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$136+ Cheap flights from Portland, ME to Milwaukee (PWM - MKE)

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 8/28. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MKE
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
1 adult, Economy
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Cheapflights Tip: The best prices from Portland to Milwaukee-Mitchell are usually found in August or July, booked 25 days in advance, depart on a Wednesday or Tuesday and return on a Tuesday

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 June 12, 2025.

Round-trip from

$271
(American Airlines)

One-way from

$136
(Delta)

Popular in

May

Cheapest in

August

Average price

$487
From Portland to Milwaukee-Mitchell
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One-way flight from Portland to Milwaukee-Mitchell
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Highest demand for flights based on searches. 11% potential increase in price ($55 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 12, 2025.

This American Airlines deal was found by Cheapflights users on 6/11. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/215:57 pmPWM - MKE
1 stop7h 14mAmerican Airlines
Wed 8/276:00 amMKE - PWM
1 stop4h 34mAmerican Airlines
Deal found 6/11$271
This Sun Country Air deal was found by Cheapflights users on 6/10. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/31:10 pmPWM - MKE
1 stop27h 25mSun Country Air
Sun 7/66:53 pmMKE - PWM
1 stop15h 24mSun Country Air
Deal found 6/10$275
This Southwest deal was found by Cheapflights users on 6/10. 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.
Thu 11/63:00 pmPWM - MKE
1 stop9h 00mSouthwest
Mon 11/106:20 amMKE - PWM
1 stop7h 05mSouthwest
Deal found 6/10$276
This Delta deal was found by Cheapflights users on 6/10. 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 8/206:00 amPWM - MKE
1 stop5h 59mDelta
Sat 8/307:05 amMKE - PWM
1 stop8h 27mDelta
Deal found 6/10$283
This United Airlines deal was found by Cheapflights users on 6/10. 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.
Thu 8/212:14 pmPWM - MKE
2 stops8h 42mUnited Airlines
Wed 8/276:00 amMKE - PWM
2 stops7h 25mUnited Airlines
Deal found 6/10$351
This Mytrip deal was found by Cheapflights users on 6/10. 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 7/31:10 pmPWM - MKE
2 stops22h 54mMultiple Airlines
Sun 7/66:53 pmMKE - PWM
1 stop15h 24mMultiple Airlines
Deal found 6/10$453

Cheapflights Fare Finder

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 June 12, 2025.
Use the filters below to find and compare flights from Portland to Milwaukee that are best for you.

Fly from

Portland

Fly to

Milwaukee

Route

Depart

Return

Price

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

Thu 8/21

5:57 pm-12:11 am

1 stop7h 14m

Milwaukee-Mitchell

Wed 8/27

6:00 am-11:34 am

1 stop4h 34m

$271

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

Thu 7/3

1:10 pm-3:35 pm

1 stop27h 25m

Milwaukee-Mitchell

Sun 7/6

6:53 pm-11:17 am

1 stop15h 24m

$275

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

Thu 11/6

3:00 pm-11:00 pm

1 stop9h 00m

Milwaukee-Mitchell

Mon 11/10

6:20 am-2:25 pm

1 stop7h 05m

$276

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

Wed 8/20

6:00 am-10:59 am

1 stop5h 59m

Milwaukee-Mitchell

Sat 8/30

7:05 am-4:32 pm

1 stop8h 27m

$283

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

Thu 8/21

2:14 pm-9:56 pm

2 stops8h 42m

Milwaukee-Mitchell

Wed 8/27

6:00 am-2:25 pm

2 stops7h 25m

$351

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

Thu 7/3

1:10 pm-11:04 am

2 stops22h 54m

Milwaukee-Mitchell

Sun 7/6

6:53 pm-11:17 am

1 stop15h 24m

$453

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

Thu 8/28

6:00 am-10:59 am

1 stop5h 59m

$136

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

Mon 6/30

6:01 pm-11:59 pm

1 stop6h 58m

$149

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

Sun 7/20

12:52 pm-5:35 pm

1 stop5h 43m

$163

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

Fri 8/29

3:30 pm-11:00 pm

2 stops8h 30m

$171

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

Showing 1-10 of 12 results
1
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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.

Cheapflights Insights

Everything you need to know about your flight from Portland to Milwaukee

How far ahead should I book a flight from Portland, Maine to Milwaukee?

Use this chart to determine the optimal time to book a round-trip flight from Portland to Milwaukee. Price data was last updated on June 9, 2025.

The price you pay for your flight from Portland, Maine to Milwaukee may vary depending on when you book. For the best chance of a lower fare, look to book 25 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 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 June 12, 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 June 12, 2025.
Southwest
8.0
Very good
4,287 reviews

Crew

8.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Southwest
8.0
Very good
4,287 reviews
Southwest
8.0
Very good
4,287 reviews

Crew

8.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Delta
8.0
Very good
7,946 reviews
Southwest
8.0
Very good
4,287 reviews

Crew

8.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
United Airlines
7.4
Good
8,790 reviews
Southwest
8.0
Very good
4,287 reviews

Crew

8.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,287 reviews

Crew

8.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.
Sun Country Air
6.9
Okay
345 reviews
Southwest
8.0
Very good
4,287 reviews

Crew

8.6

Overall

8.0

Boarding

8.2

Comfort

8.0

Food

7.1

Entertainment

7.6

Reviews

1 / 20
8.0
Excellent

John,May 2025

PVD - BNA

It’s southwest so no frills but clean, efficient and got me to my location.

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 American Airlines. Our recent data shows that you can find tickets from as low as $271 on this airline. Additional options worth looking into are Sun Country Air and Southwest, starting at $275 and $276 round-trip. Users have found that American Airlines is 34% 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 Delta. According to our data, you can fly for as low as $136. Users have also found prices from $149 and $163 on American Airlines and Sun Country Air, 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
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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$246Average$387FlexibilityNo cancel feeOn-time71%
DeltaCheapest$264Average$392FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$268Average$376FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$304Average$464FlexibilityNo cancel feeOn-time69%

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