What airlines fly to Portland, Maine?

American Airlines, Delta and JetBlue are the top three most popular airlines that fly to Portland, Maine from Madison according to our data. American Airlines is the first choice among our users, with 38% of people opting to fly with this airline when traveling to Portland, Maine. Keep in mind that there are 5 different airlines that fly to Portland, Maine on a routine basis, so you have a few additional options to choose from.

What is the cheapest airline that flies from Madison Truax Field to Portland?

American Airlines and United Airlines are the most popular carriers operating from Madison Truax Field to Portland

When did momondo last update prices for flights from Madison Truax Field Airport to Portland Airport?

Prices for flights from Madison Truax Field Airport to Portland Airport refresh daily.

How many operators does momondo search for flights from Madison Truax Field Airport to Portland Airport?

The number of operators available for flights from Madison Truax Field Airport to Portland Airport is 3 as of October 2026.

How old do you have to be to fly from Madison Truax Field Airport to Portland Airport?

The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Madison Truax Field Airport to Portland Airport.

What documentation or ID do you need to fly to Portland Airport?

The travel and health documents required for your trip to Portland Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Portland Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$175 Cheap Flights from Madison to Portland, Maine in 2026/27

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Madison to Portland

Round-trip

One-way

Last minute

Cheap round-trip flights

Enter your travel dates to find the best prices.

5:51 am - 12:02 pmMSN Madison Truax Field-PWM Portland

5h 11m1 stop Chicago O'Hare Intl

2:57 pm - 11:19 pmPWM Portland-MSN Madison Truax Field

9h 22m2 stops Washington, D.C. Reagan-National Chicago O'Hare Intl

$346American Airlines

Sat, Dec 5 - Sat, Dec 12

9:59 am - 4:10 pmMSN Madison Truax Field-PWM Portland

5h 11m1 stop Detroit Metropolitan Wayne County

4:50 pm - 9:13 pmPWM Portland-MSN Madison Truax Field

5h 23m1 stop Detroit Metropolitan Wayne County

$349Delta

Sun, Nov 15 - Sun, Nov 22

3:12 pm - 11:31 pmMSN Madison Truax Field-PWM Portland

7h 19m2 stops Chicago O'Hare Intl Washington, D.C. Reagan-National

5:00 am - 11:50 amPWM Portland-MSN Madison Truax Field

7h 50m1 stop Washington, D.C. Reagan-National

$350American Airlines

Wed, Dec 2 - Sun, Dec 6

11:49 am - 10:46 pmMSN Madison Truax Field-PWM Portland

9h 57m2 stops Chicago O'Hare Intl Washington, D.C. Reagan-National

2:57 pm - 12:08 amPWM Portland-MSN Madison Truax Field

10h 11m2 stops Washington, D.C. Reagan-National Chicago O'Hare Intl

$351American Airlines

Sat, Dec 5 - Sat, Dec 12

8:15 am - 2:16 pmMSN Madison Truax Field-PWM Portland

5h 01m1 stop Chicago O'Hare Intl

5:50 am - 2:00 pmPWM Portland-MSN Madison Truax Field

9h 10m2 stops Newark Chicago O'Hare Intl

$354United Airlines

Thu, Nov 19 - Tue, Nov 24

7:00 am - 11:58 amMSN Madison Truax Field-PWM Portland

3h 58m1 stop Detroit Metropolitan Wayne County

6:27 am - 12:50 pmPWM Portland-MSN Madison Truax Field

7h 23m2 stops New York LaGuardia Detroit Metropolitan Wayne County

$354Delta

Thu, Nov 19 - Mon, Nov 23

3:00 pm - 11:59 pmMSN Madison Truax Field-PWM Portland

7h 59m2 stops Chicago O'Hare Intl Washington, D.C. Dulles Intl

4:28 pm - 10:59 pmPWM Portland-MSN Madison Truax Field

7h 31m1 stop Chicago O'Hare Intl

$364United Airlines

Thu, Dec 24 - Thu, Dec 31

5:30 am - 1:01 pmMSN Madison Truax Field-PWM Portland

6h 31m1 stop Atlanta Hartsfield-Jackson

6:27 am - 11:18 amPWM Portland-MSN Madison Truax Field

5h 51m1 stop New York LaGuardia

$374Delta

Thu, Nov 19 - Thu, Nov 26

6:00 pm - 9:08 amMSN Madison Truax Field-PWM Portland

14h 08m1 stop Orlando

9:48 am - 5:30 pmPWM Portland-MSN Madison Truax Field

8h 42m1 stop Orlando

$710Breeze Airways

Thu, Nov 19 - Wed, Nov 25

6:00 pm - 9:08 amMSN Madison Truax Field-PWM Portland

14h 08m1 stop Orlando

9:48 am - 5:30 pmPWM Portland-MSN Madison Truax Field

8h 42m1 stop Orlando

$743Breeze Airways

Sun, Nov 22 - Wed, Nov 25

Cheap last minute flights

Enter your travel dates to find the best prices.

