HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Wisconsin

$90+ 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 7/2. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MKE
Feb 7 — Feb 141
Sat 2/7
Sat 2/14
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

Keep the following information in mind while searching for Portland to Wisconsin flight deals. Data was last updated January 8, 2026.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$195
(American Airlines)

One-way from

$90
(Sun Country Air)

Popular in

September

Cheapest in

November

Average price

$391
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 ($134 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 January 2026
Search Deals

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 January 8, 2026.

This Mytrip deal was found by Cheapflights users on 1/7. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2012:36 pmPWM - MSP
Nonstop3h 06mSun Country Air
Mon 8/247:50 amMSP - PWM
Nonstop2h 46mSun Country Air
Deal found 1/7$189
This American Airlines deal was found by Cheapflights users on 1/7. 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 2/45:20 amPWM - MSP
1 stop7h 41mAmerican Airlines
Wed 2/115:33 pmMSP - PWM
1 stop5h 10mAmerican Airlines
Deal found 1/7$195
This Delta deal was found by Cheapflights users on 1/7. 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 2/36:00 amPWM - ORD
1 stop5h 55mDelta
Tue 2/102:50 pmORD - PWM
1 stop6h 37mDelta
Deal found 1/7$197
This Delta deal was found by Cheapflights users on 1/7. 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 2/212:10 pmPWM - ORD
1 stop5h 28mDelta
Wed 2/115:40 pmORD - PWM
1 stop4h 42mDelta
Deal found 1/7$204
This CheapOair deal was found by Cheapflights users on 1/7. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/2612:40 pmPWM - MSP
Nonstop3h 08mSun Country Air
Sun 6/287:55 amMSP - PWM
Nonstop2h 42mSun Country Air
Deal found 1/7$206
This Delta deal was found by Cheapflights users on 1/7. 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.
Wed 2/45:30 amPWM - ORD
2 stops12h 27mDelta
Tue 2/1011:15 amORD - PWM
2 stops11h 07mDelta
Deal found 1/7$208
This American Airlines deal was found by Cheapflights users on 1/7. 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 5/85:45 pmPWM - ORD
Nonstop3h 10mAmerican Airlines
Mon 5/117:34 pmORD - PWM
Nonstop2h 36mAmerican Airlines
Deal found 1/7$209
This Delta deal was found by Cheapflights users on 1/8. 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 2/22:35 pmPWM - ORD
1 stop8h 00mDelta
Thu 2/56:50 amORD - PWM
1 stop4h 13mDelta
Deal found 1/8$211
This Delta deal was found by Cheapflights users on 1/7. 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 2/312:43 pmPWM - ORD
1 stop6h 45mDelta
Fri 2/137:00 amORD - PWM
1 stop5h 43mDelta
Deal found 1/7$213
This Delta deal was found by Cheapflights users on 1/8. 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 3/94:48 pmPWM - ORD
2 stops8h 11mDelta
Wed 3/117:10 amORD - PWM
2 stops5h 40mDelta
Deal found 1/8$215
This Delta deal was found by Cheapflights users on 1/7. 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.
Sun 2/82:35 pmPWM - ORD
1 stop8h 00mDelta
Wed 2/111:58 pmORD - PWM
2 stops9h 22mDelta
Deal found 1/7$218
This United Airlines deal was found by Cheapflights users on 1/6. 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.
Thu 2/126:00 amPWM - ORD
1 stop5h 49mUnited Airlines
Mon 2/1611:48 amORD - PWM
Nonstop2h 26mUnited Airlines
Deal found 1/6$219

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 January 8, 2026.
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

