HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Portland

$169+ Cheap flights from Madison to Portland, ME (MSN - 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 8/5. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — PWM
Apr 10 — Apr 171
Fri 4/10
Fri 4/17
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Madison 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 Madison to Portland

Cheapest flights from Madison to Portland
Explore the most affordable flight options available from Madison to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 11, 2026.

This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/315:44 pm
MSN
-
PWM
1 stop5h 07m
American Airlines
Sat 9/56:00 am
PWM
-
MSN
1 stop7h 01m
American Airlines
Deal found 3/6$299
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.
Tue 8/113:49 pm
MSN
-
PWM
1 stop5h 12m
United Airlines
Tue 8/185:15 am
PWM
-
MSN
2 stops7h 28m
United Airlines
Deal found 3/7$304
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.
Tue 7/72:35 pm
MSN
-
PWM
2 stops7h 55m
United Airlines
Tue 7/145:15 am
PWM
-
MSN
2 stops7h 33m
United Airlines
Deal found 3/8$309
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/236:35 pm
MSN
-
PWM
1 stop4h 38m
American Airlines
Sun 9/276:00 am
PWM
-
MSN
1 stop7h 01m
American Airlines
Deal found 3/9$319
This United Airlines deal was found by Cheapflights users on 3/10. 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 9/15:00 am
MSN
-
PWM
2 stops8h 35m
United Airlines
Sat 9/56:00 am
PWM
-
MSN
1 stop4h 44m
United Airlines
Deal found 3/10$324
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/315:45 am
MSN
-
PWM
1 stop5h 37m
Delta
Sat 9/56:00 am
PWM
-
MSN
2 stops11h 35m
Delta
Deal found 3/9$330
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.
Thu 3/123:03 pm
MSN
-
PWM
1 stop7h 31m
American Airlines
Sat 3/1412:44 pm
PWM
-
MSN
1 stop5h 03m
American Airlines
Deal found 3/8$337
This American Airlines deal was found by Cheapflights users on 3/10. 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 8/196:00 am
MSN
-
PWM
1 stop6h 29m
American Airlines
Sun 8/231:14 pm
PWM
-
MSN
1 stop6h 48m
American Airlines
Deal found 3/10$339
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.
Sat 3/283:53 pm
MSN
-
PWM
1 stop4h 11m
United Airlines
Fri 4/36:33 pm
PWM
-
MSN
1 stop6h 16m
United Airlines
Deal found 3/8$341
This Delta deal was found by Cheapflights users on 3/10. 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 4/73:08 pm
MSN
-
PWM
1 stop7h 04m
Delta
Tue 4/1412:46 pm
PWM
-
MSN
2 stops10h 41m
Delta
Deal found 3/10$350
This American Airlines deal was found by Cheapflights users on 3/10. 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 5/68:05 am
MSN
-
PWM
1 stop6h 04m
American Airlines
Sun 5/106:00 am
PWM
-
MSN
1 stop6h 14m
American Airlines
Deal found 3/10$354

Find flight deals from Madison to Portland

Discover tips and strategies to find the most affordable flight options for your journey from Madison (MSN) to Portland (PWM). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated March 11, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$299
(American Airlines)

One-way from

$169
(American Airlines)

Popular in

December

Cheapest in

September
Provider with most accurate pricing for Madison Truax Field-Portland flight deals.
Search Deals
Provider most trusted by Cheapflights users for Madison Truax Field-Portland flights.
Search Deals
From Madison Truax Field to Portland
Search Deals
One-way flight from Madison Truax Field to Portland
Search Deals
Highest demand for flights based on searches. 15% potential increase in price ($78 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($23 potential savings vs. average RT price).
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Madison 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 March 11, 2026.
Use the filters below to find and compare flights from Madison to Portland that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Mon 8/31

