Portland

$78+ 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 8/29. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — PWM
Aug 3 — Aug 101
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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 July 29, 2025.

Round-trip from

$188
(Sun Country Air)

One-way from

$78
(Cheapflightsfares)

Popular in

December

Cheapest in

April

Average price

$379
From Wisconsin to Portland
One-way flight from Wisconsin to Portland
Highest demand for flights based on searches. 18% potential increase in price ($85 potential increase over avg. RT price).
Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
Average for round-trip flights in July 2025

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 July 29, 2025.

This Sun Country Air deal was found by Cheapflights users on 7/27. 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 Sun Country Air is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/188:06 amMSP - PWM
Nonstop2h 39mSun Country Air
Thu 8/2111:42 amPWM - MSP
Nonstop3h 06mSun Country Air
Deal found 7/27$188
This United Airlines deal was found by Cheapflights users on 7/27. 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 9/910:58 amORD - PWM
Nonstop2h 28mUnited Airlines
Sat 9/136:00 amPWM - ORD
1 stop8h 07mUnited Airlines
Deal found 7/27$227
This Delta deal was found by Cheapflights users on 7/27. 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 8/266:00 amORD - PWM
1 stop5h 59mDelta
Sat 8/305:30 pmPWM - ORD
1 stop7h 26mDelta
Deal found 7/27$228
This JetBlue deal was found by Cheapflights users on 7/28. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/266:15 amORD - PWM
1 stop6h 08mJetBlue
Sun 8/316:10 amPWM - ORD
1 stop5h 37mJetBlue
Deal found 7/28$233
This American Airlines deal was found by Cheapflights users on 7/27. 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.
Wed 9/37:02 amORD - PWM
1 stop5h 05mAmerican Airlines
Sat 9/66:15 amPWM - ORD
Nonstop2h 56mAmerican Airlines
Deal found 7/27$234
This Delta deal was found by Cheapflights users on 7/28. 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 9/172:59 pmMKE - PWM
1 stop8h 12mDelta
Tue 9/234:55 pmPWM - MKE
1 stop6h 02mDelta
Deal found 7/28$237
This American Airlines deal was found by Cheapflights users on 7/27. 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 8/303:02 pmGRB - PWM
1 stop7h 57mAmerican Airlines
Sat 9/66:15 amPWM - GRB
1 stop5h 00mAmerican Airlines
Deal found 7/27$249
This United Airlines deal was found by Cheapflights users on 7/28. 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 9/273:45 pmGRB - PWM
1 stop4h 59mUnited Airlines
Tue 9/304:57 pmPWM - GRB
1 stop6h 43mUnited Airlines
Deal found 7/28$256
This Southwest deal was found by Cheapflights users on 7/28. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/131:50 pmORD - PWM
1 stop7h 35mSouthwest
Wed 8/205:50 amPWM - ORD
1 stop7h 00mSouthwest
Deal found 7/28$258
This Delta deal was found by Cheapflights users on 7/27. 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.
Sat 9/65:34 amATW - PWM
1 stop5h 55mDelta
Sat 9/1311:45 amPWM - ATW
1 stop4h 51mDelta
Deal found 7/27$259
This Delta deal was found by Cheapflights users on 7/26. 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.
Tue 10/285:18 amDLH - PWM
2 stops7h 34mDelta
Sat 11/16:00 amPWM - DLH
2 stops10h 30mDelta
Deal found 7/26$259
This Delta deal was found by Cheapflights users on 7/28. 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.
Sat 9/131:20 pmMSN - PWM
1 stop7h 40mDelta
Sat 9/207:00 amPWM - MSN
1 stop6h 41mDelta
Deal found 7/28$259

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 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

