Southwest® flights from Portland, OR to Chicago-Midway from $179

Promo Code

Low fares from Portland, OR to Chicago-Midway

$

Portland, OR (PDX)to

Chicago-Midway (MDW)
Depart: 11/24/2026

One-way

Basic

From
$179
Seen: 21 hrs ago

Portland, OR (PDX)to

Chicago-Midway (MDW)
Depart: 11/25/2026

One-way

Basic

From
$179
Seen: 19 hrs ago

Portland, OR (PDX)to

Chicago-Midway (MDW)
Depart: 10/06/2026

One-way

Basic

From
$179
Seen: 15 hrs ago

Portland, OR (PDX)to

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

One-way

Basic

From
$179
Seen: 12 hrs ago

Portland, OR (PDX)to

Chicago-Midway (MDW)
Depart: 11/16/2026

One-way

Basic

From
$179
Seen: 13 hrs ago

Portland, OR (PDX)to

Chicago-Midway (MDW)
Depart: 10/31/2026

One-way

Basic

From
$179
Seen: 19 hrs ago

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Explore flights from Portland, OR to Chicago-Midway

Sep 2026
From$239*
Seen: 13 hrs ago
One Way/Basic
Oct 2026
From$179*
Seen: 23 hrs ago
One Way/Basic
Nov 2026
From$179*
Seen: 2 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $179
cmp-daily-histogram-bars-legend-max-price-aria-label $264
Displaying fares for September-2026
  • PDX–MDW: cmp-view-offers-disclaimer. Find Offers
    11

    Fri

    SEP

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

    Sat

  • PDX–MDW, 09/13/2026: From $264
    13

    Sun

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

    Mon

  • PDX–MDW, 09/15/2026: From $239
    15

    Tue

  • PDX–MDW, 09/16/2026: From $249
    16

    Wed

  • PDX–MDW, 09/17/2026: From $254
    17

    Thu

  • PDX–MDW, 09/18/2026: From $264
    18

    Fri

  • PDX–MDW, 09/19/2026: From $239
    19

    Sat

  • PDX–MDW, 09/20/2026: From $264
    20

    Sun

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

    Mon

  • PDX–MDW, 09/22/2026: From $239
    22

    Tue

  • PDX–MDW, 09/23/2026: From $239
    23

    Wed

  • PDX–MDW, 09/24/2026: From $264
    24

    Thu

  • PDX–MDW, 09/25/2026: From $264
    25

    Fri

  • PDX–MDW, 09/26/2026: From $239
    26

    Sat

  • PDX–MDW, 09/27/2026: From $254
    27

    Sun

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

    Mon

  • PDX–MDW, 09/29/2026: From $239
    29

    Tue

  • PDX–MDW, 09/30/2026: From $239
    30

    Wed

  • PDX–MDW, 10/01/2026: From $179
    01

    Thu

    OCT

  • PDX–MDW, 10/02/2026: From $198
    02

    Fri

  • PDX–MDW, 10/03/2026: From $179
    03

    Sat

  • PDX–MDW, 10/04/2026: From $239
    04

    Sun

  • PDX–MDW: cmp-view-offers-disclaimer. Find Offers
    05

    Mon

  • PDX–MDW, 10/06/2026: From $179
    06

    Tue

  • PDX–MDW, 10/07/2026: From $179
    07

    Wed

  • PDX–MDW, 10/08/2026: From $243
    08

    Thu

  • PDX–MDW, 10/09/2026: From $198
    09

    Fri

  • PDX–MDW, 10/10/2026: From $179
    10

    Sat

    • Range$179-$264

    *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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