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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 8/21. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MKE
Aug 4 — Aug 111
Mon 8/4
Mon 8/11
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 July 30, 2025.

Round-trip from

$155
(Cheapflightsfares)

One-way from

$78
(Cheapflightsfares)

Popular in

May

Cheapest in

January

Average price

$385
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. 11% potential increase in price ($52 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 July 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 July 30, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 7/30. 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.
Thu 8/2812:54 pmPWM - MSP
Nonstop3h 06mSun Country Air
Mon 9/17:54 amMSP - PWM
Nonstop2h 46mSun Country Air
Deal found 7/30$155
This American Airlines deal was found by Cheapflights users on 7/29. 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 8/215:57 pmPWM - MKE
1 stop7h 14mAmerican Airlines
Wed 8/275:13 pmMKE - PWM
1 stop4h 46mAmerican Airlines
Deal found 7/29$252
This Southwest deal was found by Cheapflights users on 7/29. 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 9/183:30 pmPWM - MKE
1 stop6h 30mSouthwest
Sat 9/2010:50 amMKE - PWM
2 stops10h 10mSouthwest
Deal found 7/29$257
This Delta deal was found by Cheapflights users on 7/29. 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 8/202:36 pmPWM - ORD
1 stop8h 17mDelta
Mon 8/2511:05 amORD - PWM
1 stop5h 43mDelta
Deal found 7/29$258
This American Airlines deal was found by Cheapflights users on 7/30. 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 8/306:00 amPWM - MSN
1 stop7h 42mAmerican Airlines
Sat 9/67:30 amMSN - PWM
1 stop7h 47mAmerican Airlines
Deal found 7/30$259
This American Airlines deal was found by Cheapflights users on 7/30. 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 9/263:28 pmPWM - ORD
Nonstop3h 02mAmerican Airlines
Wed 10/18:15 amORD - PWM
Nonstop2h 34mAmerican Airlines
Deal found 7/30$259
This JetBlue deal was found by Cheapflights users on 7/30. 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 9/262:17 pmPWM - ORD
1 stop7h 32mJetBlue
Sun 9/286:45 amORD - PWM
1 stop5h 37mJetBlue
Deal found 7/30$260
This Delta deal was found by Cheapflights users on 7/27. 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 8/3011:48 amPWM - DLH
1 stop4h 51mDelta
Wed 9/35:10 amDLH - PWM
1 stop4h 32mDelta
Deal found 7/27$263
This United Airlines deal was found by Cheapflights users on 7/28. 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 8/166:10 amPWM - ORD
Nonstop2h 55mUnited Airlines
Tue 8/1910:58 amORD - PWM
Nonstop2h 28mUnited Airlines
Deal found 7/28$267
This Southwest deal was found by Cheapflights users on 7/30. 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.
Wed 11/512:45 pmPWM - ORD
2 stops10h 05mSouthwest
Tue 11/1111:55 amORD - PWM
2 stops9h 20mSouthwest
Deal found 7/30$268
This Delta deal was found by Cheapflights users on 7/30. 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 9/1011:48 amPWM - MKE
2 stops10h 45mDelta
Fri 9/124:47 pmMKE - PWM
1 stop6h 24mDelta
Deal found 7/30$282
This Southwest deal was found by Cheapflights users on 7/29. 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.
Sat 10/253:20 pmPWM - MSP
1 stop5h 05mSouthwest
Tue 10/287:00 amMSP - PWM
1 stop7h 10mSouthwest
Deal found 7/29$297

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 July 30, 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

Thu 8/28

12:54 pm-3:00 pm

Nonstop3h 06m

Minneapolis St Paul

Mon 9/1

7:54 am-11:40 am

Nonstop2h 46m

$155

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

Thu 8/21

5:57 pm-12:11 am

1 stop7h 14m

Milwaukee-Mitchell

Wed 8/27

5:13 pm-10:59 pm

1 stop4h 46m

$252

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

Thu 9/18

3:30 pm-9:00 pm

1 stop6h 30m

Milwaukee-Mitchell

Sat 9/20

10:50 am-10:00 pm

2 stops10h 10m

$257

PortlandChicago

PWM - ORD

PWMORD

Portland

Wed 8/20

2:36 pm-9:53 pm

1 stop8h 17m

Chicago O'Hare Intl

Mon 8/25

11:05 am-5:48 pm

1 stop5h 43m

$258

PortlandMadison

PWM - MSN

PWMMSN

Portland

Sat 8/30

6:00 am-12:42 pm

1 stop7h 42m

Madison Truax Field

Sat 9/6

7:30 am-4:17 pm

1 stop7h 47m

$259

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 9/26

3:28 pm-5:30 pm

Nonstop3h 02m

Chicago O'Hare Intl

Wed 10/1

8:15 am-11:49 am

Nonstop2h 34m

$259

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 9/26

2:17 pm-8:49 pm

1 stop7h 32m

Chicago O'Hare Intl

Sun 9/28

6:45 am-1:22 pm

1 stop5h 37m

$260

PortlandDuluth

PWM - DLH

PWMDLH

Portland

Sat 8/30

11:48 am-3:39 pm

1 stop4h 51m

Duluth Intl

Wed 9/3

5:10 am-10:42 am

1 stop4h 32m

$263

PortlandChicago

PWM - ORD

PWMORD

Portland

Sat 8/16

6:10 am-8:05 am

Nonstop2h 55m

Chicago O'Hare Intl

Tue 8/19

10:58 am-2:26 pm

Nonstop2h 28m

$267

PortlandChicago

PWM - ORD

PWMORD

Portland

Tue 8/26

9:05 am-5:55 pm

2 stops9h 50m

Chicago O'Hare Intl

Tue 9/2

1:50 pm-10:25 pm

1 stop7h 35m

$277

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/30

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 July 30, 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.

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 July 30, 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
4,241 reviews

Overall

8.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Southwest
8.0
Very good
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Overall

8.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
Delta
8.0
Very good
7,980 reviews
Southwest
8.0
Very good
4,241 reviews

Overall

8.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
United Airlines
7.4
Good
8,896 reviews
Southwest
8.0
Very good
4,241 reviews

Overall

8.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
JetBlue
7.3
Good
2,913 reviews
Southwest
8.0
Very good
4,241 reviews

Overall

8.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,241 reviews

Overall

8.0

Entertainment

7.5

Comfort

8.0

Crew

8.6

Boarding

8.1

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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 ($119), and Delta ($124).

  • 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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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 July 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$218Average$397FlexibilityNo cancel feeOn-time71%
DeltaCheapest$258Average$427FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$268Average$389FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$274Average$486FlexibilityNo cancel feeOn-time69%

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