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$78+ 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 6/5. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MKE
May 17 — May 241
Sat 5/17
Sat 5/24
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 May 12, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$155
(Cheapflightsfares)

One-way from

$78
(Cheapflightsfares)

Popular in

May

Cheapest in

August

Average price

$545
Provider with most accurate pricing for Portland-Milwaukee-Mitchell flight deals.
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Provider most trusted by Cheapflights users for Portland-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. 10% potential increase in price ($50 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in May 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 May 12, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 5/11. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/1412:58 pmPWM - MSP
Nonstop3h 08mSun Country Air
Sun 6/158:06 amMSP - PWM
Nonstop2h 39mSun Country Air
Deal found 5/11$155
This American Airlines deal was found by Cheapflights users on 5/12. 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 9/2512:03 pmPWM - ORD
Nonstop3h 00mAmerican Airlines
Sun 9/287:12 pmORD - PWM
Nonstop2h 34mAmerican Airlines
Deal found 5/12$209
This JetBlue deal was found by Cheapflights users on 5/12. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/113:35 pmPWM - ORD
1 stop7h 25mJetBlue
Sat 6/146:15 amORD - PWM
1 stop6h 08mJetBlue
Deal found 5/12$210
This United Airlines deal was found by Cheapflights users on 5/11. 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.
Tue 5/274:43 pmPWM - ORD
Nonstop2h 57mUnited Airlines
Sat 5/317:10 amORD - PWM
1 stop5h 23mUnited Airlines
Deal found 5/11$214
This Delta deal was found by Cheapflights users on 5/12. 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.
Thu 8/2811:59 amPWM - ORD
1 stop5h 51mDelta
Sun 8/317:00 amORD - PWM
1 stop4h 01mDelta
Deal found 5/12$229
This Delta deal was found by Cheapflights users on 5/10. 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 6/1311:44 amPWM - MSP
Nonstop3h 01mDelta
Sun 6/226:55 amMSP - PWM
Nonstop2h 44mDelta
Deal found 5/10$239
This American Airlines deal was found by Cheapflights users on 5/12. 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 7/47:00 amPWM - MSP
1 stop7h 33mAmerican Airlines
Tue 7/85:39 amMSP - PWM
1 stop4h 53mAmerican Airlines
Deal found 5/12$259
This Delta deal was found by Cheapflights users on 5/12. 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 6/1111:44 amPWM - MSN
1 stop7h 30mDelta
Fri 6/205:19 pmMSN - PWM
1 stop6h 07mDelta
Deal found 5/12$259
This American Airlines deal was found by Cheapflights users on 5/12. 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 6/286:01 pmPWM - MSN
1 stop6h 58mAmerican Airlines
Mon 6/305:04 pmMSN - PWM
1 stop4h 59mAmerican Airlines
Deal found 5/12$271
This Delta deal was found by Cheapflights users on 5/12. 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 7/211:44 amPWM - GRB
1 stop5h 00mDelta
Tue 7/85:30 amGRB - PWM
1 stop5h 32mDelta
Deal found 5/12$279
This United Airlines deal was found by Cheapflights users on 5/12. 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 8/2012:10 pmPWM - MKE
1 stop6h 17mUnited Airlines
Sat 8/303:44 pmMKE - PWM
1 stop5h 15mUnited Airlines
Deal found 5/12$284
This Delta deal was found by Cheapflights users on 5/12. 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 8/206:00 amPWM - MKE
2 stops10h 06mDelta
Sat 8/3011:55 amMKE - PWM
1 stop8h 49mDelta
Deal found 5/12$289

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 May 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

