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Find low faresSouthwest® flights from Portland, ME to Chicago (Midway) from $115
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Low fares from Portland, ME to Chicago (Midway)
$
Portland, ME (PWM)to
Chicago (Midway) (MDW)
Depart: 03/23/2026
One-way
Basic
From
$115
Seen: 11 hrs ago
Portland, ME (PWM)to
Chicago (Midway) (MDW)
Depart: 02/23/2026
One-way
Basic
From
$115
Seen: 50 minutes ago
Portland, ME (PWM)to
Chicago (Midway) (MDW)
Depart: 02/07/2026
One-way
Basic
From
$141
Seen: 14 hrs ago
Portland, ME (PWM)to
Chicago (Midway) (MDW)
Depart: 03/23/2026
One-way
Choice
From
$150
Seen: 11 hrs ago
Portland, ME (PWM)to
Chicago (Midway) (MDW)
Depart: 02/23/2026
One-way
Choice
From
$150
Seen: 50 minutes ago
Portland, ME (PWM)to
Chicago (Midway) (MDW)
Depart: 03/17/2026
One-way
Basic
From
$154
Seen: 15 hrs ago
Explore flights from Portland, ME to Chicago (Midway)
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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.