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$194+ Cheap flights from Portland, ME to Milwaukee (PWM - MKE)

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/31. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MKE
feb. 26 — mar. 51
jue. 2/26
jue. 3/5
1 adult, Economy
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Cheap flight deals from Portland to Milwaukee

Cheapest flights from Portland to Milwaukee
Explore the most affordable flight options available from Portland to Milwaukee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on enero 27, 2026.

This Delta deal was found by Cheapflights users on 1/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 2/2712:43 pm
PWM
-
MKE
1 stop5h 30m
Delta
lun. 3/23:59 pm
MKE
-
PWM
1 stop6h 07m
Delta
Deal found 1/26$319
This United Airlines deal was found by Cheapflights users on 1/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 2/104:10 pm
PWM
-
MKE
1 stop5h 38m
United Airlines
sáb. 2/149:44 am
MKE
-
PWM
2 stops9h 44m
United Airlines
Deal found 1/26$324
This Delta deal was found by Cheapflights users on 1/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 4/292:51 pm
PWM
-
MKE
1 stop6h 34m
Delta
lun. 5/44:25 pm
MKE
-
PWM
1 stop5h 58m
Delta
Deal found 1/25$341
This Delta deal was found by Cheapflights users on 1/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 4/155:26 pm
PWM
-
MKE
1 stop5h 04m
Delta
dom. 4/194:25 pm
MKE
-
PWM
1 stop5h 58m
Delta
Deal found 1/26$364
This American Airlines deal was found by Cheapflights users on 1/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 2/276:00 am
PWM
-
MKE
2 stops10h 51m
American Airlines
lun. 3/29:00 am
MKE
-
PWM
1 stop7h 07m
American Airlines
Deal found 1/27$372
This American Airlines deal was found by Cheapflights users on 1/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 4/36:17 am
PWM
-
MKE
1 stop6h 27m
American Airlines
dom. 4/56:30 am
MKE
-
PWM
1 stop16h 04m
American Airlines
Deal found 1/26$381
This Delta deal was found by Cheapflights users on 1/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 4/105:48 pm
PWM
-
MKE
1 stop4h 57m
Delta
dom. 4/126:45 am
MKE
-
PWM
1 stop4h 24m
Delta
Deal found 1/26$387
This United Airlines deal was found by Cheapflights users on 1/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 2/276:00 am
PWM
-
MKE
2 stops12h 31m
United Airlines
lun. 3/25:00 am
MKE
-
PWM
2 stops8h 23m
United Airlines
Deal found 1/26$400
This Southwest deal was found by Cheapflights users on 1/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 4/151:00 pm
PWM
-
MKE
2 stops9h 45m
Southwest
dom. 4/197:10 am
MKE
-
PWM
1 stop7h 35m
Southwest
Deal found 1/26$402

Find flight deals from Portland to Milwaukee

Discover tips and strategies to find the most affordable flight options for your journey from Portland (PWM) to Milwaukee (MKE). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated enero 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$319
(Delta)

One-way from

$194
(Delta)

Popular in

September

Cheapest in

November

Average price

$391
Provider with most accurate pricing for Portland-Milwaukee-Mitchell flight deals.
Search Deals
Provider most trusted by Cheapflights users for Portland-Milwaukee-Mitchell flights.
Search Deals
From Portland to Milwaukee-Mitchell
Search Deals
One-way flight from Portland to Milwaukee-Mitchell
Search Deals
Highest demand for flights based on searches. 22% potential increase in price ($139 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($26 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Portland to Milwaukee that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated enero 27, 2026.
Use the filters below to find and compare flights from Portland to Milwaukee that are best for you.

