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$85+ 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 7/18. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — PWM
Jul 8 — Jul 151
Wed 7/8
Wed 7/15
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 June 8, 2026.

This Super.com deal was found by Cheapflights users on 6/6. 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.
Sun 7/57:55 am
MSP
-
PWM
Nonstop2h 42m
Sun Country Air
Fri 7/177:41 pm
PWM
-
MSP
Nonstop3h 12m
Sun Country Air
Deal found 6/6$206
This Super.com deal was found by Cheapflights users on 6/7. 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.
Mon 10/198:25 am
MSP
-
PWM
Nonstop2h 41m
Sun Country Air
Thu 10/2212:28 pm
PWM
-
MSP
Nonstop3h 03m
Sun Country Air
Deal found 6/7$216
This Cheapflightsfares deal was found by Cheapflights users on 6/5. 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.
Sat 6/138:20 am
MSP
-
PWM
Nonstop2h 39m
Sun Country Air
Sat 6/201:02 pm
PWM
-
MSP
Nonstop3h 08m
Sun Country Air
Deal found 6/5$227
This Super.com deal was found by Cheapflights users on 6/7. 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.
Mon 7/67:35 am
MSP
-
PWM
Nonstop2h 42m
Sun Country Air
Fri 7/177:41 pm
PWM
-
MSP
Nonstop3h 12m
Sun Country Air
Deal found 6/7$236
This Cheapflightsfares deal was found by Cheapflights users on 6/4. 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.
Sat 6/138:20 am
MSP
-
PWM
Nonstop2h 39m
Sun Country Air
Sun 6/1412:40 pm
PWM
-
MSP
Nonstop3h 08m
Sun Country Air
Deal found 6/4$237
This Super.com deal was found by Cheapflights users on 6/4. 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.
Thu 6/118:00 am
MSP
-
PWM
Nonstop2h 39m
Sun Country Air
Sun 6/1412:40 pm
PWM
-
MSP
Nonstop3h 08m
Sun Country Air
Deal found 6/4$246
This Cheapflightsfares deal was found by Cheapflights users on 6/6. 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.
Sun 7/57:55 am
MSP
-
PWM
Nonstop2h 42m
Sun Country Air
Thu 7/1612:57 pm
PWM
-
MSP
Nonstop3h 09m
Sun Country Air
Deal found 6/6$247
This Super.com deal was found by Cheapflights users on 6/7. 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 7/173:10 pm
MSP
-
PWM
Nonstop2h 41m
Sun Country Air
Thu 7/2311:09 am
PWM
-
MSP
Nonstop3h 09m
Sun Country Air
Deal found 6/7$256
This Sun Country Air deal was found by Cheapflights users on 6/6. 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.
Fri 7/106:35 am
MSP
-
PWM
Nonstop2h 39m
Sun Country Air
Fri 7/177:41 pm
PWM
-
MSP
Nonstop3h 12m
Sun Country Air
Deal found 6/6$258
This CheapOair deal was found by Cheapflights users on 6/6. 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.
Sat 7/46:05 pm
ORD
-
PWM
1 stop16h 32m
Multiple Airlines
Sat 7/112:40 pm
PWM
-
ORD
1 stop8h 18m
Multiple Airlines
Deal found 6/6$279
This CheapOair deal was found by Cheapflights users on 6/7. 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.
Wed 7/156:00 am
ORD
-
PWM
1 stop6h 45m
JetBlue
Sat 7/186:41 am
PWM
-
ORD
1 stop16h 17m
JetBlue
Deal found 6/7$281
This CheapOair deal was found by Cheapflights users on 6/7. 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.
Thu 8/135:27 pm
ORD
-
PWM
1 stop5h 47m
JetBlue
Mon 8/176:00 am
PWM
-
ORD
1 stop27h 48m
JetBlue
Deal found 6/7$289

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 June 8, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$206
(Super.com)

One-way from

$85
(JetBlue)

Popular in

December

Cheapest in

January

Average price

$467
Provider with most accurate pricing for Milwaukee-Mitchell-Portland flight deals.
Search Deals
Provider most trusted by Cheapflights users for Milwaukee-Mitchell-Portland 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. 7% potential increase in price ($37 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($22 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in June 2026
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 June 8, 2026.
Use the filters below to find and compare flights from Wisconsin to Portland that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Tue 10/27

8:00 am-4:09 pm

1 stop7h 09m

Portland

Sat 10/31

4:48 pm-8:54 pm

1 stop5h 06m

$291

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Tue 8/25

2:44 pm-9:23 pm

1 stop5h 39m

Portland

Wed 9/2

7:40 am-1:42 pm

1 stop7h 02m

$291

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Thu 6/25

5:22 pm-12:25 am

1 stop6h 03m

Portland

Tue 6/30

1:25 pm-9:29 pm

1 stop9h 04m

$292

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Wed 9/23

1:30 pm-11:59 pm

2 stops9h 29m

Portland

Wed 9/30

4:45 pm-9:15 pm

1 stop5h 30m

$308

Green BayPortland

GRB - PWM

GRBPWM

Green Bay Austin-Straubel

Tue 11/10

3:44 pm-9:27 pm

1 stop4h 43m

Portland

Sat 11/14

4:48 pm-10:49 pm

1 stop7h 01m

$311

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Tue 8/11

11:22 am-12:59 am

2 stops12h 37m

Portland

Tue 8/18

6:00 am-4:20 pm

2 stops11h 20m

$323

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Sat 10/24

9:26 am-4:10 pm

1 stop5h 44m

Portland

Thu 10/29

12:50 pm-4:37 pm

1 stop4h 47m

$323

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Tue 9/1

12:29 pm-12:59 am

2 stops11h 30m

Portland

Sat 9/5

11:50 am-5:41 pm

1 stop6h 51m

$332

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Tue 7/21

2:07 pm-11:30 pm

2 stops8h 23m

Portland

Tue 7/28

6:59 pm-11:53 pm

1 stop5h 54m

$332
Quickest round-trip

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Sat 7/4

3:46 pm-9:41 pm

1 stop4h 55m

Portland

Sat 7/11

6:00 am-10:11 am

1 stop5h 11m

$338

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/5

Showing 1-10 of 60 resultsSorted by cheapest first
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6

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, July is the cheapest month in which you can book a flight from Wisconsin to Portland, Maine (average of $135). Flying from Wisconsin to Portland, Maine in December is currently the most expensive (average of $384). 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 6h 03m. The distance between Wisconsin and Portland, Maine is about 897 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 $125 and $158 on Delta and United Airlines, 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 Milwaukee-Mitchell - 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, July is the cheapest month in which you can book a flight from Wisconsin to Portland, Maine (average of $135). Flying from Wisconsin to Portland, Maine in December is currently the most expensive (average of $384). 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
Lewiston
Conway

Browse thousands of different options on Cheapflights for your next trip

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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 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 June 8, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$236Average$422FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$238Average$461FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$251Average$436FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$276Average$446FlexibilityNo cancel feeOn-time69%

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