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Wisconsin

$113+ 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 12/10. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MKE
nov. 27 — dic. 41
jue. 11/27
jue. 12/4
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 octubre 28, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$239
(Delta)

One-way from

$113
(Kiwi.com)

Popular in

September

Cheapest in

November

Average price

$421
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 ($137 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 October 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 octubre 28, 2025.

This Delta deal was found by Cheapflights users on 10/27. 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.
mié. 12/36:15 amPWM - ORD
2 stops10h 05mDelta
sáb. 12/610:45 amORD - PWM
2 stops9h 06mDelta
Deal found 10/27$239
This Delta deal was found by Cheapflights users on 10/26. 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.
vie. 12/52:34 pmPWM - ORD
1 stop8h 05mDelta
lun. 12/811:15 amORD - PWM
2 stops11h 44mDelta
Deal found 10/26$244
This Delta deal was found by Cheapflights users on 10/27. 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.
vie. 11/144:53 pmPWM - ORD
1 stop4h 36mDelta
lun. 11/171:04 pmORD - PWM
1 stop8h 15mDelta
Deal found 10/27$249
This United Airlines deal was found by Cheapflights users on 10/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/209:54 amPWM - ORD
1 stop5h 01mUnited Airlines
vie. 11/285:31 pmORD - PWM
1 stop4h 34mUnited Airlines
Deal found 10/27$250
This United Airlines deal was found by Cheapflights users on 10/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 11/145:00 pmPWM - GRB
1 stop5h 38mUnited Airlines
lun. 11/171:20 pmGRB - PWM
1 stop7h 30mUnited Airlines
Deal found 10/27$254
This Delta deal was found by Cheapflights users on 10/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/1012:53 pmPWM - ATW
1 stop5h 21mDelta
dom. 12/1411:13 amATW - PWM
1 stop3h 54mDelta
Deal found 10/28$257
This United Airlines deal was found by Cheapflights users on 10/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/317:01 pmPWM - ORD
1 stop5h 34mUnited Airlines
dom. 1/45:50 pmORD - PWM
Nonstop2h 39mUnited Airlines
Deal found 10/27$258
This American Airlines deal was found by Cheapflights users on 10/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 11/116:00 amPWM - GRB
1 stop5h 16mAmerican Airlines
sáb. 11/159:53 amGRB - PWM
1 stop6h 12mAmerican Airlines
Deal found 10/27$259
This United Airlines deal was found by Cheapflights users on 10/26. 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.
jue. 11/65:00 pmPWM - ORD
Nonstop2h 55mUnited Airlines
dom. 11/910:53 amORD - PWM
Nonstop2h 19mUnited Airlines
Deal found 10/26$259
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/86:05 pmPWM - ORD
2 stops18h 08mMultiple Airlines
jue. 12/117:40 amORD - PWM
1 stop26h 01mMultiple Airlines
Deal found 10/27$262
This United Airlines deal was found by Cheapflights users on 10/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 11/256:00 amPWM - ORD
1 stop8h 14mUnited Airlines
vie. 11/285:31 pmORD - PWM
1 stop4h 34mUnited Airlines
Deal found 10/27$263
This United Airlines deal was found by Cheapflights users on 10/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 11/116:00 amPWM - GRB
2 stops11h 46mUnited Airlines
sáb. 11/158:00 amGRB - PWM
1 stop5h 12mUnited Airlines
Deal found 10/27$264

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 octubre 28, 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

PortlandChicago

PWM - ORD

PWMORD

Portland

mié. 12/3

6:15 am-3:20 pm

2 stops10h 05m

Chicago O'Hare Intl

sáb. 12/6

10:45 am-8:51 pm

2 stops9h 06m

$239

PortlandChicago

PWM - ORD

PWMORD

Portland

mié. 11/12

3:20 pm-8:07 pm

1 stop5h 47m

Chicago O'Hare Intl

dom. 11/16

8:50 am-2:14 pm

1 stop4h 24m

$249

PortlandChicago

PWM - ORD

PWMORD

Portland

vie. 12/5

2:34 pm-12:01 am

2 stops10h 27m

Chicago O'Hare Intl

lun. 12/8

11:15 am-11:59 pm

2 stops11h 44m

$249

PortlandChicago

PWM - ORD

PWMORD

Portland

dom. 1/25

6:00 am-1:14 pm

1 stop8h 14m

Chicago O'Hare Intl

vie. 1/30

7:01 am-1:45 pm

1 stop5h 44m

$249

PortlandChicago

PWM - ORD

PWMORD

Portland

vie. 11/14

4:53 pm-8:29 pm

1 stop4h 36m

Chicago O'Hare Intl

lun. 11/17

1:04 pm-10:19 pm

1 stop8h 15m

$249

PortlandGreen Bay

PWM - GRB

PWMGRB

Portland

vie. 11/14

5:00 pm-9:38 pm

1 stop5h 38m

Green Bay Austin-Straubel

lun. 11/17

1:20 pm-9:50 pm

1 stop7h 30m

$254

PortlandGreen Bay

PWM - GRB

PWMGRB

Portland

vie. 11/14

4:53 pm-8:39 pm

1 stop4h 46m

Green Bay Austin-Straubel

dom. 11/16

11:10 am-4:07 pm

1 stop3h 57m

$254

PortlandAppleton

PWM - ATW

PWMATW

Portland

mié. 12/10

12:53 pm-5:14 pm

1 stop5h 21m

Appleton Intl

dom. 12/14

11:13 am-4:07 pm

1 stop3h 54m

$257

PortlandGreen Bay

PWM - GRB

PWMGRB

Portland

mar. 11/11

6:00 am-10:16 am

1 stop5h 16m

Green Bay Austin-Straubel

sáb. 11/15

9:53 am-5:05 pm

1 stop6h 12m

$259

PortlandMadison

PWM - MSN

PWMMSN

Portland

lun. 1/12

5:20 am-10:11 am

1 stop5h 51m

Madison Truax Field

sáb. 1/17

5:30 am-12:06 pm

1 stop5h 36m

$259

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/27

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.

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 octubre 28, 2025.

It’s typically best to fly out from Portland, Maine to Wisconsin in the evening. Doing so could potentially save you 50% 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 octubre 28, 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
4,240 reviews

Comfort

8.0

Entertainment

7.5

Overall

8.0

Crew

8.6

Food

7.0

Boarding

8.1

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
4,240 reviews
Southwest
8.0
Very good
4,240 reviews

Comfort

8.0

Entertainment

7.5

Overall

8.0

Crew

8.6

Food

7.0

Boarding

8.1

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
7.9
Good
7,994 reviews
Southwest
8.0
Very good
4,240 reviews

Comfort

8.0

Entertainment

7.5

Overall

8.0

Crew

8.6

Food

7.0

Boarding

8.1

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
9,001 reviews
Southwest
8.0
Very good
4,240 reviews

Comfort

8.0

Entertainment

7.5

Overall

8.0

Crew

8.6

Food

7.0

Boarding

8.1

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
11,032 reviews
Southwest
8.0
Very good
4,240 reviews

Comfort

8.0

Entertainment

7.5

Overall

8.0

Crew

8.6

Food

7.0

Boarding

8.1

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 5h 16m. Fly via Delta, United Airlines, or American Airlines to get the fastest option. There are 884 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 ($115), American Airlines ($170), and United Airlines ($200).

  • 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

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 octubre 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$258Average$427FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$258Average$498FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$258Average$416FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$311Average$417FlexibilityNo cancel feeOn-time63%

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