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$79+ Cheap flights from Wisconsin to Portland, ME (PWM)

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 8/18. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — PWM
Apr 5 — Apr 121
Sat 4/5
Sat 4/12
1 adult, Economy
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Cheap flight deals from Wisconsin to Portland

Keep the following information in mind while searching for Wisconsin to Portland flight deals. Data was last updated March 31, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$164
(Kiwi.com)

One-way from

$79
(FlightHub)

Popular in

December

Cheapest in

February

Average price

$363
Provider with most accurate pricing for Milwaukee-Mitchell-Portland flight deals.
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Provider most trusted by Cheapflights users for Milwaukee-Mitchell-Portland flights.
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From Wisconsin to Portland
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One-way flight from Wisconsin to Portland
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Highest demand for flights based on searches. 14% potential increase in price ($66 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in March 2025
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Find flight deals from Wisconsin to Portland

Cheapest flights from Wisconsin to Portland
Explore the most affordable flight options available from Wisconsin to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 31, 2025.

This Kiwi.com deal was found by Cheapflights users on 3/30. 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.
Sun 5/257:54 amMSP - PWM
Nonstop2h 41mSun Country Air
Thu 5/2912:47 pmPWM - MSP
Nonstop3h 13mSun Country Air
Deal found 3/30$164
This Delta deal was found by Cheapflights users on 3/30. 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.
Sat 4/197:05 amORD - PWM
1 stop5h 30mDelta
Sat 4/265:32 amPWM - ORD
2 stops10h 33mDelta
Deal found 3/30$228
This American Airlines deal was found by Cheapflights users on 3/31. 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 6/217:01 amORD - PWM
1 stop7h 19mAmerican Airlines
Sat 6/287:41 amPWM - ORD
1 stop5h 38mAmerican Airlines
Deal found 3/31$229
This JetBlue Airways deal was found by Cheapflights users on 3/31. 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 JetBlue Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/316:10 amORD - PWM
1 stop6h 10mJetBlue
Sat 6/72:15 pmPWM - ORD
1 stop9h 05mJetBlue
Deal found 3/31$232
This Booking.com deal was found by Cheapflights users on 3/29. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/119:54 amORD - PWM
1 stop22h 18mFrontier
Sun 4/1310:08 amPWM - ORD
1 stop23h 36mFrontier
Deal found 3/29$238
This Delta deal was found by Cheapflights users on 3/30. 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.
Sun 6/86:55 amMSP - PWM
Nonstop2h 44mDelta
Wed 6/1811:44 amPWM - MSP
Nonstop3h 02mDelta
Deal found 3/30$239
This United Airlines deal was found by Cheapflights users on 3/30. 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 7/114:46 pmORD - PWM
1 stop5h 28mUnited Airlines
Thu 7/246:10 amPWM - ORD
Nonstop2h 55mUnited Airlines
Deal found 3/30$240
This Delta deal was found by Cheapflights users on 3/30. 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 5/284:00 pmMSN - PWM
1 stop6h 21mDelta
Tue 6/35:30 pmPWM - MSN
1 stop6h 15mDelta
Deal found 3/30$248
This United Airlines deal was found by Cheapflights users on 3/30. 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.
Tue 5/66:44 amGRB - PWM
2 stops9h 45mUnited Airlines
Sat 5/106:13 amPWM - GRB
1 stop5h 02mUnited Airlines
Deal found 3/30$254
This Delta deal was found by Cheapflights users on 3/30. 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.
Tue 5/274:56 pmMKE - PWM
1 stop6h 03mDelta
Tue 6/35:30 pmPWM - MKE
1 stop5h 07mDelta
Deal found 3/30$257
This American Airlines deal was found by Cheapflights users on 3/30. 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.
Wed 5/281:49 pmMSP - PWM
1 stop7h 56mAmerican Airlines
Tue 6/34:01 pmPWM - MSP
1 stop5h 46mAmerican Airlines
Deal found 3/30$259
This American Airlines deal was found by Cheapflights users on 3/30. 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 8/236:52 amMSN - PWM
1 stop7h 28mAmerican Airlines
Wed 8/276:07 amPWM - MSN
1 stop7h 35mAmerican Airlines
Deal found 3/30$259

Cheapflights Fare Finder

Customize your flight search to find flights from Wisconsin to Portland 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 31, 2025.
Use the filters below to find and compare flights from Wisconsin to Portland that are best for you.

