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

Promo Code

Low fares from Chicago-Midway to Portland, OR

$

Chicago-Midway (MDW)to

Portland, OR (PDX)
Depart: 11/23/2026

One-way

Basic

From
$179
Seen: 22 hrs ago

Chicago-Midway (MDW)to

Portland, OR (PDX)
Depart: 10/19/2026

One-way

Basic

From
$179
Seen: 23 hrs ago

Chicago-Midway (MDW)to

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

One-way

Basic

From
$179
Seen: 22 hrs ago

Chicago-Midway (MDW)to

Portland, OR (PDX)
Depart: 10/29/2026

One-way

Basic

From
$179
Seen: 9 hrs ago

Chicago-Midway (MDW)to

Portland, OR (PDX)
Depart: 11/04/2026

One-way

Basic

From
$179
Seen: 11 hrs ago

Chicago-Midway (MDW)to

Portland, OR (PDX)
Depart: 10/05/2026

One-way

Basic

From
$179
Seen: 12 hrs ago

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Explore flights from Chicago-Midway to Portland, OR

Sep 2026
From$239*
Seen: 8 hrs ago
One Way/Basic
Oct 2026
From$179*
Seen: 16 hrs ago
One Way/Basic
Nov 2026
From$179*
Seen: 18 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
  • MDW–PDX, 09/11/2026: From $264
    11

    Fri

    SEP

  • MDW–PDX, 09/12/2026: From $249
    12

    Sat

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

    Sun

  • MDW–PDX, 09/14/2026: From $264
    14

    Mon

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

    Tue

  • MDW–PDX, 09/16/2026: From $255
    16

    Wed

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

    Thu

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

    Fri

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

    Sat

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

    Sun

  • MDW–PDX, 09/21/2026: From $264
    21

    Mon

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

    Tue

  • MDW–PDX: cmp-view-offers-disclaimer. Find Offers
    23

    Wed

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

    Thu

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

    Fri

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

    Sat

  • MDW–PDX, 09/27/2026: From $264
    27

    Sun

  • MDW–PDX, 09/28/2026: From $254
    28

    Mon

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

    Tue

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

    Wed

  • MDW–PDX, 10/01/2026: From $264
    01

    Thu

    OCT

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

    Fri

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

    Sat

  • MDW–PDX, 10/04/2026: From $229
    04

    Sun

  • MDW–PDX, 10/05/2026: From $179
    05

    Mon

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

    Tue

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

    Wed

  • MDW–PDX, 10/08/2026: From $224
    08

    Thu

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

    Fri

  • MDW–PDX, 10/10/2026: From $224
    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:
    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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