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Portland

$115+ 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 3/2. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — PWM
mar 7 — mar 141
sáb 3/7
sáb 3/14
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 fevereiro 5, 2026.

This Mytrip deal was found by Cheapflights users on 2/2. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb 7/48:20 am
MSP
-
PWM
Nonstop2h 39m
Sun Country Air
qui 7/912:40 pm
PWM
-
MSP
Nonstop3h 08m
Sun Country Air
Deal found 2/2$178
This Kiwi.com deal was found by Cheapflights users on 2/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb 7/188:35 am
MSP
-
PWM
Nonstop2h 39m
Sun Country Air
sex 7/2412:40 pm
PWM
-
MSP
Nonstop3h 08m
Sun Country Air
Deal found 2/4$197
This Sun Country Air deal was found by Cheapflights users on 2/4. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
seg 7/137:55 am
MSP
-
PWM
Nonstop2h 42m
Sun Country Air
qui 7/1612:58 pm
PWM
-
MSP
Nonstop3h 08m
Sun Country Air
Deal found 2/4$198
This Sun Country Air deal was found by Cheapflights users on 2/3. 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.
sex 7/177:55 am
MSP
-
PWM
Nonstop2h 42m
Sun Country Air
sáb 7/2512:34 pm
PWM
-
MSP
Nonstop3h 08m
Sun Country Air
Deal found 2/3$208
This United Airlines deal was found by Cheapflights users on 2/3. 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.
qua 6/176:25 pm
ORD
-
PWM
Nonstop2h 33m
United Airlines
qua 6/246:00 am
PWM
-
ORD
Nonstop3h 00m
United Airlines
Deal found 2/3$209
This American Airlines deal was found by Cheapflights users on 2/3. 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.
sex 3/208:02 pm
ORD
-
PWM
Nonstop2h 32m
American Airlines
sex 3/276:17 am
PWM
-
ORD
Nonstop3h 17m
American Airlines
Deal found 2/3$210
This Cheapflightsfares deal was found by Cheapflights users on 2/4. 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.
sáb 6/278:20 am
MSP
-
PWM
Nonstop2h 39m
Sun Country Air
sáb 7/412:58 pm
PWM
-
MSP
Nonstop3h 08m
Sun Country Air
Deal found 2/4$217
This Sun Country Air deal was found by Cheapflights users on 2/5. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sex 8/78:10 am
MSP
-
PWM
Nonstop2h 39m
Sun Country Air
sex 8/1412:46 pm
PWM
-
MSP
Nonstop3h 08m
Sun Country Air
Deal found 2/5$218
This Cheapflightsfares deal was found by Cheapflights users on 2/3. 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.
sáb 6/208:20 am
MSP
-
PWM
Nonstop2h 39m
Sun Country Air
sáb 7/412:58 pm
PWM
-
MSP
Nonstop3h 08m
Sun Country Air
Deal found 2/3$227
This Sun Country Air deal was found by Cheapflights users on 2/5. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom 7/198:05 am
MSP
-
PWM
Nonstop2h 39m
Sun Country Air
qui 7/231:16 pm
PWM
-
MSP
Nonstop3h 11m
Sun Country Air
Deal found 2/5$228
This Delta deal was found by Cheapflights users on 2/3. 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.
sáb 9/511:10 am
ORD
-
PWM
1 stop5h 57m
Delta
qui 9/106:50 pm
PWM
-
ORD
1 stop6h 07m
Delta
Deal found 2/3$229
This United Airlines deal was found by Cheapflights users on 2/4. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
qua 4/296:10 pm
ORD
-
PWM
Nonstop2h 30m
United Airlines
dom 5/39:39 am
PWM
-
ORD
Nonstop2h 56m
United Airlines
Deal found 2/4$230

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 fevereiro 5, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$178
(Mytrip)

One-way from

$115
(Delta)

Popular in

December

Cheapest in

April

Average price

$344
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. 17% potential increase in price ($85 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($24 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 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 fevereiro 5, 2026.
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

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

sex 5/1

5:56 pm-9:19 pm

Nonstop2h 23m

Portland

dom 5/3

9:39 am-11:35 am

Nonstop2h 56m

$209

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

sáb 3/28

8:02 pm-11:34 pm

Nonstop2h 32m

Portland

dom 4/5

6:17 am-8:34 am

Nonstop3h 17m

$209

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

sáb 3/28

5:47 pm-9:04 pm

Nonstop2h 17m

Portland

ter 3/31

6:04 am-8:00 am

Nonstop2h 56m

$209

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

sáb 3/21

8:02 pm-11:34 pm

Nonstop2h 32m

Portland

qua 3/25

5:58 pm-8:08 pm

Nonstop3h 10m

$209

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

qui 3/12

1:45 pm-5:07 pm

Nonstop2h 22m

Portland

seg 3/16

6:00 pm-8:10 pm

Nonstop3h 10m

$209

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

ter 2/24

6:25 pm-12:18 am

1 stop4h 53m

Portland

sáb 2/28

12:45 pm-4:41 pm

1 stop4h 56m

$229

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

qui 3/12

7:00 am-1:50 pm

1 stop5h 50m

Portland

seg 3/16

5:48 pm-10:12 pm

1 stop5h 24m

$229

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

qua 4/29

8:52 am-3:57 pm

1 stop6h 05m

Portland

qua 5/13

1:18 pm-7:09 pm

1 stop6h 51m

$229

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

sex 3/6

1:45 pm-5:07 pm

Nonstop2h 22m

Portland

dom 3/8

5:40 pm-7:50 pm

Nonstop3h 10m

$229

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

sex 3/20

8:02 pm-11:34 pm

Nonstop2h 32m

Portland

qua 3/25

5:58 pm-8:08 pm

Nonstop3h 10m

$229

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/1

Showing 1-10 of 60 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 December is currently the most expensive (average of $217). 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.

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 23m. 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 $118 and $124 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 December is currently the most expensive (average of $217). 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

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 fevereiro 5, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$238Average$461FlexibilityNo cancel feeOn-time71%
DeltaCheapest$238Average$392FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$246Average$386FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$258Average$431FlexibilityNo cancel feeOn-time69%

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