Southwest® flights from Chicago-Midway to Portland, OR from $141

Promo Code

Low fares from Chicago-Midway to Portland, OR

$

Chicago-Midway (MDW)to

Portland, OR (PDX)
Depart: 12/16/2026

One-way

Basic

From
$141
Seen: 6 hrs ago

Chicago-Midway (MDW)to

Portland, OR (PDX)
Depart: 01/05/2027

One-way

Basic

From
$141
Seen: 12 minutes ago

Chicago-Midway (MDW)to

Portland, OR (PDX)
Depart: 11/18/2026

One-way

Basic

From
$141
Seen: 13 hrs ago

Chicago-Midway (MDW)to

Portland, OR (PDX)
Depart: 12/07/2026

One-way

Basic

From
$146
Seen: 20 hrs ago

Chicago-Midway (MDW)to

Portland, OR (PDX)
Depart: 11/17/2026

One-way

Basic

From
$146
Seen: 19 hrs ago

Chicago-Midway (MDW)to

Portland, OR (PDX)
Depart: 12/10/2026

One-way

Basic

From
$146
Seen: 20 hrs ago

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Explore flights from Chicago-Midway to Portland, OR

Oct 2026
From$259*
Seen: 23 hrs ago
One Way/Basic
Nov 2026
From$141*
Seen: 13 hrs ago
One Way/Basic
Dec 2026
From$141*
Seen: 6 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $141
cmp-daily-histogram-bars-legend-max-price-aria-label $324
Displaying fares for October-2026
  • MDW–PDX, 10/20/2026: From $259
    20

    Tue

    OCT

  • MDW–PDX, 10/21/2026: From $259
    21

    Wed

  • MDW–PDX, 10/22/2026: From $274
    22

    Thu

  • MDW–PDX, 10/23/2026: From $324
    23

    Fri

  • MDW–PDX, 10/24/2026: From $259
    24

    Sat

  • MDW–PDX, 10/25/2026: From $274
    25

    Sun

  • MDW–PDX, 10/26/2026: From $274
    26

    Mon

  • MDW–PDX, 10/27/2026: From $259
    27

    Tue

  • MDW–PDX, 10/28/2026: From $259
    28

    Wed

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

    Thu

  • MDW–PDX, 10/30/2026: From $274
    30

    Fri

  • MDW–PDX: cmp-view-offers-disclaimer. Find Offers
    31

    Sat

  • MDW–PDX, 11/01/2026: From $282
    01

    Sun

    NOV

  • MDW–PDX, 11/02/2026: From $274
    02

    Mon

  • MDW–PDX, 11/03/2026: From $259
    03

    Tue

  • MDW–PDX, 11/04/2026: From $259
    04

    Wed

  • MDW–PDX, 11/05/2026: From $274
    05

    Thu

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

    Fri

  • MDW–PDX, 11/07/2026: From $259
    07

    Sat

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

    Sun

  • MDW–PDX, 11/09/2026: From $156
    09

    Mon

  • MDW–PDX, 11/10/2026: From $156
    10

    Tue

  • MDW–PDX, 11/11/2026: From $171
    11

    Wed

  • MDW–PDX, 11/12/2026: From $171
    12

    Thu

  • MDW–PDX, 11/13/2026: From $160
    13

    Fri

  • MDW–PDX, 11/14/2026: From $249
    14

    Sat

  • MDW–PDX, 11/15/2026: From $158
    15

    Sun

  • MDW–PDX, 11/16/2026: From $156
    16

    Mon

  • MDW–PDX, 11/17/2026: From $146
    17

    Tue

  • MDW–PDX, 11/18/2026: From $141
    18

    Wed

  • MDW–PDX, 11/19/2026: From $189
    19

    Thu

    • Range$141-$324

    *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

    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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