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Portland

$147+ 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 12/5. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — PWM
Dec 13 — Dec 201
Sat 12/13
Sat 12/20
1 adult, Economy
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Find cheap flights from Milwaukee to Portland with Cheapflights

1. Tell us where you want to go

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Cheapflights Tip: The best prices from Milwaukee-Mitchell to Portland are usually found in April or February, booked 57 days in advance, depart on a Tuesday or Sunday and return on a Wednesday

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 November 13, 2025.

This Delta deal was found by Cheapflights users on 11/11. 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 12/69:31 amMKE - PWM
1 stop5h 29mDelta
Tue 12/96:00 amPWM - MKE
1 stop5h 18mDelta
Deal found 11/11$317
This Delta deal was found by Cheapflights users on 11/12. 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.
Mon 12/85:59 pmMKE - PWM
1 stop4h 22mDelta
Mon 12/156:08 amPWM - MKE
1 stop9h 13mDelta
Deal found 11/12$341
This Southwest deal was found by Cheapflights users on 11/12. 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.
Sat 12/62:10 pmMKE - PWM
1 stop6h 45mSouthwest
Sun 12/75:30 amPWM - MKE
1 stop5h 50mSouthwest
Deal found 11/12$362
This United Airlines deal was found by Cheapflights users on 11/12. 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.
Sat 12/65:00 amMKE - PWM
2 stops8h 19mUnited Airlines
Sun 12/76:00 amPWM - MKE
2 stops10h 08mUnited Airlines
Deal found 11/12$372
This United Airlines deal was found by Cheapflights users on 11/11. 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.
Sat 12/62:30 pmMKE - PWM
1 stop5h 47mUnited Airlines
Tue 12/93:00 pmPWM - MKE
2 stops8h 30mUnited Airlines
Deal found 11/11$392
This United Airlines deal was found by Cheapflights users on 11/12. 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.
Mon 12/85:00 amMKE - PWM
2 stops8h 19mUnited Airlines
Mon 12/156:00 amPWM - MKE
1 stop5h 44mUnited Airlines
Deal found 11/12$416
This Delta deal was found by Cheapflights users on 11/12. 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.
Fri 11/285:45 amMKE - PWM
1 stop5h 45mDelta
Tue 12/24:43 pmPWM - MKE
1 stop6h 05mDelta
Deal found 11/12$467
This United Airlines deal was found by Cheapflights users on 11/12. 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.
Fri 11/286:05 amMKE - PWM
1 stop7h 07mUnited Airlines
Tue 12/23:00 pmPWM - MKE
2 stops8h 30mUnited Airlines
Deal found 11/12$472
This Southwest deal was found by Cheapflights users on 11/11. 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 12/1911:50 amMKE - PWM
1 stop11h 15mSouthwest
Sun 12/285:30 amPWM - MKE
1 stop5h 55mSouthwest
Deal found 11/11$582

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 November 13, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$315
(Delta)

One-way from

$147
(Kiwi.com)

Popular in

November

Cheapest in

April

Average price

$514
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 ($71 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
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 November 13, 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 12/6

9:31 am-4:00 pm

1 stop5h 29m

Portland

Tue 12/9

6:00 am-10:18 am

1 stop5h 18m

$317

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Sat 1/10

5:00 am-2:29 pm

2 stops8h 29m

Portland

Sun 1/18

4:10 pm-10:56 pm

1 stop7h 46m

$320

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Mon 12/8

5:59 pm-11:21 pm

1 stop4h 22m

Portland

Mon 12/15

6:08 am-2:21 pm

1 stop9h 13m

$341

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Fri 2/6

6:45 am-12:25 pm

1 stop4h 40m

Portland

Tue 2/10

5:45 am-9:50 am

1 stop5h 05m

$352

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Sat 12/6

1:10 pm-9:55 pm

2 stops7h 45m

Portland

Sun 12/7

5:30 am-10:20 am

1 stop5h 50m

$379

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Sat 12/6

2:30 pm-9:17 pm

1 stop5h 47m

Portland

Tue 12/9

3:00 pm-10:30 pm

2 stops8h 30m

$392

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Mon 12/8

6:00 am-2:19 pm

2 stops7h 19m

Portland

Mon 12/15

6:00 am-10:44 am

1 stop5h 44m

$416

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Fri 12/5

6:09 pm-10:36 am

1 stop15h 27m

$147

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Wed 1/14

5:45 pm-11:22 pm

1 stop4h 37m

$159

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Thu 12/11

10:34 am-9:06 am

1 stop21h 32m

$161

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/11

Showing 1-10 of 13 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 November.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Milwaukee-Portland, Maine flight deals on Cheapflights vs. eDreams >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 November 7, 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 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, January 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 $137). 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 November 13, 2025.
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
4,242 reviews

Crew

8.6

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,242 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
7.9
Good
8,007 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
9,017 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
11,051 reviews
Southwest
8.0
Very good
4,242 reviews

Crew

8.6

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Overall

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 29m. 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 Southwest and Delta, with the lowest prices starting at $246 and $251, respectively. American Airlines is 38% cheaper than the average price of flights available within the next 90 days to this destination.

  • 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 $88). Flying from Milwaukee to Portland, Maine in February is currently the most expensive (average of $137). 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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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 November 13, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$238Average$372FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$246Average$388FlexibilityNo cancel feeOn-time63%
DeltaCheapest$251Average$363FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$309Average$386FlexibilityNo cancel feeOn-time69%

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