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Wisconsin

$102+ 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 12/6. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MKE
dic. 6 — dic. 131
sáb. 12/6
sáb. 12/13
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 noviembre 6, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$231
(Delta)

One-way from

$102
(United Airlines)

Popular in

September

Cheapest in

November

Average price

$335
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 November 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 noviembre 6, 2025.

This Delta deal was found by Cheapflights users on 11/4. 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
2 stops10h 27mDelta
lun. 12/82:30 pmORD - PWM
2 stops7h 51mDelta
Deal found 11/4$231
This Delta deal was found by Cheapflights users on 11/5. 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. 12/34:43 pmPWM - ORD
1 stop4h 55mDelta
sáb. 12/610:45 amORD - PWM
2 stops10h 38mDelta
Deal found 11/5$234
This United Airlines deal was found by Cheapflights users on 11/6. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 11/205:00 pmPWM - ORD
Nonstop2h 55mUnited Airlines
jue. 12/114:25 pmORD - PWM
1 stop5h 44mUnited Airlines
Deal found 11/6$239
This Delta deal was found by Cheapflights users on 11/4. 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. 12/36:00 amPWM - ORD
1 stop5h 09mDelta
dom. 12/76:45 amORD - PWM
1 stop4h 28mDelta
Deal found 11/4$240
This United Airlines deal was found by Cheapflights users on 11/4. 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. 12/54:25 pmPWM - ORD
Nonstop3h 10mUnited Airlines
mar. 12/95:50 pmORD - PWM
Nonstop2h 27mUnited Airlines
Deal found 11/4$243
This Delta deal was found by Cheapflights users on 11/5. 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. 12/36:00 amPWM - ORD
2 stops11h 42mDelta
mié. 12/1010:45 amORD - PWM
2 stops12h 14mDelta
Deal found 11/5$250
This United Airlines deal was found by Cheapflights users on 11/5. 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. 12/126:00 amPWM - GRB
2 stops10h 12mUnited Airlines
mié. 1/76:31 amGRB - PWM
1 stop7h 08mUnited Airlines
Deal found 11/5$254
This Delta deal was found by Cheapflights users on 11/6. 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.
jue. 12/42:34 pmPWM - ORD
2 stops10h 27mDelta
jue. 12/116:45 amORD - PWM
1 stop4h 28mDelta
Deal found 11/6$254
This Delta deal was found by Cheapflights users on 11/6. 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.
jue. 11/276:00 amPWM - MSN
1 stop7h 55mDelta
mié. 12/33:25 pmMSN - PWM
1 stop6h 56mDelta
Deal found 11/6$259
This United Airlines deal was found by Cheapflights users on 11/4. 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. 12/116:00 amPWM - ORD
1 stop8h 09mUnited Airlines
lun. 12/1510:50 amORD - PWM
Nonstop2h 32mUnited Airlines
Deal found 11/4$263
This American Airlines deal was found by Cheapflights users on 11/4. 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.
vie. 12/56:40 pmPWM - ORD
1 stop5h 14mAmerican Airlines
lun. 12/83:52 pmORD - PWM
1 stop6h 45mAmerican Airlines
Deal found 11/4$269
This American Airlines deal was found by Cheapflights users on 11/6. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 11/245:37 pmPWM - ORD
Nonstop3h 13mAmerican Airlines
vie. 11/281:40 pmORD - PWM
Nonstop2h 25mAmerican Airlines
Deal found 11/6$274

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 noviembre 6, 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

lun. 1/26

2:35 pm-11:57 pm

2 stops10h 22m

Chicago O'Hare Intl

lun. 2/2

6:25 pm-12:20 am

1 stop4h 55m

$234

PortlandChicago

PWM - ORD

PWMORD

Portland

mié. 12/3

4:43 pm-10:30 pm

1 stop6h 47m

Chicago O'Hare Intl

mié. 12/10

2:30 pm-11:21 pm

2 stops7h 51m

$234

PortlandChicago

PWM - ORD

PWMORD

Portland

sáb. 12/13

6:00 am-3:20 pm

2 stops10h 20m

Chicago O'Hare Intl

lun. 12/15

6:00 am-4:07 pm

2 stops9h 07m

$239

PortlandChicago

PWM - ORD

PWMORD

Portland

mié. 12/3

6:00 am-10:09 am

1 stop5h 09m

Chicago O'Hare Intl

dom. 12/7

6:45 am-12:13 pm

1 stop4h 28m

$240

PortlandChicago

PWM - ORD

PWMORD

Portland

vie. 12/5

4:25 pm-6:35 pm

Nonstop3h 10m

Chicago O'Hare Intl

mar. 12/9

5:50 pm-9:17 pm

Nonstop2h 27m

$243

PortlandGreen Bay

PWM - GRB

PWMGRB

Portland

vie. 12/12

6:00 am-3:12 pm

2 stops10h 12m

Green Bay Austin-Straubel

mié. 1/7

6:31 am-2:39 pm

1 stop7h 08m

$254

PortlandChicago

PWM - ORD

PWMORD

Portland

jue. 12/4

2:34 pm-12:01 am

2 stops10h 27m

Chicago O'Hare Intl

dom. 12/7

6:45 am-12:13 pm

1 stop4h 28m

$254

PortlandChicago

PWM - ORD

PWMORD

Portland

jue. 12/4

2:34 pm-12:01 am

2 stops10h 27m

Chicago O'Hare Intl

jue. 12/11

6:45 am-12:13 pm

1 stop4h 28m

$254

PortlandChicago

PWM - ORD

PWMORD

Portland

jue. 11/20

6:00 am-3:26 pm

2 stops10h 26m

Chicago O'Hare Intl

jue. 12/11

6:45 am-12:13 pm

1 stop4h 28m

$254

PortlandGreen Bay

PWM - GRB

PWMGRB

Portland

vie. 12/12

6:00 am-3:12 pm

2 stops10h 12m

Green Bay Austin-Straubel

jue. 1/8

6:31 am-2:31 pm

2 stops7h 00m

$259

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/6

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 noviembre 6, 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 noviembre 6, 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
4,241 reviews

Food

7.0

Comfort

8.0

Boarding

8.1

Overall

8.0

Crew

8.6

Entertainment

7.5

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
4,241 reviews
Southwest
8.0
Very good
4,241 reviews

Food

7.0

Comfort

8.0

Boarding

8.1

Overall

8.0

Crew

8.6

Entertainment

7.5

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
8,001 reviews
Southwest
8.0
Very good
4,241 reviews

Food

7.0

Comfort

8.0

Boarding

8.1

Overall

8.0

Crew

8.6

Entertainment

7.5

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
9,007 reviews
Southwest
8.0
Very good
4,241 reviews

Food

7.0

Comfort

8.0

Boarding

8.1

Overall

8.0

Crew

8.6

Entertainment

7.5

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
11,040 reviews
Southwest
8.0
Very good
4,241 reviews

Food

7.0

Comfort

8.0

Boarding

8.1

Overall

8.0

Crew

8.6

Entertainment

7.5

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 6h 39m. Fly via Delta, 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 ($107), United Airlines ($107), and American Airlines ($134).

  • 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, 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 noviembre 6, 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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