MinneapolisPortland

MSP - PWM

MSPPWM

Minneapolis St Paul

Mon 8/18

8:06 am-11:45 am

Nonstop2h 39m

Portland

Thu 8/21

11:42 am-1:48 pm

Nonstop3h 06m

$188

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Tue 9/9

10:58 am-2:26 pm

Nonstop2h 28m

Portland

Sat 9/13

6:00 am-1:07 pm

1 stop8h 07m

$227

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Tue 8/26

6:00 am-12:59 pm

1 stop5h 59m

Portland

Sat 8/30

5:30 pm-11:56 pm

1 stop7h 26m

$228

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Tue 8/26

6:15 am-1:23 pm

1 stop6h 08m

Portland

Sun 8/31

6:10 am-10:47 am

1 stop5h 37m

$233

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Wed 9/3

7:02 am-1:07 pm

1 stop5h 05m

Portland

Sat 9/6

6:15 am-8:11 am

Nonstop2h 56m

$234

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Wed 9/17

2:59 pm-12:11 am

1 stop8h 12m

Portland

Tue 9/23

4:55 pm-9:57 pm

1 stop6h 02m

$237

Green BayPortland

GRB - PWM

GRBPWM

Green Bay Austin-Straubel

Sat 8/30

3:02 pm-11:59 pm

1 stop7h 57m

Portland

Sat 9/6

6:15 am-10:15 am

1 stop5h 00m

$249

Green BayPortland

GRB - PWM

GRBPWM

Green Bay Austin-Straubel

Sat 9/27

3:45 pm-9:44 pm

1 stop4h 59m

Portland

Tue 9/30

4:57 pm-10:40 pm

1 stop6h 43m

$256

AppletonPortland

ATW - PWM

ATWPWM

Appleton Intl

Sat 9/6

5:34 am-12:29 pm

1 stop5h 55m

Portland

Sat 9/13

11:45 am-3:36 pm

1 stop4h 51m

$259

DuluthPortland

DLH - PWM

DLHPWM

Duluth Intl

Tue 10/28

5:18 am-1:52 pm

2 stops7h 34m

Portland

Sat 11/1

6:00 am-3:30 pm

2 stops10h 30m

$259

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/27

Showing 1-10 of 57 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, January is the cheapest month in which you can book a flight from Wisconsin to Portland, Maine (average of $296). Flying from Wisconsin to Portland, Maine in July is currently the most expensive (average of $394). 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 Portland

Get insights into the airlines that provide service to Portland. 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 Portland. Reviews last updated July 29, 2025.
Read through reviews of airlines operating flights from Wisconsin to Portland, such as Southwest, Delta, and United Airlines. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.

Boarding

8.1

Entertainment

7.5

Crew

8.6

Comfort

8.0

Overall

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

Boarding

8.1

Entertainment

7.5

Crew

8.6

Comfort

8.0

Overall

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.
8.0
Very good

Boarding

8.1

Entertainment

7.5

Crew

8.6

Comfort

8.0

Overall

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

Boarding

8.1

Entertainment

7.5

Crew

8.6

Comfort

8.0

Overall

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

Boarding

8.1

Entertainment

7.5

Crew

8.6

Comfort

8.0

Overall

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

Boarding

8.1

Entertainment

7.5

Crew

8.6

Comfort

8.0

Overall

8.0

Food

7.0

Reviews

1 / 20
8.0
Excellent

Gina,Jul 2025

LAS - DEN

We experienced bad weather, which turned our 1.5 hour flight from Las Vegas to Denver, into 3.5. The pilot and crew kept us updated and explained that we had to circle and or possibly redirect to another airport. After circling for sometime, we were able to land smoothly in Denver. Thank you to all the flight crew, tower control, and all who got us to our destination safely.

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.

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

    For one-way options, check prices for Sun Country Air. According to our data, you can fly for as low as $78. Users have also found prices from $100 and $102 on United Airlines and JetBlue, respectively.

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

  • 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 $296). Flying from Wisconsin to Portland, Maine in July is currently the most expensive (average of $394). 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
Brunswick
North Conway
Auburn
Conway
Lewiston

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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.

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 29, 2025.
AirlineCheapestAverageFlexibilityOn-time
SouthwestCheapest$246Average$389FlexibilityNo cancel feeOn-time63%
DeltaCheapest$248Average$453FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$258Average$449FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$267Average$469FlexibilityNo cancel feeOn-time69%

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