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Cheap flights from Madison to Portland from $159

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 6/3. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

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Find the cheapest flights from Madison to Portland

Cheap round-trip flights

Enter your travel dates to find the best prices.
American Airlines Logo
10:19 am - 5:21 pm
MSN
-
PWM
6h 02m
1 stop
American Airlines Logo
3:39 pm - 9:25 pm
PWM
-
MSN
6h 46m
1 stop
$279American Airlines
Thu, Apr 9 - Mon, Apr 13
Delta Logo
7:00 am - 11:57 am
MSN
-
PWM
3h 57m
1 stop
Delta Logo
6:02 am - 5:32 pm
PWM
-
MSN
12h 30m
2 stops
$284Delta
Wed, May 27 - Sat, May 30
American Airlines Logo
8:11 am - 2:03 pm
MSN
-
PWM
4h 52m
1 stop
American Airlines Logo
1:31 pm - 7:38 pm
PWM
-
MSN
7h 07m
1 stop
$291American Airlines
Mon, Jul 20 - Tue, Aug 4
American Airlines Logo
5:36 pm - 11:27 pm
MSN
-
PWM
4h 51m
1 stop
American Airlines Logo
3:39 pm - 9:25 pm
PWM
-
MSN
6h 46m
1 stop
$294American Airlines
Wed, May 6 - Mon, May 11
American Airlines Logo
8:00 am - 3:09 pm
MSN
-
PWM
6h 09m
1 stop
American Airlines Logo
3:39 pm - 9:25 pm
PWM
-
MSN
6h 46m
1 stop
$309American Airlines
Thu, May 7 - Mon, May 11
Delta Logo
1:45 pm - 11:53 pm
MSN
-
PWM
9h 08m
2 stops
Delta Logo
3:00 pm - 8:13 pm
PWM
-
MSN
6h 13m
1 stop
$314Delta
Tue, Jul 28 - Tue, Aug 4
United Airlines Logo
2:30 pm - 9:19 pm
MSN
-
PWM
5h 49m
1 stop
United Airlines Logo
4:45 pm - 9:15 pm
PWM
-
MSN
5h 30m
1 stop
$315United Airlines
Sun, May 3 - Sat, May 9
Delta Logo
9:29 am - 4:35 pm
MSN
-
PWM
6h 06m
2 stops
Delta Logo
6:02 am - 5:32 pm
PWM
-
MSN
12h 30m
2 stops
$319Delta
Wed, May 27 - Sat, May 30
United Airlines Logo
2:30 pm - 9:19 pm
MSN
-
PWM
5h 49m
1 stop
United Airlines Logo
5:30 am - 3:02 pm
PWM
-
MSN
10h 32m
2 stops
$321United Airlines
Sun, May 3 - Sat, May 9
United Airlines Logo
10:48 am - 5:32 pm
MSN
-
PWM
5h 44m
1 stop
United Airlines Logo
6:13 pm - 11:49 pm
PWM
-
MSN
6h 36m
1 stop
$349United Airlines
Thu, Apr 2 - Mon, Apr 6

American Airlines flights from Madison to Portland, Maine

Our best American Airlines deals on Madison to Portland, Maine flight tickets
American Airlines
Apr 9
MSN10:19 amMadison Truax Field
6h 02m
1 stop
PWM5:21 pmPortland
Apr 13
PWM3:39 pmPortland
6h 46m
1 stop
MSN9:25 pmMadison Truax Field
$279
American Airlines
Jul 20
MSN8:11 amMadison Truax Field
4h 52m
1 stop
PWM2:03 pmPortland
Aug 4
PWM1:31 pmPortland
7h 07m
1 stop
MSN7:38 pmMadison Truax Field
$291
American Airlines
May 6
MSN5:36 pmMadison Truax Field
4h 51m
1 stop
PWM11:27 pmPortland
May 11
PWM3:39 pmPortland
6h 46m
1 stop
MSN9:25 pmMadison Truax Field
$294

