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$108+ 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 11/5. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — PWM
oct. 11 — oct. 181
sáb. 10/11
sáb. 10/18
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 34 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 septiembre 11, 2025.

Round-trip from

$219
(American Airlines)

One-way from

$108
(Southwest)

Popular in

December

Cheapest in

April

Average price

$352
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 ($84 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($11 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 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 septiembre 11, 2025.

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.
mar. 10/286:00 amMKE - PWM
1 stop6h 35mAmerican Airlines
sáb. 11/13:28 pmPWM - MKE
1 stop5h 18mAmerican Airlines
Deal found 9/9$219
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 10/77:00 amMKE - PWM
2 stops8h 44mUnited Airlines
sáb. 10/114:57 pmPWM - MKE
1 stop5h 59mUnited Airlines
Deal found 9/10$224
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 10/1112:05 pmMKE - PWM
2 stops10h 15mUnited Airlines
jue. 10/166:25 pmPWM - MKE
1 stop5h 06mUnited Airlines
Deal found 9/10$233
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.
jue. 10/23:34 pmMKE - PWM
1 stop7h 37mDelta
mar. 10/72:38 pmPWM - MKE
1 stop6h 29mDelta
Deal found 9/10$237
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 10/1010:50 amMKE - PWM
1 stop5h 52mUnited Airlines
mar. 10/144:57 pmPWM - MKE
1 stop5h 59mUnited Airlines
Deal found 9/10$240
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.
mar. 10/287:11 amMKE - PWM
2 stops8h 02mDelta
sáb. 11/11:27 pmPWM - MKE
1 stop8h 15mDelta
Deal found 9/10$242
This American Airlines deal was found by Cheapflights users on 9/11. 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.
vie. 10/244:44 pmMKE - PWM
1 stop5h 04mAmerican Airlines
lun. 10/275:59 pmPWM - MKE
1 stop7h 15mAmerican Airlines
Deal found 9/11$249
This American Airlines deal was found by Cheapflights users on 9/11. 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.
dom. 10/56:23 pmMKE - PWM
1 stop4h 36mAmerican Airlines
mié. 10/86:00 amPWM - MKE
1 stop6h 49mAmerican Airlines
Deal found 9/11$253
This United Airlines 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 10/1112:05 pmMKE - PWM
2 stops10h 15mUnited Airlines
mié. 10/155:41 pmPWM - MKE
1 stop6h 43mUnited Airlines
Deal found 9/10$277
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 10/236:00 pmMKE - PWM
1 stop5h 05mSouthwest
mar. 10/285:25 pmPWM - MKE
1 stop4h 45mSouthwest
Deal found 9/10$285
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 10/112:05 pmMKE - PWM
1 stop7h 57mAmerican Airlines
mié. 10/155:21 pmPWM - MKE
1 stop7h 09mAmerican Airlines
Deal found 9/10$287

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 septiembre 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

mar. 10/7

7:00 am-4:44 pm

2 stops8h 44m

Portland

sáb. 10/11

4:57 pm-9:56 pm

1 stop5h 59m

$224

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

lun. 12/8

5:59 pm-11:21 pm

1 stop4h 22m

Portland

lun. 12/15

4:43 pm-9:45 pm

1 stop6h 02m

$237

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

lun. 12/8

6:01 am-11:37 am

1 stop4h 36m

Portland

lun. 12/15

5:17 pm-11:30 pm

1 stop7h 13m

$237

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

mié. 10/15

5:47 am-12:22 pm

1 stop5h 35m

Portland

mar. 10/21

1:27 pm-8:42 pm

1 stop8h 15m

$237

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

mar. 10/14

5:43 pm-11:09 pm

1 stop4h 26m

Portland

sáb. 10/18

6:30 am-11:33 am

1 stop6h 03m

$237

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

sáb. 10/11

1:10 pm-10:19 pm

2 stops8h 09m

Portland

mié. 10/15

5:42 am-10:03 am

1 stop5h 21m

$242

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

mar. 10/28

10:45 am-4:13 pm

1 stop4h 28m

Portland

sáb. 11/1

2:38 pm-11:55 pm

2 stops10h 17m

$242

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

jue. 10/23

6:00 pm-12:05 am

1 stop5h 05m

Portland

mar. 10/28

5:25 pm-9:10 pm

1 stop4h 45m

$285

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

jue. 10/2

5:26 am-1:31 pm

1 stop7h 05m

Portland

mar. 10/7

7:44 am-11:49 am

1 stop5h 05m

$287

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

mié. 11/5

6:40 am-12:10 pm

1 stop4h 30m

$108

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

Showing 1-10 of 19 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 August 29, 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 34 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 septiembre 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
4,248 reviews

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

Crew

8.6

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

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

Crew

8.6

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

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

Crew

8.6

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

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

Crew

8.6

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

Comfort

8.0

Overall

8.0

Boarding

8.1

Food

7.0

Crew

8.6

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 Milwaukee to Portland. 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 Milwaukee to Portland, Maine?

    There are many flights that can get you from Milwaukee to Portland, Maine in 4h 22m. Fly via United Airlines, Delta, or American Airlines to get the fastest option. Milwaukee and Portland, Maine are separated by 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 Milwaukee to Portland, Maine round-trip?

    Flying on American Airlines is currently your cheapest option to Portland, Maine, with prices starting at $238. Additional round-trip tickets that might be worth considering are offered by Southwest and Delta, with the lowest prices starting at $246 and $251, respectively. American Airlines is 37% 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 $108. Users have also found prices from $110 and $115 on American Airlines and United Airlines, 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 Portland?

Book flights to Portland if you plan to visit one of these locations
Brunswick
North Conway
Auburn
Conway
Lewiston

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Top 4 airlines flying from Milwaukee to Portland

Discover the top 4 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 septiembre 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$238Average$378FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$246Average$387FlexibilityNo cancel feeOn-time63%
DeltaCheapest$251Average$362FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$309Average$376FlexibilityNo cancel feeOn-time69%

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