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$136+ 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 8/27. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — PWM
Jun 17 — Jun 241
Tue 6/17
Tue 6/24
1 adult, Economy
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Cheapflights Tip: The best prices from Milwaukee-Mitchell to Portland are usually found in April or February, booked 6 days in advance, depart on a Tuesday or Sunday and return on a Wednesday

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 June 12, 2025.

Round-trip from

$283
(American Airlines)

One-way from

$136
(Delta)

Popular in

December

Cheapest in

April

Average price

$426
From Milwaukee-Mitchell to Portland
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One-way flight from Milwaukee-Mitchell to Portland
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Highest demand for flights based on searches. 18% potential increase in price ($87 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($10 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 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 June 12, 2025.

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.
Tue 9/167:00 amMKE - PWM
1 stop6h 26mUnited Airlines
Mon 9/224:56 pmPWM - MKE
1 stop6h 00mUnited Airlines
Deal found 6/10$271
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/176:00 amMKE - PWM
1 stop7h 21mDelta
Tue 9/233:15 pmPWM - MKE
2 stops9h 10mDelta
Deal found 6/11$276
This American Airlines deal was found by Cheapflights users on 6/9. 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.
Tue 8/126:21 amMKE - PWM
1 stop4h 17mAmerican Airlines
Sat 8/165:57 pmPWM - MKE
1 stop7h 14mAmerican Airlines
Deal found 6/9$283
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/164:00 pmMKE - PWM
1 stop5h 25mSouthwest
Mon 9/222:00 pmPWM - MKE
2 stops8h 35mSouthwest
Deal found 6/11$335
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/106:30 pmMKE - PWM
1 stop14h 45mSun Country Air
Thu 7/1712:58 pmPWM - MKE
1 stop5h 37mSun Country Air
Deal found 6/10$353
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 7/102:51 pmMKE - PWM
2 stops18h 24mMultiple Airlines
Thu 7/1712:58 pmPWM - MKE
3 stops20h 52mMultiple Airlines
Deal found 6/10$534

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 June 12, 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

Tue 8/12

6:21 am-11:38 am

1 stop4h 17m

Portland

Sat 8/16

5:57 pm-12:11 am

1 stop7h 14m

$283

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Wed 7/9

12:44 pm-11:29 pm

2 stops9h 45m

Portland

Wed 7/16

6:00 am-11:38 am

1 stop6h 38m

$302

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Mon 7/7

5:10 am-4:55 pm

1 stop10h 45m

Portland

Sat 7/12

5:30 am-9:35 am

1 stop5h 05m

$347

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Thu 7/10

6:30 pm-10:15 am

1 stop14h 45m

Portland

Thu 7/17

12:58 pm-5:35 pm

1 stop5h 37m

$353

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Wed 7/9

6:05 am-1:19 pm

1 stop6h 14m

Portland

Sun 7/13

6:10 am-7:10 pm

1 stop14h 00m

$462

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Thu 7/10

2:51 pm-10:15 am

2 stops18h 24m

Portland

Thu 7/17

12:58 pm-8:50 am

3 stops20h 52m

$534

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Wed 8/27

5:25 am-12:29 pm

1 stop6h 04m

$136

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Wed 8/27

5:00 am-2:25 pm

2 stops8h 25m

$141

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Thu 7/24

6:30 pm-11:35 am

1 stop16h 05m

$148

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Mon 6/30

2:50 pm-10:47 pm

1 stop6h 57m

$180

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/10

Showing 1-10 of 12 results
1
2

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 June 9, 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 6 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, January is the cheapest month in which you can book a flight from Milwaukee to Portland, Maine (average of $296). Flying from Milwaukee to Portland, Maine in July is currently the most expensive (average of $394). 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.

Rainfall in Portland by month

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

In terms of precipitation, rainfall in Portland, Maine ranges from 2.9 - 4.5 inches per month. November is typically the wettest month, when rainfall can reach 4.5 in. August is typically the driest time to visit Portland, Maine when rainfall is around 2.9 in.

Temperature in Portland by month

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

If weather is an important factor for your trip to Portland, Maine, 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 68.0 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

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 June 12, 2025.
Read reviews from past customers who have flown Southwest, Delta and United Airlines from Milwaukee to Portland. In addition to providing an overall rating, users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,287 reviews

Food

7.1

Entertainment

7.6

Boarding

8.2

Overall

8.0

Comfort

8.0

Crew

8.6

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

Food

7.1

Entertainment

7.6

Boarding

8.2

Overall

8.0

Comfort

8.0

Crew

8.6

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

Food

7.1

Entertainment

7.6

Boarding

8.2

Overall

8.0

Comfort

8.0

Crew

8.6

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

Food

7.1

Entertainment

7.6

Boarding

8.2

Overall

8.0

Comfort

8.0

Crew

8.6

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

Food

7.1

Entertainment

7.6

Boarding

8.2

Overall

8.0

Comfort

8.0

Crew

8.6

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

Food

7.1

Entertainment

7.6

Boarding

8.2

Overall

8.0

Comfort

8.0

Crew

8.6

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 Milwaukee to Portland. 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 Milwaukee to Portland, Maine round-trip?

    Flying on American Airlines is currently your cheapest option to Portland, Maine, with prices starting at $283. Additional round-trip tickets that might be worth considering are offered by Delta and Southwest, with the lowest prices starting at $297 and $347, respectively. American Airlines is 26% 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 Delta. According to our data, you can fly for as low as $136. Users have also found prices from $141 and $148 on United Airlines and Sun Country Air, 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, January is the cheapest month in which you can book a flight from Milwaukee to Portland, Maine (average of $296). Flying from Milwaukee to Portland, Maine in July is currently the most expensive (average of $394). 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
North Conway
Bath
Brunswick
Auburn
Conway
Lewiston

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Top 5 airlines flying from Milwaukee to Portland

Discover the top 5 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 June 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$151Average$167FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$246Average$395FlexibilityNo cancel feeOn-time63%
DeltaCheapest$256Average$357FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$276Average$388FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$290Average$381FlexibilityNo cancel feeOn-time69%

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