United Airlines flights from Madison to Portland, Maine

Our best United Airlines deals on Madison to Portland, Maine flight tickets
United Airlines
May 3
MSN2:30 pmMadison Truax Field
5h 49m
1 stop
PWM9:19 pmPortland
May 9
PWM4:45 pmPortland
5h 30m
1 stop
MSN9:15 pmMadison Truax Field
$315
United Airlines
May 3
MSN2:30 pmMadison Truax Field
5h 49m
1 stop
PWM9:19 pmPortland
May 9
PWM5:30 amPortland
10h 32m
2 stops
MSN3:02 pmMadison Truax Field
$321
United Airlines
Apr 2
MSN10:48 amMadison Truax Field
5h 44m
1 stop
PWM5:32 pmPortland
Apr 6
PWM6:13 pmPortland
6h 36m
1 stop
MSN11:49 pmMadison Truax Field
$349

momondo Fare Finder

 
Customize your flight search to find flights from Madison to Portland, Maine 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, momondo users made 832,500 searches. Data last updated February 7, 2026.
Use the filters below to find and compare flights from Madison to Portland, Maine that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Thu 4/9

10:19 am-5:21 pm

1 stop6h 02m

Portland

Mon 4/13

3:39 pm-9:25 pm

1 stop6h 46m

$279

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Wed 5/27

7:00 am-11:57 am

1 stop3h 57m

Portland

Sat 5/30

6:02 am-5:32 pm

2 stops12h 30m

$284

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Mon 7/20

8:11 am-2:03 pm

1 stop4h 52m

Portland

Tue 8/4

1:31 pm-7:38 pm

1 stop7h 07m

$291

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Wed 5/6

5:36 pm-11:27 pm

1 stop4h 51m

Portland

Mon 5/11

3:39 pm-9:25 pm

1 stop6h 46m

$294

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Thu 5/7

8:00 am-3:09 pm

1 stop6h 09m

Portland

Mon 5/11

3:39 pm-9:25 pm

1 stop6h 46m

$309

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Tue 7/28

1:45 pm-11:53 pm

2 stops9h 08m

Portland

Tue 8/4

3:00 pm-8:13 pm

1 stop6h 13m

$314

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Sun 5/3

2:30 pm-9:19 pm

1 stop5h 49m

Portland

Sat 5/9

4:45 pm-9:15 pm

1 stop5h 30m

$315

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Wed 5/27

9:29 am-4:35 pm

2 stops6h 06m

Portland

Sat 5/30

6:02 am-5:32 pm

2 stops12h 30m

$319

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Sun 5/3

2:30 pm-9:19 pm

1 stop5h 49m

Portland

Sat 5/9

5:30 am-3:02 pm

2 stops10h 32m

$321

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Thu 4/2

10:48 am-5:32 pm

1 stop5h 44m

Portland

Mon 4/6

6:13 pm-11:49 pm

1 stop6h 36m

$349

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 14 resultsSorted by cheapest first
1
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See travel insights to Portland from

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

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

You are more likely to see cheaper flights to Portland, Maine from Madison when booking weeks ahead of your departure date. In general, you can expect to find flights to Portland, Maine for around $420 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Portland, Maine from Madison for as low as $308 on momondo.

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

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

Fastest flight time

3h 57m

Direct flights

None
The fastest flight from Madison to Portland, Maine takes 3h 57m
There are no direct flights from Madison to Portland, Maine. There are no popular flight routes from Madison to Portland, Maine.
Search flight deals

  • 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 57m, 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?

  • 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?

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
United AirlinesPriceFrom $258Free CancellationRating
7.4
9,244 reviews
Search United Airlines flights
American AirlinesPriceFrom $258Free CancellationRating
7.2
11,246 reviews
Search American Airlines flights
DeltaPriceFrom $258Free CancellationRating
7.9
8,159 reviews
Search Delta flights

Traveling to a place near Portland?

Book flights to Portland if you plan to visit one of these locations
North Conway
Boothbay Harbor
Jackson
Conway
Freeport
Lewiston
Brunswick
Bartlett
Gorham
Auburn
Windham
Intervale
Bath
Oxford
Georgetown
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

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