Wisconsin

$77+ 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 5/27. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MKE
Apr 4 — Apr 111
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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 5, 2026.

This Booking.com deal was found by Cheapflights users on 3/4. 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 7/1612:58 pm
PWM
-
MSP
Nonstop3h 08m
Sun Country Air
Mon 7/208:40 am
MSP
-
PWM
Nonstop2h 39m
Sun Country Air
Deal found 3/4$198
This United Airlines deal was found by Cheapflights users on 3/2. 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 4/76:04 am
PWM
-
ORD
Nonstop2h 56m
United Airlines
Mon 4/136:10 pm
ORD
-
PWM
Nonstop2h 30m
United Airlines
Deal found 3/2$209
This United Airlines deal was found by Cheapflights users on 3/2. 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 4/76:33 pm
PWM
-
ORD
Nonstop3h 10m
United Airlines
Sat 4/111:00 pm
ORD
-
PWM
1 stop5h 01m
United Airlines
Deal found 3/2$219
This Priceline deal was found by Cheapflights users on 3/2. 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 7/2412:40 pm
PWM
-
MSP
Nonstop3h 08m
Sun Country Air
Mon 7/278:00 am
MSP
-
PWM
Nonstop2h 39m
Sun Country Air
Deal found 3/2$227
This American Airlines deal was found by Cheapflights users on 3/1. 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.
Tue 4/73:39 pm
PWM
-
ORD
1 stop5h 18m
American Airlines
Sun 4/127:49 pm
ORD
-
PWM
Nonstop2h 38m
American Airlines
Deal found 3/1$230
This United Airlines deal was found by Cheapflights users on 3/1. 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 5/169:40 am
PWM
-
ORD
Nonstop2h 56m
United Airlines
Sat 5/165:56 pm
ORD
-
PWM
Nonstop2h 23m
United Airlines
Deal found 3/1$231
This Delta deal was found by Cheapflights users on 3/1. 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 5/2112:55 pm
PWM
-
ORD
1 stop6h 10m
Delta
Sun 5/241:44 pm
ORD
-
PWM
2 stops9h 59m
Delta
Deal found 3/1$234
This United Airlines deal was found by Cheapflights users on 3/3. 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 3/275:45 am
PWM
-
ORD
Nonstop3h 12m
United Airlines
Sun 3/296:10 pm
ORD
-
PWM
Nonstop2h 30m
United Airlines
Deal found 3/3$237
This United Airlines deal was found by Cheapflights users on 3/4. 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 4/96:04 am
PWM
-
ORD
Nonstop2h 56m
United Airlines
Tue 4/144:30 pm
ORD
-
PWM
1 stop5h 58m
United Airlines
Deal found 3/4$239
This United Airlines deal was found by Cheapflights users on 2/28. 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.
Sat 5/237:16 pm
PWM
-
ORD
1 stop5h 10m
United Airlines
Mon 5/256:18 pm
ORD
-
PWM
Nonstop2h 33m
United Airlines
Deal found 2/28$240
This Southwest deal was found by Cheapflights users on 3/3. 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.
Mon 4/135:30 am
PWM
-
ORD
2 stops8h 20m
Southwest
Mon 4/137:35 pm
ORD
-
PWM
2 stops15h 45m
Southwest
Deal found 3/3$245
This American Airlines deal was found by Cheapflights users on 3/2. 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 4/246:01 pm
PWM
-
ORD
Nonstop3h 13m
American Airlines
Mon 4/277:49 pm
ORD
-
PWM
Nonstop2h 38m
American Airlines
Deal found 3/2$248

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 5, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$198
(Booking.com)

One-way from

$77
(JetBlue)

Popular in

November

Cheapest in

September

Average price

$369
Provider with most accurate pricing for Boston Logan Intl-Milwaukee-Mitchell flight deals.
Provider most trusted by Cheapflights users for Boston Logan Intl-Milwaukee-Mitchell flights.
From Portland to Wisconsin
One-way flight from Portland to Wisconsin
Highest demand for flights based on searches. 14% potential increase in price ($56 potential increase over avg. RT price).
Cheapest flight prices on average. 4% potential price decrease ($13 potential savings vs. average RT price).
Average for round-trip flights in March 2026

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 5, 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

Fri 5/1

9:00 am-10:56 am

Nonstop2h 56m

Chicago O'Hare Intl

Mon 5/4

6:17 pm-11:59 pm

1 stop4h 42m

$219

PortlandChicago

PWM - ORD

PWMORD

Portland

Tue 4/14

7:12 pm-11:37 pm

1 stop5h 25m

Chicago O'Hare Intl

Tue 4/21

6:10 pm-9:40 pm

Nonstop2h 30m

$219
Quickest round-trip

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 5/15

6:00 am-7:56 am

Nonstop2h 56m

Chicago O'Hare Intl

Sun 5/17

5:56 pm-9:19 pm

Nonstop2h 23m

$229

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 4/3

5:23 am-4:43 pm

2 stops12h 20m

Chicago O'Hare Intl

Sun 4/5

7:00 am-1:50 pm

1 stop5h 50m

$234

PortlandChicago

PWM - ORD

PWMORD

Portland

Wed 7/22

6:50 pm-11:55 pm

1 stop6h 05m

Chicago O'Hare Intl

Tue 7/28

9:30 am-6:01 pm

1 stop7h 31m

$249

PortlandChicago

PWM - ORD

PWMORD

Portland

Fri 4/10

5:23 am-4:43 pm

2 stops12h 20m

Chicago O'Hare Intl

Tue 4/14

8:52 am-4:45 pm

2 stops6h 53m

$259

PortlandMinneapolis

PWM - MSP

PWMMSP

Portland

Thu 4/2

6:33 pm-11:33 pm

1 stop6h 00m

Minneapolis St Paul

Tue 4/7

10:00 am-5:32 pm

1 stop6h 32m

$289

PortlandMadison

PWM - MSN

PWMMSN

Portland

Wed 4/8

6:03 am-12:41 pm

2 stops7h 38m

Madison Truax Field

Tue 4/14

6:00 am-3:57 pm

2 stops8h 57m

$289

PortlandChicago

PWM - ORD

PWMORD

Portland

Sat 5/2

5:40 am-3:30 pm

2 stops10h 50m

Chicago O'Hare Intl

Mon 5/4

2:40 pm-11:25 pm

2 stops7h 45m

$306

PortlandChicago

PWM - ORD

PWMORD

Portland

Thu 5/28

5:15 am-9:36 am

1 stop5h 21m

Chicago O'Hare Intl

Thu 5/28

4:00 pm-11:51 pm

1 stop6h 51m

$307

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/1

Showing 1-10 of 60 resultsSorted by cheapest first
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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 5, 2026.
Read reviews from past customers who have flown Southwest, Delta, and United Airlines from Portland to Wisconsin. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.

Crew

8.6

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

8.0

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..

Crew

8.6

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

8.0

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..

Crew

8.6

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

8.0

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..

Crew

8.6

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

8.0

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..

Crew

8.6

Comfort

8.0

Entertainment

7.5

Food

7.0

Overall

8.0

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, Delta, or American Airlines 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?

  • 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

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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.

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 5, 2026.
AirlineCheapestAverageFlexibilityOn-time
United AirlinesCheapest$258Average$491FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$258Average$425FlexibilityNo cancel feeOn-time71%
DeltaCheapest$258Average$410FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$296Average$431FlexibilityNo cancel feeOn-time63%

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