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 $259 on this airline. Additional options worth looking into are Delta and United Airlines, starting at $264 and $329 round-trip. Users have found that American Airlines is 36% 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 $199 on American Airlines. Other airlines that offer cheap prices include Delta from $425 and United Airlines from $475 one-way.

What is the cheapest day to fly from Madison to Portland, Maine?

Travelers seeking maximum savings on their Madison to Portland, Maine flight should consider departing on Friday afternoons when fares are most often at their lowest. Saturday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.

What are the most popular airlines that fly from Madison to Portland, Maine?

Before booking your flight from Madison to Portland, Maine check out the most popular airlines for this route: American Airlines, Delta or United Airlines.

What is the cheapest day to fly round-trip from Madison to Portland, Maine?

Users have found that leaving on a Saturday can be a cost-effective option. It’s possible to save up to 36% on your flight compared to booking on days when demand is much higher.

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

When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 58 days in advance, which can save you up to 69% on flights from Madison to Portland, Maine compared to booking the week you need them. Waiting 58 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $379. For sooner than that we have options available in the next 3 days from $488.

What is the cheapest month to fly from Madison to Portland, Maine?

February can be a great time to fly to Portland, Maine from Madison with a flight ticket averaging about $410. Cheapflights users have found deals in the month of February for as cheap as $258. The most expensive prices can be found in the month of December.

What is the cheapest time of day to fly from MSN to PWM?

It’s optimal to fly from Madison to Portland, Maine at noon. By choosing this option you can save up to 23% on the cost of your flight, compared to a flight in the afternoon.

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 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.

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.

$199+ Flights from Madison to Portland, ME - Compare & Save Big

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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

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Cheapflights Tip: The best prices from Madison Truax Field to Portland are usually found in February or March, booked 66 days in advance, depart on a Sunday or Saturday and return on a Friday

Cheap flight deals from Madison to Portland

Most accurate provider	FlightHub 3 stars
Most trusted provider	eDreams 3 stars
Round-trip from	$259 (American Airlines)
One-way from	$199 (American Airlines)
Popular in	December
Cheapest in	February
Average price	$388

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. 3% potential increase in price ($14 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 3% potential price decrease ($14 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in April 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 April 29, 2025.

Sat 9/132:43 pmMSN - PWM

1 stop4h 37mAmerican Airlines

Sat 9/209:25 amPWM - MSN

1 stop8h 18mAmerican Airlines

Deal found 4/28

$259

Fri 8/222:00 pmMSN - PWM

2 stops8h 59mDelta

Sat 8/305:00 pmPWM - MSN

1 stop5h 04mDelta

Deal found 4/28

$264

Sun 8/246:17 amMSN - PWM

1 stop6h 05mUnited Airlines

Sat 8/305:02 pmPWM - MSN

1 stop6h 21mUnited Airlines

Deal found 4/28

$329

Best flights from Madison to Portland
Discover carefully curated flight deals from Madison to Portland that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 29, 2025.

Sat 9/132:43 pmMSN - PWM

1 stop4h 37mAmerican Airlines

Sat 9/205:57 amPWM - MSN

1 stop7h 45mAmerican Airlines

Deal found 4/29

$259

Fri 8/222:00 pmMSN - PWM

2 stops8h 59mDelta

Sat 8/305:00 pmPWM - MSN

1 stop5h 04mDelta

Deal found 4/29

$264

Sun 8/246:17 amMSN - PWM

1 stop6h 05mUnited Airlines

Sat 8/305:02 pmPWM - MSN

1 stop6h 21mUnited Airlines

Deal found 4/28

$329

Last-minute flights from Madison to Portland
Discover last-minute flight deals from Madison to Portland. Data last updated April 29, 2025 and is based on user searches.

Thu 5/17:10 amMSN - PWM

1 stop5h 46mUnited Airlines

Mon 5/512:37 pmPWM - MSN

2 stops9h 51mUnited Airlines

Deal found 4/28

$454

Fri 5/94:53 pmMSN - PWM

1 stop6h 02mAmerican Airlines

Mon 5/122:05 pmPWM - MSN

1 stop7h 56mAmerican Airlines

Deal found 4/28

$600

Fri 5/95:50 pmMSN - PWM

2 stops26h 26mUnited Airlines

Mon 5/1211:50 amPWM - MSN

1 stop5h 51mUnited Airlines

Deal found 4/28

$633

Wed 5/145:00 amMSN - PWM

1 stop6h 34mAmerican Airlines

Sun 5/186:00 amPWM - MSN

1 stop5h 10mAmerican Airlines

Deal found 4/28

$386

Sun 5/256:00 amMSN - PWM

1 stop5h 57mDelta

Fri 5/305:30 amPWM - MSN

1 stop5h 49mDelta

Deal found 4/29

$328

One-way flights from Madison to Portland
Search for one-way flight options from Madison to Portland. Find affordable one-way fares based on user searches. Data last updated April 29, 2025.

