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$160+ 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 3/1. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — PWM
Feb 26 — Mar 51
Thu 2/26
Thu 3/5
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 January 27, 2026.

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.
Sat 2/146:40 am
MKE
-
PWM
1 stop4h 20m
Delta
Tue 2/1712:13 pm
PWM
-
MKE
1 stop4h 55m
Delta
Deal found 1/25$318
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/118:33 am
MKE
-
PWM
1 stop5h 06m
United Airlines
Sun 2/156:00 am
PWM
-
MKE
1 stop5h 58m
United Airlines
Deal found 1/27$319
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/179:44 am
MKE
-
PWM
1 stop4h 30m
United Airlines
Tue 3/245:45 am
PWM
-
MKE
1 stop5h 45m
United Airlines
Deal found 1/25$341
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1912:30 pm
MKE
-
PWM
1 stop10h 11m
American Airlines
Sat 9/2612:39 pm
PWM
-
MKE
1 stop11h 39m
American Airlines
Deal found 1/25$353
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/1712:20 pm
MKE
-
PWM
2 stops9h 45m
Southwest
Tue 3/245:30 am
PWM
-
MKE
2 stops7h 15m
Southwest
Deal found 1/25$374
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.
Wed 5/204:50 pm
MKE
-
PWM
1 stop5h 20m
American Airlines
Sun 5/245:04 pm
PWM
-
MKE
1 stop7h 26m
American Airlines
Deal found 1/27$376
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.
Tue 2/107:05 am
MKE
-
PWM
1 stop5h 40m
Delta
Sat 2/142:35 pm
PWM
-
MKE
1 stop7h 01m
Delta
Deal found 1/26$379
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.
Tue 8/117:37 pm
MKE
-
PWM
1 stop14h 57m
American Airlines
Thu 8/208:01 am
PWM
-
MKE
1 stop5h 01m
American Airlines
Deal found 1/27$381
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/279:00 am
MKE
-
PWM
1 stop7h 07m
American Airlines
Mon 3/26:00 am
PWM
-
MKE
1 stop6h 40m
American Airlines
Deal found 1/25$383

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 January 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$318
(Delta)

One-way from

$160
(Delta)

Popular in

December

Cheapest in

April

Average price

$334
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. 17% potential increase in price ($84 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($25 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 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 January 27, 2026.
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 2/14

6:40 am-12:00 pm

1 stop4h 20m

Portland

Tue 2/17

12:13 pm-4:08 pm

1 stop4h 55m

$318

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Fri 2/13

2:40 pm-9:09 pm

1 stop5h 29m

Portland

Thu 2/19

6:00 am-3:20 pm

2 stops10h 20m

$324

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Wed 2/11

11:30 am-11:21 pm

2 stops10h 51m

Portland

Sun 2/15

6:00 am-10:58 am

1 stop5h 58m

$324

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Sat 4/18

2:32 pm-9:40 pm

1 stop6h 08m

Portland

Sat 4/25

6:04 am-11:32 am

1 stop6h 28m

$341

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Tue 3/17

9:44 am-3:14 pm

1 stop4h 30m

Portland

Tue 3/24

6:00 am-12:35 pm

2 stops7h 35m

$346

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Tue 3/17

12:20 pm-11:05 pm

2 stops9h 45m

Portland

Tue 3/24

5:30 am-11:45 am

2 stops7h 15m

$374

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Tue 2/10

7:05 am-1:45 pm

1 stop5h 40m

Portland

Sat 2/14

2:35 pm-8:36 pm

1 stop7h 01m

$379

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Sat 4/18

2:55 pm-11:10 pm

2 stops7h 15m

Portland

Sat 4/25

5:40 am-12:00 pm

1 stop7h 20m

$379

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Fri 2/27

9:00 am-5:07 pm

1 stop7h 07m

Portland

Mon 3/2

6:00 am-11:40 am

1 stop6h 40m

$383

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Tue 6/9

2:45 pm-11:53 pm

1 stop8h 08m

Portland

Tue 6/16

1:35 pm-7:03 pm

1 stop6h 28m

$387

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/27

Showing 1-10 of 20 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 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 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?

Use this chart to determine the optimal time to book a round-trip flight from Milwaukee to Portland. Price data was last updated on January 23, 2026.

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 55 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, October is the cheapest month in which you can book a flight from Milwaukee to Portland, Maine (average of $88). Flying from Milwaukee to Portland, Maine in February is currently the most expensive (average of $117). 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 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 January 27, 2026.
Get a feel of what it's like to fly with Southwest, Delta, and United 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
4,268 reviews

Overall

8.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Food

7.0

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

Overall

8.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Food

7.0

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

Overall

8.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Food

7.0

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

Overall

8.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Food

7.0

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

Overall

8.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Food

7.0

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 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 4h 20m. 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 American Airlines is currently your cheapest option to Portland, Maine, with prices starting at $238. Additional round-trip tickets that might be worth considering are offered by Delta and Southwest, with the lowest prices starting at $238 and $246, respectively. American Airlines is 39% 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 $124 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.

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

    Currently, October is the cheapest month in which you can book a flight from Milwaukee to Portland, Maine (average of $88). Flying from Milwaukee to Portland, Maine in February is currently the most expensive (average of $117). 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
North Conway
Brunswick
Auburn
Conway

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Alternative routes for Milwaukee to Portland

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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 January 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$238Average$382FlexibilityNo cancel feeOn-time71%
DeltaCheapest$238Average$363FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$246Average$386FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$309Average$407FlexibilityNo cancel feeOn-time69%

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