5:51 am - 1:02 pmMSN Madison Truax Field-PWM Portland

6h 11m1 stop Atlanta Hartsfield-Jackson

11:55 am - 7:06 pmPWM Portland-MSN Madison Truax Field

8h 11m1 stop Minneapolis St Paul

$420Delta

Tue, Nov 3 - Sun, Nov 8

5:51 am - 1:02 pmMSN Madison Truax Field-PWM Portland

6h 11m1 stop Atlanta Hartsfield-Jackson

11:55 am - 7:06 pmPWM Portland-MSN Madison Truax Field

8h 11m1 stop Minneapolis St Paul

$420Delta

Wed, Nov 4 - Sun, Nov 8

8:15 am - 2:16 pmMSN Madison Truax Field-PWM Portland

5h 01m1 stop Chicago O'Hare Intl

5:30 am - 11:59 amPWM Portland-MSN Madison Truax Field

7h 29m2 stops Washington, D.C. Dulles Intl Chicago O'Hare Intl

$425United Airlines

Wed, Nov 4 - Sun, Nov 8

5:51 am - 3:35 pmMSN Madison Truax Field-PWM Portland

8h 44m2 stops Atlanta Hartsfield-Jackson New York John F Kennedy Intl

11:55 am - 7:06 pmPWM Portland-MSN Madison Truax Field

8h 11m1 stop Minneapolis St Paul

$425Delta

Wed, Nov 4 - Sun, Nov 8

6:10 am - 2:27 pmMSN Madison Truax Field-PWM Portland

7h 17m2 stops Newark Washington, D.C. Dulles Intl

5:30 am - 11:59 amPWM Portland-MSN Madison Truax Field

7h 29m2 stops Washington, D.C. Dulles Intl Chicago O'Hare Intl

$430United Airlines

Wed, Nov 4 - Sun, Nov 8

3:52 pm - 9:51 pmMSN Madison Truax Field-PWM Portland

4h 59m1 stop Chicago O'Hare Intl

5:08 pm - 9:05 pmPWM Portland-MSN Madison Truax Field

4h 57m1 stop Chicago O'Hare Intl

$438United Airlines

Wed, Nov 4 - Sun, Nov 8

8:15 am - 2:16 pmMSN Madison Truax Field-PWM Portland

5h 01m1 stop Chicago O'Hare Intl

5:08 pm - 9:05 pmPWM Portland-MSN Madison Truax Field

4h 57m1 stop Chicago O'Hare Intl

$441United Airlines

Sat, Oct 31 - Tue, Nov 3

1:37 pm - 9:00 pmMSN Madison Truax Field-PWM Portland

6h 23m1 stop Atlanta Hartsfield-Jackson

11:55 am - 7:06 pmPWM Portland-MSN Madison Truax Field

8h 11m1 stop Minneapolis St Paul

$447Delta

Thu, Nov 5 - Sun, Nov 8

4:58 pm - 3:25 pmMSN Madison Truax Field-PWM Portland

21h 27m3 stops Fort Myers SW Florida Intl Greenville Pittsburgh

5:09 pm - 4:18 pmPWM Portland-MSN Madison Truax Field

24h 09m2 stops Raleigh-Durham Fort Myers SW Florida Intl

$1,084Breeze Airways

Sat, Oct 31 - Tue, Nov 3

4:58 pm - 3:25 pmMSN Madison Truax Field-PWM Portland

21h 27m3 stops Fort Myers SW Florida Intl Greenville Pittsburgh

5:09 pm - 5:20 pmPWM Portland-MSN Madison Truax Field

25h 11m2 stops Raleigh-Durham Orlando

$1,324Breeze Airways

Sat, Oct 31 - Wed, Nov 4

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United Airlines flights from Madison to Portland, Maine