Fly from

Wisconsin

Fly to

Portland

Route

Depart

Return

Price

MinneapolisPortland

MSP - PWM

MSPPWM

Minneapolis St Paul

Sun 5/25

7:54 am-11:35 am

Nonstop2h 41m

Portland

Thu 5/29

12:47 pm-3:00 pm

Nonstop3h 13m

$164

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 4/19

7:05 am-1:35 pm

1 stop5h 30m

Portland

Sat 4/26

5:32 am-3:05 pm

2 stops10h 33m

$228

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 6/21

7:01 am-3:20 pm

1 stop7h 19m

Portland

Sat 6/28

7:41 am-12:19 pm

1 stop5h 38m

$229

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 5/31

6:10 am-1:20 pm

1 stop6h 10m

Portland

Sat 6/7

2:15 pm-10:20 pm

1 stop9h 05m

$232

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Fri 4/11

9:54 am-9:12 am

1 stop22h 18m

Portland

Sun 4/13

10:08 am-8:44 am

1 stop23h 36m

$238

MinneapolisPortland

MSP - PWM

MSPPWM

Minneapolis St Paul

Sun 6/8

6:55 am-10:39 am

Nonstop2h 44m

Portland

Thu 6/19

11:44 am-1:46 pm

Nonstop3h 02m

$239

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Fri 7/11

4:46 pm-11:14 pm

1 stop5h 28m

Portland

Thu 7/24

6:10 am-8:05 am

Nonstop2h 55m

$240

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Wed 5/28

4:00 pm-11:21 pm

1 stop6h 21m

Portland

Tue 6/3

5:30 pm-10:45 pm

1 stop6h 15m

$248

Green BayPortland

GRB - PWM

GRBPWM

Green Bay Austin-Straubel

Tue 5/6

6:44 am-5:29 pm

2 stops9h 45m

Portland

Sat 5/10

6:13 am-10:15 am

1 stop5h 02m

$254

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Tue 5/27

4:56 pm-11:59 pm

1 stop6h 03m

Portland

Tue 6/3

5:30 pm-9:37 pm

1 stop5h 07m

$257

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/30

Showing 1-10 of 59 results
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Best time to book a flight from Wisconsin to Portland

Have a flexible travel schedule? Discover the best time to fly to Portland from Wisconsin 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 Wisconsin to Portland

What is the cheapest month to book a flight from Wisconsin to Portland, Maine?

Currently, January is the cheapest month in which you can book a flight from Wisconsin to Portland, Maine (average of $296). Flying from Wisconsin to Portland, Maine in May is currently the most expensive (average of $416). 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.

Rainfall in Portland by month

Plan your trip to Portland by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Portland, Maine ranges from 2.9 - 4.5 inches per month. November is typically the wettest month, when rainfall can reach 4.5 in. August is typically the driest time to visit Portland, Maine when rainfall is around 2.9 in.

Temperature in Portland by month

Plan your trip to Portland by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Portland, Maine, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 68.0 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Portland

Get insights into the airlines that provide service to Portland. 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 Portland. Reviews last updated March 31, 2025.
Read reviews from past customers who have flown Southwest, Delta and United Airlines from Wisconsin to Portland. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,275 reviews

Comfort

8.1

Boarding

8.2

Crew

8.7

Entertainment

7.6

Food

7.1

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.0
Very good
4,275 reviews
Southwest
8.0
Very good
4,275 reviews

Comfort

8.1

Boarding

8.2

Crew

8.7

Entertainment

7.6

Food

7.1

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,899 reviews
Southwest
8.0
Very good
4,275 reviews

Comfort

8.1

Boarding

8.2

Crew

8.7

Entertainment

7.6

Food

7.1

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
United Airlines
7.4
Good
8,614 reviews
Southwest
8.0
Very good
4,275 reviews

Comfort

8.1

Boarding

8.2

Crew

8.7

Entertainment

7.6

Food

7.1

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
JetBlue
7.3
Good
2,924 reviews
Southwest
8.0
Very good
4,275 reviews

Comfort

8.1

Boarding

8.2

Crew

8.7

Entertainment

7.6

Food

7.1

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,275 reviews

Comfort

8.1

Boarding

8.2

Crew

8.7

Entertainment

7.6

Food

7.1

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Related info for your journey

Find useful and relevant information for your journey from Wisconsin to Portland. 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 into for flights to Portland from Wisconsin?

    If you book a flight to Portland from Wisconsin, you will be flying to Portland, which is the city’s only airport. Portland (PWM) is located 2.9 mi from the center of Portland.

  • What are the cheapest airlines to fly from Wisconsin to Portland, Maine one-way?

    For one-way options, check prices for Sun Country Air. According to our data, you can fly for as low as $79. Users have also found prices from $90 and $92 on United Airlines and JetBlue, respectively.

  • What are the most popular routes from Wisconsin to Portland, Maine?

    The most popular route from Wisconsin to Portland, Maine is Chicago O'Hare Intl - Portland. You may also consider Minneapolis St Paul - Portland or Madison Truax Field - Portland.

  • Can I find deals for flights from Wisconsin to Portland that include hotel bookings?

    Yes. In addition to deals on Wisconsin to Portland flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Wisconsin to Portland?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Wisconsin to Portland.

  • Can I find deals for business class flights from Wisconsin to Portland?

    Yes. Cheapflights offers flight deals from Wisconsin to Portland 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 Wisconsin to Portland, Maine?

    Currently, January is the cheapest month in which you can book a flight from Wisconsin to Portland, Maine (average of $296). Flying from Wisconsin to Portland, Maine in May is currently the most expensive (average of $416). 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

Traveling to a place near Wisconsin?

Book flights to Wisconsin if you plan to visit one of these locations
North Conway
Bath
Brunswick
Auburn
Conway
Lewiston

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Top 5 airlines flying from Wisconsin to Portland

Discover the top 5 airlines that operate flights from Wisconsin to Portland. 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 31, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$151Average$167FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$217Average$423FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$246Average$406FlexibilityNo cancel feeOn-time63%
DeltaCheapest$251Average$459FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$260Average$490FlexibilityNo cancel feeOn-time69%
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