Southwest® flights from Chicago-Midway to Portland, ME from $143

Promo Code

Low fares from Chicago-Midway to Portland, ME

$

Chicago-Midway (MDW)to

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

One-way

Basic

From
$143
Seen: 5 minutes ago

Chicago-Midway (MDW)to

Portland, ME (PWM)
Depart: 11/14/2026

One-way

Basic

From
$146
Seen: 8 hrs ago

Chicago-Midway (MDW)to

Portland, ME (PWM)
Depart: 11/17/2026

One-way

Basic

From
$146
Seen: 16 hrs ago

Chicago-Midway (MDW)to

Portland, ME (PWM)
Depart: 12/15/2026

One-way

Choice

From
$155
Seen: 22 hrs ago

Chicago-Midway (MDW)to

Portland, ME (PWM)
Depart: 01/14/2027

One-way

Choice

From
$155
Seen: 9 hrs ago

Chicago-Midway (MDW)to

Portland, ME (PWM)
Depart: 11/26/2026

One-way

Basic

From
$163
Seen: 13 hrs ago

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Explore flights from Chicago-Midway to Portland, ME

Oct 2026
From$212*
Seen: 17 minutes ago
One Way/Basic
Nov 2026
From$143*
Seen: 5 minutes ago
One Way/Basic
Dec 2026
From$155*
Seen: 22 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $143
cmp-daily-histogram-bars-legend-max-price-aria-label $279
Displaying fares for October-2026
  • MDW–PWM, 10/20/2026: From $212
    20

    Tue

    OCT

  • MDW–PWM, 10/21/2026: From $212
    21

    Wed

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    22

    Thu

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    23

    Fri

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    24

    Sat

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    25

    Sun

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    26

    Mon

  • MDW–PWM, 10/27/2026: From $212
    27

    Tue

  • MDW–PWM, 10/28/2026: From $217
    28

    Wed

  • MDW–PWM, 10/29/2026: From $269
    29

    Thu

  • MDW–PWM, 10/30/2026: From $269
    30

    Fri

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

    Sat

  • MDW–PWM, 11/01/2026: From $279
    01

    Sun

    NOV

  • MDW–PWM, 11/02/2026: From $279
    02

    Mon

  • MDW–PWM, 11/03/2026: From $222
    03

    Tue

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    04

    Wed

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    05

    Thu

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    06

    Fri

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    07

    Sat

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    08

    Sun

  • MDW–PWM, 11/09/2026: From $169
    09

    Mon

  • MDW–PWM: cmp-view-offers-disclaimer. Find Offers
    10

    Tue

  • MDW–PWM, 11/11/2026: From $143
    11

    Wed

  • MDW–PWM, 11/12/2026: From $169
    12

    Thu

  • MDW–PWM, 11/13/2026: From $169
    13

    Fri

  • MDW–PWM, 11/14/2026: From $146
    14

    Sat

  • MDW–PWM, 11/15/2026: From $253
    15

    Sun

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

    Mon

  • MDW–PWM, 11/17/2026: From $146
    17

    Tue

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    18

    Wed

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    19

    Thu

    • Range$143-$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

    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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