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$136+ 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 8/30. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MKE
May 17 — May 241
Sat 5/17
Sat 5/24
1 adult, Economy
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1. Tell us where you want to go

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Cheapflights Tip: The best prices from Portland to Milwaukee-Mitchell are usually found in August or July, booked 14 days in advance, depart on a Wednesday or Tuesday and return on a Tuesday

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 May 12, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$284
(Southwest)

One-way from

$149
(American Airlines)

Popular in

May

Cheapest in

August

Average price

$545
Provider with most accurate pricing for Portland-Milwaukee-Mitchell flight deals.
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Provider most trusted by Cheapflights users for Portland-Milwaukee-Mitchell flights.
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From Portland to Milwaukee-Mitchell
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One-way flight from Portland to Milwaukee-Mitchell
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Highest demand for flights based on searches. 10% potential increase in price ($50 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in May 2025
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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 May 12, 2025.

This United Airlines deal was found by Cheapflights users on 5/12. 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.
Wed 8/2012:10 pmPWM - MKE
1 stop6h 17mUnited Airlines
Sat 8/303:44 pmMKE - PWM
1 stop5h 15mUnited Airlines
Deal found 5/12$284
This Delta deal was found by Cheapflights users on 5/12. 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.
Wed 8/206:00 amPWM - MKE
2 stops10h 06mDelta
Sat 8/3011:55 amMKE - PWM
1 stop8h 49mDelta
Deal found 5/12$289
This Southwest deal was found by Cheapflights users on 5/12. 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.
Tue 8/55:50 amPWM - MKE
1 stop4h 30mSouthwest
Tue 8/127:00 amMKE - PWM
1 stop5h 00mSouthwest
Deal found 5/12$328
This American Airlines deal was found by Cheapflights users on 5/12. 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.
Fri 8/85:57 pmPWM - MKE
1 stop7h 14mAmerican Airlines
Thu 8/142:36 pmMKE - PWM
1 stop7h 25mAmerican Airlines
Deal found 5/12$336
This Mytrip deal was found by Cheapflights users on 5/12. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/271:50 pmPWM - MKE
2 stops22h 37mMultiple Airlines
Sat 5/3112:22 pmMKE - PWM
3 stops30h 05mMultiple Airlines
Deal found 5/12$588

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 May 12, 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

Wed 8/20

12:10 pm-5:27 pm

1 stop6h 17m

Milwaukee-Mitchell

Sat 8/30

3:44 pm-9:59 pm

1 stop5h 15m

$284

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

Wed 8/20

6:00 am-3:06 pm

2 stops10h 06m

Milwaukee-Mitchell

Sat 8/30

11:55 am-9:44 pm

1 stop8h 49m

$289

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

Tue 8/5

5:50 am-9:20 am

1 stop4h 30m

Milwaukee-Mitchell

Tue 8/12

7:00 am-1:00 pm

1 stop5h 00m

$328

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

Fri 8/8

5:57 pm-12:11 am

1 stop7h 14m

Milwaukee-Mitchell

Thu 8/14

2:36 pm-11:01 pm

1 stop7h 25m

$336

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

Tue 5/27

1:50 pm-11:27 am

2 stops22h 37m

Milwaukee-Mitchell

Sat 5/31

12:22 pm-7:27 pm

3 stops30h 05m

$588

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

Sat 8/30

5:30 pm-11:25 pm

1 stop6h 55m

$136

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

Wed 7/23

6:01 pm-12:04 am

1 stop7h 03m

$149

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

Sat 6/21

6:20 am-4:55 pm

2 stops11h 35m

$189

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

Fri 9/19

2:00 pm-9:35 pm

2 stops8h 35m

$199

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

Sun 6/22

12:46 pm-5:29 pm

1 stop5h 43m

$203

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/12

Showing 1-10 of 11 results
1
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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 May.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 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 Expedia the most. Expedia 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

How far ahead should I book a flight from Portland, Maine to Milwaukee?

Use this chart to determine the optimal time to book a round-trip flight from Portland to Milwaukee. Price data was last updated on May 9, 2025.

The price you pay for your flight from Portland, Maine to Milwaukee may vary depending on when you book. For the best chance of a lower fare, look to book 14 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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

Currently, February is the cheapest month in which you can book a flight from Portland, Maine to Milwaukee (average of $280). Flying from Portland, Maine to Milwaukee in June is currently the most expensive (average of $376). 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 May 12, 2025.

It’s optimal to fly from Portland, Maine to Milwaukee in the evening. By choosing this option you can save up to 57% on the cost of your flight, compared to a flight in the afternoon.

Rainfall in Milwaukee by month

Plan your trip to Milwaukee by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Milwaukee ranges from 1.4 - 4.0 inches per month. June is typically the wettest month, when rainfall can reach 4.0 in. January is typically the driest time to visit Milwaukee when rainfall is around 1.4 in.

Temperature in Milwaukee by month

Plan your trip to Milwaukee by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Milwaukee, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 21.2 F).

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 May 12, 2025.
Southwest
8.0
Very good
4,290 reviews

Entertainment

7.6

Comfort

8.0

Crew

8.6

Food

7.1

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,290 reviews
Southwest
8.0
Very good
4,290 reviews

Entertainment

7.6

Comfort

8.0

Crew

8.6

Food

7.1

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,950 reviews
Southwest
8.0
Very good
4,290 reviews

Entertainment

7.6

Comfort

8.0

Crew

8.6

Food

7.1

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
United Airlines
7.4
Good
8,724 reviews
Southwest
8.0
Very good
4,290 reviews

Entertainment

7.6

Comfort

8.0

Crew

8.6

Food

7.1

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,290 reviews

Entertainment

7.6

Comfort

8.0

Crew

8.6

Food

7.1

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Sun Country Air
6.9
Okay
346 reviews
Southwest
8.0
Very good
4,290 reviews

Entertainment

7.6

Comfort

8.0

Crew

8.6

Food

7.1

Overall

8.0

Boarding

8.2

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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.

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

    Our cheapest airline available from Portland, Maine to Milwaukee is Southwest. Our recent data shows that you can find tickets from as low as $284 on this airline. Additional options worth looking into are Delta and American Airlines, starting at $289 and $340 round-trip. Users have found that Southwest is 31% 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 American Airlines. According to our data, you can fly for as low as $149. Users have also found prices from $189 and $203 on United Airlines and Sun Country Air, 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, February is the cheapest month in which you can book a flight from Portland, Maine to Milwaukee (average of $280). Flying from Portland, Maine to Milwaukee in June is currently the most expensive (average of $376). 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 Portland?

Book flights to Portland if you plan to visit one of these locations
Mequon
Pewaukee
Sheboygan
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 May 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$258Average$401FlexibilityNo cancel feeOn-time71%
DeltaCheapest$266Average$369FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$268Average$376FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$316Average$471FlexibilityNo cancel feeOn-time69%

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