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$80+ 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 9/29. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — PWM
Jul 16 — Jul 231
Wed 7/16
Wed 7/23
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 July 11, 2025.

Round-trip from

$159
(Southwest)

One-way from

$80
(Southwest)

Popular in

December

Cheapest in

April

Average price

$382
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 July 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 July 11, 2025.

This Southwest deal was found by Cheapflights users on 7/9. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/185:25 pmMKE - PWM
1 stop4h 55mSouthwest
Thu 8/215:50 amPWM - MKE
1 stop5h 10mSouthwest
Deal found 7/9$159
This American Airlines deal was found by Cheapflights users on 7/9. 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.
Wed 9/173:47 pmMKE - PWM
1 stop5h 42mAmerican Airlines
Tue 9/235:20 pmPWM - MKE
1 stop7h 10mAmerican Airlines
Deal found 7/9$173
This Delta deal was found by Cheapflights users on 7/9. 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 8/63:14 pmMKE - PWM
1 stop8h 24mDelta
Wed 8/136:00 amPWM - MKE
1 stop5h 09mDelta
Deal found 7/9$237
This United Airlines deal was found by Cheapflights users on 7/10. 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 8/123:45 pmMKE - PWM
1 stop5h 16mUnited Airlines
Fri 8/156:20 pmPWM - MKE
1 stop5h 25mUnited Airlines
Deal found 7/10$324

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 July 11, 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

Mon 8/18

5:25 pm-11:20 pm

1 stop4h 55m

Portland

Thu 8/21

5:50 am-10:00 am

1 stop5h 10m

$159

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Wed 9/17

3:47 pm-10:29 pm

1 stop5h 42m

Portland

Tue 9/23

5:20 pm-11:30 pm

1 stop7h 10m

$173

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Wed 8/6

3:14 pm-12:38 am

1 stop8h 24m

Portland

Wed 8/13

6:00 am-10:09 am

1 stop5h 09m

$237

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Tue 8/12

3:45 pm-10:01 pm

1 stop5h 16m

Portland

Fri 8/15

6:20 pm-10:45 pm

1 stop5h 25m

$324

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Mon 9/29

5:25 pm-11:20 pm

1 stop4h 55m

$80

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Tue 8/12

5:13 pm-10:59 pm

1 stop4h 46m

$87

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Fri 8/8

3:14 pm-12:38 am

1 stop8h 24m

$119

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Sun 7/20

6:35 pm-12:21 pm

1 stop16h 46m

$168

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Mon 8/11

9:45 am-12:13 pm

3 stops25h 28m

$276

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Mon 7/21

8:35 am-2:24 pm

1 stop4h 49m

$444

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/10

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 27, 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.

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 July 11, 2025.
Get a feel of what it's like to fly with Southwest, Delta, and United Airlines from Milwaukee to Portland by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,249 reviews

Comfort

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Overall

8.0

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
4,249 reviews
Southwest
8.0
Very good
4,249 reviews

Comfort

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Overall

8.0

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
7,951 reviews
Southwest
8.0
Very good
4,249 reviews

Comfort

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Overall

8.0

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
8,846 reviews
Southwest
8.0
Very good
4,249 reviews

Comfort

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Overall

8.0

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
4,249 reviews

Comfort

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Overall

8.0

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
335 reviews
Southwest
8.0
Very good
4,249 reviews

Comfort

8.0

Food

7.0

Crew

8.6

Boarding

8.1

Overall

8.0

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 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 Southwest is currently your cheapest option to Portland, Maine, with prices starting at $159. Additional round-trip tickets that might be worth considering are offered by American Airlines and Delta, with the lowest prices starting at $173 and $237, respectively. Southwest is 58% 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 Southwest. According to our data, you can fly for as low as $80. Users have also found prices from $87 and $119 on American Airlines and Delta, 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
Brunswick
North Conway
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 July 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$151Average$167FlexibilityNo cancel feeOn-time62%
SouthwestCheapest$246Average$392FlexibilityNo cancel feeOn-time63%
DeltaCheapest$256Average$357FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$264Average$381FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$290Average$381FlexibilityNo cancel feeOn-time69%

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