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Madison

$259+ Cheap flights from Portland, ME to Madison (PWM - MSN)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/11. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MSN
nov. 19 — nov. 261
mié. 11/19
mié. 11/26
1 adult, Economy
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Cheapflights Tip: The best prices from Portland to Madison Truax Field are usually found in January or December, booked 71 days in advance, depart on a Friday or Tuesday and return on a Sunday

Cheap flight deals from Portland to Madison

Discover tips and strategies to find the most affordable flight options for your journey from Portland (PWM) to Madison (MSN). 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 octubre 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$259
(United Airlines)

Popular in

April

Cheapest in

January

Average price

$370
Provider with most accurate pricing for Portland-Madison Truax Field flight deals.
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Provider most trusted by Cheapflights users for Portland-Madison Truax Field flights.
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From Portland to Madison Truax Field
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Highest demand for flights based on searches. 6% potential increase in price ($26 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in October 2025
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Find flight deals from Portland to Madison

Cheapest flights from Portland to Madison
Explore the most affordable flight options available from Portland to Madison. Find the lowest fares from popular airlines and budget airlines, with prices last updated on octubre 20, 2025.

This United Airlines deal was found by Cheapflights users on 10/20. 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.
mar. 11/114:57 pmPWM - MSN
1 stop4h 38mUnited Airlines
sáb. 11/152:48 pmMSN - PWM
1 stop6h 02mUnited Airlines
Deal found 10/20$259
This United Airlines deal was found by Cheapflights users on 10/19. 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.
sáb. 11/84:57 pmPWM - MSN
1 stop4h 38mUnited Airlines
sáb. 11/158:25 amMSN - PWM
1 stop4h 47mUnited Airlines
Deal found 10/19$274
This Delta deal was found by Cheapflights users on 10/19. 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.
sáb. 11/812:45 pmPWM - MSN
2 stops10h 44mDelta
sáb. 11/155:29 amMSN - PWM
1 stop6h 01mDelta
Deal found 10/19$279
This United Airlines deal was found by Cheapflights users on 10/19. 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.
vie. 11/145:30 amPWM - MSN
2 stops9h 33mUnited Airlines
lun. 11/176:30 amMSN - PWM
1 stop6h 42mUnited Airlines
Deal found 10/19$310
This American Airlines deal was found by Cheapflights users on 10/20. 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.
sáb. 11/225:21 pmPWM - MSN
1 stop4h 46mAmerican Airlines
mar. 12/23:59 pmMSN - PWM
1 stop6h 42mAmerican Airlines
Deal found 10/20$337
This United Airlines deal was found by Cheapflights users on 10/20. 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.
sáb. 11/224:57 pmPWM - MSN
1 stop4h 38mUnited Airlines
mar. 12/22:48 pmMSN - PWM
2 stops7h 21mUnited Airlines
Deal found 10/20$349
This American Airlines deal was found by Cheapflights users on 10/19. 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.
lun. 11/35:21 pmPWM - MSN
1 stop5h 44mAmerican Airlines
vie. 11/73:59 pmMSN - PWM
1 stop7h 00mAmerican Airlines
Deal found 10/19$357
This United Airlines deal was found by Cheapflights users on 10/19. 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.
lun. 11/35:30 amPWM - MSN
2 stops9h 33mUnited Airlines
vie. 11/73:58 pmMSN - PWM
1 stop4h 52mUnited Airlines
Deal found 10/19$388

Cheapflights Fare Finder

 
Customize your flight search to find flights from Portland to Madison 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 octubre 20, 2025.
Use the filters below to find and compare flights from Portland to Madison that are best for you.

