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 faresSouthwest® flights from Portland, ME to Milwaukee from $159
expand_more
1 Passenger
expand_morePromo Code
expand_moretoday
today
Low fares from Portland, ME to Milwaukee
$
Portland, ME (PWM)to
Milwaukee (MKE)
Depart: 02/25/2026
One-way
Basic
From
$159
Seen: 6 hrs ago
Portland, ME (PWM)to
Milwaukee (MKE)
Depart: 02/24/2026
One-way
Basic
From
$159
Seen: 7 hrs ago
Portland, ME (PWM)to
Milwaukee (MKE)
Depart: 02/25/2026
One-way
Choice
From
$194
Seen: 6 hrs ago
Portland, ME (PWM)to
Milwaukee (MKE)
Depart: 03/26/2026
One-way
Basic
From
$194
Seen: 12 hrs ago
Portland, ME (PWM)to
Milwaukee (MKE)
Depart: 02/24/2026
One-way
Choice
From
$194
Seen: 7 hrs ago
Portland, ME (PWM)to
Milwaukee (MKE)
Depart: 03/16/2026
One-way
Basic
From
$220
Seen: 14 hrs ago
Explore flights from Portland, ME to Milwaukee
location_on
location_on
Flight Details
Departing from:
Portland International Jetport
Arriving at:
General Mitchell Airport
Distance:
887 miles
Route Information
65† Weekly flights
† 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
There are 65 weekly flights from Portland, ME to Milwaukee on Southwest Airlines.
To find the lowest fares by day and time to fly Portland, ME to Milwaukee with Southwest, check out our Low Fare Calendar.
You can rent a car at General Mitchell Airport book yours with your flight.
Yes! Flights from Portland, ME to Milwaukee—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.