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Wisconsin

$79+ 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 6/13. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MKE
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap 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 December 18, 2025.

This United Airlines deal was found by Cheapflights users on 12/14. 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.
Mon 12/227:30 pmPWM - ORD
1 stop5h 14mUnited Airlines
Thu 12/255:50 pmORD - PWM
Nonstop2h 39mUnited Airlines
Deal found 12/14$319
This United Airlines deal was found by Cheapflights users on 12/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/247:30 pmPWM - ORD
1 stop5h 14mUnited Airlines
Tue 12/305:50 pmORD - PWM
Nonstop2h 39mUnited Airlines
Deal found 12/15$338
This United Airlines deal was found by Cheapflights users on 12/17. 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 12/254:10 pmPWM - MSP
1 stop7h 34mUnited Airlines
Fri 1/166:00 amMSP - PWM
2 stops7h 31mUnited Airlines
Deal found 12/17$354
This United Airlines deal was found by Cheapflights users on 12/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/237:30 pmPWM - ORD
1 stop5h 14mUnited Airlines
Tue 12/305:50 pmORD - PWM
Nonstop2h 39mUnited Airlines
Deal found 12/15$368
This Delta deal was found by Cheapflights users on 12/14. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/225:45 amPWM - ORD
1 stop6h 42mDelta
Thu 12/259:41 amORD - PWM
2 stops12h 02mDelta
Deal found 12/14$379
This United Airlines deal was found by Cheapflights users on 12/17. 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 12/237:30 pmPWM - ORD
1 stop5h 14mUnited Airlines
Fri 12/268:51 amORD - PWM
1 stop4h 49mUnited Airlines
Deal found 12/17$389
This United Airlines deal was found by Cheapflights users on 12/17. 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.
Sat 12/204:10 pmPWM - ORD
Nonstop3h 14mUnited Airlines
Mon 12/225:50 pmORD - PWM
Nonstop2h 39mUnited Airlines
Deal found 12/17$429
This Delta deal was found by Cheapflights users on 12/15. 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.
Mon 12/154:53 pmPWM - ORD
1 stop4h 42mDelta
Tue 12/1610:40 amORD - PWM
1 stop4h 23mDelta
Deal found 12/15$449
This United Airlines deal was found by Cheapflights users on 12/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:00 amPWM - MKE
1 stop6h 00mUnited Airlines
Sun 1/45:52 pmMKE - PWM
1 stop4h 30mUnited Airlines
Deal found 12/16$484
This United Airlines deal was found by Cheapflights users on 12/17. 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 12/189:30 amPWM - MSN
1 stop6h 35mUnited Airlines
Sun 12/216:40 amMSN - PWM
1 stop6h 34mUnited Airlines
Deal found 12/17$484
This United Airlines deal was found by Cheapflights users on 12/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/316:00 amPWM - MSP
1 stop6h 37mUnited Airlines
Sun 1/46:45 pmMSP - PWM
2 stops13h 59mUnited Airlines
Deal found 12/16$513
This United Airlines deal was found by Cheapflights users on 12/17. 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.
Mon 12/296:00 amPWM - MSP
1 stop6h 22mUnited Airlines
Sat 1/34:51 pmMSP - PWM
1 stop5h 31mUnited Airlines
Deal found 12/17$534

Find flight deals from Portland to Wisconsin

Keep the following information in mind while searching for Portland to Wisconsin flight deals. Data was last updated December 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$255
(United Airlines)

One-way from

$79
(Sun Country Air)

Popular in

November

Cheapest in

September

Average price

$389
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
Search Deals
One-way flight from Portland to Wisconsin
Search Deals
Highest demand for flights based on searches. 12% potential increase in price ($47 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 December 18, 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

PortlandMinneapolis

PWM - MSP

PWMMSP

Portland

Tue 1/27

4:10 pm-9:57 pm

1 stop6h 47m

Minneapolis St Paul

Tue 2/3

7:01 am-1:56 pm

1 stop5h 55m

$259

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 3/6

6:00 am-10:51 am

1 stop5h 51m

Chicago O'Hare Intl

Thu 3/12

11:48 am-3:14 pm

Nonstop2h 26m

$263

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 5/8

5:30 pm-7:20 pm

Nonstop2h 50m

Chicago O'Hare Intl

Mon 5/11

6:45 am-12:00 pm

1 stop4h 15m

$264

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 1/2

6:46 pm-11:35 pm

1 stop5h 49m

Chicago O'Hare Intl

Wed 1/7

6:00 am-2:31 pm

1 stop7h 31m

$265

PortlandChicago

PWM - ORD

PWMORD

Portland

Tue 4/7

5:30 am-1:16 pm

2 stops8h 46m

Chicago O'Hare Intl

Sun 4/12

7:10 am-12:00 pm

1 stop3h 50m

$274

PortlandChicago

PWM - ORD

PWMORD

Portland

Sat 2/14

3:05 pm-7:53 pm

1 stop5h 48m

Chicago O'Hare Intl

Tue 2/17

11:48 am-3:14 pm

Nonstop2h 26m

$277

PortlandMadison

PWM - MSN

PWMMSN

Portland

Wed 1/7

5:20 am-10:11 am

1 stop5h 51m

Madison Truax Field

Wed 1/14

4:47 pm-10:54 pm

1 stop5h 07m

$279

PortlandChicago

PWM - ORD

PWMORD

Portland

Sun 1/11

5:30 am-1:40 pm

1 stop9h 10m

Chicago O'Hare Intl

Tue 1/13

6:25 pm-12:26 am

1 stop5h 01m

$279

PortlandChicago

PWM - ORD

PWMORD

Portland

Tue 2/3

4:10 pm-6:18 pm

Nonstop3h 08m

Chicago O'Hare Intl

Tue 2/10

11:00 am-2:39 pm

Nonstop2h 39m

$279

PortlandMadison

PWM - MSN

PWMMSN

Portland

Tue 1/6

5:00 am-10:11 am

1 stop6h 11m

Madison Truax Field

Sat 1/10

11:23 am-9:37 pm

2 stops9h 14m

$284

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/17

Showing 1-10 of 49 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 December 18, 2025.

It’s typically best to fly out from Portland, Maine to Wisconsin in the evening. Doing so could potentially save you 51% 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 December 18, 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
7.9
Good
4,250 reviews

Food

7.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Overall

7.9

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Southwest
7.9
Good
4,250 reviews
Southwest
7.9
Good
4,250 reviews

Food

7.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Overall

7.9

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
Delta
7.9
Good
8,005 reviews
Southwest
7.9
Good
4,250 reviews

Food

7.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Overall

7.9

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
United Airlines
7.4
Good
9,091 reviews
Southwest
7.9
Good
4,250 reviews

Food

7.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Overall

7.9

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am
American Airlines
7.2
Good
11,054 reviews
Southwest
7.9
Good
4,250 reviews

Food

7.0

Boarding

8.1

Entertainment

7.5

Crew

8.6

Overall

7.9

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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 2h 50m. Fly via United Airlines, American Airlines, or Delta to get the fastest option. There are 897 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 Delta ($128), United Airlines ($134), and American Airlines ($135).

  • 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 - Milwaukee-Mitchell.

  • 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

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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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$258Average$492FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$258Average$417FlexibilityNo cancel feeOn-time71%
DeltaCheapest$258Average$416FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$311Average$396FlexibilityNo cancel feeOn-time63%

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