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Find low faresSouthwest® flights from Chicago (Midway) to Portland, ME from $113
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1 Passenger
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Low fares from Chicago (Midway) to Portland, ME
$
Chicago (Midway) (MDW)to
Portland, ME (PWM)
Depart: 02/14/2026
One-way
Basic
From
$113
Seen: 4 hrs ago
Chicago (Midway) (MDW)to
Portland, ME (PWM)
Depart: 04/01/2026
One-way
Basic
From
$115
Seen: 2 hrs ago
Chicago (Midway) (MDW)to
Portland, ME (PWM)
Depart: 05/02/2026
One-way
Basic
From
$133
Seen: 15 hrs ago
Chicago (Midway) (MDW)to
Portland, ME (PWM)
Depart: 02/15/2026
One-way
Basic
From
$135
Seen: 54 minutes ago
Chicago (Midway) (MDW)to
Portland, ME (PWM)
Depart: 03/13/2026
One-way
Basic
From
$135
Seen: 18 hrs ago
Chicago (Midway) (MDW)to
Portland, ME (PWM)
Depart: 02/14/2026
One-way
Choice
From
$141
Seen: 4 hrs ago
Explore flights from Chicago (Midway) to Portland, ME
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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.