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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 6/13. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MKE
Apr 20 — Apr 271
Mon 4/20
Mon 4/27
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 March 21, 2026.

This Travelocity deal was found by Cheapflights users on 3/17. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/182:25 pm
PWM
-
ORD
1 stop7h 19m
JetBlue
Sun 6/216:00 am
ORD
-
PWM
1 stop6h 29m
JetBlue
Deal found 3/17$213
This CheapOair deal was found by Cheapflights users on 3/16. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/1712:40 pm
PWM
-
MSP
Nonstop3h 08m
Sun Country Air
Mon 7/208:40 am
MSP
-
PWM
Nonstop2h 39m
Sun Country Air
Deal found 3/16$244
This Super.com deal was found by Cheapflights users on 3/20. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/1712:40 pm
PWM
-
MSP
Nonstop3h 08m
Sun Country Air
Sun 7/267:55 am
MSP
-
PWM
Nonstop2h 42m
Sun Country Air
Deal found 3/20$247
This KAYAK deal was found by Cheapflights users on 3/20. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/112:25 pm
PWM
-
ORD
1 stop7h 19m
JetBlue
Mon 6/156:00 am
ORD
-
PWM
1 stop6h 29m
JetBlue
Deal found 3/20$251
This Booking.com deal was found by Cheapflights users on 3/17. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/1312:46 pm
PWM
-
MSP
Nonstop3h 08m
Sun Country Air
Mon 8/178:05 am
MSP
-
PWM
Nonstop2h 39m
Sun Country Air
Deal found 3/17$258
This KAYAK deal was found by Cheapflights users on 3/20. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/222:25 pm
PWM
-
ORD
1 stop7h 19m
JetBlue
Tue 7/285:57 pm
ORD
-
PWM
1 stop5h 00m
JetBlue
Deal found 3/20$259
This Sun Country Air deal was found by Cheapflights users on 3/19. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/912:40 pm
PWM
-
MSP
Nonstop3h 08m
Sun Country Air
Sun 7/127:55 am
MSP
-
PWM
Nonstop2h 42m
Sun Country Air
Deal found 3/19$264
This United Airlines deal was found by Cheapflights users on 3/17. 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 5/226:25 pm
PWM
-
ORD
Nonstop3h 09m
United Airlines
Sun 5/246:18 pm
ORD
-
PWM
Nonstop2h 33m
United Airlines
Deal found 3/17$269
This American Airlines deal was found by Cheapflights users on 3/18. 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 4/96:01 pm
PWM
-
ORD
Nonstop3h 13m
American Airlines
Sun 4/127:49 pm
ORD
-
PWM
Nonstop2h 38m
American Airlines
Deal found 3/18$270
This Priceline deal was found by Cheapflights users on 3/19. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/912:40 pm
PWM
-
MSP
Nonstop3h 08m
Sun Country Air
Mon 7/137:55 am
MSP
-
PWM
Nonstop2h 42m
Sun Country Air
Deal found 3/19$277
This American Airlines deal was found by Cheapflights users on 3/20. 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 6/126:00 am
PWM
-
ORD
Nonstop3h 11m
American Airlines
Tue 6/163:15 pm
ORD
-
PWM
Nonstop2h 34m
American Airlines
Deal found 3/20$277
This American Airlines deal was found by Cheapflights users on 3/21. 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 7/186:25 am
PWM
-
ORD
Nonstop3h 11m
American Airlines
Tue 7/288:25 pm
ORD
-
PWM
Nonstop2h 44m
American Airlines
Deal found 3/21$278

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 March 21, 2026.

Round-trip from

$213
(Travelocity)

One-way from

$98
(Kiwi.com)

Popular in

September

Cheapest in

November

Average price

$524
From Portland to Wisconsin
Search Deals
One-way flight from Portland to Wisconsin
Search Deals
Highest demand for flights based on searches. 19% potential increase in price ($115 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($25 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 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 March 21, 2026.
Use the filters below to find and compare flights from Portland to Wisconsin that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

