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$159+ 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 1/10. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — PWM
Jan 13 — Jan 201
Tue 1/13
Tue 1/20
1 adult, Economy
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Cheapflights Tip: The best prices from Madison Truax Field to Portland are usually found in March or September, booked 47 days in advance, depart on a Sunday or Saturday and return on a Friday

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 December 14, 2025.

This American Airlines deal was found by Cheapflights users on 12/12. 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.
Sat 12/133:55 pmMSN - PWM
1 stop5h 37mAmerican Airlines
Sun 12/147:11 amPWM - MSN
1 stop8h 36mAmerican Airlines
Deal found 12/12$404
This United Airlines deal was found by Cheapflights users on 12/12. 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 12/1310:50 amMSN - PWM
2 stops11h 22mUnited Airlines
Sun 12/144:25 pmPWM - MSN
1 stop5h 22mUnited Airlines
Deal found 12/12$409
This United Airlines deal was found by Cheapflights users on 12/11. 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 12/263:46 pmMSN - PWM
1 stop4h 43mUnited Airlines
Tue 12/306:46 pmPWM - MSN
1 stop5h 11mUnited Airlines
Deal found 12/11$655
This United Airlines deal was found by Cheapflights users on 12/13. 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.
Mon 12/295:00 amMSN - PWM
3 stops17h 59mUnited Airlines
Sat 1/35:30 amPWM - MSN
2 stops10h 35mUnited Airlines
Deal found 12/13$673
This United Airlines deal was found by Cheapflights users on 12/13. 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.
Sun 12/288:15 amMSN - PWM
2 stops14h 44mUnited Airlines
Thu 1/16:46 pmPWM - MSN
1 stop5h 11mUnited Airlines
Deal found 12/13$807

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 December 14, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$279
(Delta)

One-way from

$159
(United Airlines)

Popular in

December

Cheapest in

March

Average price

$583
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. 5% potential increase in price ($26 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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 December 14, 2025.
Use the filters below to find and compare flights from Madison to Portland that are best for you.

Fly from

Madison

Fly to

Portland

Route

Depart

Return

Price

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Tue 2/24

3:30 pm-11:20 pm

1 stop6h 50m

Portland

Sat 2/28

12:45 pm-5:04 pm

1 stop5h 19m

$279

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Sat 2/14

2:48 pm-9:14 pm

1 stop5h 26m

Portland

Wed 2/18

6:00 am-5:03 pm

2 stops12h 03m

$354

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Thu 2/12

5:07 pm-11:17 pm

1 stop5h 10m

Portland

Mon 2/16

5:31 am-10:15 am

1 stop5h 44m

$401

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Sat 1/10

8:15 am-2:39 pm

1 stop5h 24m

$159

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Sat 1/10

4:47 pm-10:54 pm

1 stop5h 07m

$159

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Thu 1/8

4:47 pm-10:54 pm

1 stop5h 07m

$199

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Thu 1/8

5:38 am-5:16 pm

2 stops10h 38m

$204

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Thu 1/8

6:30 am-11:30 pm

3 stops16h 00m

$426

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Mon 12/29

9:45 am-4:08 pm

1 stop5h 23m

$450

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/11

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 December.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice 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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Madison-Portland, Maine flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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 December 12, 2025.

The best time to book flights from Madison to Portland, Maine is 35 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, October is the cheapest month in which you can book a flight from Madison to Portland, Maine (average of $88). Flying from Madison to Portland, Maine in January is currently the most expensive (average of $230). 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 Madison to Portland, Maine?

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 December 14, 2025.
Get a feel of what it's like to fly with Delta, United Airlines, and American 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
8,007 reviews

Comfort

7.9

Entertainment

7.9

Food

7.3

Overall

7.9

Crew

8.5

Boarding

8.1

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
8,007 reviews
Delta
7.9
Good
8,007 reviews

Comfort

7.9

Entertainment

7.9

Food

7.3

Overall

7.9

Crew

8.5

Boarding

8.1

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
9,094 reviews
Delta
7.9
Good
8,007 reviews

Comfort

7.9

Entertainment

7.9

Food

7.3

Overall

7.9

Crew

8.5

Boarding

8.1

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
7.2
Good
11,054 reviews
Delta
7.9
Good
8,007 reviews

Comfort

7.9

Entertainment

7.9

Food

7.3

Overall

7.9

Crew

8.5

Boarding

8.1

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 26m. The time it takes to get you to your destination can typically vary by up to 1h 24m. 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 United Airlines and Delta, starting at $258 and $258 round-trip. Users have found that American Airlines is 37% 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 $164 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, October is the cheapest month in which you can book a flight from Madison to Portland, Maine (average of $88). Flying from Madison to Portland, Maine in January is currently the most expensive (average of $230). 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
Conway

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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 December 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$258Average$408FlexibilityNo cancel feeOn-time71%
DeltaCheapest$258Average$328FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$273Average$420FlexibilityNo cancel feeOn-time69%

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