Our best United Airlines deals on Madison to Portland, Maine flight tickets

United Airlines

Nov 19

MSN8:15 amMadison Truax Field

5h 01m

1 stop

PWM2:16 pmPortland

Nov 24

PWM5:50 amPortland

9h 10m

2 stops

MSN2:00 pmMadison Truax Field

$354

United Airlines

Dec 24

MSN3:00 pmMadison Truax Field

7h 59m

2 stops

PWM11:59 pmPortland

Dec 31

PWM4:28 pmPortland

7h 31m

1 stop

MSN10:59 pmMadison Truax Field

$364

United Airlines

Dec 24

MSN3:00 pmMadison Truax Field

7h 59m

2 stops

PWM11:59 pmPortland

Dec 31

PWM3:38 pmPortland

8h 21m

2 stops

MSN10:59 pmMadison Truax Field

$369

American Airlines flights from Madison to Portland, Maine

Our best American Airlines deals on Madison to Portland, Maine flight tickets

American Airlines

Dec 5

MSN5:51 amMadison Truax Field

5h 11m

1 stop

PWM12:02 pmPortland

Dec 12

PWM2:57 pmPortland

9h 22m

2 stops

MSN11:19 pmMadison Truax Field

$346

American Airlines

Dec 2

MSN3:12 pmMadison Truax Field

7h 19m

2 stops

PWM11:31 pmPortland

Dec 6

PWM5:00 amPortland

7h 50m

1 stop

MSN11:50 amMadison Truax Field

$350

American Airlines

Dec 5

MSN11:49 amMadison Truax Field

9h 57m

2 stops

PWM10:46 pmPortland

Dec 12

PWM2:57 pmPortland

10h 11m

2 stops

MSN12:08 amMadison Truax Field

$351

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

MadisonPortland

MSN Madison Truax Field - PWM Portland

MSNPWM

Madison Truax Field

Sat 12/5

5:51 am-12:02 pm

1 stop5h 11m

Portland

Sat 12/12

2:57 pm-11:19 pm

2 stops9h 22m

$346

Quickest round-trip

MadisonPortland

MSN Madison Truax Field - PWM Portland

MSNPWM

Madison Truax Field

Sun 11/15

9:59 am-4:10 pm

1 stop5h 11m

Portland

Sun 11/22

4:50 pm-9:13 pm

1 stop5h 23m

$349

MadisonPortland

MSN Madison Truax Field - PWM Portland

MSNPWM

Madison Truax Field

Wed 12/2

3:12 pm-11:31 pm

2 stops7h 19m

Portland

Sun 12/6

5:00 am-11:50 am

1 stop7h 50m

$350

MadisonPortland

MSN Madison Truax Field - PWM Portland

MSNPWM

Madison Truax Field

Sat 12/5

11:49 am-10:46 pm

2 stops9h 57m

Portland

Sat 12/12

2:57 pm-12:08 am

2 stops10h 11m

$351

MadisonPortland

MSN Madison Truax Field - PWM Portland

MSNPWM

Madison Truax Field

Thu 11/19

8:15 am-2:16 pm

1 stop5h 01m

Portland

Tue 11/24

5:50 am-2:00 pm

2 stops9h 10m

$354

MadisonPortland

MSN Madison Truax Field - PWM Portland

MSNPWM

Madison Truax Field

Thu 11/19

7:00 am-11:58 am

1 stop3h 58m

Portland

Mon 11/23

6:27 am-12:50 pm

2 stops7h 23m

$354

MadisonPortland

MSN Madison Truax Field - PWM Portland

MSNPWM

Madison Truax Field

Thu 12/24

3:00 pm-11:59 pm

2 stops7h 59m

Portland

Thu 12/31

4:28 pm-10:59 pm

1 stop7h 31m

$364

MadisonPortland

MSN Madison Truax Field - PWM Portland

MSNPWM

Madison Truax Field

Thu 11/19

5:30 am-1:01 pm

1 stop6h 31m

Portland

Thu 11/26

6:27 am-11:18 am

1 stop5h 51m

$374

MadisonPortland

MSN Madison Truax Field - PWM Portland

MSNPWM

Madison Truax Field

Thu 11/19

6:00 pm-9:08 am

1 stop14h 08m

Portland

Wed 11/25

9:48 am-5:30 pm

1 stop8h 42m

$710

MadisonPortland

MSN Madison Truax Field - PWM Portland

MSNPWM

Madison Truax Field

Sun 11/22

6:00 pm-9:08 am

1 stop14h 08m

Portland

Wed 11/25

9:48 am-5:30 pm

1 stop8h 42m

$743

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Madison to Portland, Maine

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

What is the typical price of a round-trip flight between Madison and Portland, Maine?

Prices are currently low for flights on this route.

Typical prices usually range from $457 to $554.
The lowest price recently found on this route was $346.

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

The cheapest month to fly to Portland, Maine from Madison is in March. Flight prices, which tend to average around $0, are often lower during this time because this is during the off-season. If you aren’t able to travel to Portland, Maine during the month of March, then flying in January is also cheap. Prices for this month can be found on momondo for an average of $0.

How have Madison to Portland, Maine flight prices changed over time?

As of October 2026, prices for Madison to Portland, Maine flights are approximately 46% more expensive when compared to flights at the same time last year.

When to book flights from Madison to Portland, Maine

Are you open to changing your travel dates? Check out the ideal times to fly from Madison to Portland, Maine according to our flight data. Find out which month and days have the cheapest flights.

