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Wisconsin

$87+ 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 6/3. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MKE
Apr 9 — Apr 161
Thu 4/9
Thu 4/16
1 adult, Economy
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Cheap 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 10, 2026.

This Booking.com deal was found by Cheapflights users on 3/7. 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 8/2012:36 pm
PWM
-
MSP
Nonstop3h 06m
Sun Country Air
Sun 8/238:00 am
MSP
-
PWM
Nonstop2h 44m
Sun Country Air
Deal found 3/7$198
This United Airlines deal was found by Cheapflights users on 3/7. 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 4/46:33 pm
PWM
-
ORD
Nonstop3h 10m
United Airlines
Sun 4/126:10 pm
ORD
-
PWM
Nonstop2h 30m
United Airlines
Deal found 3/7$209
This Priceline deal was found by Cheapflights users on 3/8. 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.
Fri 7/1712:40 pm
PWM
-
MSP
Nonstop3h 08m
Sun Country Air
Mon 7/208:40 am
MSP
-
PWM
Nonstop2h 39m
Sun Country Air
Deal found 3/8$217
This United Airlines deal was found by Cheapflights users on 3/8. 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 5/611:08 am
PWM
-
ORD
1 stop6h 48m
United Airlines
Sat 5/95:56 pm
ORD
-
PWM
Nonstop2h 23m
United Airlines
Deal found 3/8$219
This Booking.com deal was found by Cheapflights users on 3/6. 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.
Fri 7/1712:40 pm
PWM
-
MSP
Nonstop3h 08m
Sun Country Air
Sun 7/198:05 am
MSP
-
PWM
Nonstop2h 39m
Sun Country Air
Deal found 3/6$228
This United Airlines deal was found by Cheapflights users on 3/8. 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 4/296:04 am
PWM
-
ORD
Nonstop2h 56m
United Airlines
Sun 5/36:55 am
ORD
-
PWM
Nonstop2h 28m
United Airlines
Deal found 3/8$229
This United Airlines deal was found by Cheapflights users on 3/8. 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 4/309:50 am
PWM
-
ORD
1 stop7h 40m
United Airlines
Sat 5/210:48 am
ORD
-
PWM
Nonstop2h 26m
United Airlines
Deal found 3/8$231
This Delta deal was found by Cheapflights users on 3/7. 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 4/44:48 pm
PWM
-
ORD
1 stop4h 34m
Delta
Tue 4/71:57 pm
ORD
-
PWM
2 stops8h 15m
Delta
Deal found 3/7$234
This Booking.com deal was found by Cheapflights users on 3/8. 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 7/3012:46 pm
PWM
-
MSP
Nonstop3h 08m
Sun Country Air
Sun 8/28:30 am
MSP
-
PWM
Nonstop2h 39m
Sun Country Air
Deal found 3/8$238
This American Airlines deal was found by Cheapflights users on 3/8. 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 5/166:01 pm
PWM
-
ORD
Nonstop3h 13m
American Airlines
Tue 5/192:05 pm
ORD
-
PWM
1 stop7h 08m
American Airlines
Deal found 3/8$238
This United Airlines deal was found by Cheapflights users on 3/9. 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.
Mon 4/66:04 am
PWM
-
ORD
Nonstop2h 56m
United Airlines
Mon 4/136:10 pm
ORD
-
PWM
Nonstop2h 30m
United Airlines
Deal found 3/9$241
This American Airlines deal was found by Cheapflights users on 3/7. 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 4/46:49 pm
PWM
-
ORD
1 stop4h 57m
American Airlines
Sun 4/127:49 pm
ORD
-
PWM
Nonstop2h 38m
American Airlines
Deal found 3/7$243

Find 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 10, 2026.

Round-trip from

$198
(Booking.com)

One-way from

$87
(JetBlue)

Popular in

September

Cheapest in

November

Average price

$524
From Portland to Wisconsin
Search Deals
One-way flight from Portland to Wisconsin
Search Deals
Highest demand for flights based on searches. 20% potential increase in price ($121 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($25 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 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 10, 2026.
Use the filters below to find and compare flights from Portland to Wisconsin that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

