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$140+ Cheap flights from Portland, ME to Milwaukee (PWM - MKE)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/7. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MKE
Jan 22 — Jan 291
Wed 1/22
Wed 1/29
1 adult, Economy
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Cheap flight deals from Portland to Milwaukee

Discover tips and strategies to find the most affordable flight options for your journey from Portland (PWM) to Milwaukee (MKE). 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 17, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$140
(Booking.com)

Popular in

December

Cheapest in

July

Average price

$357
Provider with most accurate pricing for Portland-Milwaukee-Mitchell flight deals.
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Provider most trusted by Cheapflights users for Portland-Milwaukee-Mitchell flights.
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From Portland to Milwaukee-Mitchell
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High demand for flights, 5% potential price rise
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Best time to find cheap flights, 2% potential price drop
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Average for round-trip flights in January 2025
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Find flight deals from Portland to Milwaukee

Cheapest flights from Portland to Milwaukee
Explore the most affordable flight options available from Portland to Milwaukee. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 17, 2025.

This Booking.com deal was found by Cheapflights users on 1/16. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/79:02 pmPWM - MKE
1 stop13h 52mFrontier
Sun 2/96:52 pmMKE - PWM
1 stop24h 20mFrontier
Deal found 1/16$140
This Delta deal was found by Cheapflights users on 1/16. 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 5/76:00 amPWM - MKE
1 stop6h 14mDelta
Tue 5/137:00 amMKE - PWM
1 stop6h 01mDelta
Deal found 1/16$367
This United Airlines deal was found by Cheapflights users on 1/16. 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 2/76:00 amPWM - MKE
1 stop6h 24mUnited Airlines
Sun 2/910:20 amMKE - PWM
2 stops11h 10mUnited Airlines
Deal found 1/16$392
This Southwest deal was found by Cheapflights users on 1/16. 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 5/72:20 pmPWM - MKE
2 stops8h 45mSouthwest
Wed 5/146:10 amMKE - PWM
2 stops8h 10mSouthwest
Deal found 1/16$417
This Mytrip deal was found by Cheapflights users on 1/16. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/1912:32 pmPWM - MKE
1 stop5h 57mMultiple Airlines
Sun 6/226:30 pmMKE - PWM
3 stops22h 06mMultiple Airlines
Deal found 1/16$501
This American Airlines deal was found by Cheapflights users on 1/16. 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.
Thu 6/195:15 pmPWM - MKE
1 stop7h 54mAmerican Airlines
Sun 6/226:48 amMKE - PWM
1 stop7h 11mAmerican Airlines
Deal found 1/16$529

Find flights from Portland to Milwaukee within your budget

Customize your flight search to find flights from Portland to Milwaukee 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 17, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

Fri 2/7

9:02 pm-9:54 am

1 stop13h 52m

Milwaukee-Mitchell

Sun 2/9

6:52 pm-8:12 pm

1 stop24h 20m

$140

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

Wed 5/7

6:00 am-11:14 am

1 stop6h 14m

Milwaukee-Mitchell

Tue 5/13

7:00 am-2:01 pm

1 stop6h 01m

$367

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

Fri 2/7

6:00 am-11:24 am

1 stop6h 24m

Milwaukee-Mitchell

Sun 2/9

10:20 am-10:30 pm

2 stops11h 10m

$392

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

Wed 5/7

2:20 pm-10:05 pm

2 stops8h 45m

Milwaukee-Mitchell

Wed 5/14

6:30 am-1:25 pm

1 stop5h 55m

$402

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

Thu 6/19

12:32 pm-5:29 pm

1 stop5h 57m

Milwaukee-Mitchell

Sun 6/22

6:30 pm-5:36 pm

3 stops22h 06m

$501

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

Thu 6/19

5:15 pm-12:09 am

1 stop7h 54m

Milwaukee-Mitchell

Sun 6/22

6:48 am-2:59 pm

1 stop7h 11m

$529

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

Thu 6/12

12:32 pm-5:29 pm

1 stop5h 57m

$168

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

Wed 6/11

6:00 am-10:22 am

1 stop5h 22m

$184

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

Tue 6/10

6:00 am-11:13 am

1 stop6h 13m

$189

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/15

Compare providers for flights from Portland to Milwaukee

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 Portland to Milwaukee in January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
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 Portland, Maine-Milwaukee flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Portland, Maine-Milwaukee flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Portland, Maine-Milwaukee flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Portland, Maine-Milwaukee 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 Portland, Maine-Milwaukee 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 Portland to Milwaukee

Have a flexible travel schedule? Discover the best time to fly to Milwaukee from Portland 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.

