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$105+ 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 10/25. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MKE
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
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 September 11, 2025.

Round-trip from

$197
(Southwest)

One-way from

$105
(Southwest)

Popular in

August

Cheapest in

November

Average price

$365
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. 3% potential increase in price ($14 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 11, 2025.

This Southwest deal was found by Cheapflights users on 9/8. 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 11/115:30 amPWM - MKE
1 stop5h 00mSouthwest
Sat 11/152:10 pmMKE - PWM
1 stop6h 45mSouthwest
Deal found 9/8$197
This Delta deal was found by Cheapflights users on 9/9. 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 12/32:34 pmPWM - MKE
1 stop6h 48mDelta
Wed 12/109:40 amMKE - PWM
1 stop5h 26mDelta
Deal found 9/9$237
This Delta deal was found by Cheapflights users on 9/9. 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.
Thu 11/612:45 pmPWM - MKE
2 stops8h 57mDelta
Tue 11/116:00 amMKE - PWM
1 stop5h 30mDelta
Deal found 9/9$242
This Delta deal was found by Cheapflights users on 9/9. 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.
Thu 12/46:00 amPWM - MKE
1 stop5h 18mDelta
Wed 12/107:00 amMKE - PWM
1 stop5h 54mDelta
Deal found 9/9$246
This Delta deal was found by Cheapflights users on 9/9. 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 12/36:00 amPWM - MKE
1 stop5h 18mDelta
Fri 12/59:40 amMKE - PWM
1 stop5h 26mDelta
Deal found 9/9$249
This American Airlines deal was found by Cheapflights users on 9/9. 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 10/165:59 pmPWM - MKE
1 stop7h 15mAmerican Airlines
Wed 10/224:45 pmMKE - PWM
1 stop5h 03mAmerican Airlines
Deal found 9/9$253
This Delta deal was found by Cheapflights users on 9/9. 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.
Thu 12/42:34 pmPWM - MKE
1 stop6h 48mDelta
Thu 12/119:40 amMKE - PWM
1 stop5h 26mDelta
Deal found 9/9$255
This Delta deal was found by Cheapflights users on 9/9. 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.
Thu 12/42:34 pmPWM - MKE
1 stop6h 48mDelta
Fri 12/59:40 amMKE - PWM
1 stop5h 26mDelta
Deal found 9/9$258
This Delta deal was found by Cheapflights users on 9/10. 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.
Sun 11/166:00 amPWM - MKE
1 stop5h 16mDelta
Wed 11/199:36 amMKE - PWM
1 stop5h 31mDelta
Deal found 9/10$262

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 September 11, 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

Tue 11/11

5:30 am-9:30 am

1 stop5h 00m

Milwaukee-Mitchell

Sat 11/15

2:10 pm-9:55 pm

1 stop6h 45m

$197

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

Wed 12/3

2:34 pm-8:22 pm

1 stop6h 48m

Milwaukee-Mitchell

Wed 12/10

9:40 am-4:06 pm

1 stop5h 26m

$237

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

Thu 11/20

5:43 am-12:01 pm

1 stop7h 18m

Milwaukee-Mitchell

Thu 11/27

6:00 am-11:46 am

1 stop4h 46m

$237

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

Sat 12/6

2:34 pm-8:22 pm

1 stop6h 48m

Milwaukee-Mitchell

Sat 12/13

9:31 am-4:06 pm

1 stop5h 35m

$237

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

Tue 12/2

4:53 pm-8:30 pm

1 stop4h 37m

Milwaukee-Mitchell

Tue 12/9

7:10 am-12:08 pm

1 stop3h 58m

$237

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

Tue 12/2

2:34 pm-8:22 pm

1 stop6h 48m

Milwaukee-Mitchell

Sat 12/6

7:05 am-12:08 pm

1 stop4h 03m

$237

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

Thu 11/6

1:27 pm-8:42 pm

1 stop8h 15m

Milwaukee-Mitchell

Tue 11/11

5:59 pm-11:19 pm

1 stop4h 20m

$237

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

Tue 12/2

2:34 pm-8:22 pm

1 stop6h 48m

Milwaukee-Mitchell

Thu 12/11

9:40 am-4:06 pm

1 stop5h 26m

$246

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

Wed 12/10

6:00 am-10:18 am

1 stop5h 18m

Milwaukee-Mitchell

Thu 12/11

9:40 am-4:06 pm

1 stop5h 26m

$246

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

Sat 10/25

5:50 am-11:25 am

1 stop6h 35m

$105

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

Showing 1-10 of 15 results
1
2

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

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 September 11, 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.

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 September 11, 2025.
Read reviews from past customers who have flown Southwest, Delta, and United Airlines from Portland to Milwaukee. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

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
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

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
8.0
Very good
7,960 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

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
8,937 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

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
10,000 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Food

7.0

Overall

8.0

Boarding

8.1

Comfort

8.0

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 Portland to Milwaukee. 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 Portland, Maine to Milwaukee?

    A quick flight from Portland, Maine to Milwaukee can take about 5h. Southwest provides one of the quickest options available for as low as $197. Airlines will cover 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 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 $204 on this airline. Additional options worth looking into are Delta and United Airlines, starting at $264 and $274 round-trip. Users have found that American Airlines is 52% 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 Southwest. According to our data, you can fly for as low as $105. Users have also found prices from $110 and $119 on American 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 Milwaukee?

Book flights to Milwaukee if you plan to visit one of these locations
Sheboygan
Oak Creek
New Berlin
Wauwatosa

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Alternative routes for Portland to Milwaukee

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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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$204Average$467FlexibilityNo cancel feeOn-time71%
DeltaCheapest$264Average$401FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$274Average$522FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$296Average$422FlexibilityNo cancel feeOn-time63%

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