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Cheap flights from Madison to Portland from $189

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 8/3. 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
1 adult, Economy, 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.
United Airlines Logo
6:29 am - 1:25 pm
MSN
-
PWM
5h 56m
1 stop
United Airlines Logo
6:00 am - 9:59 am
PWM
-
MSN
4h 59m
1 stop
$291United Airlines
Tue, Jun 2 - Wed, Jun 10
American Airlines Logo
6:00 am - 11:34 am
MSN
-
PWM
4h 34m
1 stop
American Airlines Logo
6:00 am - 12:41 pm
PWM
-
MSN
7h 41m
1 stop
$312American Airlines
Mon, Aug 31 - Sat, Sep 5
American Airlines Logo
4:12 pm - 11:54 pm
MSN
-
PWM
6h 42m
1 stop
American Airlines Logo
7:23 pm - 11:28 pm
PWM
-
MSN
5h 05m
1 stop
$328American Airlines
Wed, May 6 - Sun, May 10
United Airlines Logo
6:29 am - 1:25 pm
MSN
-
PWM
5h 56m
1 stop
United Airlines Logo
5:15 am - 11:48 am
PWM
-
MSN
7h 33m
2 stops
$331United Airlines
Tue, Jun 2 - Wed, Jun 10
Delta Logo
5:45 am - 12:22 pm
MSN
-
PWM
5h 37m
1 stop
Delta Logo
3:00 pm - 9:57 pm
PWM
-
MSN
7h 57m
2 stops
$341Delta
Mon, Aug 31 - Sat, Sep 5
American Airlines Logo
5:52 pm - 11:51 pm
MSN
-
PWM
4h 59m
1 stop
American Airlines Logo
6:00 am - 12:03 pm
PWM
-
MSN
7h 03m
1 stop
$358American Airlines
Fri, May 22 - Tue, May 26
American Airlines Logo
4:12 pm - 11:54 pm
MSN
-
PWM
6h 42m
1 stop
American Airlines Logo
7:23 pm - 11:28 pm
PWM
-
MSN
5h 05m
1 stop
$362American Airlines
Wed, May 6 - Sun, May 10
United Airlines Logo
6:30 am - 2:34 pm
MSN
-
PWM
7h 04m
2 stops
United Airlines Logo
6:00 am - 9:54 am
PWM
-
MSN
4h 54m
1 stop
$364United Airlines
Tue, Jun 9 - Sat, Jun 13
Delta Logo
1:29 pm - 12:43 am
MSN
-
PWM
10h 14m
2 stops
Delta Logo
6:25 am - 4:25 pm
PWM
-
MSN
11h 00m
2 stops
$367Delta
Thu, May 7 - Mon, May 11
United Airlines Logo
6:30 am - 2:35 pm
MSN
-
PWM
7h 05m
2 stops
United Airlines Logo
9:15 am - 2:53 pm
PWM
-
MSN
6h 38m
1 stop
$374United Airlines
Tue, Aug 25 - Tue, Sep 8

American Airlines flights from Madison to Portland, Maine

Our best American Airlines deals on Madison to Portland, Maine flight tickets
American Airlines
Aug 31
MSN6:00 amMadison Truax Field
4h 34m
1 stop
PWM11:34 amPortland
Sep 5
PWM6:00 amPortland
7h 41m
1 stop
MSN12:41 pmMadison Truax Field
$312
American Airlines
May 6
MSN4:12 pmMadison Truax Field
6h 42m
1 stop
PWM11:54 pmPortland
May 10
PWM7:23 pmPortland
5h 05m
1 stop
MSN11:28 pmMadison Truax Field
$328
American Airlines
May 22
MSN5:52 pmMadison Truax Field
4h 59m
1 stop
PWM11:51 pmPortland
May 26
PWM6:00 amPortland
7h 03m
1 stop
MSN12:03 pmMadison Truax Field
$358

United Airlines flights from Madison to Portland, Maine

Our best United Airlines deals on Madison to Portland, Maine flight tickets
United Airlines
Jun 2
MSN6:29 amMadison Truax Field
5h 56m
1 stop
PWM1:25 pmPortland
Jun 10
PWM6:00 amPortland
4h 59m
1 stop
MSN9:59 amMadison Truax Field
$291
United Airlines
Jun 2
MSN6:29 amMadison Truax Field
5h 56m
1 stop
PWM1:25 pmPortland
Jun 10
PWM5:15 amPortland
7h 33m
2 stops
MSN11:48 amMadison Truax Field
$331
United Airlines
Jun 9
MSN6:30 amMadison Truax Field
7h 04m
2 stops
PWM2:34 pmPortland
Jun 13
PWM6:00 amPortland
4h 54m
1 stop
MSN9:54 amMadison Truax Field
$364

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 April 1, 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

Cheapest round-trip
Quickest round-trip

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Tue 6/2

6:29 am-1:25 pm

1 stop5h 56m

Portland

Wed 6/10

6:00 am-9:59 am

1 stop4h 59m

$291

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Mon 8/31

6:00 am-11:34 am

1 stop4h 34m

Portland

Sat 9/5

6:00 am-12:41 pm

1 stop7h 41m

$312

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Wed 5/6

4:12 pm-11:54 pm

1 stop6h 42m

Portland

Sun 5/10

7:23 pm-11:28 pm

1 stop5h 05m

$328

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Tue 6/2

6:29 am-1:25 pm

1 stop5h 56m

Portland

Wed 6/10

5:15 am-11:48 am

2 stops7h 33m

$331

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Mon 8/31

5:45 am-12:22 pm

1 stop5h 37m

Portland

Sat 9/5

3:00 pm-9:57 pm

2 stops7h 57m

$341

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Fri 5/22

5:52 pm-11:51 pm

1 stop4h 59m

Portland

Tue 5/26

6:00 am-12:03 pm

1 stop7h 03m

$358

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Wed 5/6

4:12 pm-11:54 pm

1 stop6h 42m

Portland

Sun 5/10

7:23 pm-11:28 pm

1 stop5h 05m

$362

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Tue 6/9

6:30 am-2:34 pm

2 stops7h 04m

Portland

Sat 6/13

6:00 am-9:54 am

1 stop4h 54m

$364

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Thu 5/7

1:29 pm-12:43 am

2 stops10h 14m

Portland

Mon 5/11

6:25 am-4:25 pm

2 stops11h 00m

$367

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Tue 8/25

6:30 am-2:35 pm

2 stops7h 05m

Portland

Tue 9/8

9:15 am-2:53 pm

1 stop6h 38m

$374

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 18 resultsSorted by cheapest first
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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

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

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

4h 09m

Direct flights

None
The fastest flight from Madison to Portland, Maine takes 4h 09m
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 4h 09m, 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
DeltaPriceFrom $258Free CancellationRating
7.9
8,368 reviews
Search Delta flights
American AirlinesPriceFrom $258Free CancellationRating
7.1
11,544 reviews
Search American Airlines flights
United AirlinesPriceFrom $273Free CancellationRating
7.4
9,529 reviews
Search United Airlines 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.

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