Fly from

Portland

Fly to

Madison

Route

Depart

Return

Price

PortlandMadison

PWM - MSN

PWMMSN

Portland

mar. 11/11

4:57 pm-8:35 pm

1 stop4h 38m

Madison Truax Field

sáb. 11/15

2:48 pm-9:50 pm

1 stop6h 02m

$259

PortlandMadison

PWM - MSN

PWMMSN

Portland

vie. 11/14

5:43 am-10:12 am

1 stop5h 29m

Madison Truax Field

lun. 11/17

6:00 am-11:46 am

1 stop4h 46m

$259

PortlandMadison

PWM - MSN

PWMMSN

Portland

sáb. 11/8

12:45 pm-10:29 pm

2 stops10h 44m

Madison Truax Field

sáb. 11/15

5:29 am-12:30 pm

1 stop6h 01m

$279

PortlandMadison

PWM - MSN

PWMMSN

Portland

vie. 11/14

5:30 am-2:03 pm

2 stops9h 33m

Madison Truax Field

lun. 11/17

6:30 am-2:12 pm

1 stop6h 42m

$310

PortlandMadison

PWM - MSN

PWMMSN

Portland

sáb. 11/22

5:21 pm-9:07 pm

1 stop4h 46m

Madison Truax Field

mar. 12/2

3:59 pm-11:41 pm

1 stop6h 42m

$337

PortlandMadison

PWM - MSN

PWMMSN

Portland

sáb. 11/22

4:57 pm-8:35 pm

1 stop4h 38m

Madison Truax Field

mar. 12/2

2:48 pm-11:09 pm

2 stops7h 21m

$349

PortlandMadison

PWM - MSN

PWMMSN

Portland

lun. 11/3

5:21 pm-10:05 pm

1 stop5h 44m

Madison Truax Field

vie. 11/7

3:59 pm-11:59 pm

1 stop7h 00m

$357

PortlandMadison

PWM - MSN

PWMMSN

Portland

mié. 4/8

11:50 am-4:51 pm

1 stop6h 01m

Madison Truax Field

sáb. 4/11

2:25 pm-9:27 pm

1 stop6h 02m

$378

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/20

Compare providers for flights from Portland to Madison

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 Portland to Madison in October.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars
eDreamsPrice 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 Portland, Maine-Madison flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Portland, Maine-Madison flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Portland, Maine-Madison flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Portland, Maine-Madison 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 Portland, Maine-Madison 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 Portland to Madison

Have a flexible travel schedule? Discover the best time to fly to Madison from Portland 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 Portland to Madison

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

Use this chart to determine the optimal time to book a round-trip flight from Portland to Madison. Price data was last updated on October 17, 2025.

The price you pay for your flight from Portland, Maine to Madison may vary depending on when you book. For the best chance of a lower fare, look to book 27 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.

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

Currently, September is the cheapest month in which you can book a flight from Portland, Maine to Madison (average of $98). Flying from Portland, Maine to Madison in February is currently the most expensive (average of $258). 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.

Reviews of airlines servicing Madison

Get insights into the airlines that provide service to Madison. 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 Madison. Reviews last updated octubre 20, 2025.
Get a feel of what it's like to fly with Delta, United Airlines, and American Airlines from Portland to Madison by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
7,978 reviews

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Delta
7.9
Good
7,978 reviews
Delta
7.9
Good
7,978 reviews

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
United Airlines
7.4
Good
8,991 reviews
Delta
7.9
Good
7,978 reviews

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
American Airlines
7.2
Good
11,024 reviews
Delta
7.9
Good
7,978 reviews

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.9

Food

7.3

Overall

7.9

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.

Related info for your journey

Find useful and relevant information for your journey from Portland to Madison. 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 Portland, Maine to Madison?

    For as low as $259, United Airlines can have you in Madison from Portland, Maine in 4h 38m. Airlines will cover a distance of 953 mi. This flight may include one or multiple stops.

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

    Cheapflights users have booked flights from Portland, Maine to Madison round-trip from $258. Other airlines that can offer you cheap pricing are American Airlines, from $258, and United Airlines, from $273. Delta is priced at 31% lower than the current average price of a flight leaving 3 months from now.

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

    Yes. In addition to deals on Portland to Madison flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Portland to Madison?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Portland to Madison.

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

    Yes. Cheapflights offers flight deals from Portland to Madison 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 Portland, Maine to Madison?

    Currently, September is the cheapest month in which you can book a flight from Portland, Maine to Madison (average of $98). Flying from Portland, Maine to Madison in February is currently the most expensive (average of $258). 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

Traveling to a place near Madison?

Book flights to Madison if you plan to visit one of these locations
Portage
Middleton
Baraboo
Fitchburg

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Top 3 airlines flying from Portland to Madison

Discover the top 3 airlines that operate flights from Portland to Madison. 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 octubre 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$258Average$362FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$258Average$369FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$273Average$377FlexibilityNo cancel feeOn-time69%

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