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$149+ Cheap flights from Milwaukee to Portland, ME (MKE - PWM)

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 6/24. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — PWM
Apr 29 — May 61
Tue 4/29
Tue 5/6
1 adult, Economy
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Cheapflights Tip: The best prices from Milwaukee-Mitchell to Portland are usually found in February or September, booked 6 days in advance, depart on a Tuesday or Sunday and return on a Wednesday

Cheap flight deals from Milwaukee to Portland

Discover tips and strategies to find the most affordable flight options for your journey from Milwaukee (MKE) to Portland (PWM). 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 April 24, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$284
(Delta)

One-way from

$149
(American Airlines)

Popular in

December

Cheapest in

February

Average price

$398
Provider with most accurate pricing for Milwaukee-Mitchell-Portland flight deals.
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Provider most trusted by Cheapflights users for Milwaukee-Mitchell-Portland flights.
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From Milwaukee-Mitchell to Portland
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One-way flight from Milwaukee-Mitchell to Portland
Search Deals
Highest demand for flights based on searches. 16% potential increase in price ($77 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in April 2025
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Find flight deals from Milwaukee to Portland

Cheapest flights from Milwaukee to Portland
Explore the most affordable flight options available from Milwaukee to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 24, 2025.

This Delta deal was found by Cheapflights users on 4/22. 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.
Sat 8/237:00 amMKE - PWM
1 stop8h 44mDelta
Sat 8/306:00 amPWM - MKE
1 stop5h 02mDelta
Deal found 4/22$284
This American Airlines deal was found by Cheapflights users on 4/22. 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 6/165:13 pmMKE - PWM
1 stop4h 34mAmerican Airlines
Fri 6/206:01 pmPWM - MKE
1 stop6h 58mAmerican Airlines
Deal found 4/22$367
This Southwest deal was found by Cheapflights users on 4/23. 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.
Fri 7/1811:40 amMKE - PWM
2 stops11h 25mSouthwest
Thu 7/245:40 amPWM - MKE
1 stop4h 50mSouthwest
Deal found 4/23$370
This United Airlines deal was found by Cheapflights users on 4/23. 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.
Thu 8/712:10 pmMKE - PWM
2 stops10h 49mUnited Airlines
Mon 8/114:56 pmPWM - MKE
1 stop6h 49mUnited Airlines
Deal found 4/23$403
This Mytrip deal was found by Cheapflights users on 4/23. 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.
Fri 6/69:15 amMKE - PWM
3 stops25h 38mMultiple Airlines
Sun 6/812:40 pmPWM - MKE
1 stop5h 49mMultiple Airlines
Deal found 4/23$458
This Sun Country Air deal was found by Cheapflights users on 4/22. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/136:30 pmMKE - PWM
1 stop16h 05mSun Country Air
Sun 7/2012:46 pmPWM - MKE
1 stop5h 37mSun Country Air
Deal found 4/22$465

Cheapflights Fare Finder

Customize your flight search to find flights from Milwaukee to Portland 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 April 24, 2025.
Use the filters below to find and compare flights from Milwaukee to Portland that are best for you.

