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$171+ 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 1/5. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MKE
Dec 13 — Dec 201
Sat 12/13
Sat 12/20
1 adult, Economy
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Find 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 November 13, 2025.

This United Airlines deal was found by Cheapflights users on 11/10. 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.
Tue 12/94:25 pmPWM - MKE
1 stop7h 05mUnited Airlines
Tue 12/168:40 amMKE - PWM
1 stop4h 42mUnited Airlines
Deal found 11/10$387
This American Airlines deal was found by Cheapflights users on 11/12. 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.
Mon 12/15:37 pmPWM - MKE
1 stop6h 29mAmerican Airlines
Fri 12/53:45 pmMKE - PWM
1 stop4h 52mAmerican Airlines
Deal found 11/12$437
This American Airlines deal was found by Cheapflights users on 11/11. 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.
Sat 12/205:20 pmPWM - MKE
1 stop4h 56mAmerican Airlines
Wed 12/246:02 amMKE - PWM
1 stop11h 57mAmerican Airlines
Deal found 11/11$444
This United Airlines deal was found by Cheapflights users on 11/12. 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.
Mon 12/14:52 pmPWM - MKE
1 stop6h 51mUnited Airlines
Fri 12/52:30 pmMKE - PWM
2 stops7h 39mUnited Airlines
Deal found 11/12$461
This Delta deal was found by Cheapflights users on 11/12. 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.
Thu 11/202:30 pmPWM - MKE
1 stop6h 37mDelta
Thu 11/275:45 amMKE - PWM
1 stop5h 45mDelta
Deal found 11/12$505
This Delta deal was found by Cheapflights users on 11/11. 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.
Sun 12/215:45 amPWM - MKE
1 stop6h 48mDelta
Fri 12/263:38 pmMKE - PWM
1 stop6h 05mDelta
Deal found 11/11$508
This Southwest deal was found by Cheapflights users on 11/12. 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.
Mon 12/15:30 amPWM - MKE
2 stops11h 05mSouthwest
Fri 12/512:45 pmMKE - PWM
2 stops8h 30mSouthwest
Deal found 11/12$512
This Southwest deal was found by Cheapflights users on 11/11. 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.
Sat 12/205:15 amPWM - MKE
2 stops10h 15mSouthwest
Wed 12/2411:30 amMKE - PWM
2 stops9h 45mSouthwest
Deal found 11/11$528

Cheap 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 November 13, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$341
(Delta)

One-way from

$171
(Delta)

Popular in

September

Cheapest in

November

Average price

$312
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 ($137 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 November 2025
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 November 13, 2025.
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

Tue 12/9

4:25 pm-10:30 pm

1 stop7h 05m

Milwaukee-Mitchell

Tue 12/16

8:40 am-2:22 pm

1 stop4h 42m

$387

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

Thu 2/5

4:10 pm-9:59 pm

1 stop6h 49m

Milwaukee-Mitchell

Mon 2/9

7:00 am-6:50 pm

2 stops10h 50m

$416

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

Mon 12/1

5:37 pm-11:06 pm

1 stop6h 29m

Milwaukee-Mitchell

Fri 12/5

3:45 pm-9:37 pm

1 stop4h 52m

$437

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

Sat 12/20

5:20 pm-9:16 pm

1 stop4h 56m

Milwaukee-Mitchell

Wed 12/24

6:02 am-6:59 pm

1 stop11h 57m

$444

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

Mon 12/1

4:52 pm-10:43 pm

1 stop6h 51m

Milwaukee-Mitchell

Fri 12/5

2:30 pm-11:09 pm

2 stops7h 39m

$461

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

Mon 1/5

6:00 am-1:13 pm

1 stop8h 13m

$171

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

Sun 1/4

5:45 am-10:25 am

1 stop5h 40m

$194

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

Sat 1/3

4:41 pm-10:14 pm

1 stop6h 33m

$194

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

Sat 11/22

11:16 am-11:40 am

1 stop25h 24m

$204

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

Wed 11/26

4:40 pm-10:43 pm

1 stop7h 03m

$234

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/13

Showing 1-10 of 14 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 November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice 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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Portland, Maine-Milwaukee flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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 $123). 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.

What is the cheapest time of day to fly from PWM to MKE?

Find hourly flight availability from Portland to Milwaukee. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 13, 2025.

It’s optimal to fly from Portland, Maine to Milwaukee in the evening. By choosing this option you can save up to 56% on the cost of your flight, compared to a flight in the afternoon.

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 November 13, 2025.
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
4,242 reviews

Crew

8.6

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
7.9
Good
8,007 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
9,017 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
11,051 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

8.0

Boarding

8.1

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 7h 05m. United Airlines provides one of the quickest options available for as low as $387. Airlines will cover a distance of 883 mi.

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

    Our cheapest airline available from Portland, Maine to Milwaukee is Delta. Our recent data shows that you can find tickets from as low as $287 on this airline. Additional options worth looking into are Southwest and United Airlines, starting at $311 and $312 round-trip. Users have found that Delta is 39% 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 $171. Users have also found prices from $194 and $234 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 $123). 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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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 November 13, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$287Average$419FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$311Average$417FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$312Average$496FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$315Average$467FlexibilityNo cancel feeOn-time71%

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