Tue 2/17

6:18 am-1:29 pm

1 stop8h 11m

Chicago O'Hare Intl

Wed 2/18

6:25 pm-12:18 am

1 stop4h 53m

$197

PortlandChicago

PWM - ORD

PWMORD

Portland

Tue 2/17

6:18 am-1:29 pm

1 stop8h 11m

Chicago O'Hare Intl

Tue 2/24

6:30 am-12:00 pm

1 stop4h 30m

$197

PortlandChicago

PWM - ORD

PWMORD

Portland

Wed 2/11

5:59 pm-10:34 pm

1 stop5h 35m

Chicago O'Hare Intl

Tue 2/24

5:20 pm-11:20 pm

1 stop5h 00m

$197

PortlandChicago

PWM - ORD

PWMORD

Portland

Thu 7/2

4:48 pm-6:45 pm

Nonstop2h 57m

Chicago O'Hare Intl

Sun 7/5

1:55 pm-5:12 pm

Nonstop2h 17m

$209

PortlandChicago

PWM - ORD

PWMORD

Portland

Tue 2/3

12:43 pm-6:28 pm

1 stop6h 45m

Chicago O'Hare Intl

Fri 2/13

7:00 am-1:43 pm

1 stop5h 43m

$213

PortlandChicago

PWM - ORD

PWMORD

Portland

Sun 2/8

2:35 pm-9:35 pm

1 stop8h 00m

Chicago O'Hare Intl

Wed 2/11

7:00 am-1:45 pm

1 stop5h 45m

$213

PortlandChicago

PWM - ORD

PWMORD

Portland

Tue 4/7

5:48 pm-10:12 pm

1 stop5h 24m

Chicago O'Hare Intl

Sun 4/12

6:00 am-4:06 pm

2 stops9h 06m

$218

PortlandChicago

PWM - ORD

PWMORD

Portland

Sun 2/8

2:35 pm-9:35 pm

1 stop8h 00m

Chicago O'Hare Intl

Tue 2/10

1:58 pm-12:20 am

2 stops9h 22m

$218

PortlandChicago

PWM - ORD

PWMORD

Portland

Sat 1/31

2:35 pm-11:56 pm

2 stops10h 21m

Chicago O'Hare Intl

Tue 2/3

5:40 pm-11:22 pm

1 stop4h 42m

$218

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 7/3

6:00 am-7:57 am

Nonstop2h 57m

Chicago O'Hare Intl

Wed 7/8

3:45 pm-10:57 pm

1 stop6h 12m

$219

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/5

Showing 1-10 of 60 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.

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 January 8, 2026.
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
4,248 reviews

Crew

8.6

Overall

8.0

Food

7.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

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
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Overall

8.0

Food

7.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

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
8,025 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Overall

8.0

Food

7.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

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
9,139 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Overall

8.0

Food

7.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

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
11,095 reviews
Southwest
8.0
Very good
4,248 reviews

Crew

8.6

Overall

8.0

Food

7.0

Comfort

8.0

Boarding

8.1

Entertainment

7.5

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 57m. Fly via Delta, United Airlines, 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 - Appleton Intl.

  • 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 Tampa flights
Boston to Fort Lauderdale flights
Boston to Miami flights
Boston to Orlando flights
Boston to Los Angeles flights
Boston to Fort Myers flights
Boston to Dallas/Fort Worth flights
Boston to West Palm Beach flights
Boston to Las Vegas flights
Boston to Sky Harbor Intl flights
Boston to Denver flights
Boston to Sarasota flights
Boston to Salt Lake City flights
Boston to Atlanta flights
Boston to Baltimore flights
Boston to New Orleans flights
Boston to Hobby flights
Boston to Seattle flights
Boston to O'Hare Intl flights
Boston to Dulles Intl flights
Boston to Reagan-National flights
Boston to George Bush Intcntl flights
Boston to Austin flights
Boston to San Diego flights
Boston to Newark flights
Boston to Charleston flights
Boston to Charlotte flights
Boston to LaGuardia flights
Boston to San Francisco flights
Boston to Raleigh flights
Boston to Key West flights
Boston to Jacksonville flights
Boston to John F Kennedy Intl flights
Boston to Nashville flights
Boston to Savannah flights
Boston to Myrtle Beach flights
Boston to Philadelphia flights
Boston to Ontario flights
Boston to Honolulu flights
Boston to Detroit flights
Boston to Daytona Beach flights
Boston to Midway flights
Boston to Love Field flights
Boston to Minneapolis flights
Boston to Bozeman flights
Boston to Cincinnati flights
Portland to Orlando flights
Boston to Portland flights
Boston to Pittsburgh flights
Boston to San Antonio 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 January 8, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$258Average$490FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$258Average$418FlexibilityNo cancel feeOn-time71%
DeltaCheapest$258Average$424FlexibilityNo 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.