Southwest® flights from Chicago-Midway to Portland, ME from $185

Promo Code

Low fares from Chicago-Midway to Portland, ME

$

Chicago-Midway (MDW)to

Portland, ME (PWM)
Depart: 12/14/2026

One-way

Basic

From
$185
Seen: 14 hrs ago

Chicago-Midway (MDW)to

Portland, ME (PWM)
Depart: 12/03/2026

One-way

Basic

From
$185
Seen: 16 hrs ago

Chicago-Midway (MDW)to

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

One-way

Basic

From
$185
Seen: 37 minutes ago

Chicago-Midway (MDW)to

Portland, ME (PWM)
Depart: 12/16/2026

One-way

Basic

From
$185
Seen: 4 hrs ago

Chicago-Midway (MDW)to

Portland, ME (PWM)
Depart: 12/02/2026

One-way

Basic

From
$200
Seen: 18 hrs ago

Chicago-Midway (MDW)to

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

One-way

Basic

From
$205
Seen: 35 minutes ago

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Explore flights from Chicago-Midway to Portland, ME

Nov 2026
From$225*
Seen: 8 hrs ago
One Way/Basic
Dec 2026
From$185*
Seen: 4 hrs ago
One Way/Basic
Jan 2027
No result for this month.
cmp-daily-histogram-bars-legend-min-price-aria-label $185
cmp-daily-histogram-bars-legend-max-price-aria-label $510
Displaying fares for November-2026
  • MDW–PWM: cmp-view-offers-disclaimer. Find Offers
    10

    Tue

    NOV

  • MDW–PWM: cmp-view-offers-disclaimer. Find Offers
    11

    Wed

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

    Thu

  • MDW–PWM, 11/13/2026: From $225
    13

    Fri

  • MDW–PWM, 11/14/2026: From $230
    14

    Sat

  • MDW–PWM, 11/15/2026: From $225
    15

    Sun

  • MDW–PWM, 11/16/2026: From $300
    16

    Mon

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

    Tue

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

    Wed

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

    Thu

  • MDW–PWM, 11/20/2026: From $225
    20

    Fri

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

    Sat

  • MDW–PWM: cmp-view-offers-disclaimer. Find Offers
    22

    Sun

  • MDW–PWM: cmp-view-offers-disclaimer. Find Offers
    23

    Mon

  • MDW–PWM, 11/24/2026: From $264
    24

    Tue

  • MDW–PWM, 11/25/2026: From $264
    25

    Wed

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

    Thu

  • MDW–PWM, 11/27/2026: From $225
    27

    Fri

  • MDW–PWM: cmp-view-offers-disclaimer. Find Offers
    28

    Sat

  • MDW–PWM, 11/29/2026: From $510
    29

    Sun

  • MDW–PWM, 11/30/2026: From $391
    30

    Mon

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

    Tue

    DEC

  • MDW–PWM, 12/02/2026: From $200
    02

    Wed

  • MDW–PWM, 12/03/2026: From $185
    03

    Thu

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

    Fri

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

    Sat

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    06

    Sun

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

    Mon

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

    Tue

  • MDW–PWM, 12/09/2026: From $185
    09

    Wed

    • Range$185-$510

    *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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