HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Portland

$67+ 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 10/18. Fares are subject to change and may not be available on all flights or dates of travel.
MKE — PWM
Oct 14 — Oct 211
Tue 10/14
Tue 10/21
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Wisconsin to Portland with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 September 14, 2025.

Round-trip from

$219
(American Airlines)

One-way from

$67
(United Airlines)

Popular in

December

Cheapest in

April

Average price

$352
From Wisconsin to Portland
Search Deals
One-way flight from Wisconsin to Portland
Search Deals
Highest demand for flights based on searches. 18% potential increase in price ($84 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
Search Deals

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 September 14, 2025.

This American Airlines deal was found by Cheapflights users on 9/11. 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 10/288:00 amMKE - PWM
1 stop5h 38mAmerican Airlines
Sat 11/16:20 amPWM - MKE
1 stop4h 58mAmerican Airlines
Deal found 9/11$219
This American Airlines deal was found by Cheapflights users on 9/12. 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.
Mon 10/277:10 pmMSP - PWM
1 stop15h 18mAmerican Airlines
Thu 10/303:28 pmPWM - MSP
1 stop9h 12mAmerican Airlines
Deal found 9/12$235
This American Airlines deal was found by Cheapflights users on 9/12. 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 10/175:19 pmORD - PWM
1 stop5h 32mAmerican Airlines
Wed 11/55:37 pmPWM - ORD
Nonstop3h 13mAmerican Airlines
Deal found 9/12$237
This American Airlines deal was found by Cheapflights users on 9/12. 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 11/206:00 amMKE - PWM
1 stop4h 46mAmerican Airlines
Mon 11/245:43 amPWM - MKE
1 stop7h 18mAmerican Airlines
Deal found 9/12$237
This Southwest deal was found by Cheapflights users on 9/12. 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 10/221:50 pmORD - PWM
1 stop5h 05mSouthwest
Tue 10/285:45 amPWM - ORD
2 stops8h 00mSouthwest
Deal found 9/12$239
This United Airlines deal was found by Cheapflights users on 9/13. 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 10/1812:00 pmORD - PWM
1 stop5h 38mUnited Airlines
Sat 10/256:14 amPWM - ORD
Nonstop2h 51mUnited Airlines
Deal found 9/13$241
This United Airlines deal was found by Cheapflights users on 9/12. 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 9/274:05 pmORD - PWM
1 stop6h 15mUnited Airlines
Wed 10/17:25 pmPWM - ORD
1 stop4h 50mUnited Airlines
Deal found 9/12$242
This Delta deal was found by Cheapflights users on 9/11. 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 10/286:00 amMKE - PWM
1 stop6h 06mDelta
Sat 11/14:48 pmPWM - MKE
2 stops8h 07mDelta
Deal found 9/11$242
This American Airlines deal was found by Cheapflights users on 9/13. 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 10/256:45 amORD - PWM
1 stop9h 53mAmerican Airlines
Tue 10/287:00 amPWM - ORD
1 stop9h 58mAmerican Airlines
Deal found 9/13$244
This Cheapflightsfares deal was found by Cheapflights users on 9/12. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/2811:12 amMSP - PWM
Nonstop2h 40mSun Country Air
Thu 10/212:33 pmPWM - MSP
Nonstop3h 02mSun Country Air
Deal found 9/12$246
This United Airlines deal was found by Cheapflights users on 9/11. 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 10/3110:53 amORD - PWM
Nonstop2h 19mUnited Airlines
Sun 11/25:00 amPWM - ORD
1 stop5h 45mUnited Airlines
Deal found 9/11$248
This American Airlines deal was found by Cheapflights users on 9/13. 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 10/182:41 pmORD - PWM
1 stop5h 17mAmerican Airlines
Sat 10/257:44 amPWM - ORD
1 stop7h 27mAmerican Airlines
Deal found 9/13$251

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 September 14, 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

