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Wisconsin

$66+ 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 2/26. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MKE
Jan 26 — Feb 21
Sun 1/26
Sun 2/2
1 adult, Economy
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Cheap flight deals from Portland to Wisconsin

Discover tips and strategies to find the most affordable flight options for your journey from Portland (PWM) to Wisconsin (USWI). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated January 21, 2025.

Round-trip from

$241
(United Airlines)

One-way from

$66
(CheapOair)
From Portland to Wisconsin
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One-way flight from Portland to Wisconsin
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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 January 21, 2025.

This FlightHub deal was found by Cheapflights users on 1/20. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/1112:32 pmPWM - MSP
Nonstop3h 08mSun Country Air
Mon 8/187:54 amMSP - PWM
Nonstop2h 41mSun Country Air
Deal found 1/20$193
This United Airlines deal was found by Cheapflights users on 1/20. 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.
Fri 2/76:00 amPWM - ORD
1 stop5h 44mUnited Airlines
Mon 2/103:15 pmORD - PWM
1 stop6h 15mUnited Airlines
Deal found 1/20$239
This Delta deal was found by Cheapflights users on 1/20. 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 2/76:00 amPWM - ORD
2 stops10h 45mDelta
Mon 2/104:55 pmORD - PWM
1 stop6h 00mDelta
Deal found 1/20$244
This American Airlines deal was found by Cheapflights users on 1/20. 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 7/97:19 amPWM - ORD
Nonstop2h 51mAmerican Airlines
Mon 7/146:20 pmORD - PWM
Nonstop2h 30mAmerican Airlines
Deal found 1/20$258
This American Airlines deal was found by Cheapflights users on 1/19. 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 2/275:45 amPWM - MSN
1 stop6h 18mAmerican Airlines
Wed 3/56:01 amMSN - PWM
1 stop4h 46mAmerican Airlines
Deal found 1/19$259
This JetBlue deal was found by Cheapflights users on 1/20. 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.
Fri 4/46:10 amPWM - ORD
1 stop7h 19mJetBlue
Fri 4/111:22 pmORD - PWM
1 stop8h 38mJetBlue
Deal found 1/20$273
This Southwest deal was found by Cheapflights users on 1/20. 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 1/303:35 pmPWM - ORD
1 stop7h 45mSouthwest
Wed 2/54:35 pmORD - PWM
1 stop4h 40mSouthwest
Deal found 1/20$279
This Delta deal was found by Cheapflights users on 1/20. 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 2/45:25 pmPWM - MSN
1 stop5h 36mDelta
Sun 2/94:00 pmMSN - PWM
1 stop6h 10mDelta
Deal found 1/20$289
This Mytrip deal was found by Cheapflights users on 1/20. 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.
Fri 6/611:53 amPWM - MSP
1 stop12h 38mMultiple Airlines
Sun 6/87:54 amMSP - PWM
Nonstop2h 41mMultiple Airlines
Deal found 1/20$292
This Delta deal was found by Cheapflights users on 1/20. 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 2/273:04 pmPWM - MKE
1 stop5h 31mDelta
Sun 3/25:05 pmMKE - PWM
1 stop5h 05mDelta
Deal found 1/20$302
This United Airlines deal was found by Cheapflights users on 1/20. 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 3/14:04 pmPWM - MKE
1 stop5h 29mUnited Airlines
Wed 3/511:11 amMKE - PWM
1 stop6h 20mUnited Airlines
Deal found 1/20$332
This Delta deal was found by Cheapflights users on 1/20. 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 2/204:46 pmPWM - ATW
1 stop4h 43mDelta
Wed 3/57:05 amATW - PWM
2 stops6h 17mDelta
Deal found 1/20$334

Find flights from Portland to Wisconsin within your budget

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 21, 2025.

