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$98+ 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 8/27. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — PWM
Aug 24 — Aug 311
Mon 8/24
Mon 8/31
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 July 25, 2026.

This United Airlines deal was found by Cheapflights users on 7/22. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/275:50 pm
ORD
-
PWM
Nonstop2h 33m
United Airlines
Tue 9/15:03 pm
PWM
-
ORD
Nonstop2h 57m
United Airlines
Deal found 7/22$272
This American Airlines deal was found by Cheapflights users on 7/24. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2210:53 am
ORD
-
PWM
1 stop4h 40m
American Airlines
Mon 8/246:09 pm
PWM
-
ORD
Nonstop3h 21m
American Airlines
Deal found 7/24$273
This Delta deal was found by Cheapflights users on 7/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/178:55 am
ORD
-
PWM
2 stops11h 06m
Delta
Sat 10/318:00 am
PWM
-
ORD
2 stops11h 59m
Delta
Deal found 7/22$275
This American Airlines deal was found by Cheapflights users on 7/23. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/227:13 pm
ORD
-
PWM
Nonstop2h 35m
American Airlines
Sat 8/296:46 am
PWM
-
ORD
Nonstop3h 14m
American Airlines
Deal found 7/23$276
This American Airlines deal was found by Cheapflights users on 7/22. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/36:00 am
ORD
-
PWM
1 stop5h 40m
American Airlines
Sat 9/55:13 pm
PWM
-
ORD
1 stop5h 28m
American Airlines
Deal found 7/22$277
This Cheapflightsfares deal was found by Cheapflights users on 7/24. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/238:00 am
MSP
-
PWM
Nonstop2h 41m
Sun Country Air
Fri 8/2812:25 pm
PWM
-
MSP
Nonstop3h 03m
Sun Country Air
Deal found 7/24$277
This American Airlines deal was found by Cheapflights users on 7/20. 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.
Thu 9/177:59 pm
ORD
-
PWM
Nonstop2h 48m
American Airlines
Mon 9/216:30 am
PWM
-
ORD
Nonstop3h 08m
American Airlines
Deal found 7/20$279
This Delta deal was found by Cheapflights users on 7/20. 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.
Wed 8/266:00 am
ORD
-
PWM
1 stop7h 13m
Delta
Sat 9/56:10 am
PWM
-
ORD
2 stops11h 41m
Delta
Deal found 7/20$282
This Priceline deal was found by Cheapflights users on 7/23. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/36:00 am
ORD
-
PWM
1 stop6h 45m
JetBlue
Thu 9/106:00 am
PWM
-
ORD
1 stop4h 58m
JetBlue
Deal found 7/23$284
This Super.com deal was found by Cheapflights users on 7/22. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/227:45 am
MSP
-
PWM
Nonstop2h 44m
Sun Country Air
Sun 10/2512:28 pm
PWM
-
MSP
Nonstop3h 03m
Sun Country Air
Deal found 7/22$286
This Delta deal was found by Cheapflights users on 7/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/245:40 pm
ORD
-
PWM
1 stop4h 50m
Delta
Wed 8/262:53 pm
PWM
-
ORD
1 stop7h 59m
Delta
Deal found 7/21$287
This Cheapflightsfares deal was found by Cheapflights users on 7/21. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/168:10 am
MSP
-
PWM
Nonstop2h 39m
Sun Country Air
Thu 8/2012:36 pm
PWM
-
MSP
Nonstop3h 03m
Sun Country Air
Deal found 7/21$287

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 July 25, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$272
(United Airlines)

One-way from

$98
(Super.com)

Popular in

December

Cheapest in

January

Average price

$486
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 ($95 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 8% potential price decrease ($38 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 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 July 25, 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

Mon 8/17

1:41 pm-11:30 pm

2 stops8h 49m

Portland

Thu 8/20

11:50 am-7:30 pm

1 stop8h 40m

$292

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Tue 9/8

6:00 am-12:30 pm

1 stop5h 30m

Portland

Tue 9/15

6:00 am-9:58 am

1 stop4h 58m

$294

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Tue 9/8

6:00 am-1:16 pm

1 stop6h 16m

Portland

Tue 9/15

6:30 am-4:37 pm

2 stops11h 07m

$297

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Sat 9/26

4:10 pm-11:59 pm

2 stops6h 49m

Portland

Wed 9/30

8:03 am-1:37 pm

2 stops6h 34m

$301

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Mon 8/17

1:41 pm-11:30 pm

2 stops8h 49m

Portland

Mon 8/24

12:47 pm-4:17 pm

1 stop4h 30m

$304

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Tue 9/29

6:49 am-2:38 pm

2 stops6h 49m

Portland

Sat 10/3

8:03 am-1:37 pm

2 stops6h 34m

$310

Green BayPortland

GRB - PWM

GRBPWM

Green Bay Austin-Straubel

Tue 8/18

5:24 am-4:50 pm

2 stops10h 26m

Portland

Mon 8/24

12:47 pm-4:55 pm

1 stop5h 08m

$314

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Sat 9/26

5:00 am-10:40 am

1 stop4h 40m

Portland

Sat 10/3

6:00 am-10:48 am

1 stop5h 48m

$317

DuluthPortland

DLH - PWM

DLHPWM

Duluth Intl

Fri 10/30

5:14 am-10:50 am

1 stop4h 36m

Portland

Tue 11/3

11:55 am-3:41 pm

1 stop4h 46m

$318

Green BayPortland

GRB - PWM

GRBPWM

Green Bay Austin-Straubel

Sat 8/22

2:31 pm-9:23 pm

1 stop5h 52m

Portland

Sat 8/29

6:03 am-11:55 am

1 stop6h 52m

$319

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/20

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, January is the cheapest month in which you can book a flight from Wisconsin to Portland, Maine (average of $340). Flying from Wisconsin to Portland, Maine in December is currently the most expensive (average of $583). 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?

Airfare is below average for this route at the moment.
Wisconsin to Portland, Maine flights typically cost between $428 and $605 in September.
The cheapest round-trip price found within the last 5 days was $317 on American Airlines (Sep 19-Sep 26).

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 30m. 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 Delta. According to our data, you can fly for as low as $125. Users have also found prices from $133 and $158 on American Airlines 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 Appleton Intl - 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 $340). Flying from Wisconsin to Portland, Maine in December is currently the most expensive (average of $583). 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
Lewiston
Brunswick
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 July 25, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$236Average$427FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$238Average$472FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$266Average$508FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$276Average$450FlexibilityNo cancel feeOn-time69%

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