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Portland

$88+ 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 6/15. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — PWM
May 4 — May 111
Sun 5/4
Sun 5/11
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 April 29, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$239
(Delta)

One-way from

$88
(Cheapflightsfares)

Popular in

December

Cheapest in

February

Average price

$398
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. 16% potential increase in price ($78 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 29, 2025.

This Sun Country Air 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/117:54 amMSP - PWM
Nonstop2h 41mSun Country Air
Thu 8/1412:32 pmPWM - MSP
Nonstop3h 08mSun Country Air
Deal found 4/29$238
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.
Fri 7/256:55 amMSP - PWM
Nonstop2h 40mDelta
Wed 7/3011:40 amPWM - MSP
Nonstop3h 05mDelta
Deal found 4/28$239
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/217:00 amORD - PWM
1 stop5h 59mDelta
Wed 8/2711:25 amPWM - ORD
2 stops10h 09mDelta
Deal found 4/29$244
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/255:51 pmMSP - PWM
1 stop5h 08mAmerican Airlines
Tue 7/15:08 amPWM - MSP
1 stop8h 01mAmerican Airlines
Deal found 4/28$248
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.
Wed 7/163:33 pmORD - PWM
1 stop7h 20mAmerican Airlines
Wed 7/306:00 amPWM - ORD
1 stop5h 22mAmerican Airlines
Deal found 4/29$251
This Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/241:50 pmORD - PWM
1 stop9h 15mSouthwest
Tue 10/287:40 amPWM - ORD
1 stop5h 10mSouthwest
Deal found 4/29$254
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.
Wed 8/63:02 pmGRB - PWM
1 stop6h 43mAmerican Airlines
Tue 8/1212:14 pmPWM - GRB
2 stops12h 14mAmerican Airlines
Deal found 4/29$254
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/156:15 amORD - PWM
1 stop7h 25mJetBlue
Tue 5/203:35 pmPWM - ORD
1 stop7h 19mJetBlue
Deal found 4/29$255
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/214:50 pmORD - PWM
1 stop5h 11mUnited Airlines
Sun 8/246:00 amPWM - ORD
1 stop5h 38mUnited Airlines
Deal found 4/29$256
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/46:41 amATW - PWM
1 stop6h 45mUnited Airlines
Tue 9/94:56 pmPWM - ATW
1 stop5h 47mUnited Airlines
Deal found 4/29$259
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/132:43 pmMSN - PWM
1 stop4h 37mAmerican Airlines
Sat 9/209:25 amPWM - MSN
1 stop8h 18mAmerican Airlines
Deal found 4/28$259
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.
Fri 8/222:00 pmMSN - PWM
2 stops8h 59mDelta
Sat 8/305:00 pmPWM - MSN
1 stop5h 04mDelta
Deal found 4/28$264

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 April 29, 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

Fri 7/25

6:55 am-10:35 am

Nonstop2h 40m

Portland

Wed 7/30

11:40 am-1:45 pm

Nonstop3h 05m

$239

MinneapolisPortland

MSP - PWM

MSPPWM

Minneapolis St Paul

Sat 6/14

8:18 am-11:57 am

Nonstop2h 39m

Portland

Sat 6/21

12:58 pm-3:06 pm

Nonstop3h 08m

$242

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Thu 8/21

7:00 am-1:59 pm

1 stop5h 59m

Portland

Wed 8/27

11:25 am-8:34 pm

2 stops10h 09m

$244

MinneapolisPortland

MSP - PWM

MSPPWM

Minneapolis St Paul

Wed 6/25

5:51 pm-11:59 pm

1 stop5h 08m

Portland

Tue 7/1

5:08 am-12:09 pm

1 stop8h 01m

$248

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Wed 7/16

3:33 pm-11:53 pm

1 stop7h 20m

Portland

Wed 7/30

6:00 am-10:22 am

1 stop5h 22m

$251

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Fri 10/24

1:50 pm-12:05 am

1 stop9h 15m

Portland

Tue 10/28

7:40 am-11:50 am

1 stop5h 10m

$254

Green BayPortland

GRB - PWM

GRBPWM

Green Bay Austin-Straubel

Wed 8/6

3:02 pm-10:45 pm

1 stop6h 43m

Portland

Tue 8/12

12:14 pm-11:28 pm

2 stops12h 14m

$254

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Thu 5/15

6:15 am-2:40 pm

1 stop7h 25m

Portland

Tue 5/20

3:35 pm-9:54 pm

1 stop7h 19m

$255

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Thu 8/21

4:50 pm-11:01 pm

1 stop5h 11m

Portland

Sun 8/24

6:00 am-10:38 am

1 stop5h 38m

$256

AppletonPortland

ATW - PWM

ATWPWM

Appleton Intl

Thu 9/4

6:41 am-2:26 pm

1 stop6h 45m

Portland

Tue 9/9

4:56 pm-9:43 pm

1 stop5h 47m

$259

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/28

Showing 1-10 of 55 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 April 29, 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
4,295 reviews

Boarding

8.2

Comfort

8.0

Entertainment

7.6

Crew

8.6

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Southwest
8.0
Very good
4,295 reviews
Southwest
8.0
Very good
4,295 reviews

Boarding

8.2

Comfort

8.0

Entertainment

7.6

Crew

8.6

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
Delta
8.0
Very good
7,936 reviews
Southwest
8.0
Very good
4,295 reviews

Boarding

8.2

Comfort

8.0

Entertainment

7.6

Crew

8.6

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
United Airlines
7.4
Good
8,696 reviews
Southwest
8.0
Very good
4,295 reviews

Boarding

8.2

Comfort

8.0

Entertainment

7.6

Crew

8.6

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
JetBlue
7.3
Good
2,922 reviews
Southwest
8.0
Very good
4,295 reviews

Boarding

8.2

Comfort

8.0

Entertainment

7.6

Crew

8.6

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!
American Airlines
7.2
Good
10,000 reviews
Southwest
8.0
Very good
4,295 reviews

Boarding

8.2

Comfort

8.0

Entertainment

7.6

Crew

8.6

Food

7.1

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Gina,Apr 2025

LAS - DEN

Good, the crew was friendly and helpful. The pilot had great skills in keeping the plane stable through rough turbulence. Smooth landing, too! Thank you!

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 $88. Users have also found prices from $90 and $93 on American 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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Alternative routes for Wisconsin to Portland

See prices for flight routes from nearby airports that may be better suited for you.
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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 April 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
JetBlueCheapest$151Average$167FlexibilityNo cancel feeOn-time62%
American AirlinesCheapest$222Average$402FlexibilityNo cancel feeOn-time71%
DeltaCheapest$243Average$459FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$246Average$396FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$260Average$484FlexibilityNo cancel feeOn-time69%

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