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$189+ 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 11/12. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — PWM
Nov 27 — Dec 41
Thu 11/27
Thu 12/4
1 adult, Economy
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Cheapflights Tip: The best prices from Madison Truax Field to Portland are usually found in February or March, booked 35 days in advance, depart on a Sunday or Saturday and return on a Friday

Cheap 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 October 28, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$274
(United Airlines)

One-way from

$189
(Delta)

Popular in

December

Cheapest in

February

Average price

$398
Provider with most accurate pricing for Madison Truax Field-Portland flight deals.
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Provider most trusted by Cheapflights users for Madison Truax Field-Portland flights.
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From Madison Truax Field to Portland
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One-way flight from Madison Truax Field to Portland
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Highest demand for flights based on searches. 6% potential increase in price ($28 potential increase over avg. RT price).
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Cheapest flight prices on average. 4% potential price decrease ($18 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Find 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 October 28, 2025.

This United Airlines deal was found by Cheapflights users on 10/27. 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 11/116:15 amMSN - PWM
1 stop6h 21mUnited Airlines
Fri 1/26:46 pmPWM - MSN
1 stop5h 11mUnited Airlines
Deal found 10/27$274
This United Airlines deal was found by Cheapflights users on 10/27. 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.
Fri 11/148:25 amMSN - PWM
1 stop4h 47mUnited Airlines
Tue 11/259:45 amPWM - MSN
1 stop6h 09mUnited Airlines
Deal found 10/27$313
This American Airlines deal was found by Cheapflights users on 10/27. 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.
Fri 11/73:37 pmMSN - PWM
1 stop4h 58mAmerican Airlines
Wed 11/127:02 amPWM - MSN
1 stop8h 55mAmerican Airlines
Deal found 10/27$328
This Delta deal was found by Cheapflights users on 10/27. 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.
Fri 11/73:49 pmMSN - PWM
1 stop6h 20mDelta
Wed 11/126:00 amPWM - MSN
2 stops7h 45mDelta
Deal found 10/27$333
This American Airlines deal was found by Cheapflights users on 10/27. 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 11/126:00 amMSN - PWM
1 stop4h 46mAmerican Airlines
Sun 11/165:43 amPWM - MSN
1 stop5h 39mAmerican Airlines
Deal found 10/27$344
This United Airlines deal was found by Cheapflights users on 10/28. 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.
Wed 11/52:48 pmMSN - PWM
1 stop6h 02mUnited Airlines
Sat 11/84:57 pmPWM - MSN
1 stop4h 38mUnited Airlines
Deal found 10/28$367
This United Airlines deal was found by Cheapflights users on 10/28. 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.
Thu 11/68:25 amMSN - PWM
1 stop4h 47mUnited Airlines
Sun 11/95:30 amPWM - MSN
2 stops9h 33mUnited Airlines
Deal found 10/28$372

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 October 28, 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 11/11

6:15 am-1:36 pm

1 stop6h 21m

Portland

Fri 1/2

6:46 pm-10:57 pm

1 stop5h 11m

$274

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Thu 4/9

4:22 pm-11:39 pm

1 stop6h 17m

Portland

Mon 4/13

12:09 pm-7:02 pm

1 stop7h 53m

$289

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Fri 11/14

8:25 am-2:12 pm

1 stop4h 47m

Portland

Tue 11/25

9:45 am-2:54 pm

1 stop6h 09m

$313

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Fri 11/7

3:59 pm-11:59 pm

1 stop7h 00m

Portland

Wed 11/12

5:43 am-10:12 am

1 stop5h 29m

$328

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Fri 11/7

3:49 pm-11:09 pm

1 stop6h 20m

Portland

Wed 11/12

6:00 am-12:45 pm

2 stops7h 45m

$333

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Wed 2/18

4:23 pm-11:49 pm

1 stop6h 26m

Portland

Sat 2/21

5:35 am-5:02 pm

2 stops12h 27m

$334

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Wed 2/18

2:48 pm-9:14 pm

1 stop5h 26m

Portland

Sat 2/21

6:00 am-3:02 pm

2 stops10h 02m

$334

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Wed 11/12

5:29 am-12:30 pm

1 stop6h 01m

$189

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Wed 12/17

3:35 pm-9:37 pm

1 stop5h 02m

$194

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Mon 12/22

4:05 pm-11:42 pm

1 stop6h 37m

$329

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/26

Showing 1-10 of 14 results
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 October.
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 October 24, 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 $222). 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 October 28, 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
7,994 reviews

Overall

7.9

Comfort

7.9

Entertainment

7.9

Food

7.3

Boarding

8.2

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Delta
7.9
Good
7,994 reviews
Delta
7.9
Good
7,994 reviews

Overall

7.9

Comfort

7.9

Entertainment

7.9

Food

7.3

Boarding

8.2

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
United Airlines
7.4
Good
9,001 reviews
Delta
7.9
Good
7,994 reviews

Overall

7.9

Comfort

7.9

Entertainment

7.9

Food

7.3

Boarding

8.2

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
American Airlines
7.2
Good
11,032 reviews
Delta
7.9
Good
7,994 reviews

Overall

7.9

Comfort

7.9

Entertainment

7.9

Food

7.3

Boarding

8.2

Crew

8.5

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.

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 United Airlines and American Airlines fly from Madison to Portland, Maine in about 6h 17m. The time it takes to get you to your destination can typically vary by up to 04m. 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 $273 round-trip. Users have found that American Airlines is 33% cheaper than the other options available to this destination.

  • 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 $222). 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 October 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$258Average$408FlexibilityNo cancel feeOn-time71%
DeltaCheapest$258Average$331FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$273Average$420FlexibilityNo cancel feeOn-time69%

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