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Wisconsin

$98+ 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 7/27. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MKE
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
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 January 29, 2026.

This United Airlines deal was found by Cheapflights users on 1/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/254:15 pm
PWM
-
ORD
Nonstop3h 12m
United Airlines
Tue 3/311:48 am
ORD
-
PWM
Nonstop2h 26m
United Airlines
Deal found 1/28$209
This American Airlines deal was found by Cheapflights users on 1/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/146:17 am
PWM
-
ORD
Nonstop3h 17m
American Airlines
Sat 3/218:02 pm
ORD
-
PWM
Nonstop2h 32m
American Airlines
Deal found 1/28$211
This United Airlines deal was found by Cheapflights users on 1/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/256:00 am
PWM
-
ORD
1 stop6h 38m
United Airlines
Mon 3/25:45 pm
ORD
-
PWM
Nonstop2h 24m
United Airlines
Deal found 1/28$219
This United Airlines deal was found by Cheapflights users on 1/26. 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.
Wed 2/256:00 am
PWM
-
ORD
1 stop6h 38m
United Airlines
Wed 3/44:10 pm
ORD
-
PWM
1 stop6h 10m
United Airlines
Deal found 1/26$229
This American Airlines deal was found by Cheapflights users on 1/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/217:00 am
PWM
-
ORD
1 stop6h 02m
American Airlines
Sat 2/282:05 pm
ORD
-
PWM
Nonstop2h 22m
American Airlines
Deal found 1/28$230
This Delta deal was found by Cheapflights users on 1/26. 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.
Wed 2/255:59 pm
PWM
-
ORD
1 stop5h 06m
Delta
Wed 3/411:18 am
ORD
-
PWM
2 stops11h 02m
Delta
Deal found 1/26$234
This Cheapflightsfares deal was found by Cheapflights users on 1/27. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/2112:40 pm
PWM
-
MSP
Nonstop3h 08m
Sun Country Air
Sat 6/278:20 am
MSP
-
PWM
Nonstop2h 39m
Sun Country Air
Deal found 1/27$237
This American Airlines deal was found by Cheapflights users on 1/27. 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.
Tue 3/176:00 am
PWM
-
ORD
1 stop5h 57m
American Airlines
Sat 3/218:02 pm
ORD
-
PWM
Nonstop2h 32m
American Airlines
Deal found 1/27$239
This United Airlines deal was found by Cheapflights users on 1/27. 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.
Sat 3/216:00 am
PWM
-
ORD
1 stop6h 58m
United Airlines
Fri 3/274:30 pm
ORD
-
PWM
1 stop4h 48m
United Airlines
Deal found 1/27$249
This United Airlines deal was found by Cheapflights users on 1/26. 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.
Thu 4/26:04 am
PWM
-
ORD
Nonstop2h 56m
United Airlines
Sun 4/56:00 am
ORD
-
PWM
1 stop7h 37m
United Airlines
Deal found 1/26$253
This United Airlines deal was found by Cheapflights users on 1/27. 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.
Mon 4/67:36 pm
PWM
-
ORD
1 stop5h 07m
United Airlines
Mon 4/131:00 pm
ORD
-
PWM
1 stop5h 01m
United Airlines
Deal found 1/27$254
This United Airlines deal was found by Cheapflights users on 1/27. 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.
Sat 2/284:15 pm
PWM
-
MSP
1 stop6h 44m
United Airlines
Wed 3/48:05 am
MSP
-
PWM
1 stop6h 09m
United Airlines
Deal found 1/27$259

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 January 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$209
(United Airlines)

One-way from

$98
(Kiwi.com)

Popular in

September

Cheapest in

November

Average price

$391
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 ($139 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 January 2026
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 January 29, 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

Thu 3/19

6:17 am-8:34 am

Nonstop3h 17m

Chicago O'Hare Intl

Mon 3/23

8:02 pm-11:34 pm

Nonstop2h 32m

$209

PortlandChicago

PWM - ORD

PWMORD

Portland

Wed 2/25

6:00 am-11:38 am

1 stop6h 38m

Chicago O'Hare Intl

Wed 3/4

11:48 am-3:14 pm

Nonstop2h 26m

$219

PortlandChicago

PWM - ORD

PWMORD

Portland

Wed 2/25

3:05 pm-9:34 pm

1 stop7h 29m

Chicago O'Hare Intl

Tue 3/3

11:48 am-3:14 pm

Nonstop2h 26m

$219

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 5/8

12:50 pm-6:41 pm

1 stop6h 51m

Chicago O'Hare Intl

Mon 5/11

6:00 am-12:18 pm

1 stop5h 18m

$229

PortlandChicago

PWM - ORD

PWMORD

Portland

Wed 7/22

6:50 pm-11:57 pm

1 stop6h 07m

Chicago O'Hare Intl

Tue 7/28

6:00 am-12:22 pm

1 stop5h 22m

$229

PortlandChicago

PWM - ORD

PWMORD

Portland

Sat 2/28

6:00 am-1:03 pm

1 stop8h 03m

Chicago O'Hare Intl

Mon 3/2

8:50 am-2:23 pm

1 stop4h 33m

$229

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 5/22

4:50 pm-8:24 pm

1 stop4h 34m

Chicago O'Hare Intl

Mon 5/25

8:55 am-4:15 pm

1 stop6h 20m

$229

PortlandChicago

PWM - ORD

PWMORD

Portland

Wed 2/25

5:59 pm-10:05 pm

1 stop5h 06m

Chicago O'Hare Intl

Wed 3/4

11:18 am-11:20 pm

2 stops11h 02m

$234

PortlandChicago

PWM - ORD

PWMORD

Portland

Sat 2/28

12:45 pm-4:41 pm

1 stop4h 56m

Chicago O'Hare Intl

Mon 3/2

2:05 pm-12:18 am

2 stops9h 13m

$234

PortlandMadison

PWM - MSN

PWMMSN

Portland

Wed 2/11

6:00 am-3:44 pm

2 stops10h 44m

Madison Truax Field

Tue 2/17

3:30 pm-11:20 pm

1 stop6h 50m

$299

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/28

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 November is currently the most expensive (average of $248). 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 29, 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
4,267 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Overall

8.0

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
4,267 reviews
Southwest
8.0
Very good
4,267 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Overall

8.0

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
8,128 reviews
Southwest
8.0
Very good
4,267 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Overall

8.0

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
9,215 reviews
Southwest
8.0
Very good
4,267 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Overall

8.0

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
11,205 reviews
Southwest
8.0
Very good
4,267 reviews

Comfort

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Overall

8.0

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 17m. Fly via American Airlines, 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 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 - Madison Truax Field.

  • 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 November is currently the most expensive (average of $248). 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 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$244Average$489FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$258Average$419FlexibilityNo cancel feeOn-time71%
DeltaCheapest$258Average$383FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$311Average$396FlexibilityNo cancel feeOn-time63%

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