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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 6/20. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MKE
Jan 24 — Jan 311
Sat 1/24
Sat 1/31
1 adult, Economy
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Cheap 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 December 25, 2025.

This Delta deal was found by Cheapflights users on 12/23. 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 12/294:48 pmPWM - ORD
1 stop4h 48mDelta
Thu 1/17:00 amORD - PWM
1 stop4h 17mDelta
Deal found 12/23$414
This United Airlines deal was found by Cheapflights users on 12/23. 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.
Mon 12/296:46 pmPWM - ORD
1 stop5h 49mUnited Airlines
Thu 1/110:35 amORD - PWM
Nonstop2h 39mUnited Airlines
Deal found 12/23$424
This American Airlines deal was found by Cheapflights users on 12/24. 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 12/245:20 pmPWM - MSP
1 stop24h 54mAmerican Airlines
Wed 1/285:33 pmMSP - PWM
1 stop17h 33mAmerican Airlines
Deal found 12/24$433
This American Airlines deal was found by Cheapflights users on 12/24. 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 12/255:45 amPWM - MSP
1 stop6h 00mAmerican Airlines
Wed 1/286:00 amMSP - PWM
1 stop5h 05mAmerican Airlines
Deal found 12/24$529
This United Airlines deal was found by Cheapflights users on 12/24. 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 12/2410:19 amPWM - MSP
2 stops10h 12mUnited Airlines
Wed 1/2812:10 pmMSP - PWM
2 stops10h 20mUnited Airlines
Deal found 12/24$539
This United Airlines deal was found by Cheapflights users on 12/23. 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 12/286:00 amPWM - GRB
2 stops11h 47mUnited Airlines
Sat 1/38:00 amGRB - PWM
1 stop5h 14mUnited Airlines
Deal found 12/23$585
This Delta deal was found by Cheapflights users on 12/25. 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 12/284:48 pmPWM - GRB
1 stop4h 54mDelta
Sat 1/311:11 amGRB - PWM
1 stop3h 57mDelta
Deal found 12/25$679
This American Airlines deal was found by Cheapflights users on 12/23. 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.
Sun 12/285:20 pmPWM - GRB
2 stops7h 16mAmerican Airlines
Sat 1/37:00 amGRB - PWM
2 stops8h 36mAmerican Airlines
Deal found 12/23$689
This American Airlines deal was found by Cheapflights users on 12/25. 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.
Mon 12/295:45 amPWM - MSP
1 stop6h 46mAmerican Airlines
Wed 12/311:44 pmMSP - PWM
1 stop8h 07mAmerican Airlines
Deal found 12/25$719
This United Airlines deal was found by Cheapflights users on 12/25. 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.
Mon 12/296:00 amPWM - MSP
1 stop6h 22mUnited Airlines
Wed 12/315:18 pmMSP - PWM
2 stops15h 26mUnited Airlines
Deal found 12/25$720
This American Airlines deal was found by Cheapflights users on 12/24. 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 12/265:45 amPWM - ORD
1 stop5h 18mAmerican Airlines
Sun 12/284:07 pmORD - PWM
1 stop6h 38mAmerican Airlines
Deal found 12/24$744
This American Airlines deal was found by Cheapflights users on 12/25. 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 12/275:45 amPWM - MKE
2 stops13h 04mAmerican Airlines
Tue 12/306:00 amMKE - PWM
2 stops9h 39mAmerican Airlines
Deal found 12/25$754

Find flight deals from Portland to Wisconsin

Keep the following information in mind while searching for Portland to Wisconsin flight deals. Data was last updated December 25, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$188
(Booking.com)

One-way from

$99
(Sun Country Air)

Popular in

September

Cheapest in

November

Average price

$558
Provider with most accurate pricing for Portland-Milwaukee-Mitchell flight deals.
Search Deals
Provider most trusted by Cheapflights users for Portland-Milwaukee-Mitchell flights.
Search Deals
From Portland to Wisconsin
Search Deals
One-way flight from Portland to Wisconsin
Search Deals
Highest demand for flights based on searches. 22% potential increase in price ($137 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($26 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 December 25, 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 6/18

12:34 pm-2:42 pm

Nonstop3h 08m

Minneapolis St Paul

Sat 6/20

8:20 am-11:59 am

Nonstop2h 39m

$188

PortlandChicago

PWM - ORD

PWMORD

Portland

Sat 1/31

4:10 pm-6:18 pm

Nonstop3h 08m

Chicago O'Hare Intl

Tue 2/3

11:00 am-2:39 pm

Nonstop2h 39m

$209

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 1/23

4:10 pm-6:18 pm

Nonstop3h 08m

Chicago O'Hare Intl

Sun 1/25

11:00 am-2:39 pm

Nonstop2h 39m

$209

PortlandChicago

PWM - ORD

PWMORD

Portland

Wed 1/21

4:10 pm-6:18 pm

Nonstop3h 08m

Chicago O'Hare Intl

Wed 1/28

11:00 am-2:39 pm

Nonstop2h 39m

$209

PortlandChicago

PWM - ORD

PWMORD

Portland

Thu 2/5

3:12 pm-9:06 pm

1 stop6h 54m

Chicago O'Hare Intl

Mon 2/9

11:00 am-2:39 pm

Nonstop2h 39m

$219

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 2/6

4:10 pm-6:18 pm

Nonstop3h 08m

Chicago O'Hare Intl

Sun 2/8

4:15 pm-11:30 pm

1 stop6h 15m

$219

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 2/6

8:40 am-4:06 pm

1 stop8h 26m

Chicago O'Hare Intl

Tue 2/10

11:00 am-2:39 pm

Nonstop2h 39m

$219

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 3/13

5:38 pm-7:55 pm

Nonstop3h 17m

Chicago O'Hare Intl

Mon 3/16

1:29 pm-4:54 pm

Nonstop2h 25m

$229

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 1/16

8:40 am-4:06 pm

1 stop8h 26m

Chicago O'Hare Intl

Sun 1/18

8:52 am-2:31 pm

1 stop4h 39m

$229

PortlandMinneapolis

PWM - MSP

PWMMSP

Portland

Sat 1/17

5:09 pm-9:47 pm

1 stop5h 38m

Minneapolis St Paul

Sat 1/24

6:00 am-12:10 pm

1 stop5h 10m

$259

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/23

Showing 1-10 of 58 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.

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 December 25, 2025.

It’s typically best to fly out from Portland, Maine to Wisconsin in the evening. Doing so could potentially save you 51% on the flight price compared to flying in the afternoon, which is usually more expensive.

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 December 25, 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
4,257 reviews

Food

7.0

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

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
4,257 reviews
Southwest
8.0
Very good
4,257 reviews

Food

7.0

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

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
8,011 reviews
Southwest
8.0
Very good
4,257 reviews

Food

7.0

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

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
9,116 reviews
Southwest
8.0
Very good
4,257 reviews

Food

7.0

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

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
11,056 reviews
Southwest
8.0
Very good
4,257 reviews

Food

7.0

Crew

8.6

Overall

8.0

Comfort

8.0

Entertainment

7.5

Boarding

8.1

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 08m. Fly via Sun Country Air, United Airlines, or American Airlines to get the fastest option. There are 1132 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 - Minneapolis St Paul, Portland - Chicago O'Hare Intl 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, 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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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 December 25, 2025.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$258Average$490FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$258Average$418FlexibilityNo cancel feeOn-time71%
DeltaCheapest$258Average$416FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$311Average$396FlexibilityNo cancel feeOn-time63%

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