HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
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 5/28. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MKE
трав. 29 — черв. 51
пт 5/29
пт 6/5
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Portland to Wisconsin with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 квітень 29, 2026.

This Cheapflightsfares deal was found by Cheapflights users on 4/24. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
чт 10/112:16 pm
PWM
-
MSP
Nonstop3h 03m
Sun Country Air
нд 10/117:45 am
MSP
-
PWM
Nonstop2h 44m
Sun Country Air
Deal found 4/24$267
This United Airlines deal was found by Cheapflights users on 4/25. 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.
пт 5/226:00 am
PWM
-
ORD
Nonstop3h 00m
United Airlines
нд 5/2410:55 am
ORD
-
PWM
Nonstop2h 31m
United Airlines
Deal found 4/25$269
This American Airlines deal was found by Cheapflights users on 4/25. 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.
пт 6/56:00 am
PWM
-
ORD
Nonstop3h 12m
American Airlines
нд 6/78:54 pm
ORD
-
PWM
Nonstop2h 43m
American Airlines
Deal found 4/25$271
This Sun Country Air deal was found by Cheapflights users on 4/28. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
пт 6/2612:45 pm
PWM
-
MSP
Nonstop3h 08m
Sun Country Air
сб 7/48:20 am
MSP
-
PWM
Nonstop2h 39m
Sun Country Air
Deal found 4/28$274
This Cheapflightsfares deal was found by Cheapflights users on 4/27. 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.
нд 6/712:47 pm
PWM
-
MSP
Nonstop3h 08m
Sun Country Air
нд 6/147:55 am
MSP
-
PWM
Nonstop2h 42m
Sun Country Air
Deal found 4/27$277
This American Airlines deal was found by Cheapflights users on 4/29. 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.
сб 6/67:28 pm
PWM
-
ORD
Nonstop3h 09m
American Airlines
нд 6/78:59 pm
ORD
-
PWM
Nonstop2h 43m
American Airlines
Deal found 4/29$278
This American Airlines deal was found by Cheapflights users on 4/25. 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.
чт 6/257:23 pm
PWM
-
ORD
Nonstop3h 09m
American Airlines
нд 6/285:00 am
ORD
-
PWM
1 stop4h 37m
American Airlines
Deal found 4/25$280
This Sun Country Air deal was found by Cheapflights users on 4/26. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
чт 6/412:50 pm
PWM
-
MSP
Nonstop3h 08m
Sun Country Air
нд 6/147:55 am
MSP
-
PWM
Nonstop2h 42m
Sun Country Air
Deal found 4/26$284
This Cheapflightsfares deal was found by Cheapflights users on 4/25. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
нд 9/274:57 pm
PWM
-
MSP
Nonstop3h 03m
Sun Country Air
нд 10/412:50 pm
MSP
-
PWM
Nonstop2h 41m
Sun Country Air
Deal found 4/25$287
This American Airlines deal was found by Cheapflights users on 4/29. 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.
вт 7/76:59 pm
PWM
-
ORD
1 stop6h 30m
American Airlines
нд 7/129:03 pm
ORD
-
PWM
Nonstop2h 34m
American Airlines
Deal found 4/29$288
This Delta deal was found by Cheapflights users on 4/28. 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.
пт 5/222:05 pm
PWM
-
ORD
1 stop8h 48m
Delta
ср 5/2711:09 am
ORD
-
PWM
1 stop3h 58m
Delta
Deal found 4/28$289
This United Airlines deal was found by Cheapflights users on 4/28. 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.
вт 6/26:00 am
PWM
-
MSN
1 stop4h 59m
United Airlines
вт 6/93:53 pm
MSN
-
PWM
1 stop4h 59m
United Airlines
Deal found 4/28$291

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 квітень 29, 2026.

Round-trip from

$267
(Cheapflightsfares)

One-way from

$98
(Kiwi.com)

Popular in

September

Cheapest in

November

Average price

$557
From Portland to Wisconsin
Search Deals
One-way flight from Portland to Wisconsin
Search Deals
Highest demand for flights based on searches. 18% potential increase in price ($111 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($24 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 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 квітень 29, 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
Quickest round-trip

