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Portland

$99+ 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 4/22. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — PWM
Apr 25 — May 21
Sat 4/25
Sat 5/2
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 March 26, 2026.

This Sun Country Air deal was found by Cheapflights users on 3/21. 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.
Sun 8/238:00 am
MSP
-
PWM
Nonstop2h 44m
Sun Country Air
Fri 8/2812:29 pm
PWM
-
MSP
Nonstop3h 06m
Sun Country Air
Deal found 3/21$208
This Super.com deal was found by Cheapflights users on 3/25. 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 7/58:00 am
MSP
-
PWM
Nonstop2h 39m
Sun Country Air
Thu 7/912:40 pm
PWM
-
MSP
Nonstop3h 08m
Sun Country Air
Deal found 3/25$217
This Sun Country Air deal was found by Cheapflights users on 3/25. 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.
Sat 7/48:20 am
MSP
-
PWM
Nonstop2h 39m
Sun Country Air
Thu 7/912:40 pm
PWM
-
MSP
Nonstop3h 08m
Sun Country Air
Deal found 3/25$224
This Priceline deal was found by Cheapflights users on 3/22. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/247:50 am
MSP
-
PWM
Nonstop2h 46m
Sun Country Air
Fri 8/2812:29 pm
PWM
-
MSP
Nonstop3h 06m
Sun Country Air
Deal found 3/22$227
This Delta deal was found by Cheapflights users on 3/25. 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 5/296:31 pm
ORD
-
PWM
1 stop5h 12m
Delta
Wed 6/312:55 pm
PWM
-
ORD
1 stop6h 10m
Delta
Deal found 3/25$231
This Delta deal was found by Cheapflights users on 3/25. 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 6/61:44 pm
ORD
-
PWM
2 stops9h 59m
Delta
Mon 6/86:57 pm
PWM
-
ORD
1 stop6h 02m
Delta
Deal found 3/25$234
This Sun Country Air deal was found by Cheapflights users on 3/24. 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.
Sun 9/2011:10 am
MSP
-
PWM
Nonstop2h 41m
Sun Country Air
Thu 9/2412:18 pm
PWM
-
MSP
Nonstop3h 03m
Sun Country Air
Deal found 3/24$234
This KAYAK deal was found by Cheapflights users on 3/23. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/146:00 am
ORD
-
PWM
1 stop6h 29m
JetBlue
Tue 6/162:25 pm
PWM
-
ORD
1 stop7h 19m
JetBlue
Deal found 3/23$239
This Southwest deal was found by Cheapflights users on 3/22. 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 5/292:40 pm
ORD
-
PWM
2 stops7h 45m
Southwest
Tue 6/21:00 pm
PWM
-
ORD
2 stops9h 55m
Southwest
Deal found 3/22$240
This Delta deal was found by Cheapflights users on 3/24. 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 5/86:31 pm
ORD
-
PWM
1 stop5h 12m
Delta
Tue 5/1211:03 am
PWM
-
ORD
1 stop6h 31m
Delta
Deal found 3/24$243
This Delta deal was found by Cheapflights users on 3/25. 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 4/166:04 am
ORD
-
PWM
1 stop7h 07m
Delta
Mon 4/205:26 pm
PWM
-
ORD
1 stop5h 49m
Delta
Deal found 3/25$247
This Cheapflightsfares deal was found by Cheapflights users on 3/25. 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.
Fri 7/177:55 am
MSP
-
PWM
Nonstop2h 42m
Sun Country Air
Fri 7/2412:40 pm
PWM
-
MSP
Nonstop3h 08m
Sun Country Air
Deal found 3/25$247

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 March 26, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$208
(Sun Country Air)

One-way from

$99
(Delta)

Popular in

December

Cheapest in

April

Average price

$416
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. 16% potential increase in price ($76 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 March 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 March 26, 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

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Fri 5/29

11:09 am-11:09 pm

2 stops11h 00m

Portland

Tue 6/2

5:51 pm-10:36 pm

1 stop5h 45m

$270

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Fri 5/8

5:56 pm-9:19 pm

Nonstop2h 23m

Portland

Tue 5/12

7:10 pm-11:44 pm

1 stop5h 34m

$274

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Fri 5/29

3:53 pm-11:51 pm

1 stop6h 58m

Portland

Mon 6/1

6:25 pm-8:34 pm

Nonstop3h 09m

$279

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Thu 6/4

3:53 pm-11:51 pm

1 stop6h 58m

Portland

Mon 6/8

6:00 am-8:00 am

Nonstop3h 00m

$279

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Fri 6/5

6:18 pm-9:51 pm

Nonstop2h 33m

Portland

Sun 6/7

5:15 am-11:54 am

1 stop7h 39m

$279

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Fri 5/8

6:31 pm-12:43 am

1 stop5h 12m

Portland

Fri 5/15

4:48 pm-8:14 pm

1 stop4h 26m

$289

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Fri 7/31

11:20 am-5:52 pm

1 stop5h 32m

Portland

Tue 8/4

6:57 pm-11:53 pm

1 stop5h 56m

$289

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Thu 5/7

2:00 pm-12:43 am

2 stops9h 43m

Portland

Thu 5/14

12:55 pm-6:05 pm

1 stop6h 10m

$294

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Thu 5/28

2:50 pm-11:51 pm

2 stops8h 01m

Portland

Tue 6/2

6:00 am-10:09 am

1 stop5h 09m

$295
Quickest round-trip

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Tue 4/7

10:45 am-2:20 pm

Nonstop2h 35m

Portland

Sat 4/11

6:33 pm-8:43 pm

Nonstop3h 10m

$309

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/26

Showing 1-10 of 60 resultsSorted by cheapest first
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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, September is the cheapest month in which you can book a flight from Wisconsin to Portland, Maine (average of $93). 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.

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 5h 12m. 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 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, September is the cheapest month in which you can book a flight from Wisconsin to Portland, Maine (average of $93). 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
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 March 26, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$236Average$433FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$238Average$435FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$258Average$422FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$266Average$394FlexibilityNo cancel feeOn-time63%

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