Southwest® flights from Portland, ME to Chicago-Midway from $169

Promo Code

Low fares from Portland, ME to Chicago-Midway

$

Portland, ME (PWM)to

Chicago-Midway (MDW)
Depart: 10/01/2026

One-way

Basic

From
$169
Seen: 17 hrs ago

Portland, ME (PWM)to

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

One-way

Basic

From
$179
Seen: 11 hrs ago

Portland, ME (PWM)to

Chicago-Midway (MDW)
Depart: 12/17/2026

One-way

Basic

From
$179
Seen: 10 hrs ago

Portland, ME (PWM)to

Chicago-Midway (MDW)
Depart: 10/26/2026

One-way

Basic

From
$179
Seen: 2 hrs ago

Portland, ME (PWM)to

Chicago-Midway (MDW)
Depart: 11/05/2026

One-way

Basic

From
$184
Seen: 1 hour ago

Portland, ME (PWM)to

Chicago-Midway (MDW)
Depart: 10/23/2026

One-way

Basic

From
$185
Seen: 5 hrs ago

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Explore flights from Portland, ME to Chicago-Midway

Sep 2026
From$199*
Seen: 20 hrs ago
One Way/Basic
Oct 2026
From$169*
Seen: 17 hrs ago
One Way/Basic
Nov 2026
From$179*
Seen: 11 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $169
cmp-daily-histogram-bars-legend-max-price-aria-label $406
Displaying fares for September-2026
  • PWM–MDW: cmp-view-offers-disclaimer. Find Offers
    11

    Fri

    SEP

  • PWM–MDW: cmp-view-offers-disclaimer. Find Offers
    12

    Sat

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

    Sun

  • PWM–MDW: cmp-view-offers-disclaimer. Find Offers
    14

    Mon

  • PWM–MDW, 09/15/2026: From $209
    15

    Tue

  • PWM–MDW: cmp-view-offers-disclaimer. Find Offers
    16

    Wed

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

    Thu

  • PWM–MDW, 09/18/2026: From $388
    18

    Fri

  • PWM–MDW, 09/19/2026: From $199
    19

    Sat

  • PWM–MDW: cmp-view-offers-disclaimer. Find Offers
    20

    Sun

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

    Mon

  • PWM–MDW, 09/22/2026: From $381
    22

    Tue

  • PWM–MDW, 09/23/2026: From $239
    23

    Wed

  • PWM–MDW, 09/24/2026: From $259
    24

    Thu

  • PWM–MDW, 09/25/2026: From $249
    25

    Fri

  • PWM–MDW, 09/26/2026: From $209
    26

    Sat

  • PWM–MDW, 09/27/2026: From $406
    27

    Sun

  • PWM–MDW, 09/28/2026: From $341
    28

    Mon

  • PWM–MDW, 09/29/2026: From $209
    29

    Tue

  • PWM–MDW, 09/30/2026: From $199
    30

    Wed

  • PWM–MDW, 10/01/2026: From $169
    01

    Thu

    OCT

  • PWM–MDW, 10/02/2026: From $185
    02

    Fri

  • PWM–MDW, 10/03/2026: From $229
    03

    Sat

  • PWM–MDW, 10/04/2026: From $336
    04

    Sun

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

    Mon

  • PWM–MDW, 10/06/2026: From $298
    06

    Tue

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

    Wed

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

    Thu

  • PWM–MDW: cmp-view-offers-disclaimer. Find Offers
    09

    Fri

  • PWM–MDW, 10/10/2026: From $346
    10

    Sat

    • Range$169-$406

    *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 Jetport
    Arriving at:
    Chicago Midway International Airport
    Average flight time:
    2 hours 34 minutes
    Distance:
    895 miles

    Route Information

    93† Weekly flights
    • 1‡ Nonstop flight 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 Portland, ME to Chicago (Midway) is 2 hours 34 minutes.
    There are 93 weekly flights from Portland, ME to Chicago (Midway) on Southwest Airlines.
    Yes, Southwest flies nonstop from Portland, ME to Chicago (Midway) once per day from Monday through Friday.
    Yes, Southwest flies nonstop from Portland, ME to Chicago (Midway) once per day on Saturdays and Sundays.
    To find the lowest fares by day and time to fly Portland, ME 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, ME 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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