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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 6/13. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — PWM
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap 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 December 18, 2025.

This United Airlines deal was found by Cheapflights users on 12/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/306:21 pmORD - PWM
1 stop4h 38mUnited Airlines
Fri 1/26:46 pmPWM - ORD
1 stop5h 49mUnited Airlines
Deal found 12/16$269
This United Airlines deal was found by Cheapflights users on 12/15. 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 12/265:50 pmORD - PWM
Nonstop2h 39mUnited Airlines
Thu 8/204:48 pmPWM - ORD
Nonstop2h 57mUnited Airlines
Deal found 12/15$278
This United Airlines deal was found by Cheapflights users on 12/15. 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 12/266:21 pmORD - PWM
1 stop4h 38mUnited Airlines
Thu 5/284:48 pmPWM - ORD
Nonstop2h 57mUnited Airlines
Deal found 12/15$283
This American Airlines deal was found by Cheapflights users on 12/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/3111:35 amORD - PWM
1 stop4h 04mAmerican Airlines
Tue 1/65:07 pmPWM - ORD
1 stop6h 27mAmerican Airlines
Deal found 12/16$285
This United Airlines deal was found by Cheapflights users on 12/15. 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 12/265:50 pmORD - PWM
Nonstop2h 39mUnited Airlines
Thu 1/88:40 amPWM - ORD
1 stop5h 35mUnited Airlines
Deal found 12/15$287
This United Airlines deal was found by Cheapflights users on 12/17. 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.
Thu 12/2510:35 amORD - PWM
Nonstop2h 39mUnited Airlines
Thu 1/17:30 pmPWM - ORD
1 stop5h 14mUnited Airlines
Deal found 12/17$289
This United Airlines deal was found by Cheapflights users on 12/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/266:21 pmORD - PWM
1 stop4h 38mUnited Airlines
Wed 5/277:22 pmPWM - ORD
1 stop4h 50mUnited Airlines
Deal found 12/16$294
This United Airlines deal was found by Cheapflights users on 12/17. 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.
Thu 12/255:50 pmORD - PWM
Nonstop2h 39mUnited Airlines
Wed 12/319:30 amPWM - ORD
Nonstop3h 14mUnited Airlines
Deal found 12/17$303
This United Airlines deal was found by Cheapflights users on 12/15. 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 12/316:21 pmORD - PWM
1 stop4h 38mUnited Airlines
Tue 1/64:10 pmPWM - ORD
Nonstop3h 08mUnited Airlines
Deal found 12/15$309
This United Airlines deal was found by Cheapflights users on 12/16. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/243:18 pmMSP - PWM
2 stops7h 41mUnited Airlines
Wed 12/316:00 amPWM - MSP
1 stop6h 37mUnited Airlines
Deal found 12/16$364
This American Airlines deal was found by Cheapflights users on 12/15. 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 12/246:02 amMKE - PWM
1 stop4h 47mAmerican Airlines
Fri 1/25:45 amPWM - MKE
1 stop5h 40mAmerican Airlines
Deal found 12/15$393
This United Airlines deal was found by Cheapflights users on 12/15. 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 12/243:48 pmMKE - PWM
2 stops7h 11mUnited Airlines
Fri 1/26:00 amPWM - MKE
1 stop5h 45mUnited Airlines
Deal found 12/15$494

Find flight deals from Wisconsin to Portland

Keep the following information in mind while searching for Wisconsin to Portland flight deals. Data was last updated December 18, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$208
(Booking.com)

One-way from

$79
(Sun Country Air)

Popular in

January

Cheapest in

September

Average price

$478
Provider with most accurate pricing for Milwaukee-Mitchell-Boston Logan Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for Milwaukee-Mitchell-Boston Logan Intl flights.
Search Deals
From Wisconsin to Portland
Search Deals
One-way flight from Wisconsin to Portland
Search Deals
Highest demand for flights based on searches. 22% potential increase in price ($100 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($18 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 December 18, 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

Sat 6/13

8:20 am-11:59 am

Nonstop2h 39m

Portland

Sat 6/20

12:58 pm-3:06 pm

Nonstop3h 08m

$168

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Mon 1/5

8:51 am-2:40 pm

1 stop4h 49m

Portland

Sat 1/10

4:10 pm-6:18 pm

Nonstop3h 08m

$219

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 4/4

9:37 am-4:10 pm

1 stop5h 33m

Portland

Tue 4/7

5:45 pm-10:12 pm

1 stop5h 27m

$229

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Tue 2/3

6:05 am-1:56 pm

1 stop6h 51m

Portland

Tue 2/10

6:00 am-1:15 pm

1 stop8h 15m

$229

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Thu 1/8

7:01 am-1:45 pm

1 stop5h 44m

Portland

Mon 1/12

5:57 pm-10:34 pm

1 stop5h 37m

$229

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sun 1/11

6:50 am-12:08 pm

1 stop4h 18m

Portland

Wed 1/14

2:35 pm-9:35 pm

1 stop8h 00m

$229

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Tue 1/13

5:20 pm-11:22 pm

1 stop5h 02m

Portland

Thu 1/15

5:57 pm-10:34 pm

1 stop5h 37m

$229

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Mon 1/12

5:20 pm-11:22 pm

1 stop5h 02m

Portland

Tue 1/20

5:57 pm-10:34 pm

1 stop5h 37m

$229

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Wed 4/1

10:50 am-5:05 pm

1 stop5h 15m

Portland

Tue 4/7

5:45 pm-10:12 pm

1 stop5h 27m

$229

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Mon 1/5

6:25 pm-12:20 am

1 stop4h 55m

Portland

Mon 1/12

5:57 pm-10:34 pm

1 stop5h 37m

$229

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/15

Showing 1-10 of 51 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, October is the cheapest month in which you can book a flight from Wisconsin to Portland, Maine (average of $88). Flying from Wisconsin to Portland, Maine in January is currently the most expensive (average of $230). 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 Wisconsin to Portland, Maine?

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.

  • How long is the flight from Wisconsin to Portland, Maine?

    Departing from Wisconsin to Portland, Maine will take you 2h 39m. The distance between Wisconsin and Portland, Maine is about 1132 mi. This flight may include one or multiple stops.

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

    For one-way options, check prices for American Airlines. According to our data, you can fly for as low as $86. Users have also found prices from $118 and $125 on Southwest and Delta, 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, October is the cheapest month in which you can book a flight from Wisconsin to Portland, Maine (average of $88). Flying from Wisconsin to Portland, Maine in January is currently the most expensive (average of $230). 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 Portland?

Book flights to Portland if you plan to visit one of these locations
North Conway
Brunswick
Auburn
Conway

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Top 4 airlines flying from Wisconsin to Portland

Discover the top 4 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 December 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$238Average$462FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$246Average$387FlexibilityNo cancel feeOn-time63%
DeltaCheapest$251Average$395FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$267Average$442FlexibilityNo cancel feeOn-time69%

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