Southwest® flights from Chicago-Midway to Portland, OR from $174

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
$174
Seen: 22 hrs ago

Chicago-Midway (MDW)to

Portland, OR (PDX)
Depart: 01/13/2027

One-way

Basic

From
$174
Seen: 10 hrs ago

Chicago-Midway (MDW)to

Portland, OR (PDX)
Depart: 02/06/2027

One-way

Basic

From
$174
Seen: 20 hrs ago

Chicago-Midway (MDW)to

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

One-way

Basic

From
$174
Seen: 14 hrs ago

Chicago-Midway (MDW)to

Portland, OR (PDX)
Depart: 01/09/2027

One-way

Basic

From
$174
Seen: 6 hrs ago

Chicago-Midway (MDW)to

Portland, OR (PDX)
Depart: 12/15/2026

One-way

Basic

From
$174
Seen: 16 hrs ago

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Explore flights from Chicago-Midway to Portland, OR

Nov 2026
From$269*
Seen: 21 hrs ago
One Way/Basic
Dec 2026
From$174*
Seen: 14 hrs ago
One Way/Basic
Jan 2027
From$174*
Seen: 6 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $194
cmp-daily-histogram-bars-legend-max-price-aria-label $468
Displaying fares for November-2026
  • MDW–PDX, 11/12/2026: From $329
    12

    Thu

    NOV

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

    Fri

  • MDW–PDX, 11/14/2026: From $269
    14

    Sat

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

    Sun

  • MDW–PDX, 11/16/2026: From $279
    16

    Mon

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

    Tue

  • MDW–PDX, 11/18/2026: From $269
    18

    Wed

  • MDW–PDX, 11/19/2026: From $279
    19

    Thu

  • MDW–PDX, 11/20/2026: From $279
    20

    Fri

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

    Sat

  • MDW–PDX, 11/22/2026: From $279
    22

    Sun

  • MDW–PDX, 11/23/2026: From $279
    23

    Mon

  • MDW–PDX, 11/24/2026: From $269
    24

    Tue

  • MDW–PDX: cmp-view-offers-disclaimer. Find Offers
    25

    Wed

  • MDW–PDX, 11/26/2026: From $279
    26

    Thu

  • MDW–PDX, 11/27/2026: From $316
    27

    Fri

  • MDW–PDX, 11/28/2026: From $468
    28

    Sat

  • MDW–PDX, 11/29/2026: From $458
    29

    Sun

  • MDW–PDX, 11/30/2026: From $355
    30

    Mon

  • MDW–PDX, 12/01/2026: From $269
    01

    Tue

    DEC

  • MDW–PDX, 12/02/2026: From $195
    02

    Wed

  • MDW–PDX, 12/03/2026: From $215
    03

    Thu

  • MDW–PDX: cmp-view-offers-disclaimer. Find Offers
    04

    Fri

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

    Sat

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

    Sun

  • MDW–PDX, 12/07/2026: From $215
    07

    Mon

  • MDW–PDX, 12/08/2026: From $195
    08

    Tue

  • MDW–PDX, 12/09/2026: From $195
    09

    Wed

  • MDW–PDX, 12/10/2026: From $194
    10

    Thu

  • MDW–PDX: cmp-view-offers-disclaimer. Find Offers
    11

    Fri

    • Range$194-$468

    *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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