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Wisconsin

$90+ Cheap flights from Portland, ME (PWM) to Wisconsin

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 4/29. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MKE
Apr 2 — Apr 91
Wed 4/2
Wed 4/9
1 adult, Economy
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Cheap flight deals from Portland to Wisconsin

Keep the following information in mind while searching for Portland to Wisconsin flight deals. Data was last updated March 28, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$158
(Booking.com)

One-way from

$90
(United Airlines)

Popular in

December

Cheapest in

July

Average price

$466
Provider with most accurate pricing for Portland-Milwaukee-Mitchell flight deals.
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Provider most trusted by Cheapflights users for Portland-Milwaukee-Mitchell flights.
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From Portland to Wisconsin
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One-way flight from Portland to Wisconsin
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Highest demand for flights based on searches. 4% potential increase in price ($17 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in March 2025
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Find flight deals from Portland to Wisconsin

Cheapest flights from Portland to Wisconsin
Explore the most affordable flight options available from Portland to Wisconsin. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 28, 2025.

This Booking.com deal was found by Cheapflights users on 3/27. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/2212:41 pmPWM - MSP
Nonstop3h 13mSun Country Air
Sun 5/257:54 amMSP - PWM
Nonstop2h 41mSun Country Air
Deal found 3/27$158
This Delta deal was found by Cheapflights users on 3/27. 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.
Thu 5/2911:33 amPWM - ORD
2 stops8h 04mDelta
Tue 6/31:30 pmORD - PWM
2 stops9h 44mDelta
Deal found 3/27$227
This United Airlines deal was found by Cheapflights users on 3/27. 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.
Wed 5/76:13 amPWM - ORD
Nonstop2h 52mUnited Airlines
Fri 5/95:53 pmORD - PWM
Nonstop2h 23mUnited Airlines
Deal found 3/27$228
This American Airlines deal was found by Cheapflights users on 3/27. 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.
Thu 5/296:00 amPWM - MSN
1 stop5h 10mAmerican Airlines
Tue 6/34:53 pmMSN - PWM
1 stop6h 02mAmerican Airlines
Deal found 3/27$229
This American Airlines deal was found by Cheapflights users on 3/27. 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.
Sat 6/76:00 amPWM - ORD
Nonstop2h 59mAmerican Airlines
Wed 6/117:10 pmORD - PWM
Nonstop2h 33mAmerican Airlines
Deal found 3/27$234
This Delta deal was found by Cheapflights users on 3/26. 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 7/1011:59 amPWM - MSP
Nonstop3h 11mDelta
Mon 7/147:05 amMSP - PWM
Nonstop2h 51mDelta
Deal found 3/26$239
This Delta deal was found by Cheapflights users on 3/26. 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 5/12:59 pmPWM - MKE
1 stop6h 13mDelta
Mon 5/56:44 pmMKE - PWM
1 stop3h 30mDelta
Deal found 3/26$239
This Booking.com deal was found by Cheapflights users on 3/27. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/1310:08 amPWM - ORD
1 stop23h 36mFrontier
Wed 4/1611:45 amORD - PWM
1 stop20h 27mFrontier
Deal found 3/27$248
This JetBlue deal was found by Cheapflights users on 3/27. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/133:35 pmPWM - ORD
1 stop7h 19mJetBlue
Fri 5/164:03 pmORD - PWM
1 stop5h 56mJetBlue
Deal found 3/27$252
This United Airlines deal was found by Cheapflights users on 3/27. 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.
Sat 5/246:00 amPWM - MKE
1 stop5h 13mUnited Airlines
Tue 5/275:15 amMKE - PWM
1 stop4h 34mUnited Airlines
Deal found 3/27$257
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/44:01 pmPWM - MSP
1 stop5h 46mAmerican Airlines
Wed 6/112:08 pmMSP - PWM
1 stop5h 47mAmerican Airlines
Deal found 3/25$259
This Delta deal was found by Cheapflights users on 3/26. 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 4/167:00 amPWM - MSN
1 stop6h 44mDelta
Mon 4/214:00 pmMSN - PWM
1 stop6h 15mDelta
Deal found 3/26$259

Cheapflights Fare Finder

Customize your flight search to find flights from Portland to Wisconsin 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 28, 2025.
Use the filters below to find and compare flights from Portland to Wisconsin that are best for you.