PortlandMinneapolis

PWM - MSP

PWMMSP

Portland

Sat 6/14

12:58 pm-3:06 pm

Nonstop3h 08m

Minneapolis St Paul

Sun 6/15

8:06 am-11:45 am

Nonstop2h 39m

$155

PortlandChicago

PWM - ORD

PWMORD

Portland

Thu 9/25

12:03 pm-2:03 pm

Nonstop3h 00m

Chicago O'Hare Intl

Sun 9/28

7:12 pm-10:46 pm

Nonstop2h 34m

$209

PortlandChicago

PWM - ORD

PWMORD

Portland

Mon 5/26

6:10 am-10:39 am

1 stop5h 29m

Chicago O'Hare Intl

Fri 5/30

7:10 am-10:49 am

Nonstop2h 39m

$214

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 6/6

3:35 pm-9:54 pm

1 stop7h 19m

Chicago O'Hare Intl

Mon 6/9

6:15 am-2:40 pm

1 stop7h 25m

$225

PortlandChicago

PWM - ORD

PWMORD

Portland

Wed 7/30

6:53 pm-12:09 am

1 stop6h 16m

Chicago O'Hare Intl

Tue 8/5

9:25 am-4:05 pm

1 stop5h 40m

$229

PortlandMinneapolis

PWM - MSP

PWMMSP

Portland

Fri 6/13

11:44 am-1:45 pm

Nonstop3h 01m

Minneapolis St Paul

Sun 6/22

6:55 am-10:39 am

Nonstop2h 44m

$239

PortlandMinneapolis

PWM - MSP

PWMMSP

Portland

Fri 7/4

7:00 am-1:33 pm

1 stop7h 33m

Minneapolis St Paul

Tue 7/8

5:39 am-11:32 am

1 stop4h 53m

$259

PortlandMadison

PWM - MSN

PWMMSN

Portland

Wed 6/11

11:44 am-6:14 pm

1 stop7h 30m

Madison Truax Field

Fri 6/20

5:19 pm-12:26 am

1 stop6h 07m

$259

PortlandMadison

PWM - MSN

PWMMSN

Portland

Sat 6/28

6:01 pm-11:59 pm

1 stop6h 58m

Madison Truax Field

Mon 6/30

5:04 pm-11:03 pm

1 stop4h 59m

$271

PortlandGreen Bay

PWM - GRB

PWMGRB

Portland

Wed 7/2

11:44 am-3:44 pm

1 stop5h 00m

Green Bay Austin-Straubel

Tue 7/8

5:30 am-12:02 pm

1 stop5h 32m

$279

Flights are sorted by cheapest round-trip flights first.

Deals found on 5/11

Showing 1-10 of 51 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, February is the cheapest month in which you can book a flight from Portland, Maine to Wisconsin (average of $280). Flying from Portland, Maine to Wisconsin in June is currently the most expensive (average of $376). 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 May 12, 2025.

When flying from Portland, Maine to Wisconsin, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Rainfall in Wisconsin by month

Plan your trip to Wisconsin by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Wisconsin ranges from 1.4 - 4.0 inches per month. June is typically the wettest month, when rainfall can reach 4.0 in. January is typically the driest time to visit Wisconsin when rainfall is around 1.4 in.

Temperature in Wisconsin by month

Plan your trip to Wisconsin by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Wisconsin, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 21.2 F).

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 May 12, 2025.
Read reviews from past customers who have flown Southwest, Delta and United Airlines from Portland to Wisconsin. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,290 reviews

Boarding

8.2

Food

7.1

Comfort

8.0

Entertainment

7.6

Crew

8.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,290 reviews
Southwest
8.0
Very good
4,290 reviews

Boarding

8.2

Food

7.1

Comfort

8.0

Entertainment

7.6

Crew

8.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,950 reviews
Southwest
8.0
Very good
4,290 reviews

Boarding

8.2

Food

7.1

Comfort

8.0

Entertainment

7.6

Crew

8.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
United Airlines
7.4
Good
8,724 reviews
Southwest
8.0
Very good
4,290 reviews

Boarding

8.2

Food

7.1

Comfort

8.0

Entertainment

7.6

Crew

8.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
JetBlue
7.3
Good
2,924 reviews
Southwest
8.0
Very good
4,290 reviews

Boarding

8.2

Food

7.1

Comfort

8.0

Entertainment

7.6

Crew

8.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,290 reviews

Boarding

8.2

Food

7.1

Comfort

8.0

Entertainment

7.6

Crew

8.6

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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.

  • 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 Sun Country Air ($78), American Airlines ($90), and United Airlines ($100).

  • 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, February is the cheapest month in which you can book a flight from Portland, Maine to Wisconsin (average of $280). Flying from Portland, Maine to Wisconsin in June is currently the most expensive (average of $376). 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 May 12, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$206Average$374FlexibilityNo cancel feeOn-time71%
DeltaCheapest$248Average$370FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$268Average$376FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$281Average$485FlexibilityNo cancel feeOn-time69%

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