Southwest® flights from Chicago (Midway) to Portland, ME from $132

Promo Code

Low fares from Chicago (Midway) to Portland, ME

$

Chicago (Midway) (MDW)to

Portland, ME (PWM)
Depart: 10/03/2026

One-way

Basic

From
$132
Seen: 6 hrs ago

Chicago (Midway) (MDW)to

Portland, ME (PWM)
Depart: 09/12/2026

One-way

Basic

From
$149
Seen: 14 hrs ago

Chicago (Midway) (MDW)to

Portland, ME (PWM)
Depart: 10/26/2026

One-way

Basic

From
$149
Seen: 10 hrs ago

Chicago (Midway) (MDW)to

Portland, ME (PWM)
Depart: 11/12/2026

One-way

Basic

From
$159
Seen: 15 hrs ago

Chicago (Midway) (MDW)to

Portland, ME (PWM)
Depart: 10/06/2026

One-way

Basic

From
$159
Seen: 15 hrs ago

Chicago (Midway) (MDW)to

Portland, ME (PWM)
Depart: 11/11/2026

One-way

Basic

From
$159
Seen: 15 hrs ago

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Explore flights from Chicago (Midway) to Portland, ME

Aug 2026
From$189*
Seen: 18 hrs ago
One Way/Basic
Sep 2026
From$149*
Seen: 14 hrs ago
One Way/Basic
Oct 2026
From$132*
Seen: 6 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $149
cmp-daily-histogram-bars-legend-max-price-aria-label $396
Displaying fares for August-2026
  • MDW–PWM, 08/21/2026: From $239
    21

    Fri

    AUG

  • MDW–PWM, 08/22/2026: From $199
    22

    Sat

  • MDW–PWM, 08/23/2026: From $239
    23

    Sun

  • MDW–PWM: cmp-view-offers-disclaimer. Find Offers
    24

    Mon

  • MDW–PWM, 08/25/2026: From $189
    25

    Tue

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

    Wed

  • MDW–PWM, 08/27/2026: From $272
    27

    Thu

  • MDW–PWM, 08/28/2026: From $239
    28

    Fri

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

    Sat

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

    Sun

  • MDW–PWM, 08/31/2026: From $269
    31

    Mon

  • MDW–PWM: cmp-view-offers-disclaimer. Find Offers
    01

    Tue

    SEP

  • MDW–PWM, 09/02/2026: From $189
    02

    Wed

  • MDW–PWM, 09/03/2026: From $336
    03

    Thu

  • MDW–PWM, 09/04/2026: From $262
    04

    Fri

  • MDW–PWM, 09/05/2026: From $169
    05

    Sat

  • MDW–PWM, 09/06/2026: From $159
    06

    Sun

  • MDW–PWM, 09/07/2026: From $239
    07

    Mon

  • MDW–PWM, 09/08/2026: From $189
    08

    Tue

  • MDW–PWM, 09/09/2026: From $204
    09

    Wed

  • MDW–PWM, 09/10/2026: From $321
    10

    Thu

  • MDW–PWM, 09/11/2026: From $174
    11

    Fri

  • MDW–PWM, 09/12/2026: From $149
    12

    Sat

  • MDW–PWM, 09/13/2026: From $239
    13

    Sun

  • MDW–PWM, 09/14/2026: From $186
    14

    Mon

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

    Tue

  • MDW–PWM, 09/16/2026: From $186
    16

    Wed

  • MDW–PWM, 09/17/2026: From $396
    17

    Thu

  • MDW–PWM, 09/18/2026: From $257
    18

    Fri

  • MDW–PWM: cmp-view-offers-disclaimer. Find Offers
    19

    Sat

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

    Sun

    • Range$149-$396

    *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 Jetport
    Average flight time:
    2 hours 10 minutes
    Distance:
    895 miles

    Route Information

    86† 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 Chicago (Midway) to Portland, ME is 2 hours 10 minutes.
    There are 86 weekly flights from Chicago (Midway) to Portland, ME on Southwest Airlines.
    Yes, Southwest flies nonstop from Chicago (Midway) to Portland, ME once per day from Monday through Friday.
    Yes, Southwest flies nonstop from Chicago (Midway) to Portland, ME once per day on Saturdays and Sundays.
    To find the lowest fares by day and time to fly Chicago (Midway) to Portland, ME with Southwest, check out our Low Fare Calendar.
    You can rent a car at Portland International Jetport book yours with your flight.
    Yes! Flights from Chicago (Midway) to Portland, ME—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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