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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 6 — Feb 131
Fri 2/6
Fri 2/13
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 January 7, 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.
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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. 22% potential increase in price ($134 potential increase over avg. RT price).
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Cheapest flight prices on average. 5% potential price decrease ($26 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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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 7, 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 2/35:30 amPWM - ORD
1 stop9h 10mDelta
Wed 2/112:50 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 2/412:43 pmPWM - ORD
2 stops9h 22mDelta
Wed 2/112:50 pmORD - PWM
2 stops8h 30mDelta
Deal found 1/7$208
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 2/22:35 pmPWM - ORD
2 stops10h 21mDelta
Tue 2/105:40 pmORD - PWM
1 stop4h 42mDelta
Deal found 1/7$209
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 2/22:35 pmPWM - ORD
1 stop8h 00mDelta
Mon 2/96:50 amORD - PWM
1 stop4h 13mDelta
Deal found 1/7$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 1/7. 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 1/282:35 pmPWM - ORD
2 stops10h 21mDelta
Thu 1/2910:35 amORD - PWM
2 stops10h 52mDelta
Deal found 1/7$215
This Delta 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 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
Thu 3/127:00 amORD - PWM
1 stop5h 50mDelta
Deal found 1/6$216
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
Tue 2/101:58 pmORD - PWM
2 stops9h 22mDelta
Deal found 1/7$218

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 7, 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 1/27

6:17 am-1:14 pm

1 stop7h 57m

Chicago O'Hare Intl

Wed 1/28

2:50 pm-12:20 am

2 stops8h 30m

$202

PortlandChicago

PWM - ORD

PWMORD

Portland

Mon 2/2

2:35 pm-9:35 pm

1 stop8h 00m

Chicago O'Hare Intl

Wed 2/4

9:35 am-5:16 pm

1 stop6h 41m

$204

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 5/8

7:07 am-9:10 am

Nonstop3h 03m

Chicago O'Hare Intl

Mon 5/11

7:34 pm-11:10 pm

Nonstop2h 36m

$209

PortlandChicago

PWM - ORD

PWMORD

Portland

Wed 2/11

4:10 pm-6:18 pm

Nonstop3h 08m

Chicago O'Hare Intl

Sun 2/15

5:45 pm-9:09 pm

Nonstop2h 24m

$209

PortlandChicago

PWM - ORD

PWMORD

Portland

Tue 2/3

6:00 am-4:55 pm

2 stops11h 55m

Chicago O'Hare Intl

Thu 2/5

6:50 am-12:03 pm

1 stop4h 13m

$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

Tue 4/7

5:48 pm-10:12 pm

1 stop5h 24m

Chicago O'Hare Intl

Sun 4/12

9:50 am-4:06 pm

1 stop5h 16m

$213

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 2/6

12:43 pm-6:28 pm

1 stop6h 45m

Chicago O'Hare Intl

Wed 2/11

5:40 pm-11:22 pm

1 stop4h 42m

$213

PortlandChicago

PWM - ORD

PWMORD

Portland

Wed 1/28

2:35 pm-11:56 pm

2 stops10h 21m

Chicago O'Hare Intl

Thu 1/29

10:35 am-10:27 pm

2 stops10h 52m

$215

PortlandChicago

PWM - ORD

PWMORD

Portland

Mon 2/2

2:35 pm-11:56 pm

2 stops10h 21m

Chicago O'Hare Intl

Thu 2/5

6:50 am-12:03 pm

1 stop4h 13m

$216

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/5

Showing 1-10 of 60 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, 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 7, 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

Entertainment

7.5

Overall

8.0

Comfort

8.0

Boarding

8.1

Food

7.0

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

Entertainment

7.5

Overall

8.0

Comfort

8.0

Boarding

8.1

Food

7.0

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

Entertainment

7.5

Overall

8.0

Comfort

8.0

Boarding

8.1

Food

7.0

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

Entertainment

7.5

Overall

8.0

Comfort

8.0

Boarding

8.1

Food

7.0

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

Entertainment

7.5

Overall

8.0

Comfort

8.0

Boarding

8.1

Food

7.0

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 3h 03m. Fly via Delta, American Airlines, or United 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 - Green Bay Austin-Straubel.

  • 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

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Alternative routes for Portland to Wisconsin

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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 7, 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%

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