PortlandChicago

PWM - ORD

PWMORD

Portland

пт 7/10

6:00 am-8:00 am

Nonstop3h 00m

Chicago O'Hare Intl

пн 7/13

10:55 am-2:26 pm

Nonstop2h 31m

$269

PortlandChicago

PWM - ORD

PWMORD

Portland

пт 8/28

5:15 am-9:33 am

1 stop5h 18m

Chicago O'Hare Intl

пн 8/31

6:35 am-10:12 am

Nonstop2h 37m

$279

PortlandChicago

PWM - ORD

PWMORD

Portland

чт 7/2

11:48 am-5:02 pm

1 stop6h 14m

Chicago O'Hare Intl

сб 7/11

3:35 pm-11:14 pm

1 stop6h 39m

$289

PortlandChicago

PWM - ORD

PWMORD

Portland

вт 8/25

5:15 am-9:33 am

1 stop5h 18m

Chicago O'Hare Intl

ср 9/2

6:18 pm-11:59 pm

1 stop4h 41m

$289

PortlandChicago

PWM - ORD

PWMORD

Portland

ср 8/26

3:00 pm-11:57 pm

2 stops9h 57m

Chicago O'Hare Intl

сб 8/29

1:15 pm-10:33 pm

1 stop8h 18m

$294

PortlandChicago

PWM - ORD

PWMORD

Portland

вт 5/19

1:18 pm-10:27 pm

2 stops10h 09m

Chicago O'Hare Intl

нд 5/24

6:07 am-1:58 pm

1 stop6h 51m

$294

PortlandChicago

PWM - ORD

PWMORD

Portland

ср 5/20

6:02 am-1:01 pm

2 stops7h 59m

Chicago O'Hare Intl

ср 5/27

11:09 am-11:09 pm

2 stops11h 00m

$300

PortlandChicago

PWM - ORD

PWMORD

Portland

нд 6/21

6:00 am-8:00 am

Nonstop3h 00m

Chicago O'Hare Intl

вт 6/23

3:53 pm-11:51 pm

1 stop6h 58m

$309

PortlandMadison

PWM - MSN

PWMMSN

Portland

чт 6/18

11:48 am-5:52 pm

1 stop7h 04m

Madison Truax Field

вт 6/23

1:31 pm-11:05 pm

2 stops8h 34m

$317

PortlandChicago

PWM - ORD

PWMORD

Portland

нд 6/7

11:48 am-7:31 pm

1 stop8h 43m

Chicago O'Hare Intl

ср 6/10

6:30 am-3:55 pm

2 stops8h 25m

$325

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/27

Showing 1-10 of 60 resultsSorted by cheapest first
1
2
3
...
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, December is the cheapest month in which you can book a flight from Portland, Maine to Wisconsin (average of $193). Flying from Portland, Maine to Wisconsin in March is currently the most expensive (average of $329). 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.

How much does it cost to fly round-trip from Portland, Maine to Wisconsin?

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 квітень 29, 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
4,314 reviews

Overall

8.0

Entertainment

7.5

Food

7.0

Comfort

8.0

Crew

8.6

Boarding

8.1

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
4,314 reviews
Southwest
8.0
Very good
4,314 reviews

Overall

8.0

Entertainment

7.5

Food

7.0

Comfort

8.0

Crew

8.6

Boarding

8.1

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
8,467 reviews
Southwest
8.0
Very good
4,314 reviews

Overall

8.0

Entertainment

7.5

Food

7.0

Comfort

8.0

Crew

8.6

Boarding

8.1

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
9,680 reviews
Southwest
8.0
Very good
4,314 reviews

Overall

8.0

Entertainment

7.5

Food

7.0

Comfort

8.0

Crew

8.6

Boarding

8.1

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
11,678 reviews
Southwest
8.0
Very good
4,314 reviews

Overall

8.0

Entertainment

7.5

Food

7.0

Comfort

8.0

Crew

8.6

Boarding

8.1

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 3h. Fly via United Airlines, Delta, 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 American Airlines ($135), Delta ($135), and United Airlines ($148).

  • 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, December is the cheapest month in which you can book a flight from Portland, Maine to Wisconsin (average of $193). Flying from Portland, Maine to Wisconsin in March is currently the most expensive (average of $329). 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Portland to Wisconsin

See prices for flight routes from nearby airports that may be better suited for you.
Boston to Seattle flights
Boston to Miami flights
Boston to Dallas/Fort Worth flights
Boston to Orlando flights
Boston to Los Angeles flights
Boston to San Francisco flights
Boston to Las Vegas flights
Boston to Atlanta flights
Boston to O'Hare Intl flights
Boston to Fort Lauderdale flights
Boston to Tampa flights
Boston to Baltimore flights
Boston to Denver flights
Boston to Reagan-National flights
Boston to Nashville flights
Boston to San Diego flights
Boston to Dulles Intl flights
Boston to Hobby flights
Boston to Raleigh flights
Boston to Charlotte flights
Boston to Sky Harbor Intl flights
Boston to LaGuardia flights
Boston to Detroit flights
Boston to Charleston flights
Boston to John F Kennedy Intl flights
Boston to Philadelphia flights
Boston to New Orleans flights
Boston to George Bush Intcntl flights
Boston to Minneapolis flights
Boston to Newark flights
Boston to Austin flights
Boston to Pittsburgh flights
Boston to Fort Myers flights
Boston to Portland flights
Boston to West Palm Beach flights
Boston to Love Field flights
Boston to Savannah flights
Boston to Midway flights
Boston to Ontario flights
Boston to Salt Lake City flights
Boston to Richmond flights
Boston to Columbus flights
Boston to Cincinnati flights
Boston to Indianapolis flights
Boston to Kansas City flights
Boston to Myrtle Beach flights
Boston to Bozeman flights
Boston to Jacksonville flights
Boston to Cleveland flights
Boston to Sarasota flights

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 квітень 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$258Average$437FlexibilityNo cancel feeOn-time71%
DeltaCheapest$258Average$418FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$262Average$442FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$311Average$477FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.