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

Promo Code

Low fares from Portland, ME to Chicago-Midway

$

Portland, ME (PWM)to

Chicago-Midway (MDW)
Depart: 12/02/2026

One-way

Basic

From
$185
Seen: 15 hrs ago

Portland, ME (PWM)to

Chicago-Midway (MDW)
Depart: 12/09/2026

One-way

Basic

From
$185
Seen: 8 hrs ago

Portland, ME (PWM)to

Chicago-Midway (MDW)
Depart: 01/15/2027

One-way

Basic

From
$185
Seen: 13 hrs ago

Portland, ME (PWM)to

Chicago-Midway (MDW)
Depart: 12/10/2026

One-way

Basic

From
$185
Seen: 6 hrs ago

Portland, ME (PWM)to

Chicago-Midway (MDW)
Depart: 12/19/2026

One-way

Basic

From
$204
Seen: 21 hrs ago

Portland, ME (PWM)to

Chicago-Midway (MDW)
Depart: 12/04/2026

One-way

Basic

From
$205
Seen: 9 hrs ago

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Explore flights from Portland, ME to Chicago-Midway

Nov 2026
From$215*
Seen: 1 hour ago
One Way/Basic
Dec 2026
From$185*
Seen: 15 hrs ago
One Way/Basic
Jan 2027
From$185*
Seen: 13 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $185
cmp-daily-histogram-bars-legend-max-price-aria-label $329
Displaying fares for November-2026
  • PWM–MDW: cmp-view-offers-disclaimer. Find Offers
    12

    Thu

    NOV

  • PWM–MDW, 11/13/2026: From $215
    13

    Fri

  • PWM–MDW, 11/14/2026: From $215
    14

    Sat

  • PWM–MDW, 11/15/2026: From $329
    15

    Sun

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

    Mon

  • PWM–MDW, 11/17/2026: From $215
    17

    Tue

  • PWM–MDW, 11/18/2026: From $215
    18

    Wed

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    19

    Thu

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    20

    Fri

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    21

    Sat

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    22

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    23

    Mon

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    24

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    25

    Wed

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    26

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  • PWM–MDW: cmp-view-offers-disclaimer. Find Offers
    27

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    28

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

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    30

    Mon

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

    Tue

    DEC

  • PWM–MDW, 12/02/2026: From $185
    02

    Wed

  • PWM–MDW, 12/03/2026: From $205
    03

    Thu

  • PWM–MDW, 12/04/2026: From $205
    04

    Fri

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

    Sat

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    06

    Sun

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

    Mon

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

    Tue

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

    Wed

  • PWM–MDW, 12/10/2026: From $185
    10

    Thu

  • PWM–MDW, 12/11/2026: From $205
    11

    Fri

    • Range$185-$329

    *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

    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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