Southwest® flights from Portland, OR to Chicago (O'Hare)

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Low fares from Portland, OR to Chicago (O'Hare)

$

Portland, OR (PDX)to

Chicago (Midway) (MDW)
Depart: 09/06/2026

One-way

Basic

From
$179
Seen: 17 hrs ago

Portland, OR (PDX)to

Chicago (Midway) (MDW)
Depart: 09/05/2026

One-way

Basic

From
$179
Seen: 4 hrs ago

Portland, OR (PDX)to

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

One-way

Basic

From
$179
Seen: 1 hour ago

Portland, OR (PDX)to

Chicago (Midway) (MDW)
Depart: 10/30/2026

One-way

Basic

From
$179
Seen: 18 hrs ago

Portland, OR (PDX)to

Chicago (Midway) (MDW)
Depart: 10/24/2026

One-way

Basic

From
$195
Seen: 21 hrs ago

Portland, OR (PDX)to

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

One-way

Basic

From
$195
Seen: 20 hrs ago

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Explore flights from Portland, OR to Chicago (O'Hare)

Aug 2026
From$198*
Seen: 1 hour ago
One Way/Basic
Sep 2026
From$179*
Seen: 1 hour ago
One Way/Basic
Oct 2026
From$179*
Seen: 18 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $198
cmp-daily-histogram-bars-legend-max-price-aria-label $252
Displaying fares for August-2026
  • PDX–MDW: cmp-view-offers-disclaimer. Find Offers
    05

    Wed

    AUG

  • PDX–MDW, 08/06/2026: From $242
    06

    Thu

  • PDX–MDW, 08/07/2026: From $242
    07

    Fri

  • PDX–MDW, 08/08/2026: From $229
    08

    Sat

  • PDX–MDW, 08/09/2026: From $252
    09

    Sun

  • PDX–MDW, 08/10/2026: From $252
    10

    Mon

  • PDX–MDW, 08/11/2026: From $229
    11

    Tue

  • PDX–MDW, 08/12/2026: From $219
    12

    Wed

  • PDX–MDW, 08/13/2026: From $242
    13

    Thu

  • PDX–MDW, 08/14/2026: From $252
    14

    Fri

  • PDX–MDW, 08/15/2026: From $229
    15

    Sat

  • PDX–MDW, 08/16/2026: From $242
    16

    Sun

  • PDX–MDW, 08/17/2026: From $242
    17

    Mon

  • PDX–MDW, 08/18/2026: From $219
    18

    Tue

  • PDX–MDW, 08/19/2026: From $219
    19

    Wed

  • PDX–MDW, 08/20/2026: From $242
    20

    Thu

  • PDX–MDW, 08/21/2026: From $242
    21

    Fri

  • PDX–MDW, 08/22/2026: From $219
    22

    Sat

  • PDX–MDW, 08/23/2026: From $242
    23

    Sun

  • PDX–MDW, 08/24/2026: From $242
    24

    Mon

  • PDX–MDW, 08/25/2026: From $198
    25

    Tue

  • PDX–MDW, 08/26/2026: From $243
    26

    Wed

  • PDX–MDW, 08/27/2026: From $198
    27

    Thu

  • PDX–MDW, 08/28/2026: From $219
    28

    Fri

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

    Sat

  • PDX–MDW: cmp-view-offers-disclaimer. Find Offers
    30

    Sun

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

    Mon

  • PDX–MDW, 09/01/2026: From $198
    01

    Tue

    SEP

  • PDX–MDW: cmp-view-offers-disclaimer. Find Offers
    02

    Wed

  • PDX–MDW, 09/03/2026: From $198
    03

    Thu

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

    Fri

    • Range$198-$252

    *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:
    O'Hare International Airport
    Distance:
    1739 miles

    Route Information

    79† Weekly flights

    † 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

    There are 79 weekly flights from Portland, OR to Chicago (O'Hare) on Southwest Airlines.
    To find the lowest fares by day and time to fly Portland, OR to Chicago (O'Hare) with Southwest, check out our Low Fare Calendar.
    You can rent a car at O'Hare International Airport book yours with your flight.
    Yes! Flights from Portland, OR to Chicago (O'Hare)—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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