5:45 am-12:22 pm

1 stop5h 37m

Portland

Sat 9/5

6:00 am-4:35 pm

2 stops11h 35m

$356

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Tue 9/1

2:45 pm-11:59 pm

2 stops8h 14m

Portland

Sat 9/5

9:15 am-1:43 pm

1 stop5h 28m

$374

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Tue 6/30

5:00 am-1:25 pm

2 stops7h 25m

Portland

Wed 7/15

6:00 am-9:59 am

1 stop4h 59m

$374
Quickest round-trip

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Wed 4/8

2:44 pm-9:40 pm

1 stop5h 56m

Portland

Sat 4/11

6:33 pm-10:53 pm

1 stop5h 20m

$424

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Sat 5/23

10:36 am-11:51 pm

2 stops12h 15m

Portland

Wed 5/27

5:15 am-2:00 pm

3 stops9h 45m

$460

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Tue 6/9

10:40 am-11:51 pm

2 stops12h 11m

Portland

Sat 6/13

6:00 am-2:00 pm

2 stops9h 00m

$463

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Mon 8/31

6:30 am-7:19 pm

2 stops11h 49m

Portland

Sat 9/5

5:15 am-1:43 pm

2 stops9h 28m

$490

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Fri 6/26

9:40 am-11:51 pm

2 stops13h 11m

Portland

Tue 6/30

6:00 am-9:59 am

1 stop4h 59m

$493
Cheapest one-way
Quickest one-way

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Wed 8/5

8:10 am-2:26 pm

1 stop5h 16m

$169

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Tue 8/4

6:30 am-2:34 pm

2 stops7h 04m

$174

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/6

Showing 1-10 of 15 resultsSorted by cheapest first
1
2

Compare providers for flights from Madison to Portland

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Madison to Portland in March.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on Madison-Portland, Maine flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Madison-Portland, Maine flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Madison-Portland, Maine flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Madison-Portland, Maine flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Madison-Portland, Maine flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from Madison to Portland

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

How far ahead should I book a flight from Madison to Portland, Maine?

Use this chart to determine the optimal time to book a round-trip flight from Madison to Portland. Price data was last updated on March 6, 2026.

The best time to book flights from Madison to Portland, Maine is 45 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

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

Currently, September is the cheapest month in which you can book a flight from Madison to Portland, Maine (average of $93). Flying from Madison to Portland, Maine in December is currently the most expensive (average of $217). 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 March 11, 2026.
Get a feel of what it's like to fly with Delta,United Airlines, andAmerican Airlines from Madison to Portland by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,278 reviews

Entertainment

7.8

Boarding

8.1

Crew

8.5

Overall

7.9

Comfort

7.9

Food

7.2

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,278 reviews
Delta
7.9
Good
8,278 reviews

Entertainment

7.8

Boarding

8.1

Crew

8.5

Overall

7.9

Comfort

7.9

Food

7.2

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
United Airlines
7.4
Good
9,414 reviews
Delta
7.9
Good
8,278 reviews

Entertainment

7.8

Boarding

8.1

Crew

8.5

Overall

7.9

Comfort

7.9

Food

7.2

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.1
Good
11,419 reviews
Delta
7.9
Good
8,278 reviews

Entertainment

7.8

Boarding

8.1

Crew

8.5

Overall

7.9

Comfort

7.9

Food

7.2

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

Related info for your journey

Find useful and relevant information for your journey from Madison to Portland. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

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

    Airlines like Delta and United Airlines fly from Madison to Portland, Maine in about 5h 37m. The time it takes to get you to your destination can typically vary by up to 2h 37m. There are 953 mi between Madison and Portland, Maine. This flight may include one or multiple stops.

  • What are the cheapest airlines flying from Madison to Portland, Maine round-trip?

    Our cheapest airline available from Madison to Portland, Maine is American Airlines. Our recent data shows that you can find tickets from as low as $258 on this airline. Additional options worth looking into are Delta and United Airlines, starting at $258 and $258 round-trip. Users have found that American Airlines is 38% cheaper than the other options available to this destination.

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

    One-way options have recently been found by users for as low as $141 on American Airlines. Other airlines that offer cheap prices include Delta from $158 and United Airlines from $168 one-way.

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

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

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

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

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

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

    Currently, September is the cheapest month in which you can book a flight from Madison to Portland, Maine (average of $93). Flying from Madison to Portland, Maine in December is currently the most expensive (average of $217). 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
North Conway
Brunswick
Auburn
Lewiston
Conway

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.

Top 3 airlines flying from Madison to Portland

Discover the top 3 airlines that operate flights from Madison 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 March 11, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$258Average$323FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$258Average$407FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$258Average$395FlexibilityNo cancel feeOn-time71%

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.
Site
©2026 Cheapflights