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$269+ 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 8/21. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — PWM
Aug 27 — Sep 31
Thu 8/27
Thu 9/3
1 adult, Economy
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Cheap 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 July 28, 2026.

This United Airlines deal was found by Cheapflights users on 7/23. 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 10/135:00 am
MSN
-
PWM
1 stop4h 40m
United Airlines
Sat 10/176:00 am
PWM
-
MSN
2 stops8h 37m
United Airlines
Deal found 7/23$296
This Delta deal was found by Cheapflights users on 7/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/215:51 am
MSN
-
PWM
1 stop6h 11m
Delta
Wed 10/2811:55 am
PWM
-
MSN
1 stop8h 11m
Delta
Deal found 7/28$301
This American Airlines deal was found by Cheapflights users on 7/26. 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.
Sat 10/105:26 pm
MSN
-
PWM
1 stop5h 15m
American Airlines
Sat 10/175:09 pm
PWM
-
MSN
2 stops8h 03m
American Airlines
Deal found 7/26$306
This Delta deal was found by Cheapflights users on 7/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/215:51 am
MSN
-
PWM
2 stops8h 44m
Delta
Tue 10/272:09 pm
PWM
-
MSN
2 stops7h 52m
Delta
Deal found 7/28$311
This American Airlines deal was found by Cheapflights users on 7/26. 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.
Mon 8/319:48 am
MSN
-
PWM
1 stop6h 44m
American Airlines
Sat 9/510:56 am
PWM
-
MSN
1 stop7h 21m
American Airlines
Deal found 7/26$315
This American Airlines deal was found by Cheapflights users on 7/27. 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 8/195:00 am
MSN
-
PWM
2 stops6h 40m
American Airlines
Wed 8/265:13 pm
PWM
-
MSN
2 stops7h 57m
American Airlines
Deal found 7/27$325
This American Airlines deal was found by Cheapflights users on 7/26. 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.
Tue 8/181:25 pm
MSN
-
PWM
1 stop6h 56m
American Airlines
Sat 8/226:46 pm
PWM
-
MSN
1 stop5h 43m
American Airlines
Deal found 7/26$329
This American Airlines deal was found by Cheapflights users on 7/27. 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.
Thu 10/14:23 pm
MSN
-
PWM
1 stop6h 36m
American Airlines
Tue 10/65:37 pm
PWM
-
MSN
1 stop6h 48m
American Airlines
Deal found 7/27$332

Find 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 July 28, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$296
(United Airlines)

One-way from

$269
(American Airlines)

Popular in

December

Cheapest in

September

Average price

$497
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. 13% potential increase in price ($66 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($22 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals

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 July 28, 2026.
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

Cheapest round-trip

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Tue 10/20

5:51 am-3:35 pm

2 stops8h 44m

Portland

Wed 10/28

1:52 pm-7:15 pm

1 stop6h 23m

$306

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Fri 10/16

2:49 pm-9:46 pm

1 stop5h 57m

Portland

Tue 10/27

5:30 am-11:54 am

2 stops7h 24m

$320

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Thu 10/22

1:29 pm-11:35 pm

2 stops9h 06m

Portland

Wed 10/28

1:52 pm-7:15 pm

1 stop6h 23m

$320

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Tue 10/13

5:00 am-10:40 am

1 stop4h 40m

Portland

Sat 10/17

7:58 am-3:04 pm

1 stop8h 06m

$334

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Sat 9/12

12:41 pm-9:23 pm

1 stop7h 42m

Portland

Sat 9/19

6:00 am-9:40 am

1 stop4h 40m

$381

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Sat 11/14

8:14 am-7:02 pm

2 stops9h 48m

Portland

Wed 11/18

3:10 pm-10:59 pm

2 stops8h 49m

$381
Quickest round-trip

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Fri 9/18

2:44 pm-9:23 pm

1 stop5h 39m

Portland

Sun 9/20

6:00 am-9:40 am

1 stop4h 40m

$409
Cheapest one-way

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Fri 8/21

3:54 pm-11:47 pm

1 stop6h 53m

$269
Quickest one-way

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Tue 8/4

3:46 pm-9:41 pm

1 stop4h 55m

$366

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Sun 8/2

3:46 pm-9:41 pm

1 stop4h 55m

$416

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/23

Showing 1-10 of 11 resultsSorted by cheapest first
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 July.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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 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 FlightHub the most. FlightHub 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 much does it cost to fly round-trip from Madison to Portland, Maine?

Airfare is below average for this route at the moment.

Madison to Portland, Maine flights typically cost between $340 and $519 in October.
The cheapest round-trip price found within the last 5 days was $296 on United Airlines (Oct 13-Oct 17).

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 July 28, 2026.
Get a feel of what it's like to fly with Delta,United Airlines, andAmerican 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
7.8
Good
8,482 reviews

Crew

8.5

Overall

7.8

Entertainment

7.8

Boarding

8.1

Comfort

7.8

Food

7.2

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

The snacks were not very good, not everyone was very friendly and professional
Delta
7.8
Good
8,482 reviews
Delta
7.8
Good
8,482 reviews

Crew

8.5

Overall

7.8

Entertainment

7.8

Boarding

8.1

Comfort

7.8

Food

7.2

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

The snacks were not very good, not everyone was very friendly and professional
United Airlines
7.4
Good
10,046 reviews
Delta
7.8
Good
8,482 reviews

Crew

8.5

Overall

7.8

Entertainment

7.8

Boarding

8.1

Comfort

7.8

Food

7.2

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

The snacks were not very good, not everyone was very friendly and professional
American Airlines
7.1
Good
11,839 reviews
Delta
7.8
Good
8,482 reviews

Crew

8.5

Overall

7.8

Entertainment

7.8

Boarding

8.1

Comfort

7.8

Food

7.2

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

The snacks were not very good, not everyone was very friendly and professional

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 Delta and United Airlines fly from Madison to Portland, Maine in about 5h 57m. The time it takes to get you to your destination can typically vary by up to 2h 47m. 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 Delta. Our recent data shows that you can find tickets from as low as $258 on this airline. Additional options worth looking into are American Airlines and United Airlines, starting at $285 and $300 round-trip. Users have found that Delta is 40% 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 $158 on Delta. Other airlines that offer cheap prices include United Airlines from $168 and American Airlines from $193 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.

See more FAQs

Traveling to a place near Portland?

Book flights to Portland if you plan to visit one of these locations
North Conway
Lewiston
Brunswick
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 July 28, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$258Average$307FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$285Average$413FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$300Average$457FlexibilityNo cancel feeOn-time69%

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