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$67+ 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 10/28. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MKE
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
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 September 11, 2025.

Round-trip from

$197
(Southwest)

One-way from

$67
(American Airlines)

Popular in

August

Cheapest in

November

Average price

$365
From Portland to Wisconsin
Search Deals
One-way flight from Portland to Wisconsin
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($14 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in September 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 September 11, 2025.

This Southwest deal was found by Cheapflights users on 9/8. 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.
Tue 11/115:30 amPWM - MKE
1 stop5h 00mSouthwest
Sat 11/152:10 pmMKE - PWM
1 stop6h 45mSouthwest
Deal found 9/8$197
This Delta deal was found by Cheapflights users on 9/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/225:42 amPWM - ORD
1 stop5h 29mDelta
Wed 10/2910:30 amORD - PWM
2 stops10h 49mDelta
Deal found 9/11$222
This United Airlines deal was found by Cheapflights users on 9/11. 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.
Fri 10/34:57 pmPWM - ORD
Nonstop2h 51mUnited Airlines
Sun 10/56:10 pmORD - PWM
Nonstop2h 34mUnited Airlines
Deal found 9/11$235
This Delta deal was found by Cheapflights users on 9/9. 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 12/32:34 pmPWM - MKE
1 stop6h 48mDelta
Wed 12/109:40 amMKE - PWM
1 stop5h 26mDelta
Deal found 9/9$237
This JetBlue deal was found by Cheapflights users on 9/10. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/167:30 amPWM - ORD
1 stop5h 40mJetBlue
Mon 10/206:45 amORD - PWM
1 stop5h 37mJetBlue
Deal found 9/10$237
This United Airlines deal was found by Cheapflights users on 9/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/85:41 pmPWM - ORD
1 stop6h 49mUnited Airlines
Fri 10/2411:05 amORD - PWM
Nonstop2h 28mUnited Airlines
Deal found 9/10$241
This Delta deal was found by Cheapflights users on 9/9. 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 11/612:45 pmPWM - MKE
2 stops8h 57mDelta
Tue 11/116:00 amMKE - PWM
1 stop5h 30mDelta
Deal found 9/9$242
This Southwest deal was found by Cheapflights users on 9/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/15:50 amPWM - ORD
1 stop7h 00mSouthwest
Thu 10/21:50 pmORD - PWM
1 stop9h 15mSouthwest
Deal found 9/10$242
This American Airlines deal was found by Cheapflights users on 9/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/176:14 amPWM - ORD
Nonstop2h 54mAmerican Airlines
Mon 10/207:58 amORD - PWM
Nonstop2h 30mAmerican Airlines
Deal found 9/10$243
This United Airlines deal was found by Cheapflights users on 9/11. 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.
Fri 10/34:57 pmPWM - ORD
Nonstop2h 51mUnited Airlines
Sat 10/412:00 pmORD - PWM
1 stop5h 38mUnited Airlines
Deal found 9/11$245
This Delta deal was found by Cheapflights users on 9/9. 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 12/46:00 amPWM - MKE
1 stop5h 18mDelta
Wed 12/107:00 amMKE - PWM
1 stop5h 54mDelta
Deal found 9/9$246
This United Airlines deal was found by Cheapflights users on 9/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/410:30 amPWM - ORD
1 stop5h 25mUnited Airlines
Sun 10/56:10 pmORD - PWM
Nonstop2h 34mUnited Airlines
Deal found 9/10$246

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 September 11, 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

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

Tue 11/11

5:30 am-9:30 am

1 stop5h 00m

Milwaukee-Mitchell

Sat 11/15

2:10 pm-9:55 pm

1 stop6h 45m

$197

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 10/3

4:57 pm-6:48 pm

Nonstop2h 51m

Chicago O'Hare Intl

Sun 10/5

6:10 pm-9:44 pm

Nonstop2h 34m

$235

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

Wed 12/3

2:34 pm-8:22 pm

1 stop6h 48m

Milwaukee-Mitchell

Wed 12/10

9:40 am-4:06 pm

1 stop5h 26m

$237

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

Thu 11/20

5:43 am-12:01 pm

1 stop7h 18m

Milwaukee-Mitchell

Thu 11/27

6:00 am-11:46 am

1 stop4h 46m

$237

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

Sat 12/6

2:34 pm-8:22 pm

1 stop6h 48m

Milwaukee-Mitchell

Sat 12/13

9:31 am-4:06 pm

1 stop5h 35m

$237

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

Tue 12/2

4:53 pm-8:30 pm

1 stop4h 37m

Milwaukee-Mitchell

Tue 12/9

7:10 am-12:08 pm

1 stop3h 58m

$237

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

Tue 12/2

2:34 pm-8:22 pm

1 stop6h 48m

Milwaukee-Mitchell

Sat 12/6

7:05 am-12:08 pm

1 stop4h 03m

$237

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

Thu 11/6

1:27 pm-8:42 pm

1 stop8h 15m

Milwaukee-Mitchell

Tue 11/11

5:59 pm-11:19 pm

1 stop4h 20m

$237

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 11/7

4:48 pm-8:23 pm

1 stop4h 35m

Chicago O'Hare Intl

Tue 11/11

7:00 am-1:50 pm

1 stop5h 50m

$245

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

Tue 12/2

2:34 pm-8:22 pm

1 stop6h 48m

Milwaukee-Mitchell

Thu 12/11

9:40 am-4:06 pm

1 stop5h 26m

$246

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

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, 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 September 11, 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 September 11, 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
4,248 reviews

Food

7.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Southwest
8.0
Very good
4,248 reviews
Southwest
8.0
Very good
4,248 reviews

Food

7.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
Delta
8.0
Very good
7,960 reviews
Southwest
8.0
Very good
4,248 reviews

Food

7.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
United Airlines
7.4
Good
8,937 reviews
Southwest
8.0
Very good
4,248 reviews

Food

7.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,248 reviews

Food

7.0

Boarding

8.1

Overall

8.0

Entertainment

7.5

Crew

8.6

Comfort

8.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 2h 51m. Fly via Southwest, United Airlines, or Delta 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 United Airlines ($67), Southwest ($103), and American Airlines ($110).

  • 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

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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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$204Average$418FlexibilityNo cancel feeOn-time71%
DeltaCheapest$258Average$421FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$258Average$484FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$296Average$422FlexibilityNo cancel feeOn-time63%

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