Fly from

Portland

Fly to

Wisconsin

Route

Depart

Return

Price

PortlandMinneapolis

PWM - MSP

PWMMSP

Portland

Thu 5/22

12:41 pm-2:54 pm

Nonstop3h 13m

Minneapolis St Paul

Sun 5/25

7:54 am-11:35 am

Nonstop2h 41m

$158

PortlandChicago

PWM - ORD

PWMORD

Portland

Thu 5/29

11:33 am-6:37 pm

2 stops8h 04m

Chicago O'Hare Intl

Tue 6/3

1:30 pm-12:14 am

2 stops9h 44m

$227

PortlandChicago

PWM - ORD

PWMORD

Portland

Wed 5/7

6:13 am-8:05 am

Nonstop2h 52m

Chicago O'Hare Intl

Fri 5/9

5:53 pm-9:16 pm

Nonstop2h 23m

$228

PortlandMadison

PWM - MSN

PWMMSN

Portland

Thu 5/29

6:00 am-10:10 am

1 stop5h 10m

Madison Truax Field

Tue 6/3

4:53 pm-11:55 pm

1 stop6h 02m

$229

PortlandChicago

PWM - ORD

PWMORD

Portland

Sat 6/7

6:00 am-7:59 am

Nonstop2h 59m

Chicago O'Hare Intl

Wed 6/11

7:10 pm-10:43 pm

Nonstop2h 33m

$234

PortlandMinneapolis

PWM - MSP

PWMMSP

Portland

Thu 7/10

11:59 am-2:10 pm

Nonstop3h 11m

Minneapolis St Paul

Mon 7/14

7:05 am-10:56 am

Nonstop2h 51m

$239

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

Thu 5/1

2:59 pm-8:12 pm

1 stop6h 13m

Milwaukee-Mitchell

Mon 5/5

6:44 pm-11:14 pm

1 stop3h 30m

$239

PortlandChicago

PWM - ORD

PWMORD

Portland

Mon 4/7

7:22 pm-8:27 am

1 stop14h 05m

Chicago O'Hare Intl

Wed 4/9

11:45 am-9:27 am

1 stop20h 42m

$248

PortlandChicago

PWM - ORD

PWMORD

Portland

Tue 5/13

3:35 pm-9:54 pm

1 stop7h 19m

Chicago O'Hare Intl

Fri 5/16

4:03 pm-10:59 pm

1 stop5h 56m

$252

PortlandMilwaukee

PWM - MKE

PWMMKE

Portland

Sat 5/24

6:00 am-10:13 am

1 stop5h 13m

Milwaukee-Mitchell

Tue 5/27

5:15 am-10:49 am

1 stop4h 34m

$257

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/27

Showing 1-10 of 55 results
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Best time to book a flight from Portland to Wisconsin

Have a flexible travel schedule? Discover the best time to fly to Wisconsin from Portland 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 Portland to Wisconsin

What is the cheapest month to book a flight from Portland, Maine to Wisconsin?

Currently, February is the cheapest month in which you can book a flight from Portland, Maine to Wisconsin (average of $280). Flying from Portland, Maine to Wisconsin in June is currently the most expensive (average of $376). 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.

What is the cheapest time of day to fly from PWM to WI?

Find hourly flight availability from Portland to Wisconsin. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated March 28, 2025.