PortlandChicago

PWM - ORD

PWMORD

Portland

Wed 4/29

6:04 am-8:00 am

Nonstop2h 56m

Chicago O'Hare Intl

Sun 5/3

6:55 am-10:23 am

Nonstop2h 28m

$229

PortlandChicago

PWM - ORD

PWMORD

Portland

Thu 5/7

4:50 pm-6:48 pm

Nonstop2h 58m

Chicago O'Hare Intl

Mon 5/11

10:48 am-2:14 pm

Nonstop2h 26m

$229

PortlandMinneapolis

PWM - MSP

PWMMSP

Portland

Fri 7/17

12:40 pm-2:48 pm

Nonstop3h 08m

Minneapolis St Paul

Mon 7/20

8:40 am-12:19 pm

Nonstop2h 39m

$234

PortlandChicago

PWM - ORD

PWMORD

Portland

Wed 5/6

2:51 pm-11:59 pm

2 stops10h 08m

Chicago O'Hare Intl

Sat 5/9

1:44 pm-12:43 am

2 stops9h 59m

$239

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 7/17

7:16 pm-11:26 pm

1 stop5h 10m

Chicago O'Hare Intl

Mon 7/20

6:18 pm-9:51 pm

Nonstop2h 33m

$239

PortlandChicago

PWM - ORD

PWMORD

Portland

Wed 8/26

3:00 pm-7:22 pm

1 stop5h 22m

Chicago O'Hare Intl

Sat 8/29

1:15 pm-10:33 pm

1 stop8h 18m

$249

PortlandChicago

PWM - ORD

PWMORD

Portland

Tue 5/19

6:25 am-12:21 pm

1 stop6h 56m

Chicago O'Hare Intl

Mon 5/25

7:00 am-12:00 pm

1 stop4h 00m

$249

PortlandChicago

PWM - ORD

PWMORD

Portland

Thu 5/21

12:55 pm-6:05 pm

1 stop6h 10m

Chicago O'Hare Intl

Mon 5/25

7:00 am-12:00 pm

1 stop4h 00m

$249

PortlandChicago

PWM - ORD

PWMORD

Portland

Thu 7/16

6:00 am-8:00 am

Nonstop3h 00m

Chicago O'Hare Intl

Mon 7/20

6:12 pm-11:51 pm

1 stop4h 39m

$259

PortlandChicago

PWM - ORD

PWMORD

Portland

Wed 7/22

3:00 pm-7:22 pm

1 stop5h 22m

Chicago O'Hare Intl

Tue 7/28

7:00 am-1:21 pm

1 stop5h 21m

$268

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/8

Showing 1-10 of 60 resultsSorted by cheapest first
1
2
3
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6

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, September is the cheapest month in which you can book a flight from Portland, Maine to Wisconsin (average of $98). Flying from Portland, Maine to Wisconsin in November is currently the most expensive (average of $248). 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.

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 10, 2026.
Read reviews from past customers who have flown Southwest,Delta, andUnited Airlines from Portland to Wisconsin. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,317 reviews

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Mar 2026

KOA - HNL

pretty smooth and fast service ever, that flight is very helpful each and everyone for price and also fright for free..
Southwest
8.0
Very good
4,317 reviews
Southwest
8.0
Very good
4,317 reviews

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Mar 2026

KOA - HNL

pretty smooth and fast service ever, that flight is very helpful each and everyone for price and also fright for free..
Delta
7.9
Good
8,276 reviews
Southwest
8.0
Very good
4,317 reviews

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Mar 2026

KOA - HNL

pretty smooth and fast service ever, that flight is very helpful each and everyone for price and also fright for free..
United Airlines
7.4
Good
9,409 reviews
Southwest
8.0
Very good
4,317 reviews

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Mar 2026

KOA - HNL

pretty smooth and fast service ever, that flight is very helpful each and everyone for price and also fright for free..
American Airlines
7.1
Good
11,414 reviews
Southwest
8.0
Very good
4,317 reviews

Comfort

8.0

Overall

8.0

Crew

8.6

Entertainment

7.5

Food

7.0

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,Mar 2026

KOA - HNL

pretty smooth and fast service ever, that flight is very helpful each and everyone for price and also fright for free..

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.

  • How long is the flight from Portland, Maine to Wisconsin?

    There are many flights that can get you from Portland, Maine to Wisconsin in 2h 56m. Fly via United Airlines, Sun Country Air, or Delta to get the fastest option. There are 897 mi between Portland, Maine and Wisconsin. This flight may include one or multiple stops.

  • 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 Delta ($128), American Airlines ($135), and United Airlines ($148).

  • 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 - Appleton Intl.

  • 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, September is the cheapest month in which you can book a flight from Portland, Maine to Wisconsin (average of $98). Flying from Portland, Maine to Wisconsin in November is currently the most expensive (average of $248). 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

Browse thousands of different options on Cheapflights for your next trip

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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 10, 2026.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$258Average$426FlexibilityNo cancel feeOn-time71%
DeltaCheapest$258Average$410FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$273Average$479FlexibilityNo cancel feeOn-time69%
SouthwestCheapest$296Average$431FlexibilityNo cancel feeOn-time63%

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