Fly from

Any airport

Fly to

Any airport

Route

Depart

Return

Price

PortlandChicago

PWM - ORD

PWMORD

Portland

Sat 5/24

5:00 pm-8:34 pm

1 stop4h 34m

Chicago O'Hare Intl

Tue 5/27

7:00 am-11:54 am

1 stop3h 54m

$239

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 4/4

6:00 am-10:48 am

1 stop5h 48m

Chicago O'Hare Intl

Mon 4/14

7:30 am-11:02 am

Nonstop2h 32m

$241

PortlandChicago

PWM - ORD

PWMORD

Portland

Sun 2/23

5:45 am-10:50 am

1 stop6h 05m

Chicago O'Hare Intl

Fri 2/28

6:06 am-11:47 am

1 stop4h 41m

$243

PortlandMadison

PWM - MSN

PWMMSN

Portland

Thu 2/27

5:45 am-11:03 am

1 stop6h 18m

Madison Truax Field

Wed 3/5

6:01 am-11:47 am

1 stop4h 46m

$259

PortlandChicago

PWM - ORD

PWMORD

Portland

Sun 2/23

5:35 am-2:00 pm

1 stop9h 25m

Chicago O'Hare Intl

Sat 3/1

1:30 pm-11:15 pm

2 stops8h 45m

$269

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 4/4

6:10 am-12:29 pm

1 stop7h 19m

Chicago O'Hare Intl

Fri 4/11

1:22 pm-11:00 pm

1 stop8h 38m

$273

PortlandMadison

PWM - MSN

PWMMSN

Portland

Tue 2/4

5:25 pm-10:01 pm

1 stop5h 36m

Madison Truax Field

Sun 2/9

4:00 pm-11:10 pm

1 stop6h 10m

$289

PortlandMinneapolis

PWM - MSP

PWMMSP

Portland

Fri 6/6

11:53 am-11:31 pm

1 stop12h 38m

Minneapolis St Paul

Sun 6/8

7:54 am-11:35 am

Nonstop2h 41m

$292

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

Thu 2/27

3:04 pm-7:35 pm

1 stop5h 31m

Milwaukee-Mitchell

Sun 3/2

5:05 pm-11:10 pm

1 stop5h 05m

$302

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

Sat 3/1

4:04 pm-8:33 pm

1 stop5h 29m

Milwaukee-Mitchell

Wed 3/5

11:11 am-6:31 pm

1 stop6h 20m

$332

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/20

Showing 1-10 of 45 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.

Travel insights for flights from Portland to Wisconsin

Get recent, data-driven insights about flights from Portland to Wisconsin including ideal travel times, pricing trends, and more.

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 January 21, 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 January 21, 2025.
Read reviews from past customers who have flown United Airlines, American Airlines and Southwest from Portland to Wisconsin. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,659 reviews

Food

7.2

Entertainment

7.7

Overall

8.1

Comfort

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Southwest
8.1
Very good
4,659 reviews
Southwest
8.1
Very good
4,659 reviews

Food

7.2

Entertainment

7.7

Overall

8.1

Comfort

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Alaska Airlines
8.0
Very good
9,696 reviews
Southwest
8.1
Very good
4,659 reviews

Food

7.2

Entertainment

7.7

Overall

8.1

Comfort

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

Delta
8.0
Very good
8,521 reviews
Southwest
8.1
Very good
4,659 reviews

Food

7.2

Entertainment

7.7

Overall

8.1

Comfort

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

JetBlue
7.4
Good
3,201 reviews
Southwest
8.1
Very good
4,659 reviews

Food

7.2

Entertainment

7.7

Overall

8.1

Comfort

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

United Airlines
7.4
Good
8,982 reviews
Southwest
8.1
Very good
4,659 reviews

Food

7.2

Entertainment

7.7

Overall

8.1

Comfort

8.1

Crew

8.7

Boarding

8.2

Reviews

1 / 10

We BARELY made the connection and when we got onboard we were treated like disobedient children who should have arrived earlier because we had to ask other passengers to move so we could sit with our kids. The flight attendants on the first flight were nice but the second one, they were snippy and fairly rude.

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 Frontier ($66), Sun Country Air ($88), and Delta ($115).

  • 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.

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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 January 21, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$206Average$364FlexibilityNo cancel feeOn-time71%
DeltaCheapest$258Average$429FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$268Average$376FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$283Average$569FlexibilityNo cancel feeOn-time69%
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