Estimated round-trip price

Cheap Madison to Portland, Maine (MSN to PWM) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Madison to Portland, Maine

Best Price Found	$175
Fastest flight time	3h 58m
Direct flights	None

The best one-way flight to Portland, Maine from Madison in the past 72 hours is $175. The best round-trip flight deal from Madison to Portland, Maine found on momondo in the last 72 hours is $346.

The fastest flight from Madison to Portland, Maine takes 3h 58m

There are no direct flights from Madison to Portland, Maine. There are no popular flight routes from Madison to Portland, Maine.

Search flight deals

Frequently asked questions about flying from Madison to Portland, Maine

How far is Madison Truax Field to Portland by plane?
A flight from Madison Truax Field to Portland will travel around 959.7 mi. Flights usually cover this in 3h 58m, depending on flying conditions and air traffic around both airports.
When did momondo last update prices for flights from Madison Truax Field Airport to Portland Airport?
Prices for flights from Madison Truax Field Airport to Portland Airport refresh daily.
How many operators does momondo search for flights from Madison Truax Field Airport to Portland Airport?
The number of operators available for flights from Madison Truax Field Airport to Portland Airport is 3 as of October 2026.
How old do you have to be to fly from Madison Truax Field Airport to Portland Airport?
The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Madison Truax Field Airport to Portland Airport.
What documentation or ID do you need to fly to Portland Airport?
The travel and health documents required for your trip to Portland Airport can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Portland Airport. We always recommend checking with your airline or a trusted third party such as IATA to get advice.
What is the most popular airline from Madison to Portland, Maine?
momondo data reveals that the most frequently booked airline on the route from Madison to Portland, Maine is American Airlines, representing 60% of all bookings. The subsequent popular airlines are United Airlines at 29% and Delta at 10%.

Best airlines flying from Madison to Portland, Maine

Compare and see reviews for airlines that fly from Madison to Portland, Maine with momondo

Airline	Rating	Free Cancellation	Price
Delta	PriceFrom $258	Free Cancellation	Rating 7.8 8,692 reviews	Search Delta flights
American Airlines	PriceFrom $290	Free Cancellation	Rating 7.0 12,210 reviews	Search American Airlines flights
United Airlines	PriceFrom $300	Free Cancellation	Rating 7.3 10,451 reviews	Search United Airlines flights

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Freeport

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Auburn

Bartlett

Bath

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Intervale

Georgetown

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Falmouth

Tamworth

Why use momondo?

Why should I use momondo to find a flight deal from Madison to Portland?

Finding the right flight to Portland from Madison is quick and easy when you have a range of options in front of you, from reputable agents and recognisable airlines. Options that can then be filtered down to find the best fit. That is what momondo does. We make finding flights to Portland quick and easy, saving you time and money.

Can I find flights from Madison to Portland with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Madison to Portland flights to just show those with flexible booking policies.

How can momondo help me find flights from Madison to Portland?

momondo helps you find the best flight between Madison and Portland by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

I’m not ready to book a flight from Madison to Portland right now. Can momondo alert me if prices change?

If you are not ready to book a flight from Madison to Portland now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Portland and let you know when they change.

An easier way to manage your Portland, Maine trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

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Rockland Knox County Regional Airport

Cheap flights from Madison to Portland from $175

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Madison to Portland departing on 11/23. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.

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United Airlines flights from Madison to Portland, Maine

Our best United Airlines deals on Madison to Portland, Maine flight tickets

American Airlines flights from Madison to Portland, Maine

Our best American Airlines deals on Madison to Portland, Maine flight tickets

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How to get the cheapest flight ticket from Madison to Portland, Maine

What is the typical price of a round-trip flight between Madison and Portland, Maine?

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

How have Madison to Portland, Maine flight prices changed over time?

What is the cheapest airline that flies from Madison Truax Field to Portland?

What airlines fly to Portland, Maine?

When to book flights from Madison to Portland, Maine

Cheap Madison to Portland, Maine (MSN to PWM) flight deals and tips

Best Price Found

Fastest flight time

Direct flights

Frequently asked questions about flying from Madison to Portland, Maine

Best airlines flying from Madison to Portland, Maine

Compare and see reviews for airlines that fly from Madison to Portland, Maine with momondo

Traveling to a place near Portland?

Why use momondo?

An easier way to manage your Portland, Maine trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.

Find better results for your trip to the United States

Airports servicing Maine

Fly your favorite airline to Portland

Airlines are sorted and displayed according to clicks in the past 7 days on momondo

Cabin classes currently available on flights to Portland

List of cabin classes available on flights landing in Portland. Availability may vary depending on flight origin and airline.

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Popular flights according to clicks in the last 7 days on momondo

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According to popular flight searches on momondo this year

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