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Wisconsin

$96+ Cheap flights from Portland, ME (PWM) to Wisconsin

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 4/7. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MKE
nov 15 — nov 221
sáb 11/15
sáb 11/22
1 adult, Economy
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Cheap flight deals from Portland to Wisconsin

Keep the following information in mind while searching for Portland to Wisconsin flight deals. Data was last updated outubro 16, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$259
(American Airlines)

One-way from

$96
(Priceline)

Popular in

November

Cheapest in

September

Average price

$296
Provider with most accurate pricing for Boston Logan Intl-Milwaukee-Mitchell flight deals.
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Provider most trusted by Cheapflights users for Boston Logan Intl-Milwaukee-Mitchell flights.
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From Portland to Wisconsin
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One-way flight from Portland to Wisconsin
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Highest demand for flights based on searches. 12% potential increase in price ($47 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 October 2025
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Find flight deals from Portland to Wisconsin

Cheapest flights from Portland to Wisconsin
Explore the most affordable flight options available from Portland to Wisconsin. Find the lowest fares from popular airlines and budget airlines, with prices last updated on outubro 16, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/15. 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.
qui 10/2312:34 pmPWM - MSP
Nonstop3h 02mSun Country Air
dom 10/267:48 amMSP - PWM
Nonstop2h 43mSun Country Air
Deal found 10/15$216
This American Airlines deal was found by Cheapflights users on 10/15. 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.
qua 12/105:17 pmPWM - MSN
1 stop5h 39mAmerican Airlines
qua 12/1710:20 amMSN - PWM
1 stop6h 55mAmerican Airlines
Deal found 10/15$259
This Delta deal was found by Cheapflights users on 10/15. 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.
qua 12/1012:53 pmPWM - MSN
1 stop5h 45mDelta
qua 12/175:28 amMSN - PWM
2 stops9h 35mDelta
Deal found 10/15$264
This American Airlines deal was found by Cheapflights users on 10/14. 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.
qua 10/291:05 pmPWM - ORD
1 stop9h 20mAmerican Airlines
sex 10/317:58 amORD - PWM
Nonstop2h 30mAmerican Airlines
Deal found 10/14$265
This Kiwi.com deal was found by Cheapflights users on 10/14. 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.
qua 10/2911:16 amPWM - ORD
1 stop31h 33mMultiple Airlines
sex 10/311:55 pmORD - PWM
1 stop19h 46mMultiple Airlines
Deal found 10/14$269
This Delta deal was found by Cheapflights users on 10/16. 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.
qui 11/206:00 amPWM - MKE
1 stop5h 16mDelta
qui 11/275:45 amMKE - PWM
1 stop5h 45mDelta
Deal found 10/16$282
This Kiwi.com deal was found by Cheapflights users on 10/13. 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.
qua 12/36:18 pmPWM - ORD
1 stop18h 16mMultiple Airlines
dom 12/77:49 pmORD - PWM
1 stop12h 17mMultiple Airlines
Deal found 10/13$288
This American Airlines deal was found by Cheapflights users on 10/14. 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.
qui 10/305:21 pmPWM - MSN
1 stop4h 57mAmerican Airlines
seg 11/33:59 pmMSN - PWM
1 stop7h 00mAmerican Airlines
Deal found 10/14$289
This United Airlines deal was found by Cheapflights users on 10/14. 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.
qui 10/306:00 amPWM - MSN
2 stops9h 03mUnited Airlines
seg 11/36:30 amMSN - PWM
1 stop6h 42mUnited Airlines
Deal found 10/14$294
This Kiwi.com deal was found by Cheapflights users on 10/14. 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.
qua 11/511:16 amPWM - ORD
1 stop26h 10mMultiple Airlines
dom 11/95:25 amORD - PWM
1 stop26h 41mMultiple Airlines
Deal found 10/14$299
This Kiwi.com deal was found by Cheapflights users on 10/15. 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.
qui 10/305:40 pmPWM - ORD
1 stop15h 36mMultiple Airlines
seg 11/34:42 pmORD - PWM
1 stop24h 07mMultiple Airlines
Deal found 10/15$309
This Kiwi.com deal was found by Cheapflights users on 10/15. 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.
qui 10/2312:34 pmPWM - MSP
Nonstop3h 02mMultiple Airlines
dom 10/262:18 pmMSP - PWM
1 stop22h 33mMultiple Airlines
Deal found 10/15$310

Cheapflights Fare Finder

 
Customize your flight search to find flights from Portland to Wisconsin 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 outubro 16, 2025.
Use the filters below to find and compare flights from Portland to Wisconsin that are best for you.

