Southwest® flights from Chicago (Midway) to Portland, ME from $118

Promo Code

Low fares from Chicago (Midway) to Portland, ME

$

Chicago (Midway) (MDW)to

Portland, ME (PWM)
Depart: 10/20/2026

One-way

Basic

From
$118
Seen: 20 hrs ago

Chicago (Midway) (MDW)to

Portland, ME (PWM)
Depart: 10/28/2026

One-way

Basic

From
$118
Seen: 5 hrs ago

Chicago (Midway) (MDW)to

Portland, ME (PWM)
Depart: 09/07/2026

One-way

Basic

From
$118
Seen: 14 hrs ago

Chicago (Midway) (MDW)to

Portland, ME (PWM)
Depart: 10/29/2026

One-way

Basic

From
$118
Seen: 14 hrs ago

Chicago (Midway) (MDW)to

Portland, ME (PWM)
Depart: 08/24/2026

One-way

Basic

From
$128
Seen: 10 hrs ago

Chicago (Midway) (MDW)to

Portland, ME (PWM)
Depart: 09/22/2026

One-way

Basic

From
$128
Seen: 21 hrs ago

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Explore flights from Chicago (Midway) to Portland, ME

Try alternate month or interact with individual days below in order to find offers.
Jul 2026
No result for this month.
Aug 2026
From$128*
Seen: 10 hrs ago
One Way/Basic
Sep 2026
From$118*
Seen: 14 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $128
cmp-daily-histogram-bars-legend-max-price-aria-label $279
Displaying fares for July-2026
  • MDW–PWM: cmp-view-offers-disclaimer. Find Offers
    31

    Fri

    JUL

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

    Sat

  • MDW–PWM, 08/02/2026: From $279
    02

    Sun

  • MDW–PWM, 08/03/2026: From $239
    03

    Mon

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    04

    Tue

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

    Wed

  • MDW–PWM, 08/06/2026: From $269
    06

    Thu

  • MDW–PWM, 08/07/2026: From $262
    07

    Fri

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

    Sat

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    09

    Sun

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    10

    Mon

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    11

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    12

    Wed

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    13

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    14

    Fri

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    15

    Sat

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    16

    Sun

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

    Mon

  • MDW–PWM: cmp-view-offers-disclaimer. Find Offers
    18

    Tue

  • MDW–PWM, 08/19/2026: From $189
    19

    Wed

  • MDW–PWM, 08/20/2026: From $249
    20

    Thu

  • MDW–PWM, 08/21/2026: From $178
    21

    Fri

  • MDW–PWM, 08/22/2026: From $193
    22

    Sat

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

    Sun

  • MDW–PWM, 08/24/2026: From $128
    24

    Mon

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    25

    Tue

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    26

    Wed

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    27

    Thu

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    28

    Fri

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    29

    Sat

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    30

    Sun

    • Range$128-$279

    *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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