Thu 5/154:53 pmMSN - PWM

1 stop6h 02mAmerican Airlines

Deal found 4/27

$199

Thu 5/155:30 amMSN - PWM

2 stops10h 20mDelta

Deal found 4/27

$425

Thu 5/152:27 pmMSN - PWM

1 stop5h 49mUnited Airlines

Deal found 4/29

$475

Cheapflights Fare Finder

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

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Sat 9/13

2:43 pm-8:20 pm

1 stop4h 37m

Portland

Sat 9/20

5:57 am-12:42 pm

1 stop7h 45m

$259

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Fri 8/22

2:00 pm-11:59 pm

2 stops8h 59m

Portland

Sat 8/30

5:00 pm-9:04 pm

1 stop5h 04m

$264

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Sun 8/24

6:17 am-1:22 pm

1 stop6h 05m

Portland

Sat 8/30

5:02 pm-10:23 pm

1 stop6h 21m

$329

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Thu 5/15

4:53 pm-11:55 pm

1 stop6h 02m

$199

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Thu 5/15

5:30 am-4:50 pm

2 stops10h 20m

$425

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Thu 5/15

2:27 pm-9:16 pm

1 stop5h 49m

$475

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/27

Compare providers for flights from Madison to Portland

Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Madison to Portland in April.

Provider	Price Accuracy	Trust Score*
Expedia	Price Accuracy1 star	Trust Score*3 stars
FlightHub	Price Accuracy3 stars	Trust Score*2 stars
eDreams	Price Accuracy3 stars	Trust 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 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?

The best time to book flights from Madison to Portland, Maine is 66 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, January is the cheapest month in which you can book a flight from Madison to Portland, Maine (average of $296). Flying from Madison to Portland, Maine in May is currently the most expensive (average of $416). 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.

Rainfall in Portland by month

In terms of precipitation, rainfall in Portland, Maine ranges from 2.9 - 4.5 inches per month. November is typically the wettest month, when rainfall can reach 4.5 in. August is typically the driest time to visit Portland, Maine when rainfall is around 2.9 in.

Temperature in Portland by month

If weather is an important factor for your trip to Portland, Maine, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 68.0 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 23.0 F).

Reviews of airlines servicing Portland

Read reviews from past customers who have flown Delta, United Airlines and American Airlines from Madison to Portland. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.

Delta

8.0

Very good

7,929 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Delta

8.0

Very good

7,929 reviews

Delta

8.0

Very good

7,929 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

United Airlines

7.4

Good

8,696 reviews

Delta

8.0

Very good

7,929 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

American Airlines

7.2

Good

10,000 reviews

Delta

8.0

Very good

7,929 reviews

Reviews

1 / 20

10.0

Excellent

Aaron,Oct 2024

TUS - LAX

Delta has consistently been the best U.S. airline for my travels and this flight was no exception

Related info for your journey

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 $259 on this airline. Additional options worth looking into are Delta and United Airlines, starting at $264 and $329 round-trip. Users have found that American Airlines is 36% 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 $199 on American Airlines. Other airlines that offer cheap prices include Delta from $425 and United Airlines from $475 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, January is the cheapest month in which you can book a flight from Madison to Portland, Maine (average of $296). Flying from Madison to Portland, Maine in May is currently the most expensive (average of $416). 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

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Top 3 airlines flying from Madison to Portland

Airline	Cheapest	Average	Flexibility	On-time
American Airlines	Cheapest$240	Average$417	FlexibilityNo cancel fee	On-time71%
Delta	Cheapest$251	Average$377	FlexibilityNo cancel fee	On-timeN/A
United Airlines	Cheapest$260	Average$463	FlexibilityNo cancel fee	On-time69%

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$199+ 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 5/15. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Madison to Portland with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheapflights Tip: The best prices from Madison Truax Field to Portland are usually found in February or March, booked 66 days in advance, depart on a Sunday or Saturday and return on a Friday

Cheap flight deals from Madison to Portland

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Find flight deals from Madison to Portland

Cheapest flights from Madison to PortlandExplore 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 April 29, 2025.

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 April 29, 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from Madison to Portland that are best for you.

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 April.

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.

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 April 25, 2025.

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

Rainfall in Portland by month

Plan your trip to Portland by taking into account the average rainfall totals by month.

Temperature in Portland by month

Plan your trip to Portland by taking into account the average temperature totals by month.

Reviews of airlines servicing Portland

Read reviews from past customers who have flown Delta, United Airlines and American Airlines from Madison to Portland. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.

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.

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

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

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

How can I find direct flights from Madison to Portland?

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

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

Traveling to a place near Madison?

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Alternative routes for Madison to Portland

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Top 3 airlines flying from Madison to Portland

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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 April 29, 2025.