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Mon 12/8

6:01 am-11:37 am

1 stop4h 36m

Portland

Mon 12/15

5:46 am-12:04 pm

1 stop7h 18m

$237

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Thu 11/20

6:00 am-11:46 am

1 stop4h 46m

Portland

Mon 11/24

5:43 am-12:01 pm

1 stop7h 18m

$237

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Sat 10/4

7:10 pm-10:43 pm

Nonstop2h 33m

Portland

Tue 10/7

6:00 am-12:03 pm

1 stop7h 03m

$241

MilwaukeePortland

MKE - PWM

MKEPWM

Milwaukee-Mitchell

Tue 10/28

6:00 am-1:06 pm

1 stop6h 06m

Portland

Sat 11/1

4:48 pm-11:55 pm

2 stops8h 07m

$242

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Tue 10/7

4:50 pm-11:13 pm

1 stop5h 23m

Portland

Tue 10/14

5:41 pm-11:30 pm

1 stop6h 49m

$251

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Wed 11/5

6:06 am-11:46 am

1 stop4h 40m

Portland

Sat 11/8

5:21 pm-9:23 pm

1 stop5h 02m

$251

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Tue 3/3

2:45 pm-11:21 pm

1 stop7h 36m

Portland

Wed 3/4

6:00 am-10:49 am

1 stop5h 49m

$255

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Tue 9/30

11:05 am-2:33 pm

Nonstop2h 28m

Portland

Sat 10/4

4:57 pm-6:48 pm

Nonstop2h 51m

$255

ChicagoPortland

ORD - PWM

ORDPWM

Chicago O'Hare Intl

Wed 11/12

6:45 am-12:08 pm

1 stop4h 23m

Portland

Sat 11/15

6:00 am-4:52 pm

2 stops11h 52m

$256

MinneapolisPortland

MSP - PWM

MSPPWM

Minneapolis St Paul

Mon 10/27

5:45 pm-12:05 am

1 stop5h 20m

Portland

Thu 10/30

5:45 am-1:50 pm

2 stops9h 05m

$258

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/12

Showing 1-10 of 60 results
1
2
3
...
6

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.

How much does it cost to fly round-trip from Wisconsin to Portland, Maine?

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 4h 36m. The distance between Wisconsin and Portland, Maine is about 883 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 United Airlines. According to our data, you can fly for as low as $67. Users have also found prices from $108 and $119 on Southwest and Delta, 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, 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Wisconsin to Portland

See prices for flight routes from nearby airports that may be better suited for you.
Dallas/Fort Worth to Boston flights
Los Angeles to Boston flights
Baltimore to Boston flights
San Francisco to Boston flights
Reagan-National to Boston flights
O'Hare Intl to Boston flights
Atlanta to Boston flights
Newark to Boston flights
Denver to Boston flights
Dulles Intl to Boston flights
LaGuardia to Boston flights
Raleigh to Boston flights
Orlando to Boston flights
Hobby to Boston flights
Seattle to Boston flights
Philadelphia to Boston flights
Charlotte to Boston flights
Sky Harbor Intl to Boston flights
John F Kennedy Intl to Boston flights
Austin to Boston flights
George Bush Intcntl to Boston flights
Tampa to Boston flights
Fort Lauderdale to Boston flights
Midway to Boston flights
Cincinnati to Boston flights
Miami to Boston flights
Detroit to Boston flights
Columbus to Boston flights
Minneapolis to Boston flights
Cleveland to Boston flights
Pittsburgh to Boston flights
Portland to Boston flights
Ontario to Boston flights
Love Field to Boston flights
San Diego to Boston flights
Santa Ana to Boston flights
Indianapolis to Boston flights
St. Louis to Boston flights
West Palm Beach to Boston flights
Dulles Intl to Portland flights
Islip to Boston flights
Reagan-National to Portland flights
Richmond to Boston flights
Jacksonville to Boston flights
Nashville to Boston flights
Salt Lake City to Boston flights
Louisville to Boston flights
Milwaukee to Boston flights
LaGuardia to Portland flights
San Antonio to Boston flights

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 September 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$238Average$455FlexibilityNo cancel feeOn-time71%
SouthwestCheapest$246Average$387FlexibilityNo cancel feeOn-time63%
DeltaCheapest$248Average$409FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$267Average$454FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.