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$101+ 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 4/1. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — PWM
Nov 28 — Dec 51
Fri 11/28
Fri 12/5
1 adult, Economy
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Cheap flight deals from Wisconsin to Portland

Keep the following information in mind while searching for Wisconsin to Portland flight deals. Data was last updated October 29, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$245
(United Airlines)

One-way from

$101
(Priceline)

Popular in

December

Cheapest in

April

Average price

$452
Provider with most accurate pricing for Milwaukee-Mitchell-Portland flight deals.
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Provider most trusted by Cheapflights users for Milwaukee-Mitchell-Portland flights.
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From Wisconsin to Portland
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One-way flight from Wisconsin to Portland
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Highest demand for flights based on searches. 22% potential increase in price ($117 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Find 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 October 29, 2025.

This Delta deal was found by Cheapflights users on 10/28. 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 11/121:29 pmORD - PWM
1 stop7h 50mDelta
Tue 11/1811:25 amPWM - ORD
1 stop7h 55mDelta
Deal found 10/28$249
This American Airlines deal was found by Cheapflights users on 10/27. 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.
Fri 11/216:06 amORD - PWM
1 stop4h 40mAmerican Airlines
Sun 11/235:37 pmPWM - ORD
Nonstop3h 13mAmerican Airlines
Deal found 10/27$259
This United Airlines deal was found by Cheapflights users on 10/28. 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 12/52:32 pmATW - PWM
2 stops7h 37mUnited Airlines
Sat 12/136:00 amPWM - ATW
2 stops10h 07mUnited Airlines
Deal found 10/28$267
This Delta deal was found by Cheapflights users on 10/28. 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 11/1210:30 amORD - PWM
1 stop4h 30mDelta
Mon 11/171:25 pmPWM - ORD
1 stop6h 27mDelta
Deal found 10/28$269
This American Airlines deal was found by Cheapflights users on 10/28. 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 12/106:00 amGRB - PWM
2 stops8h 27mAmerican Airlines
Wed 12/175:46 amPWM - GRB
2 stops9h 43mAmerican Airlines
Deal found 10/28$270
This Delta deal was found by Cheapflights users on 10/28. 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 12/511:13 amATW - PWM
1 stop3h 54mDelta
Sat 12/1312:53 pmPWM - ATW
1 stop5h 36mDelta
Deal found 10/28$273
This Delta deal was found by Cheapflights users on 10/28. 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 11/127:00 amORD - PWM
1 stop5h 50mDelta
Thu 11/136:00 amPWM - ORD
2 stops11h 46mDelta
Deal found 10/28$274
This United Airlines deal was found by Cheapflights users on 10/27. 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 11/116:15 amMSN - PWM
1 stop6h 21mUnited Airlines
Fri 1/26:46 pmPWM - MSN
1 stop5h 11mUnited Airlines
Deal found 10/27$274
This Delta deal was found by Cheapflights users on 10/27. 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.
Tue 11/1110:35 amORD - PWM
1 stop12h 19mDelta
Mon 11/174:40 pmPWM - ORD
1 stop5h 04mDelta
Deal found 10/27$277
This Delta deal was found by Cheapflights users on 10/27. 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 11/75:20 amORD - PWM
1 stop6h 02mDelta
Sat 11/154:53 pmPWM - ORD
1 stop4h 36mDelta
Deal found 10/27$279
This Delta deal was found by Cheapflights users on 10/28. 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 11/75:20 amORD - PWM
1 stop6h 02mDelta
Tue 11/116:00 amPWM - ORD
2 stops11h 46mDelta
Deal found 10/28$284
This Delta deal was found by Cheapflights users on 10/27. 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.
Tue 11/111:25 pmORD - PWM
1 stop9h 29mDelta
Sat 11/154:53 pmPWM - ORD
1 stop4h 36mDelta
Deal found 10/27$287

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 October 29, 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

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Wed 3/11

7:30 am-1:51 pm

1 stop5h 21m

Portland

Thu 3/19

4:50 pm-8:38 pm

1 stop4h 48m

$249

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Wed 11/12

5:50 pm-11:19 pm

1 stop4h 29m

Portland

Sat 11/15

4:53 pm-8:29 pm

1 stop4h 36m

$249

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Mon 11/10

8:55 am-4:07 pm

1 stop6h 12m

Portland

Wed 11/12

4:40 pm-8:44 pm

1 stop5h 04m

$249

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Thu 11/13

7:00 am-1:50 pm

1 stop5h 50m

Portland

Sat 11/15

4:53 pm-8:29 pm

1 stop4h 36m

$249

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Mon 11/10

8:55 am-4:07 pm

1 stop6h 12m

Portland

Sat 11/15

6:00 am-1:55 pm

2 stops8h 55m

$254

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Tue 11/11

1:29 pm-11:19 pm

2 stops8h 50m

Portland

Tue 11/18

4:53 pm-8:29 pm

1 stop4h 36m

$254

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Tue 3/3

5:50 am-3:56 pm

2 stops9h 06m

Portland

Wed 3/4

6:00 am-10:22 am

1 stop5h 22m

$254

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Wed 11/12

1:29 pm-11:54 pm

2 stops9h 25m

Portland

Tue 11/18

2:30 pm-9:27 pm

1 stop7h 57m

$254

AppletonPortland

ATW - PWM

ATWPWM

Appleton Intl

Fri 12/5

2:32 pm-11:09 pm

2 stops7h 37m

Portland

Sat 12/13

6:00 am-3:07 pm

2 stops10h 07m

$267

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 11/8

7:10 am-12:00 pm

1 stop3h 50m

Portland

Tue 11/18

6:00 am-10:13 am

1 stop5h 13m

$269

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/29

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 January is currently the most expensive (average of $222). 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 5h 21m. 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 $115. Users have also found prices from $157 and $170 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 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 $222). 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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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 October 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$238Average$455FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$246Average$388FlexibilityNo cancel feeOn-time63%
DeltaCheapest$248Average$397FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$267Average$428FlexibilityNo cancel feeOn-time69%

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