HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
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 1/12. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MKE
Jan 11 — Jan 181
Sun 1/11
Sun 1/18
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Portland to Wisconsin with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 12, 2025.

This United Airlines deal was found by Cheapflights users on 12/10. 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.
Thu 12/189:30 amPWM - ORD
Nonstop3h 14mUnited Airlines
Sun 12/216:21 pmORD - PWM
1 stop4h 38mUnited Airlines
Deal found 12/10$319
This United Airlines deal was found by Cheapflights users on 12/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/214:10 pmPWM - ORD
Nonstop3h 14mUnited Airlines
Sun 12/285:50 pmORD - PWM
Nonstop2h 39mUnited Airlines
Deal found 12/11$349
This United Airlines deal was found by Cheapflights users on 12/10. 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.
Wed 12/316:00 amPWM - MKE
1 stop6h 00mUnited Airlines
Fri 1/25:39 pmMKE - PWM
1 stop4h 43mUnited Airlines
Deal found 12/10$354
This Delta deal was found by Cheapflights users on 12/10. 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.
Tue 12/164:43 pmPWM - ORD
1 stop4h 55mDelta
Thu 12/185:50 pmORD - PWM
1 stop4h 31mDelta
Deal found 12/10$389
This United Airlines deal was found by Cheapflights users on 12/10. 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.
Thu 12/184:10 pmPWM - ORD
Nonstop3h 14mUnited Airlines
Sat 12/206:21 pmORD - PWM
1 stop4h 38mUnited Airlines
Deal found 12/10$403
This United Airlines deal was found by Cheapflights users on 12/10. 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.
Thu 12/256:00 amPWM - ORD
1 stop8h 15mUnited Airlines
Mon 12/295:50 pmORD - PWM
Nonstop2h 39mUnited Airlines
Deal found 12/10$430
This United Airlines deal was found by Cheapflights users on 12/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/184:10 pmPWM - MSP
1 stop6h 49mUnited Airlines
Thu 12/256:15 amMSP - PWM
2 stops7h 25mUnited Airlines
Deal found 12/11$449
This Delta deal was found by Cheapflights users on 12/10. 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.
Fri 12/126:08 amPWM - ORD
1 stop7h 02mDelta
Sun 12/145:50 pmORD - PWM
1 stop4h 31mDelta
Deal found 12/10$449
This United Airlines deal was found by Cheapflights users on 12/10. 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.
Thu 12/184:10 pmPWM - MSN
1 stop7h 20mUnited Airlines
Sun 12/212:29 pmMSN - PWM
2 stops8h 30mUnited Airlines
Deal found 12/10$484
This Southwest deal was found by Cheapflights users on 12/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/183:00 pmPWM - MSP
1 stop5h 45mSouthwest
Thu 12/256:10 amMSP - PWM
1 stop7h 45mSouthwest
Deal found 12/11$524
This United Airlines deal was found by Cheapflights users on 12/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/184:10 pmPWM - DLH
1 stop7h 45mUnited Airlines
Sat 12/203:03 pmDLH - PWM
2 stops7h 56mUnited Airlines
Deal found 12/9$538
This American Airlines deal was found by Cheapflights users on 12/11. 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.
Wed 12/175:46 amPWM - MSN
1 stop5h 30mAmerican Airlines
Sat 12/205:01 pmMSN - PWM
1 stop4h 54mAmerican Airlines
Deal found 12/11$549

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 12, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$259
(American Airlines)

One-way from

$96
(Kiwi.com)

Popular in

November

Cheapest in

September

Average price

$389
Provider with most accurate pricing for Boston Logan Intl-Milwaukee-Mitchell flight deals.
Search Deals
Provider most trusted by Cheapflights users for Boston Logan Intl-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. 11% potential increase in price ($45 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 12, 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

