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$159+ 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 6/8. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — PWM
May 24 — May 311
Sun 5/24
Sun 5/31
1 adult, Economy
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Cheap 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, 2026.

This Delta deal was found by Cheapflights users on 4/21. 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.
Tue 9/226:00 am
MKE
-
PWM
1 stop6h 21m
Delta
Tue 9/293:00 pm
PWM
-
MKE
1 stop6h 52m
Delta
Deal found 4/21$263
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/16:00 am
MKE
-
PWM
2 stops7h 35m
United Airlines
Tue 9/225:05 pm
PWM
-
MKE
1 stop6h 31m
United Airlines
Deal found 4/22$268
This American Airlines deal was found by Cheapflights users on 4/20. 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.
Tue 5/266:45 pm
MKE
-
PWM
1 stop4h 50m
American Airlines
Sat 5/306:00 am
PWM
-
MKE
1 stop7h 02m
American Airlines
Deal found 4/20$290
This American Airlines deal was found by Cheapflights users on 4/20. 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 9/1910:21 am
MKE
-
PWM
1 stop5h 37m
American Airlines
Sat 9/265:30 pm
PWM
-
MKE
1 stop6h 48m
American Airlines
Deal found 4/20$317
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.
Mon 5/257:30 am
MKE
-
PWM
1 stop5h 56m
United Airlines
Sat 5/306:00 am
PWM
-
MKE
2 stops7h 48m
United Airlines
Deal found 4/23$322
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/26:00 am
MKE
-
PWM
1 stop6h 21m
Delta
Sun 9/66:00 am
PWM
-
MKE
1 stop5h 07m
Delta
Deal found 4/23$335
This United Airlines deal was found by Cheapflights users on 4/21. 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 9/15:05 am
MKE
-
PWM
2 stops8h 30m
United Airlines
Sun 9/66:00 am
PWM
-
MKE
1 stop5h 00m
United Airlines
Deal found 4/21$340
This Southwest deal was found by Cheapflights users on 4/21. 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.
Wed 9/23:40 pm
MKE
-
PWM
1 stop5h 25m
Southwest
Sun 9/66:10 am
PWM
-
MKE
2 stops7h 00m
Southwest
Deal found 4/21$341
This United Airlines deal was found by Cheapflights users on 4/21. 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 8/246:00 am
MKE
-
PWM
1 stop7h 28m
United Airlines
Fri 8/285:05 pm
PWM
-
MKE
1 stop6h 31m
United Airlines
Deal found 4/21$344
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/306:00 am
MKE
-
PWM
1 stop6h 21m
Delta
Sun 10/46:00 am
PWM
-
MKE
1 stop5h 07m
Delta
Deal found 4/23$345
This Southwest deal was found by Cheapflights users on 4/19. 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.
Sun 6/74:45 pm
MKE
-
PWM
1 stop5h 25m
Southwest
Wed 6/101:05 pm
PWM
-
MKE
1 stop4h 25m
Southwest
Deal found 4/19$346
This United Airlines deal was found by Cheapflights users on 4/21. 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 9/225:05 am
MKE
-
PWM
2 stops7h 49m
United Airlines
Tue 9/296:55 pm
PWM
-
MKE
1 stop5h 41m
United Airlines
Deal found 4/21$348

Find 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, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$263
(Delta)

One-way from

$159
(Southwest)

Popular in

December

Cheapest in

January
Provider with most accurate pricing for Milwaukee-Mitchell-Portland flight deals.
Search Deals
Provider most trusted by Cheapflights users for Milwaukee-Mitchell-Portland flights.
Search Deals
From Milwaukee-Mitchell to Portland
Search Deals
One-way flight from Milwaukee-Mitchell to Portland
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($45 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($23 potential savings vs. average RT price).
Search Deals

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, 2026.
Use the filters below to find and compare flights from Milwaukee to Portland that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Tue 9/22

6:00 am-1:21 pm

1 stop6h 21m

Portland

Tue 9/29

3:00 pm-8:52 pm

1 stop6h 52m

$263

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Mon 5/25

7:30 am-2:26 pm

1 stop5h 56m

Portland

Sat 5/30

6:00 am-12:48 pm

2 stops7h 48m

$322

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Tue 9/22

5:05 am-1:54 pm

2 stops7h 49m

Portland

Tue 9/29

6:55 pm-11:36 pm

1 stop5h 41m

$348

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Tue 6/2

1:30 pm-9:52 pm

1 stop7h 22m

Portland

Wed 6/3

6:00 am-11:08 am

1 stop6h 08m

$367

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Wed 9/23

5:05 am-1:54 pm

2 stops7h 49m

Portland

Wed 9/30

6:55 pm-11:36 pm

1 stop5h 41m

$372

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Mon 5/25

6:50 am-4:15 pm

2 stops8h 25m

Portland

Sat 5/30

5:40 am-2:55 pm

2 stops10h 15m

$380
Quickest round-trip

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Wed 10/7

7:00 am-1:53 pm

1 stop5h 53m

Portland

Sun 10/11

6:00 am-10:14 am

1 stop5h 14m

$407
Cheapest one-way

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Mon 6/8

6:45 pm-12:05 am

1 stop4h 20m

$159

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Fri 9/11

5:51 pm-11:51 pm

1 stop5h 00m

$186

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Sun 8/30

6:00 am-1:21 pm

1 stop6h 21m

$204

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/19

Showing 1-10 of 17 resultsSorted by cheapest first
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*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 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 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?

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 54 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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, 2026.
Get a feel of what it's like to fly with Southwest,Delta, andUnited Airlines from Milwaukee to Portland by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,332 reviews

Boarding

8.1

Entertainment

7.5

Overall

8.0

Crew

8.6

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,332 reviews
Southwest
8.0
Very good
4,332 reviews

Boarding

8.1

Entertainment

7.5

Overall

8.0

Crew

8.6

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Delta
7.9
Good
8,450 reviews
Southwest
8.0
Very good
4,332 reviews

Boarding

8.1

Entertainment

7.5

Overall

8.0

Crew

8.6

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
United Airlines
7.4
Good
9,643 reviews
Southwest
8.0
Very good
4,332 reviews

Boarding

8.1

Entertainment

7.5

Overall

8.0

Crew

8.6

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
American Airlines
7.1
Good
11,666 reviews
Southwest
8.0
Very good
4,332 reviews

Boarding

8.1

Entertainment

7.5

Overall

8.0

Crew

8.6

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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.

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

    There are many flights that can get you from Milwaukee to Portland, Maine in 5h 56m. Fly via Delta or United Airlines to get the fastest option. Milwaukee and Portland, Maine are separated by 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 Milwaukee to Portland, Maine round-trip?

    Flying on Delta is currently your cheapest option to Portland, Maine, with prices starting at $236. Additional round-trip tickets that might be worth considering are offered by American Airlines and Southwest, with the lowest prices starting at $238 and $266, respectively. Delta is 45% 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 $86. Users have also found prices from $118 and $125 on Southwest and Delta, 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.

See more FAQs

Traveling to a place near Portland?

Book flights to Portland if you plan to visit one of these locations
North Conway
Brunswick
Auburn
Lewiston
Conway

Browse thousands of different options on Cheapflights for your next trip

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Top 4 airlines flying from Milwaukee to Portland

Discover the top 4 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, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$236Average$401FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$238Average$411FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$266Average$401FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$329Average$426FlexibilityNo cancel feeOn-time69%

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