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

Promo Code

Low fares from Portland, OR to Chicago-Midway

$

Portland, OR (PDX)to

Chicago-Midway (MDW)
Depart: 11/09/2026

One-way

Basic

From
$141
Seen: 22 hrs ago

Portland, OR (PDX)to

Chicago-Midway (MDW)
Depart: 01/06/2027

One-way

Basic

From
$141
Seen: 20 hrs ago

Portland, OR (PDX)to

Chicago-Midway (MDW)
Depart: 11/17/2026

One-way

Basic

From
$141
Seen: 16 hrs ago

Portland, OR (PDX)to

Chicago-Midway (MDW)
Depart: 11/18/2026

One-way

Basic

From
$141
Seen: 9 hrs ago

Portland, OR (PDX)to

Chicago-Midway (MDW)
Depart: 12/15/2026

One-way

Basic

From
$141
Seen: 21 hrs ago

Portland, OR (PDX)to

Chicago-Midway (MDW)
Depart: 01/23/2027

One-way

Basic

From
$141
Seen: 22 hrs ago

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Explore flights from Portland, OR to Chicago-Midway

Oct 2026
From$259*
Seen: 14 hrs ago
One Way/Basic
Nov 2026
From$141*
Seen: 21 minutes ago
One Way/Basic
Dec 2026
From$141*
Seen: 23 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $141
cmp-daily-histogram-bars-legend-max-price-aria-label $274
Displaying fares for October-2026
  • PDX–MDW, 10/22/2026: From $274
    22

    Thu

    OCT

  • PDX–MDW, 10/23/2026: From $274
    23

    Fri

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

    Sat

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

    Sun

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

    Mon

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

    Tue

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

    Wed

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

    Thu

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

    Fri

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

    Sat

  • PDX–MDW, 11/01/2026: From $274
    01

    Sun

    NOV

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

    Mon

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

    Tue

  • PDX–MDW, 11/04/2026: From $269
    04

    Wed

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

    Thu

  • PDX–MDW, 11/06/2026: From $274
    06

    Fri

  • PDX–MDW: cmp-view-offers-disclaimer. Find Offers
    07

    Sat

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

    Sun

  • PDX–MDW, 11/09/2026: From $141
    09

    Mon

  • PDX–MDW, 11/10/2026: From $171
    10

    Tue

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

    Wed

  • PDX–MDW, 11/12/2026: From $151
    12

    Thu

  • PDX–MDW, 11/13/2026: From $145
    13

    Fri

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

    Sat

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

    Sun

  • PDX–MDW, 11/16/2026: From $249
    16

    Mon

  • PDX–MDW, 11/17/2026: From $141
    17

    Tue

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

    Wed

  • PDX–MDW, 11/19/2026: From $254
    19

    Thu

  • PDX–MDW, 11/20/2026: From $249
    20

    Fri

  • PDX–MDW, 11/21/2026: From $141
    21

    Sat

    • Range$141-$274

    *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

    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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