Wed 1/7

5:20 am-10:11 am

1 stop5h 51m

Madison Truax Field

Sat 1/10

4:47 pm-10:54 pm

1 stop5h 07m

$259

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

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 3/4

5:59 pm-10:05 pm

1 stop5h 06m

Chicago O'Hare Intl

Sun 3/8

6:30 am-12:00 pm

1 stop4h 30m

$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 1/31

4:10 pm-6:18 pm

Nonstop3h 08m

Chicago O'Hare Intl

Tue 2/3

11:00 am-2:39 pm

Nonstop2h 39m

$279

PortlandChicago

PWM - ORD

PWMORD

Portland

Wed 1/28

4:10 pm-6:18 pm

Nonstop3h 08m

Chicago O'Hare Intl

Mon 2/2

11:00 am-2:39 pm

Nonstop2h 39m

$279

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 1/9

4:10 pm-6:18 pm

Nonstop3h 08m

Chicago O'Hare Intl

Mon 1/12

11:00 am-2:39 pm

Nonstop2h 39m

$280

PortlandChicago

PWM - ORD

PWMORD

Portland

Wed 1/14

12:48 pm-6:28 pm

1 stop6h 40m

Chicago O'Hare Intl

Fri 1/16

1:55 pm-12:20 am

2 stops9h 25m

$284

PortlandChicago

PWM - ORD

PWMORD

Portland

Mon 1/12

6:00 am-1:08 pm

2 stops8h 08m

Chicago O'Hare Intl

Tue 1/13

12:00 pm-11:22 pm

2 stops10h 22m

$289

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/10

Showing 1-10 of 53 results
1
2
3
...
6

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 12, 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 12, 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
4,253 reviews

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Crew

8.6

Overall

7.9

Food

7.0

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
4,253 reviews
Southwest
7.9
Good
4,253 reviews

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Crew

8.6

Overall

7.9

Food

7.0

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
8,008 reviews
Southwest
7.9
Good
4,253 reviews

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Crew

8.6

Overall

7.9

Food

7.0

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
9,095 reviews
Southwest
7.9
Good
4,253 reviews

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Crew

8.6

Overall

7.9

Food

7.0

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
11,050 reviews
Southwest
7.9
Good
4,253 reviews

Boarding

8.1

Entertainment

7.5

Comfort

8.0

Crew

8.6

Overall

7.9

Food

7.0

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 3h 08m. Fly via American Airlines, United 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 - Madison Truax Field.

  • 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Portland to Wisconsin

See prices for flight routes from nearby airports that may be better suited for you.
Boston to Fort Lauderdale flights
Boston to Miami flights
Boston to Los Angeles flights
Boston to Orlando flights
Boston to Las Vegas flights
Boston to Dallas/Fort Worth flights
Boston to Tampa flights
Boston to Fort Myers flights
Boston to Denver flights
Boston to San Francisco flights
Boston to West Palm Beach flights
Boston to Atlanta flights
Boston to Sky Harbor Intl flights
Boston to Baltimore flights
Boston to Salt Lake City flights
Boston to Hobby flights
Boston to New Orleans flights
Boston to Seattle flights
Boston to O'Hare Intl flights
Boston to Dulles Intl flights
Boston to Newark flights
Boston to George Bush Intcntl flights
Boston to San Diego flights
Boston to LaGuardia flights
Boston to Austin flights
Boston to Sarasota flights
Boston to Reagan-National flights
Boston to Charlotte flights
Boston to John F Kennedy Intl flights
Boston to Nashville flights
Boston to Charleston flights
Boston to Key West flights
Boston to Ontario flights
Boston to Honolulu flights
Boston to Philadelphia flights
Boston to Raleigh flights
Boston to Minneapolis flights
Boston to Midway flights
Boston to Jacksonville flights
Boston to Savannah flights
Boston to Detroit flights
Boston to Indianapolis flights
Boston to Columbus flights
Boston to Love Field flights
Boston to Bozeman flights
Boston to Cincinnati flights
Boston to Pittsburgh flights
Boston to Kansas City flights
Boston to Daytona Beach flights
Boston to Buffalo flights

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 12, 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%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.