Fly from

Milwaukee

Fly to

Portland

Route

Depart

Return

Price

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Sat 8/23

7:00 am-4:44 pm

1 stop8h 44m

Portland

Sat 8/30

6:00 am-10:02 am

1 stop5h 02m

$284

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Mon 6/16

5:13 pm-10:47 pm

1 stop4h 34m

Portland

Fri 6/20

6:01 pm-11:59 pm

1 stop6h 58m

$367

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Fri 7/18

11:40 am-12:05 am

2 stops11h 25m

Portland

Thu 7/24

5:40 am-9:30 am

1 stop4h 50m

$370

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Thu 8/7

12:10 pm-11:59 pm

2 stops10h 49m

Portland

Mon 8/11

4:56 pm-10:45 pm

1 stop6h 49m

$403

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Fri 6/6

9:15 am-11:53 am

3 stops25h 38m

Portland

Sun 6/8

12:40 pm-5:29 pm

1 stop5h 49m

$458

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Sun 7/13

6:30 pm-11:35 am

1 stop16h 05m

Portland

Sun 7/20

12:46 pm-5:23 pm

1 stop5h 37m

$465

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Tue 6/24

5:13 pm-10:47 pm

1 stop4h 34m

$149

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Thu 7/31

4:20 pm-11:59 pm

1 stop6h 39m

$152

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Tue 6/24

5:15 am-5:43 pm

2 stops11h 28m

$171

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Fri 8/1

6:35 pm-12:05 am

1 stop4h 30m

$194

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/22

Showing 1-10 of 11 results
1
2

Compare providers for flights from Milwaukee to Portland

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 Milwaukee to Portland in April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 stars
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 Milwaukee-Portland, Maine flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Milwaukee-Portland, Maine flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Milwaukee-Portland, Maine flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Milwaukee-Portland, Maine 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 Milwaukee-Portland, Maine 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 Milwaukee to Portland

Have a flexible travel schedule? Discover the best time to fly to Portland from Milwaukee 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 Milwaukee to Portland

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

Use this chart to determine the optimal time to book a round-trip flight from Milwaukee to Portland. Price data was last updated on April 18, 2025.

The price you pay for your flight from Milwaukee to Portland, Maine may vary depending on when you book. For the best chance of a lower fare, look to book 6 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 Milwaukee to Portland, Maine?

Currently, January is the cheapest month in which you can book a flight from Milwaukee to Portland, Maine (average of $296). Flying from Milwaukee to Portland, Maine in May is currently the most expensive (average of $416). 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.

Rainfall in Portland by month

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

In terms of precipitation, rainfall in Portland, Maine ranges from 2.9 - 4.5 inches per month. November is typically the wettest month, when rainfall can reach 4.5 in. August is typically the driest time to visit Portland, Maine when rainfall is around 2.9 in.

Temperature in Portland by month

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

If weather is an important factor for your trip to Portland, Maine, 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 68.0 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Portland

Get insights into the airlines that provide service to Portland. 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 Portland. Reviews last updated April 24, 2025.
Southwest
8.0
Very good
4,287 reviews

Entertainment

7.6

Comfort

8.0

Crew

8.6

Boarding

8.2

Food

7.1

Overall

8.0

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
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Entertainment

7.6

Comfort

8.0

Crew

8.6

Boarding

8.2

Food

7.1

Overall

8.0

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
7,920 reviews
Southwest
8.0
Very good
4,287 reviews

Entertainment

7.6

Comfort

8.0

Crew

8.6

Boarding

8.2

Food

7.1

Overall

8.0

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
8,685 reviews
Southwest
8.0
Very good
4,287 reviews

Entertainment

7.6

Comfort

8.0

Crew

8.6

Boarding

8.2

Food

7.1

Overall

8.0

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
4,287 reviews

Entertainment

7.6

Comfort

8.0

Crew

8.6

Boarding

8.2

Food

7.1

Overall

8.0

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
349 reviews
Southwest
8.0
Very good
4,287 reviews

Entertainment

7.6

Comfort

8.0

Crew

8.6

Boarding

8.2

Food

7.1

Overall

8.0

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 Milwaukee to Portland. 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 Milwaukee to Portland, Maine round-trip?

    Flying on Delta is currently your cheapest option to Portland, Maine, with prices starting at $284. Additional round-trip tickets that might be worth considering are offered by American Airlines and Southwest, with the lowest prices starting at $367 and $370, respectively. Delta is 27% cheaper than the average price of flights available within the next 90 days to this destination.

  • What are the cheapest airlines to fly from Milwaukee to Portland, Maine 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 $152 and $171 on Delta and United Airlines, respectively.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Milwaukee to Portland 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 Milwaukee to Portland, Maine?

    Currently, January is the cheapest month in which you can book a flight from Milwaukee to Portland, Maine (average of $296). Flying from Milwaukee to Portland, Maine in May is currently the most expensive (average of $416). 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
North Conway
Bath
Brunswick
Auburn
Conway
Lewiston

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Top 5 airlines flying from Milwaukee to Portland

Discover the top 5 airlines that operate flights from Milwaukee to Portland. 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 April 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$151Average$167FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$246Average$396FlexibilityNo cancel feeOn-time63%
DeltaCheapest$256Average$365FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$266Average$386FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$309Average$429FlexibilityNo cancel feeOn-time69%

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