When flying from Portland, Maine to Wisconsin, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Rainfall in Wisconsin by month

Plan your trip to Wisconsin by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Wisconsin ranges from 1.4 - 4.0 inches per month. June is typically the wettest month, when rainfall can reach 4.0 in. January is typically the driest time to visit Wisconsin when rainfall is around 1.4 in.

Temperature in Wisconsin by month

Plan your trip to Wisconsin by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Wisconsin, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 21.2 F).

Reviews of airlines servicing Wisconsin

Get insights into the airlines that provide service to Wisconsin. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Wisconsin. Reviews last updated March 28, 2025.
Read reviews from past customers who have flown Southwest, Delta and United Airlines from Portland to Wisconsin. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.1
Very good
4,273 reviews

Entertainment

7.6

Overall

8.1

Food

7.1

Comfort

8.1

Boarding

8.2

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Southwest
8.1
Very good
4,273 reviews
Southwest
8.1
Very good
4,273 reviews

Entertainment

7.6

Overall

8.1

Food

7.1

Comfort

8.1

Boarding

8.2

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
Delta
8.0
Very good
7,896 reviews
Southwest
8.1
Very good
4,273 reviews

Entertainment

7.6

Overall

8.1

Food

7.1

Comfort

8.1

Boarding

8.2

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
United Airlines
7.4
Good
8,603 reviews
Southwest
8.1
Very good
4,273 reviews

Entertainment

7.6

Overall

8.1

Food

7.1

Comfort

8.1

Boarding

8.2

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
JetBlue
7.3
Good
2,923 reviews
Southwest
8.1
Very good
4,273 reviews

Entertainment

7.6

Overall

8.1

Food

7.1

Comfort

8.1

Boarding

8.2

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.
American Airlines
7.2
Good
10,000 reviews
Southwest
8.1
Very good
4,273 reviews

Entertainment

7.6

Overall

8.1

Food

7.1

Comfort

8.1

Boarding

8.2

Crew

8.6

Reviews

1 / 20
8.0
Excellent

Ila,Mar 2025

HOU - DAL

Our original flight was delayed. We were able to change our flight and got home at close to the same time. Looking forward to when you have assigned seating.

Related info for your journey

Find useful and relevant information for your journey from Portland to Wisconsin. 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 from for flights from Portland to Wisconsin?

    Portland (PWM), located 2.9 mi from the city center, is the airport you fly out of when you book flights from Portland to Wisconsin.

  • What are the cheapest airlines to fly from Portland, Maine to Wisconsin one-way?

    The cheapest airlines for a one-way flight from Portland, Maine to Wisconsin are United Airlines ($90), JetBlue ($92), and Southwest ($100).

  • What are the most popular routes from Portland, Maine to Wisconsin?

    The most popular flight routes from Portland, Maine to Wisconsin are Portland - Chicago O'Hare Intl, Portland - Minneapolis St Paul and Portland - Milwaukee-Mitchell.

  • Can I find deals for flights from Portland to Wisconsin that include hotel bookings?

    Yes. In addition to deals on Portland to Wisconsin flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Portland to Wisconsin?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Portland to Wisconsin.

  • Can I find deals for business class flights from Portland to Wisconsin?

    Yes. Cheapflights offers flight deals from Portland to Wisconsin 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 Portland, Maine to Wisconsin?

    Currently, February is the cheapest month in which you can book a flight from Portland, Maine to Wisconsin (average of $280). Flying from Portland, Maine to Wisconsin in June is currently the most expensive (average of $376). 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

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Alternative routes for Portland to Wisconsin

See prices for flight routes from nearby airports that may be better suited for you.
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Top 4 airlines flying from Portland to Wisconsin

Discover the top 4 airlines that operate flights from Portland to Wisconsin. 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 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$206Average$364FlexibilityNo cancel feeOn-time71%
DeltaCheapest$248Average$408FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$268Average$376FlexibilityNo cancel feeOn-time63%
United AirlinesCheapest$281Average$484FlexibilityNo cancel feeOn-time69%
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