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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 8/24. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — PWM
Aug 26 — Sep 21
Wed 8/26
Wed 9/2
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 July 27, 2026.

This Delta deal was found by Cheapflights users on 7/23. 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 9/165:47 pm
MKE
-
PWM
1 stop4h 30m
Delta
Tue 9/2911:35 am
PWM
-
MKE
1 stop6h 32m
Delta
Deal found 7/23$317
This American Airlines deal was found by Cheapflights users on 7/23. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/212:58 pm
MKE
-
PWM
1 stop7h 23m
American Airlines
Sun 9/66:00 am
PWM
-
MKE
1 stop7h 10m
American Airlines
Deal found 7/23$322
This Delta deal was found by Cheapflights users on 7/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/128:05 am
MKE
-
PWM
1 stop6h 56m
Delta
Sat 9/196:30 am
PWM
-
MKE
1 stop6h 07m
Delta
Deal found 7/27$325
This United Airlines deal was found by Cheapflights users on 7/26. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/25:00 am
MKE
-
PWM
2 stops8h 38m
United Airlines
Tue 9/86:00 am
PWM
-
MKE
1 stop5h 00m
United Airlines
Deal found 7/26$330
This Delta deal was found by Cheapflights users on 7/24. 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 9/2310:47 am
MKE
-
PWM
1 stop5h 02m
Delta
Wed 9/304:20 pm
PWM
-
MKE
1 stop5h 30m
Delta
Deal found 7/24$335
This Southwest deal was found by Cheapflights users on 7/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/2510:30 am
MKE
-
PWM
2 stops9h 40m
Southwest
Tue 9/110:30 am
PWM
-
MKE
2 stops11h 00m
Southwest
Deal found 7/26$340
This Southwest deal was found by Cheapflights users on 7/23. 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.
Wed 9/163:40 pm
MKE
-
PWM
1 stop5h 30m
Southwest
Tue 9/295:45 am
PWM
-
MKE
2 stops11h 05m
Southwest
Deal found 7/23$353
This American Airlines deal was found by Cheapflights users on 7/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/216:00 pm
MKE
-
PWM
1 stop4h 37m
American Airlines
Thu 8/276:46 pm
PWM
-
MKE
1 stop5h 28m
American Airlines
Deal found 7/26$355
This American Airlines deal was found by Cheapflights users on 7/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/55:10 pm
MKE
-
PWM
1 stop5h 36m
American Airlines
Tue 10/136:00 am
PWM
-
MKE
1 stop7h 08m
American Airlines
Deal found 7/26$358
This United Airlines deal was found by Cheapflights users on 7/22. 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.
Fri 9/41:19 pm
MKE
-
PWM
1 stop7h 04m
United Airlines
Tue 9/86:00 am
PWM
-
MKE
1 stop5h 00m
United Airlines
Deal found 7/22$367
This Southwest deal was found by Cheapflights users on 7/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/2811:35 am
MKE
-
PWM
2 stops9h 00m
Southwest
Thu 10/155:20 am
PWM
-
MKE
2 stops6h 25m
Southwest
Deal found 7/26$370

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 July 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$317
(Delta)

One-way from

$159
(Southwest)

Popular in

December

Cheapest in

January

Average price

$470
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. 15% potential increase in price ($88 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 8% potential price decrease ($38 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 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 July 27, 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

Wed 9/2

1:19 pm-9:23 pm

1 stop7h 04m

Portland

Tue 9/8

6:00 am-11:30 am

1 stop6h 30m

$325

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Mon 9/21

5:00 pm-10:30 pm

1 stop4h 30m

Portland

Sat 9/26

5:40 am-12:40 pm

2 stops8h 00m

$335

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Sat 10/3

2:05 pm-10:10 pm

2 stops7h 05m

Portland

Wed 10/7

5:40 am-1:50 pm

2 stops9h 10m

$349

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Fri 9/18

2:20 pm-9:23 pm

1 stop6h 03m

Portland

Thu 9/24

5:08 pm-10:59 pm

1 stop6h 51m

$355
Quickest round-trip

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Sun 9/20

3:52 pm-9:23 pm

1 stop4h 31m

Portland

Tue 9/22

4:57 pm-9:00 pm

1 stop5h 03m

$371

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Fri 10/2

5:00 pm-9:50 pm

1 stop3h 50m

Portland

Mon 10/5

5:20 am-10:40 am

1 stop6h 20m

$401

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Sat 9/19

3:52 pm-11:59 pm

2 stops7h 07m

Portland

Sat 9/26

6:00 am-11:30 am

1 stop6h 30m

$402

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Sat 9/12

2:20 pm-9:23 pm

1 stop6h 03m

Portland

Sat 9/19

6:06 am-2:33 pm

2 stops9h 27m

$402

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Sat 10/17

8:30 am-2:38 pm

1 stop5h 08m

Portland

Wed 10/21

6:00 am-10:07 am

1 stop5h 07m

$405
Cheapest one-way

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Sat 9/12

11:45 am-6:29 pm

1 stop5h 44m

$163

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/26

Showing 1-10 of 19 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 July.
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 much does it cost to fly round-trip from Milwaukee to Portland, Maine?

Airfare is below average for this route at the moment.

Milwaukee to Portland, Maine flights typically cost between $462 and $596 in September.
The cheapest round-trip price found within the last 5 days was $317 on Delta (Sep 16-Sep 29).

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 July 27, 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
4,228 reviews

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Libby,Jun 2026

TUS - LAS

One delay in a 2 layover flight=a good trip. The crew was great.
Southwest
8.0
Very good
4,228 reviews
Southwest
8.0
Very good
4,228 reviews

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Libby,Jun 2026

TUS - LAS

One delay in a 2 layover flight=a good trip. The crew was great.
Delta
7.8
Good
8,482 reviews
Southwest
8.0
Very good
4,228 reviews

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Libby,Jun 2026

TUS - LAS

One delay in a 2 layover flight=a good trip. The crew was great.
United Airlines
7.4
Good
10,041 reviews
Southwest
8.0
Very good
4,228 reviews

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Libby,Jun 2026

TUS - LAS

One delay in a 2 layover flight=a good trip. The crew was great.
American Airlines
7.1
Good
11,836 reviews
Southwest
8.0
Very good
4,228 reviews

Comfort

8.0

Boarding

8.1

Entertainment

7.5

Food

7.0

Overall

8.0

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Libby,Jun 2026

TUS - LAS

One delay in a 2 layover flight=a good trip. The crew was great.

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 30m. Fly via United Airlines or Southwest 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 Southwest and American Airlines, with the lowest prices starting at $301 and $314, respectively. Delta is 50% 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 Delta. According to our data, you can fly for as low as $125. Users have also found prices from $133 and $158 on American Airlines 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.

See more FAQs

Traveling to a place near Portland?

Book flights to Portland if you plan to visit one of these locations
North Conway
Lewiston
Brunswick
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 July 27, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$236Average$416FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$301Average$521FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$314Average$462FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$340Average$437FlexibilityNo cancel feeOn-time69%

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