Southwest® flights from Portland, ME to Chicago (Midway) from $135

Promo Code

Low fares from Portland, ME to Chicago (Midway)

$

Portland, ME (PWM)to

Chicago (Midway) (MDW)
Depart: 06/16/2026

One-way

Basic

From
$125
Seen: 4 hrs ago

Portland, ME (PWM)to

Chicago (Midway) (MDW)
Depart: 04/06/2026

One-way

Basic

From
$135
Seen: 8 hrs ago

Portland, ME (PWM)to

Chicago (Midway) (MDW)
Depart: 05/24/2026

One-way

Basic

From
$140
Seen: 7 hrs ago

Portland, ME (PWM)to

Chicago (Midway) (MDW)
Depart: 06/06/2026

One-way

Basic

From
$144
Seen: 2 hrs ago

Portland, ME (PWM)to

Chicago (Midway) (MDW)
Depart: 06/16/2026

One-way

Choice

From
$160
Seen: 4 hrs ago

Portland, ME (PWM)to

Chicago (Midway) (MDW)
Depart: 04/06/2026

One-way

Choice

From
$170
Seen: 8 hrs ago

Looking for more low-fare flights?

Check out the Low Fare Calendar to find a fare that works for you. Just choose the month you want to depart and return, and we’ll show you the best fares available.

Find low fares

Explore flights from Portland, ME to Chicago (Midway)

Mar 2026
From$190*
Seen: 3 hrs ago
One Way/Basic
Apr 2026
From$135*
Seen: 8 hrs ago
One Way/Basic
May 2026
From$140*
Seen: 7 hrs ago
One Way/Basic
$135
$353
Displaying fares for March-2026
  • 13

    Fri

    MAR

  • 14

    Sat

  • 15

    Sun

  • 16

    Mon

  • 17

    Tue

  • 18

    Wed

  • 19

    Thu

  • 20

    Fri

  • 21

    Sat

  • 22

    Sun

  • 23

    Mon

  • 24

    Tue

  • 25

    Wed

  • 26

    Thu

  • 27

    Fri

  • 28

    Sat

  • 29

    Sun

  • 30

    Mon

  • 31

    Tue

  • 01

    Wed

    APR

  • 02

    Thu

  • 03

    Fri

  • 04

    Sat

  • 05

    Sun

  • 06

    Mon

  • 07

    Tue

  • 08

    Wed

  • 09

    Thu

  • 10

    Fri

  • 11

    Sat

  • 12

    Sun

    • Range$135-$353

    *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

    Route Information

    93† 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 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.

    Explore Flights from Other Popular Origins

    Popular Flights from Portland, ME