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$199+ Cheap flights from Portland, ME to Madison (PWM - MSN)

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 11/18. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MSN
Nov 29 — Dec 61
Sat 11/29
Sat 12/6
1 adult, Economy
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Cheapflights Tip: The best prices from Portland to Madison Truax Field are usually found in January or March, 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 October 30, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$259
(Delta)

One-way from

$199
(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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One-way flight 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 October 30, 2025.

This Delta deal was found by Cheapflights users on 10/29. 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.
Thu 11/276:00 amPWM - MSN
1 stop7h 55mDelta
Wed 12/33:25 pmMSN - PWM
1 stop6h 56mDelta
Deal found 10/29$259
This Delta deal was found by Cheapflights users on 10/30. 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 12/36:00 amPWM - MSN
2 stops11h 21mDelta
Wed 12/103:25 pmMSN - PWM
1 stop6h 56mDelta
Deal found 10/30$264
This United Airlines deal was found by Cheapflights users on 10/29. 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.
Thu 11/2710:45 amPWM - MSN
1 stop6h 03mUnited Airlines
Mon 12/12:48 pmMSN - PWM
2 stops8h 11mUnited Airlines
Deal found 10/29$273
This American Airlines deal was found by Cheapflights users on 10/29. 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 11/135:43 amPWM - MSN
1 stop5h 29mAmerican Airlines
Mon 11/176:00 amMSN - PWM
1 stop4h 46mAmerican Airlines
Deal found 10/29$309
This Delta deal was found by Cheapflights users on 10/29. 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.
Thu 11/136:00 amPWM - MSN
2 stops7h 45mDelta
Mon 11/175:29 amMSN - PWM
1 stop6h 01mDelta
Deal found 10/29$314
This American Airlines deal was found by Cheapflights users on 10/30. 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 11/225:21 pmPWM - MSN
1 stop4h 46mAmerican Airlines
Tue 12/23:59 pmMSN - PWM
1 stop6h 42mAmerican Airlines
Deal found 10/30$322
This United Airlines deal was found by Cheapflights users on 10/29. 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.
Sat 11/224:57 pmPWM - MSN
1 stop4h 38mUnited Airlines
Tue 12/23:59 pmMSN - PWM
1 stop4h 18mUnited Airlines
Deal found 10/29$328
This American Airlines deal was found by Cheapflights users on 10/27. 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 11/207:02 amPWM - MSN
1 stop8h 42mAmerican Airlines
Sun 11/236:00 amMSN - PWM
1 stop4h 46mAmerican Airlines
Deal found 10/27$329

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 October 30, 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

Wed 12/3

5:34 am-10:06 am

1 stop5h 32m

Madison Truax Field

Wed 12/10

12:18 pm-9:37 pm

1 stop8h 19m

$259

PortlandMadison

PWM - MSN

PWMMSN

Portland

Wed 12/3

6:00 am-4:21 pm

2 stops11h 21m

Madison Truax Field

Wed 12/10

9:40 am-4:07 pm

1 stop5h 27m

$264

PortlandMadison

PWM - MSN

PWMMSN

Portland

Mon 1/12

8:40 am-7:07 pm

2 stops11h 27m

Madison Truax Field

Sat 1/17

8:15 am-2:39 pm

1 stop5h 24m

$264

PortlandMadison

PWM - MSN

PWMMSN

Portland

Fri 1/23

12:20 pm-5:36 pm

1 stop6h 16m

Madison Truax Field

Sun 1/25

8:35 am-5:16 pm

1 stop7h 41m

$319

PortlandMadison

PWM - MSN

PWMMSN

Portland

Thu 11/13

6:00 am-12:45 pm

2 stops7h 45m

Madison Truax Field

Mon 11/17

1:30 pm-11:19 pm

2 stops8h 49m

$319

PortlandMadison

PWM - MSN

PWMMSN

Portland

Sat 11/22

5:21 pm-9:07 pm

1 stop4h 46m

Madison Truax Field

Tue 12/2

3:59 pm-11:41 pm

1 stop6h 42m

$322

PortlandMadison

PWM - MSN

PWMMSN

Portland

Wed 1/21

2:35 pm-10:37 pm

2 stops9h 02m

Madison Truax Field

Mon 1/26

3:20 pm-11:22 pm

1 stop7h 02m

$324

PortlandMadison

PWM - MSN

PWMMSN

Portland

Sat 11/22

4:57 pm-8:35 pm

1 stop4h 38m

Madison Truax Field

Tue 12/2

3:59 pm-9:17 pm

1 stop4h 18m

$328

PortlandMadison

PWM - MSN

PWMMSN

Portland

Thu 11/20

5:43 am-10:10 am

1 stop5h 27m

Madison Truax Field

Sun 11/23

6:00 am-11:46 am

1 stop4h 46m

$328

PortlandMadison

PWM - MSN

PWMMSN

Portland

Thu 11/20

6:00 am-12:45 pm

2 stops7h 45m

Madison Truax Field

Sun 11/23

1:30 pm-11:54 pm

2 stops9h 24m

$328

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/30

Showing 1-10 of 13 results
1
2

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
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

*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 eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on Portland, Maine-Madison flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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 24, 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 October 30, 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
7,998 reviews

Overall

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

Comfort

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
7,998 reviews
Delta
7.9
Good
7,998 reviews

Overall

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

Comfort

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
8,998 reviews
Delta
7.9
Good
7,998 reviews

Overall

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

Comfort

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
11,035 reviews
Delta
7.9
Good
7,998 reviews

Overall

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

Comfort

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, American Airlines can have you in Madison from Portland, Maine in 5h 32m. 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 Delta, from $258, and United Airlines, from $273. American Airlines is priced at 30% 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 October 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$258Average$383FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$258Average$365FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$273Average$378FlexibilityNo cancel feeOn-time69%

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