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Wisconsin

$99+ 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 7/10. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MKE
Jul 8 — Jul 151
Tue 7/8
Tue 7/15
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 3, 2025.

Round-trip from

$165
(Cheapflightsfares)

One-way from

$99
(FlightHub)

Popular in

May

Cheapest in

August

Average price

$365
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 ($54 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 3, 2025.

This Cheapflightsfares deal was found by Cheapflights users on 7/3. 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 7/3$165
This Delta deal was found by Cheapflights users on 7/1. 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 8/111:40 amPWM - MSP
Nonstop3h 05mDelta
Mon 8/46:55 amMSP - PWM
Nonstop2h 40mDelta
Deal found 7/1$199
This American Airlines deal was found by Cheapflights users on 7/3. 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 8/1312:08 pmPWM - ORD
Nonstop3h 02mAmerican Airlines
Wed 8/206:45 pmORD - PWM
Nonstop2h 43mAmerican Airlines
Deal found 7/3$231
This Delta deal was found by Cheapflights users on 7/3. 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 8/236:00 amPWM - ORD
1 stop7h 17mDelta
Sun 8/317:15 amORD - PWM
1 stop3h 53mDelta
Deal found 7/3$235
This American Airlines deal was found by Cheapflights users on 7/3. 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 7/3$237
This JetBlue deal was found by Cheapflights users on 7/1. 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 8/66:10 amPWM - ORD
1 stop6h 08mJetBlue
Mon 8/116:15 amORD - PWM
1 stop6h 08mJetBlue
Deal found 7/1$237
This United Airlines deal was found by Cheapflights users on 6/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/316:14 amPWM - ORD
Nonstop2h 51mUnited Airlines
Sat 9/66:00 amORD - PWM
1 stop6h 22mUnited Airlines
Deal found 6/30$239
This Delta deal was found by Cheapflights users on 7/3. 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 8/305:30 pmPWM - GRB
1 stop6h 52mDelta
Wed 9/312:06 pmGRB - PWM
2 stops10h 57mDelta
Deal found 7/3$254
This Southwest deal was found by Cheapflights users on 7/1. 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 9/255:50 amPWM - MSP
1 stop5h 25mSouthwest
Sat 9/276:15 amMSP - PWM
1 stop5h 05mSouthwest
Deal found 7/1$255
This Delta deal was found by Cheapflights users on 7/3. 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 8/204:50 pmPWM - MKE
2 stops7h 39mDelta
Sat 8/302:54 pmMKE - PWM
1 stop8h 09mDelta
Deal found 7/3$257
This American Airlines deal was found by Cheapflights users on 7/2. 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 7/236:01 pmPWM - MSN
1 stop6h 49mAmerican Airlines
Wed 7/305:06 pmMSN - PWM
1 stop5h 13mAmerican Airlines
Deal found 7/2$259
This American Airlines deal was found by Cheapflights users on 7/3. 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 8/3012:08 pmPWM - GRB
1 stop7h 03mAmerican Airlines
Wed 9/34:39 pmGRB - PWM
1 stop5h 04mAmerican Airlines
Deal found 7/3$260

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 3, 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

$165

PortlandMinneapolis

PWM - MSP

PWMMSP

Portland

Fri 8/1

11:40 am-1:45 pm

Nonstop3h 05m

Minneapolis St Paul

Mon 8/4

6:55 am-10:35 am

Nonstop2h 40m

$199

PortlandChicago

PWM - ORD

PWMORD

Portland

Wed 8/13

12:08 pm-2:10 pm

Nonstop3h 02m

Chicago O'Hare Intl

Wed 8/20

6:45 pm-10:28 pm

Nonstop2h 43m

$231

PortlandChicago

PWM - ORD

PWMORD

Portland

Sat 8/23

6:00 am-12:17 pm

1 stop7h 17m

Chicago O'Hare Intl

Sun 8/31

7:15 am-12:08 pm

1 stop3h 53m

$235

PortlandChicago

PWM - ORD

PWMORD

Portland

Wed 8/6

6:10 am-11:18 am

1 stop6h 08m

Chicago O'Hare Intl

Mon 8/11

6:15 am-1:23 pm

1 stop6h 08m

$237

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

$237

PortlandChicago

PWM - ORD

PWMORD

Portland

Sun 8/31

6:14 am-8:05 am

Nonstop2h 51m

Chicago O'Hare Intl

Sat 9/6

6:00 am-1:22 pm

1 stop6h 22m

$239

PortlandMinneapolis

PWM - MSP

PWMMSP

Portland

Thu 9/25

5:50 am-10:15 am

1 stop5h 25m

Minneapolis St Paul

Sat 9/27

6:15 am-12:20 pm

1 stop5h 05m

$255

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

Wed 8/20

4:50 pm-11:29 pm

2 stops7h 39m

Milwaukee-Mitchell

Sat 8/30

2:54 pm-12:03 am

1 stop8h 09m

$257

PortlandMadison

PWM - MSN

PWMMSN

Portland

Wed 7/23

6:01 pm-11:50 pm

1 stop6h 49m

Madison Truax Field

Wed 7/30

5:06 pm-11:19 pm

1 stop5h 13m

$259

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/3

Showing 1-10 of 57 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 3, 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 3, 2025.
Read reviews from past customers who have flown Breeze Airways, Southwest, and Delta from Portland to Wisconsin. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Breeze Airways
8.1
Very good
183 reviews

Comfort

8.2

Entertainment

6.6

Boarding

8.3

Food

6.8

Overall

8.1

Crew

8.8

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Breeze Airways
8.1
Very good
183 reviews
Breeze Airways
8.1
Very good
183 reviews

Comfort

8.2

Entertainment

6.6

Boarding

8.3

Food

6.8

Overall

8.1

Crew

8.8

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Southwest
8.0
Very good
4,266 reviews
Breeze Airways
8.1
Very good
183 reviews

Comfort

8.2

Entertainment

6.6

Boarding

8.3

Food

6.8

Overall

8.1

Crew

8.8

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Delta
8.0
Very good
7,982 reviews
Breeze Airways
8.1
Very good
183 reviews

Comfort

8.2

Entertainment

6.6

Boarding

8.3

Food

6.8

Overall

8.1

Crew

8.8

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
United Airlines
7.4
Good
8,861 reviews
Breeze Airways
8.1
Very good
183 reviews

Comfort

8.2

Entertainment

6.6

Boarding

8.3

Food

6.8

Overall

8.1

Crew

8.8

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
JetBlue
7.3
Good
2,916 reviews
Breeze Airways
8.1
Very good
183 reviews

Comfort

8.2

Entertainment

6.6

Boarding

8.3

Food

6.8

Overall

8.1

Crew

8.8

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!

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 ($99), Delta ($119), and JetBlue ($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.

See more FAQs

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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 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$211Average$351FlexibilityNo cancel feeOn-time71%
DeltaCheapest$258Average$400FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$268Average$379FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$281Average$471FlexibilityNo cancel feeOn-time69%

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