Fly from

Portland

Fly to

Wisconsin

Route

Depart

Return

Price

PortlandMadison

PWM - MSN

PWMMSN

Portland

qua 12/10

12:53 pm-5:38 pm

1 stop5h 45m

Madison Truax Field

qua 12/17

5:28 am-4:03 pm

2 stops9h 35m

$264

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

qui 11/20

6:00 am-10:16 am

1 stop5h 16m

Milwaukee-Mitchell

qui 11/27

7:12 am-12:08 pm

1 stop3h 56m

$282

PortlandMadison

PWM - MSN

PWMMSN

Portland

qui 10/30

5:21 pm-9:18 pm

1 stop4h 57m

Madison Truax Field

seg 11/3

3:59 pm-11:59 pm

1 stop7h 00m

$289

PortlandMadison

PWM - MSN

PWMMSN

Portland

qui 10/30

6:00 am-2:03 pm

2 stops9h 03m

Madison Truax Field

seg 11/3

6:30 am-2:12 pm

1 stop6h 42m

$294

PortlandChicago

PWM - ORD

PWMORD

Portland

sáb 1/17

1:15 pm-7:25 pm

1 stop7h 10m

Chicago O'Hare Intl

seg 1/19

2:45 pm-9:59 pm

1 stop6h 14m

$299

PortlandChicago

PWM - ORD

PWMORD

Portland

qua 11/12

4:40 pm-6:41 pm

Nonstop3h 01m

Chicago O'Hare Intl

qui 11/13

6:15 pm-9:50 pm

Nonstop2h 35m

$311

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

qui 11/6

5:21 pm-11:42 pm

1 stop7h 21m

Milwaukee-Mitchell

ter 11/11

6:00 am-11:46 am

1 stop4h 46m

$313

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

qui 2/5

11:25 am-5:10 pm

1 stop6h 45m

Milwaukee-Mitchell

seg 2/9

2:45 pm-9:59 pm

1 stop6h 14m

$313

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

sáb 11/8

5:37 pm-11:05 pm

1 stop6h 28m

Milwaukee-Mitchell

ter 11/11

6:00 am-11:46 am

1 stop4h 46m

$315

PortlandMadison

PWM - MSN

PWMMSN

Portland

qua 11/26

4:40 pm-8:35 pm

1 stop4h 55m

Madison Truax Field

sex 11/28

6:00 am-1:36 pm

1 stop6h 36m

$329

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/15

Showing 1-10 of 60 results
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Best time to book a flight from Portland to Wisconsin

Have a flexible travel schedule? Discover the best time to fly to Wisconsin 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 Wisconsin

What is the cheapest month to book a flight from Portland, Maine to Wisconsin?

Currently, September is the cheapest month in which you can book a flight from Portland, Maine to Wisconsin (average of $98). Flying from Portland, Maine to Wisconsin in February is currently the most expensive (average of $258). 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 WI?

Find hourly flight availability from Portland to Wisconsin. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated outubro 16, 2025.

It’s typically best to fly out from Portland, Maine to Wisconsin in the evening. Doing so could potentially save you 50% on the flight price compared to flying in the afternoon, which is usually more expensive.

Reviews of airlines servicing Wisconsin

Get insights into the airlines that provide service to Wisconsin. 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 Wisconsin. Reviews last updated outubro 16, 2025.
Read reviews from past customers who have flown Southwest, Delta, and United Airlines from Portland to Wisconsin. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,239 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.0

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
4,239 reviews
Southwest
8.0
Very good
4,239 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.0

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
7,977 reviews
Southwest
8.0
Very good
4,239 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.0

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
8,979 reviews
Southwest
8.0
Very good
4,239 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.0

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
11,041 reviews
Southwest
8.0
Very good
4,239 reviews

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Overall

8.0

Crew

8.6

Food

7.0

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 Wisconsin. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Portland to Wisconsin?

    Portland (PWM), located 2.9 mi from the city center, is the airport you fly out of when you book flights from Portland to Wisconsin.

  • How long is the flight from Portland, Maine to Wisconsin?

    There are many flights that can get you from Portland, Maine to Wisconsin in 4h 57m. Fly via Delta, American Airlines, or United Airlines to get the fastest option. There are 953 mi between Portland, Maine and Wisconsin. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Portland, Maine to Wisconsin one-way?

    The cheapest airlines for a one-way flight from Portland, Maine to Wisconsin are United Airlines ($124), Delta ($139), and Southwest ($170).

  • What are the most popular routes from Portland, Maine to Wisconsin?

    The most popular flight routes from Portland, Maine to Wisconsin are Portland - Chicago O'Hare Intl, Portland - Minneapolis St Paul and Portland - Green Bay Austin-Straubel.

  • Can I find deals for flights from Portland to Wisconsin that include hotel bookings?

    Yes. In addition to deals on Portland to Wisconsin flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Portland to Wisconsin?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Portland to Wisconsin.

  • Can I find deals for business class flights from Portland to Wisconsin?

    Yes. Cheapflights offers flight deals from Portland to Wisconsin 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 Wisconsin?

    Currently, September is the cheapest month in which you can book a flight from Portland, Maine to Wisconsin (average of $98). Flying from Portland, Maine to Wisconsin in February is currently the most expensive (average of $258). 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

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Alternative routes for Portland to Wisconsin

See prices for flight routes from nearby airports that may be better suited for you.
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Top 4 airlines flying from Portland to Wisconsin

Discover the top 4 airlines that operate flights from Portland to Wisconsin. 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 outubro 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$258Average$420FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$258Average$498FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$258Average$418FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$311Average$422FlexibilityNo cancel feeOn-time63%

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