Fly from

Portland

Fly to

Milwaukee

Route

Depart

Return

Price

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

vie. 2/27

12:43 pm-5:13 pm

1 stop5h 30m

Milwaukee-Mitchell

lun. 3/2

3:59 pm-11:06 pm

1 stop6h 07m

$319

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

mar. 2/10

4:10 pm-8:48 pm

1 stop5h 38m

Milwaukee-Mitchell

sáb. 2/14

7:00 am-3:14 pm

1 stop7h 14m

$319

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

vie. 2/27

5:07 pm-11:24 pm

1 stop7h 17m

Milwaukee-Mitchell

lun. 3/2

9:00 am-5:07 pm

1 stop7h 07m

$319

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

mié. 4/15

5:26 pm-9:30 pm

1 stop5h 04m

Milwaukee-Mitchell

dom. 4/19

4:25 pm-11:23 pm

1 stop5h 58m

$364

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

mié. 7/1

11:38 am-4:42 pm

1 stop6h 04m

Milwaukee-Mitchell

sáb. 7/4

5:25 pm-11:53 pm

1 stop5h 28m

$387

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

vie. 4/10

5:48 pm-9:45 pm

1 stop4h 57m

Milwaukee-Mitchell

dom. 4/12

6:45 am-12:09 pm

1 stop4h 24m

$387

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

dom. 5/31

6:00 am-10:07 am

1 stop5h 07m

Milwaukee-Mitchell

mié. 6/3

12:20 pm-10:03 pm

1 stop8h 43m

$387

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

mar. 7/21

8:01 am-12:02 pm

1 stop5h 01m

$194

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

dom. 5/31

6:00 am-10:07 am

1 stop5h 07m

$194

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

mar. 7/21

6:00 am-1:43 pm

2 stops8h 43m

$199

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

Showing 1-10 of 17 results
1
2

Compare providers for flights from Portland to Milwaukee

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Portland to Milwaukee in January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Portland, Maine-Milwaukee flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Portland, Maine-Milwaukee flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Portland, Maine-Milwaukee flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Portland, Maine-Milwaukee flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Portland, Maine-Milwaukee flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Portland to Milwaukee

Have a flexible travel schedule? Discover the best time to fly to Milwaukee from Portland with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Portland to Milwaukee

What is the cheapest month to book a flight from Portland, Maine to Milwaukee?

Currently, April is the cheapest month in which you can book a flight from Portland, Maine to Milwaukee (average of $89). Flying from Portland, Maine to Milwaukee in January is currently the most expensive (average of $126). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Reviews of airlines servicing Milwaukee

Get insights into the airlines that provide service to Milwaukee. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Milwaukee. Reviews last updated enero 27, 2026.
Read reviews from past customers who have flown Southwest, Delta, and United Airlines from Portland to Milwaukee. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,268 reviews

Food

7.0

Boarding

8.1

Overall

8.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
8.0
Very good
4,268 reviews
Southwest
8.0
Very good
4,268 reviews

Food

7.0

Boarding

8.1

Overall

8.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Delta
7.9
Good
8,118 reviews
Southwest
8.0
Very good
4,268 reviews

Food

7.0

Boarding

8.1

Overall

8.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
United Airlines
7.4
Good
9,205 reviews
Southwest
8.0
Very good
4,268 reviews

Food

7.0

Boarding

8.1

Overall

8.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
American Airlines
7.2
Good
11,197 reviews
Southwest
8.0
Very good
4,268 reviews

Food

7.0

Boarding

8.1

Overall

8.0

Comfort

8.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Related info for your journey

Find useful and relevant information for your journey from Portland to Milwaukee. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from Portland, Maine to Milwaukee?

    A quick flight from Portland, Maine to Milwaukee can take about 5h 30m. Delta provides one of the quickest options available for as low as $319. Airlines will cover a distance of 883 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines flying from Portland, Maine to Milwaukee round-trip?

    Our cheapest airline available from Portland, Maine to Milwaukee is United Airlines. Our recent data shows that you can find tickets from as low as $244 on this airline. Additional options worth looking into are Delta and Southwest, starting at $279 and $311 round-trip. Users have found that United Airlines is 47% cheaper than the other options available to this destination.

  • What are the cheapest airlines to fly from Portland, Maine to Milwaukee one-way?

    For one-way options, check prices for Delta. According to our data, you can fly for as low as $128. Users have also found prices from $135 and $148 on American Airlines and United Airlines, respectively.

  • Can I find deals for flights from Portland to Milwaukee that include hotel bookings?

    Yes. In addition to deals on Portland to Milwaukee flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Portland to Milwaukee?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Portland to Milwaukee.

  • Can I find deals for business class flights from Portland to Milwaukee?

    Yes. Cheapflights offers flight deals from Portland to Milwaukee by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Portland, Maine to Milwaukee?

    Currently, April is the cheapest month in which you can book a flight from Portland, Maine to Milwaukee (average of $89). Flying from Portland, Maine to Milwaukee in January is currently the most expensive (average of $126). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Traveling to a place near Milwaukee?

Book flights to Milwaukee if you plan to visit one of these locations
Sheboygan
New Berlin
Oak Creek
Wauwatosa

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Alternative routes for Portland to Milwaukee

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Top 4 airlines flying from Portland to Milwaukee

Discover the top 4 airlines that operate flights from Portland to Milwaukee. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated enero 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$244Average$496FlexibilityNo cancel feeOn-time69%
DeltaCheapest$279Average$406FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$311Average$396FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$315Average$467FlexibilityNo cancel feeOn-time71%

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