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$119+ 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 10/4. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MKE
Aug 5 — Aug 121
Tue 8/5
Tue 8/12
1 adult, Economy
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Cheapflights Tip: The best prices from Portland to Milwaukee-Mitchell are usually found in January or February, 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 July 31, 2025.

Round-trip from

$237
(Southwest)

One-way from

$119
(American Airlines)

Popular in

May

Cheapest in

January

Average price

$385
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 ($52 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 July 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 July 31, 2025.

This American Airlines deal was found by Cheapflights users on 7/31. 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 8/275:13 pmMKE - PWM
1 stop4h 46mAmerican Airlines
Deal found 7/31$252
This Southwest deal was found by Cheapflights users on 7/29. 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 9/183:30 pmPWM - MKE
1 stop6h 30mSouthwest
Sat 9/2010:50 amMKE - PWM
2 stops10h 10mSouthwest
Deal found 7/29$257
This Delta deal was found by Cheapflights users on 7/30. 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 9/1011:48 amPWM - MKE
2 stops10h 45mDelta
Fri 9/124:47 pmMKE - PWM
1 stop6h 24mDelta
Deal found 7/30$282
This United Airlines deal was found by Cheapflights users on 7/31. 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 11/206:00 amPWM - MKE
2 stops10h 07mUnited Airlines
Thu 11/276:05 amMKE - PWM
1 stop7h 07mUnited Airlines
Deal found 7/31$392
This Mytrip deal was found by Cheapflights users on 7/30. 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 8/148:52 pmPWM - MKE
3 stops20h 47mMultiple Airlines
Mon 8/186:00 amMKE - PWM
1 stop10h 25mMultiple Airlines
Deal found 7/30$658

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 July 31, 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

Sat 8/30

5:45 am-10:10 am

1 stop5h 25m

Milwaukee-Mitchell

Sat 9/6

1:50 pm-10:00 pm

1 stop7h 10m

$237

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

Thu 8/21

5:57 pm-12:11 am

1 stop7h 14m

Milwaukee-Mitchell

Wed 8/27

5:13 pm-10:59 pm

1 stop4h 46m

$252

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

Wed 9/10

11:48 am-9:33 pm

2 stops10h 45m

Milwaukee-Mitchell

Fri 9/12

4:47 pm-12:11 am

1 stop6h 24m

$282

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

Thu 8/21

6:41 pm-11:29 pm

1 stop5h 48m

Milwaukee-Mitchell

Wed 8/27

7:00 am-2:25 pm

2 stops6h 25m

$474

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

Thu 8/14

8:52 pm-4:39 pm

3 stops20h 47m

Milwaukee-Mitchell

Mon 8/18

6:00 am-5:25 pm

1 stop10h 25m

$658

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

Sat 10/4

6:15 am-10:08 am

1 stop4h 53m

$119

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

Wed 9/10

1:39 pm-11:36 pm

2 stops10h 57m

$124

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

Wed 9/3

4:56 pm-9:56 pm

1 stop6h 00m

$154

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

Sun 10/26

5:30 am-9:25 am

1 stop4h 55m

$184

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

Thu 8/7

12:46 pm-8:50 am

3 stops21h 04m

$380

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

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 July 25, 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 July 31, 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 July 31, 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
4,246 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,246 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,981 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
United Airlines
7.4
Good
8,900 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,246 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

Crew

8.6

Entertainment

7.5

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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 Southwest. Our recent data shows that you can find tickets from as low as $237 on this airline. Additional options worth looking into are American Airlines and Delta, starting at $252 and $282 round-trip. Users have found that Southwest is 43% 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 American Airlines. According to our data, you can fly for as low as $119. Users have also found prices from $124 and $154 on Delta and United Airlines, 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
Mequon
Oak Creek
Sheboygan
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 July 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$246Average$394FlexibilityNo cancel feeOn-time71%
DeltaCheapest$264Average$406FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$268Average$389FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$274Average$496FlexibilityNo cancel feeOn-time69%

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