Southwest® flights from Chicago-Midway to Portland, ME from $177

Promo Code

Low fares from Chicago-Midway to Portland, ME

$

Chicago-Midway (MDW)to

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

One-way

Basic

From
$177
Seen: 20 hrs ago

Chicago-Midway (MDW)to

Portland, ME (PWM)
Depart: 10/27/2026

One-way

Basic

From
$177
Seen: 9 hrs ago

Chicago-Midway (MDW)to

Portland, ME (PWM)
Depart: 10/22/2026

One-way

Basic

From
$177
Seen: 6 hrs ago

Chicago-Midway (MDW)to

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

One-way

Basic

From
$177
Seen: 17 hrs ago

Chicago-Midway (MDW)to

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

One-way

Basic

From
$177
Seen: 18 hrs ago

Chicago-Midway (MDW)to

Portland, ME (PWM)
Depart: 10/21/2026

One-way

Basic

From
$177
Seen: 19 hrs ago

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Explore flights from Chicago-Midway to Portland, ME

Sep 2026
From$209*
Seen: 20 hrs ago
One Way/Basic
Oct 2026
From$177*
Seen: 17 hrs ago
One Way/Basic
Nov 2026
From$187*
Seen: 16 hrs ago
One Way/Basic
cmp-daily-histogram-bars-legend-min-price-aria-label $177
cmp-daily-histogram-bars-legend-max-price-aria-label $593
Displaying fares for September-2026
  • MDW–PWM, 09/30/2026: From $209
    30

    Wed

    SEP

  • MDW–PWM, 10/01/2026: From $425
    01

    Thu

  • MDW–PWM, 10/02/2026: From $259
    02

    Fri

  • MDW–PWM, 10/03/2026: From $209
    03

    Sat

  • MDW–PWM, 10/04/2026: From $259
    04

    Sun

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

    Mon

  • MDW–PWM: cmp-view-offers-disclaimer. Find Offers
    06

    Tue

  • MDW–PWM, 10/07/2026: From $234
    07

    Wed

  • MDW–PWM, 10/08/2026: From $593
    08

    Thu

  • MDW–PWM: cmp-view-offers-disclaimer. Find Offers
    09

    Fri

  • MDW–PWM, 10/10/2026: From $219
    10

    Sat

  • MDW–PWM, 10/11/2026: From $259
    11

    Sun

  • MDW–PWM, 10/12/2026: From $274
    12

    Mon

  • MDW–PWM: cmp-view-offers-disclaimer. Find Offers
    13

    Tue

  • MDW–PWM, 10/14/2026: From $219
    14

    Wed

  • MDW–PWM, 10/15/2026: From $336
    15

    Thu

  • MDW–PWM, 10/16/2026: From $269
    16

    Fri

  • MDW–PWM, 10/17/2026: From $209
    17

    Sat

  • MDW–PWM, 10/18/2026: From $259
    18

    Sun

  • MDW–PWM, 10/19/2026: From $259
    19

    Mon

  • MDW–PWM, 10/20/2026: From $177
    20

    Tue

  • MDW–PWM, 10/21/2026: From $177
    21

    Wed

  • MDW–PWM, 10/22/2026: From $177
    22

    Thu

  • MDW–PWM, 10/23/2026: From $195
    23

    Fri

  • MDW–PWM, 10/24/2026: From $177
    24

    Sat

  • MDW–PWM: cmp-view-offers-disclaimer. Find Offers
    25

    Sun

  • MDW–PWM, 10/26/2026: From $177
    26

    Mon

  • MDW–PWM, 10/27/2026: From $177
    27

    Tue

  • MDW–PWM, 10/28/2026: From $177
    28

    Wed

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

    Thu

    • Range$177-$593

    *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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