HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Portland

$157+ 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 12/3. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — PWM
Nov 27 — Dec 41
Thu 11/27
Thu 12/4
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Milwaukee to Portland with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 October 28, 2025.

This Delta deal was found by Cheapflights users on 10/28. 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 10/28$313
This Delta deal was found by Cheapflights users on 10/28. 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 11/185:59 pmMKE - PWM
1 stop4h 20mDelta
Wed 11/192:30 pmPWM - MKE
1 stop6h 37mDelta
Deal found 10/28$317
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/137:03 pmMKE - PWM
1 stop13h 03mMultiple Airlines
Wed 11/1911:21 amPWM - MKE
2 stops25h 19mMultiple Airlines
Deal found 10/27$346
This Kiwi.com deal was found by Cheapflights users on 10/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/167:03 pmMKE - PWM
1 stop13h 03mMultiple Airlines
Wed 11/1911:16 amPWM - MKE
1 stop25h 24mMultiple Airlines
Deal found 10/26$356
This Delta deal was found by Cheapflights users on 10/27. 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.
Mon 11/177:12 amMKE - PWM
1 stop3h 56mDelta
Tue 11/186:00 amPWM - MKE
1 stop5h 16mDelta
Deal found 10/27$362

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 October 28, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$313
(Delta)

One-way from

$157
(American Airlines)

Popular in

December

Cheapest in

April

Average price

$452
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. 22% potential increase in price ($117 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 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 October 28, 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

Mon 12/8

5:59 pm-11:21 pm

1 stop4h 22m

Portland

Mon 12/15

4:53 pm-8:30 pm

1 stop4h 37m

$313

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Tue 11/18

11:37 am-11:54 pm

2 stops11h 17m

Portland

Wed 11/19

6:00 am-2:13 pm

2 stops9h 13m

$327

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Tue 3/3

7:00 am-1:51 pm

1 stop5h 51m

Portland

Thu 3/5

2:35 pm-8:12 pm

1 stop6h 37m

$360

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Tue 11/18

5:45 am-12:30 pm

1 stop5h 45m

Portland

Thu 11/20

2:30 pm-8:07 pm

1 stop6h 37m

$362

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Mon 11/17

1:22 pm-11:19 pm

2 stops8h 57m

Portland

Tue 11/18

4:40 pm-9:45 pm

1 stop6h 05m

$367

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Wed 12/3

3:45 pm-9:37 pm

1 stop4h 52m

$157

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Wed 12/3

11:41 am-11:59 pm

2 stops11h 18m

$162

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Thu 11/13

7:03 pm-9:06 am

1 stop13h 03m

$180

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Tue 12/2

2:30 pm-11:09 pm

2 stops7h 39m

$181

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Mon 12/1

6:05 am-2:12 pm

1 stop7h 07m

$194

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/27

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 October.
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 October 24, 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, November is the cheapest month in which you can book a flight from Milwaukee to Portland, Maine (average of $71). 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 October 28, 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
4,240 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.0

Entertainment

7.5

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
4,240 reviews
Southwest
8.0
Very good
4,240 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.0

Entertainment

7.5

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
7,994 reviews
Southwest
8.0
Very good
4,240 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.0

Entertainment

7.5

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
9,001 reviews
Southwest
8.0
Very good
4,240 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.0

Entertainment

7.5

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
11,032 reviews
Southwest
8.0
Very good
4,240 reviews

Boarding

8.1

Crew

8.6

Overall

8.0

Comfort

8.0

Food

7.0

Entertainment

7.5

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 4h 22m. Fly via Delta to get the fastest option. Milwaukee and Portland, Maine are separated by a distance of 883 mi.

  • 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 40% 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 $157. Users have also found prices from $162 and $181 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, November is the cheapest month in which you can book a flight from Milwaukee to Portland, Maine (average of $71). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Milwaukee to Portland

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to Boston flights
Minneapolis to Boston flights
Milwaukee to Boston flights
O'Hare Intl to Portland flights
Madison to Boston flights
Appleton to Boston flights
Minneapolis to Portland flights
O'Hare Intl to Bangor flights
Madison to Portland flights
Eau Claire to Boston flights
Milwaukee to Bangor flights
Green Bay to Boston flights
Minneapolis to Bangor flights
Wausau to Boston flights
Appleton to Portland flights
Madison to Bangor flights
Green Bay to Portland flights
Duluth to Boston flights
O'Hare Intl to Augusta flights
La Crosse to Boston flights
O'Hare Intl to Rockland flights
Wausau to Portland flights
La Crosse to Portland flights
Escanaba to Boston flights
O'Hare Intl to Bar Harbor flights
Appleton to Bangor flights
Minneapolis to Bar Harbor flights
Rhinelander to Boston flights
Escanaba to Portland flights
Duluth to Portland flights
Minneapolis to Augusta flights
Milwaukee to Bar Harbor flights
Dubuque to Portland flights
Madison to Presque Isle flights
Madison to Bar Harbor flights
Minneapolis to Rockland flights
Dubuque to Boston flights

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 October 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$238Average$369FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$246Average$388FlexibilityNo cancel feeOn-time63%
DeltaCheapest$251Average$364FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$309Average$386FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.