Travel insights for flights from Portland to Milwaukee

Get recent, data-driven insights about flights from Portland to Milwaukee including ideal travel times, pricing trends, and more.

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

Currently, February is the cheapest month in which you can book a flight from Portland, Maine to Milwaukee (average of $280). Flying from Portland, Maine to Milwaukee in June is currently the most expensive (average of $376). 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.

What is the cheapest time of day to fly from PWM to MKE?

Find hourly flight availability from Portland to Milwaukee. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated January 17, 2025.

It’s optimal to fly from Portland, Maine to Milwaukee in the evening. By choosing this option you can save up to 57% on the cost of your flight, compared to a flight in the afternoon.

Rainfall in Milwaukee by month

Plan your trip to Milwaukee by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Milwaukee ranges from 1.4 - 4.0 inches per month. June is typically the wettest month, when rainfall can reach 4.0 in. January is typically the driest time to visit Milwaukee when rainfall is around 1.4 in.

Temperature in Milwaukee by month

Plan your trip to Milwaukee by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Milwaukee, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 21.2 F).

Reviews of airlines servicing Milwaukee

Get insights into the airlines that provide service to Milwaukee. 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 Milwaukee. Reviews last updated January 17, 2025.
Southwest
8.1
Very good
4,659 reviews

Boarding

8.2

Crew

8.7

Overall

8.1

Comfort

8.1

Entertainment

7.7

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,659 reviews
Southwest
8.1
Very good
4,659 reviews

Boarding

8.2

Crew

8.7

Overall

8.1

Comfort

8.1

Entertainment

7.7

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,511 reviews
Southwest
8.1
Very good
4,659 reviews

Boarding

8.2

Crew

8.7

Overall

8.1

Comfort

8.1

Entertainment

7.7

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

United Airlines
7.4
Good
8,964 reviews
Southwest
8.1
Very good
4,659 reviews

Boarding

8.2

Crew

8.7

Overall

8.1

Comfort

8.1

Entertainment

7.7

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,659 reviews

Boarding

8.2

Crew

8.7

Overall

8.1

Comfort

8.1

Entertainment

7.7

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Sun Country Air
7.0
Good
384 reviews
Southwest
8.1
Very good
4,659 reviews

Boarding

8.2

Crew

8.7

Overall

8.1

Comfort

8.1

Entertainment

7.7

Food

7.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Related info for your journey

Find useful and relevant information for your journey from Portland to Milwaukee. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the cheapest airlines flying from Portland, Maine to Milwaukee round-trip?

    Our cheapest airline available from Portland, Maine to Milwaukee is Frontier. Our recent data shows that you can find tickets from as low as $140 on this airline. Additional options worth looking into are Delta and United Airlines, starting at $367 and $392 round-trip. Users have found that Frontier is 64% cheaper than the other options available to this destination.

  • What are the cheapest airlines to fly from Portland, Maine to Milwaukee one-way?

    For one-way options, check prices for Sun Country Air. According to our data, you can fly for as low as $168. Users have also found prices from $184 and $189 on United Airlines and Delta, respectively.

  • Can I find deals for flights from Portland to Milwaukee that include hotel bookings?

    Yes. In addition to deals on Portland to Milwaukee flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Portland to Milwaukee?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Portland to Milwaukee.

  • Can I find deals for business class flights from Portland to Milwaukee?

    Yes. Cheapflights offers flight deals from Portland to Milwaukee 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 Portland, Maine to Milwaukee?

    Currently, February is the cheapest month in which you can book a flight from Portland, Maine to Milwaukee (average of $280). Flying from Portland, Maine to Milwaukee in June is currently the most expensive (average of $376). 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
Mequon
Pewaukee
Sheboygan
Oak Creek
Wauwatosa

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Top 4 airlines flying from Portland to Milwaukee

Discover the top 4 airlines that operate flights from Portland to Milwaukee. 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 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$258Average$371FlexibilityNo cancel feeOn-time71%
DeltaCheapest$264Average$363FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$268Average$376FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$316Average$436FlexibilityNo cancel feeOn-time69%
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