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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 6/4. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MKE
Jan 6 — Jan 131
Tue 1/6
Tue 1/13
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 7, 2025.

This United Airlines deal was found by Cheapflights users on 12/5. 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
Thu 12/256:21 pmORD - PWM
1 stop4h 38mUnited Airlines
Deal found 12/5$269
This United Airlines deal was found by Cheapflights users on 12/5. 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
Thu 12/256:21 pmORD - PWM
1 stop4h 38mUnited Airlines
Deal found 12/5$289
This United Airlines deal was found by Cheapflights users on 12/5. 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 12/139:45 amPWM - ORD
Nonstop3h 10mUnited Airlines
Mon 12/155:50 pmORD - PWM
Nonstop2h 27mUnited Airlines
Deal found 12/5$309
This American Airlines deal was found by Cheapflights users on 12/6. 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.
Thu 12/185:39 amPWM - ORD
1 stop7h 28mAmerican Airlines
Mon 12/224:05 pmORD - PWM
1 stop5h 46mAmerican Airlines
Deal found 12/6$324
This American Airlines deal was found by Cheapflights users on 12/5. 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.
Fri 12/125:34 amPWM - ORD
1 stop6h 21mAmerican Airlines
Sun 12/143:52 pmORD - PWM
1 stop6h 45mAmerican Airlines
Deal found 12/5$329
This Delta deal was found by Cheapflights users on 12/5. 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.
Sat 12/134:45 pmPWM - ORD
1 stop4h 50mDelta
Mon 12/155:30 amORD - PWM
2 stops9h 33mDelta
Deal found 12/5$334
This United Airlines deal was found by Cheapflights users on 12/6. 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
Wed 12/313:53 pmORD - PWM
1 stop6h 29mUnited Airlines
Deal found 12/6$345
This American Airlines deal was found by Cheapflights users on 12/5. 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.
Sat 12/205:20 pmPWM - ORD
1 stop4h 56mAmerican Airlines
Wed 12/241:27 pmORD - PWM
1 stop4h 32mAmerican Airlines
Deal found 12/5$359
This United Airlines deal was found by Cheapflights users on 12/5. 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 12/116:00 amPWM - MSN
2 stops8h 51mUnited Airlines
Sat 12/136:15 amMSN - PWM
1 stop6h 23mUnited Airlines
Deal found 12/5$393
This American Airlines deal was found by Cheapflights users on 12/5. 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.
Thu 12/115:34 amPWM - MSN
1 stop5h 42mAmerican Airlines
Sat 12/133:55 pmMSN - PWM
1 stop5h 37mAmerican Airlines
Deal found 12/5$404
This American Airlines deal was found by Cheapflights users on 12/6. 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.
Thu 12/187:17 amPWM - MKE
2 stops11h 32mAmerican Airlines
Mon 12/226:05 amMKE - PWM
1 stop4h 44mAmerican Airlines
Deal found 12/6$525
This American Airlines deal was found by Cheapflights users on 12/4. 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.
Mon 12/153:55 pmPWM - MSP
1 stop8h 23mAmerican Airlines
Thu 12/181:41 pmMSP - PWM
1 stop8h 10mAmerican Airlines
Deal found 12/4$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 7, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$218
(Booking.com)

One-way from

$93
(Southwest)

Popular in

September

Cheapest in

November

Average price

$558
Provider with most accurate pricing for Portland-Milwaukee-Mitchell flight deals.
Search Deals
Provider most trusted by Cheapflights users for Portland-Milwaukee-Mitchell flights.
Search Deals
From Portland to Wisconsin
Search Deals
One-way flight from Portland to Wisconsin
Search Deals
Highest demand for flights based on searches. 22% potential increase in price ($137 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($26 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 7, 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

PortlandChicago

PWM - ORD

PWMORD

Portland

Wed 12/24

7:30 pm-11:44 pm

1 stop5h 14m

Chicago O'Hare Intl

Thu 12/25

6:21 pm-11:59 pm

1 stop4h 38m

$269

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 1/16

2:35 pm-11:59 pm

2 stops10h 24m

Chicago O'Hare Intl

Sun 1/18

1:55 pm-12:20 am

2 stops9h 25m

$279

PortlandChicago

PWM - ORD

PWMORD

Portland

Wed 1/28

4:10 pm-6:18 pm

Nonstop3h 08m

Chicago O'Hare Intl

Sat 1/31

11:00 am-2:39 pm

Nonstop2h 39m

$279

PortlandChicago

PWM - ORD

PWMORD

Portland

Wed 1/14

5:30 am-10:59 am

1 stop6h 29m

Chicago O'Hare Intl

Fri 1/16

6:25 pm-12:20 am

1 stop4h 55m

$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

PortlandChicago

PWM - ORD

PWMORD

Portland

Sat 5/16

6:01 am-11:08 am

1 stop6h 07m

Chicago O'Hare Intl

Mon 5/18

1:25 pm-4:55 pm

Nonstop2h 30m

$284

PortlandChicago

PWM - ORD

PWMORD

Portland

Wed 4/8

6:00 am-12:50 pm

1 stop7h 50m

Chicago O'Hare Intl

Sun 4/12

1:45 pm-11:36 pm

1 stop8h 51m

$285

PortlandChicago

PWM - ORD

PWMORD

Portland

Thu 1/29

12:20 pm-11:56 pm

2 stops12h 36m

Chicago O'Hare Intl

Sat 1/31

8:50 am-7:38 pm

2 stops9h 48m

$289

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

Wed 1/14

4:10 pm-10:56 pm

1 stop7h 46m

Milwaukee-Mitchell

Sat 1/17

5:39 pm-11:30 pm

1 stop4h 51m

$295

PortlandMinneapolis

PWM - MSP

PWMMSP

Portland

Fri 5/8

5:30 pm-9:53 pm

1 stop5h 23m

Minneapolis St Paul

Tue 5/12

6:08 am-12:00 pm

1 stop4h 52m

$319

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/5

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 December 7, 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 7, 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
4,253 reviews

Boarding

8.1

Overall

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

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
8.0
Very good
4,253 reviews
Southwest
8.0
Very good
4,253 reviews

Boarding

8.1

Overall

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

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
8,013 reviews
Southwest
8.0
Very good
4,253 reviews

Boarding

8.1

Overall

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

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
9,072 reviews
Southwest
8.0
Very good
4,253 reviews

Boarding

8.1

Overall

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

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
11,046 reviews
Southwest
8.0
Very good
4,253 reviews

Boarding

8.1

Overall

8.0

Food

7.0

Crew

8.6

Entertainment

7.5

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 5h 14m. Fly via United Airlines, Delta, or American Airlines 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 - 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 December 7, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$258Average$492FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$258Average$416FlexibilityNo cancel feeOn-time71%
DeltaCheapest$258Average$416FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$311Average$396FlexibilityNo cancel feeOn-time63%

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