Midway)

$

Portland, OR (PDX)to

Chicago (Midway) (MDW)
Depart: 09/05/2026

One-way

Basic

From
$149
Seen: 8 hrs ago

Portland, OR (PDX)to

Chicago (Midway) (MDW)
Depart: 09/29/2026

One-way

Basic

From
$149
Seen: 5 hrs ago

Portland, OR (PDX)to

Chicago (Midway) (MDW)
Depart: 09/30/2026

One-way

Basic

From
$149
Seen: 5 hrs ago

Portland, OR (PDX)to

Chicago (Midway) (MDW)
Depart: 11/03/2026

One-way

Basic

From
$149
Seen: 22 hrs ago

Portland, OR (PDX)to

Chicago (Midway) (MDW)
Depart: 10/20/2026

One-way

Basic

From
$149
Seen: 5 hrs ago

Portland, OR (PDX)to

Chicago (Midway) (MDW)
Depart: 08/29/2026

One-way

Basic

From
$149
Seen: 1 hour ago

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Explore flights from Portland, OR to Chicago (Midway)

Aug 2026
From$149*
Seen: 1 hour ago
One Way/Basic
Sep 2026
From$149*
Seen: 1 hour ago
One Way/Basic
Oct 2026
From$149*
Seen: 17 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $149
cmp-daily-histogram-bars-legend-max-price-aria-label $252
Displaying fares for August-2026
  • PDX–MDW: cmp-view-offers-disclaimer. Find Offers
    01

    Sat

    AUG

  • PDX–MDW, 08/02/2026: From $252
    02

    Sun

  • PDX–MDW, 08/03/2026: From $242
    03

    Mon

  • PDX–MDW, 08/04/2026: From $219
    04

    Tue

  • PDX–MDW, 08/05/2026: From $219
    05

    Wed

  • PDX–MDW, 08/06/2026: From $242
    06

    Thu

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

    Fri

  • PDX–MDW, 08/08/2026: From $229
    08

    Sat

  • PDX–MDW, 08/09/2026: From $252
    09

    Sun

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

    Mon

  • PDX–MDW, 08/11/2026: From $229
    11

    Tue

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

    Wed

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

    Thu

  • PDX–MDW, 08/14/2026: From $252
    14

    Fri

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

    Sat

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

    Sun

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

    Mon

  • PDX–MDW, 08/18/2026: From $219
    18

    Tue

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

    Wed

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

    Thu

  • PDX–MDW, 08/21/2026: From $219
    21

    Fri

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

    Sat

  • PDX–MDW, 08/23/2026: From $219
    23

    Sun

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

    Mon

  • PDX–MDW, 08/25/2026: From $198
    25

    Tue

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

    Wed

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

    Thu

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

    Fri

  • PDX–MDW, 08/29/2026: From $149
    29

    Sat

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

    Sun

  • PDX–MDW, 08/31/2026: From $159
    31

    Mon

    • Range$149-$252

    *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:
    Chicago Midway International Airport
    Average flight time:
    3 hours 53 minutes
    Distance:
    1751 miles

    Route Information

    150† 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 Portland, OR to Chicago (Midway) is 3 hours 53 minutes.
    There are 150 weekly flights from Portland, OR to Chicago (Midway) on Southwest Airlines.
    Yes, Southwest flies nonstop from Portland, OR to Chicago (Midway) 2 times per day from Monday through Friday.
    Yes, Southwest flies nonstop from Portland, OR to Chicago (Midway) once per day on Saturdays and Sundays.
    To find the lowest fares by day and time to fly Portland, OR to Chicago (Midway) with Southwest, check out our Low Fare Calendar.
    You can rent a car at Chicago Midway International Airport book yours with your flight.
    Yes! Flights from Portland, OR to Chicago (Midway)—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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