PortlandChicago

PWM - ORD

PWMORD

Portland

Thu 6/11

6:00 am-8:00 am

Nonstop3h 00m

Chicago O'Hare Intl

Sat 6/13

6:18 pm-9:51 pm

Nonstop2h 33m

$269
Quickest round-trip

PortlandChicago

PWM - ORD

PWMORD

Portland

Mon 4/13

6:04 am-8:00 am

Nonstop2h 56m

Chicago O'Hare Intl

Mon 4/20

6:10 pm-9:40 pm

Nonstop2h 30m

$269

PortlandMinneapolis

PWM - MSP

PWMMSP

Portland

Fri 7/17

12:40 pm-2:48 pm

Nonstop3h 08m

Minneapolis St Paul

Mon 7/20

8:40 am-12:19 pm

Nonstop2h 39m

$274

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 7/10

7:16 pm-11:26 pm

1 stop5h 10m

Chicago O'Hare Intl

Mon 7/13

6:08 pm-9:41 pm

Nonstop2h 33m

$279

PortlandChicago

PWM - ORD

PWMORD

Portland

Sun 7/19

6:00 am-8:00 am

Nonstop3h 00m

Chicago O'Hare Intl

Mon 7/27

6:08 pm-9:41 pm

Nonstop2h 33m

$315

PortlandAppleton

PWM - ATW

PWMATW

Portland

Wed 4/22

6:33 pm-11:03 pm

1 stop5h 30m

Appleton Intl

Tue 4/28

12:34 pm-11:28 pm

2 stops9h 54m

$322

PortlandChicago

PWM - ORD

PWMORD

Portland

Mon 4/13

2:51 pm-11:59 pm

2 stops10h 08m

Chicago O'Hare Intl

Mon 4/20

5:59 pm-11:24 pm

1 stop4h 25m

$325

PortlandChicago

PWM - ORD

PWMORD

Portland

Sun 4/26

4:43 pm-8:40 pm

1 stop4h 57m

Chicago O'Hare Intl

Tue 4/28

11:19 am-11:24 pm

2 stops11h 05m

$325

PortlandChicago

PWM - ORD

PWMORD

Portland

Mon 4/27

5:26 pm-10:15 pm

1 stop5h 49m

Chicago O'Hare Intl

Tue 4/28

11:19 am-11:24 pm

2 stops11h 05m

$325

PortlandMinneapolis

PWM - MSP

PWMMSP

Portland

Sat 5/16

9:40 am-2:18 pm

1 stop5h 38m

Minneapolis St Paul

Tue 6/2

12:29 pm-7:27 pm

1 stop5h 58m

$329

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/16

Showing 1-10 of 60 resultsSorted by cheapest first
1
2
3
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6

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 March 21, 2026.
Read reviews from past customers who have flown Southwest,Delta, andUnited 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
4,325 reviews

Comfort

8.0

Boarding

8.1

Overall

8.0

Food

7.0

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Southwest
8.0
Very good
4,325 reviews
Southwest
8.0
Very good
4,325 reviews

Comfort

8.0

Boarding

8.1

Overall

8.0

Food

7.0

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
Delta
7.9
Good
8,312 reviews
Southwest
8.0
Very good
4,325 reviews

Comfort

8.0

Boarding

8.1

Overall

8.0

Food

7.0

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
United Airlines
7.4
Good
9,452 reviews
Southwest
8.0
Very good
4,325 reviews

Comfort

8.0

Boarding

8.1

Overall

8.0

Food

7.0

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.
American Airlines
7.1
Good
11,488 reviews
Southwest
8.0
Very good
4,325 reviews

Comfort

8.0

Boarding

8.1

Overall

8.0

Food

7.0

Entertainment

7.5

Crew

8.6

Reviews

1 / 20
2.0
Mediocre

Dominic,Mar 2026

MCO - SMF

I had to try and sleep on the floor of the Austin airport. I spent 12 hours there. The airline policies were so poor, that a near violent argument broke out between the people in front of me and the flight attendants - making for a super stressful situation at 30,000 feet. Garbage airline choice by Kayak Garbage idea to book a flight with a layover. Next time I will pay for a quality booking myself, and somehow force the company to reimburse it.

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 55m. Fly via Sun Country Air, United Airlines, or American Airlines 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), American Airlines ($135), and United Airlines ($158).

  • 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 March 21, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$258Average$429FlexibilityNo cancel feeOn-time71%
DeltaCheapest$258Average$410FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$273Average$476FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$296Average$431FlexibilityNo cancel feeOn-time63%

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