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$100+ 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 5/24. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MSN
Apr 29 — May 61
Tue 4/29
Tue 5/6
1 adult, Economy
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Cheapflights Tip: The best prices from Portland to Madison Truax Field are usually found in January or December, booked 44 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 April 24, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$259
(Delta)

One-way from

$100
(American Airlines)

Popular in

July

Cheapest in

January

Average price

$502
Provider with most accurate pricing for Portland-Madison Truax Field flight deals.
Search Deals
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
Search Deals
Highest demand for flights based on searches. 16% potential increase in price ($86 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($27 potential savings vs. average RT price).
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Average for round-trip flights in April 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 April 24, 2025.

This Delta deal was found by Cheapflights users on 4/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/1112:49 pmPWM - MSN
1 stop4h 36mDelta
Fri 6/205:19 pmMSN - PWM
1 stop6h 07mDelta
Deal found 4/23$259
This American Airlines deal was found by Cheapflights users on 4/23. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/86:01 pmPWM - MSN
1 stop7h 01mAmerican Airlines
Sun 7/136:24 amMSN - PWM
1 stop10h 21mAmerican Airlines
Deal found 4/23$309
This United Airlines deal was found by Cheapflights users on 4/23. 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 7/86:00 amPWM - MSN
2 stops8h 54mUnited Airlines
Sun 7/136:30 amMSN - PWM
1 stop6h 54mUnited Airlines
Deal found 4/23$494
This KAYAK deal was found by Cheapflights users on 4/23. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/123:17 pmPWM - MSN
3 stops43h 22mBreeze Airways
Wed 6/186:25 pmMSN - PWM
2 stops24h 02mBreeze Airways
Deal found 4/23$888

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 April 24, 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 6/11

12:49 pm-4:25 pm

1 stop4h 36m

Madison Truax Field

Fri 6/20

5:19 pm-12:26 am

1 stop6h 07m

$259

PortlandMadison

PWM - MSN

PWMMSN

Portland

Tue 7/8

6:01 pm-12:02 am

1 stop7h 01m

Madison Truax Field

Sun 7/13

6:24 am-5:45 pm

1 stop10h 21m

$309

PortlandMadison

PWM - MSN

PWMMSN

Portland

Tue 7/8

6:00 am-1:54 pm

2 stops8h 54m

Madison Truax Field

Sun 7/13

6:30 am-2:24 pm

1 stop6h 54m

$494

PortlandMadison

PWM - MSN

PWMMSN

Portland

Thu 6/12

3:17 pm-9:39 am

3 stops43h 22m

Madison Truax Field

Wed 6/18

6:25 pm-7:27 pm

2 stops24h 02m

$888

PortlandMadison

PWM - MSN

PWMMSN

Portland

Sat 5/24

6:00 am-10:10 am

1 stop5h 10m

$100

PortlandMadison

PWM - MSN

PWMMSN

Portland

Sat 5/24

2:30 pm-11:21 pm

2 stops9h 51m

$124

PortlandMadison

PWM - MSN

PWMMSN

Portland

Sat 5/24

6:00 am-10:11 am

1 stop5h 11m

$205

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/23

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 April.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
eDreamsPrice Accuracy3 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*2 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 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 April 18, 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 44 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, January is the cheapest month in which you can book a flight from Portland, Maine to Madison (average of $338). Flying from Portland, Maine to Madison in June is currently the most expensive (average of $423). 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.

Rainfall in Madison by month

Plan your trip to Madison by taking into account the average rainfall totals by month.

In terms of precipitation, rainfall in Madison ranges from 1.2 - 4.5 inches per month. June is typically the wettest month, when rainfall can reach 4.5 in. January is typically the driest time to visit Madison when rainfall is around 1.2 in.

Temperature in Madison by month

Plan your trip to Madison by taking into account the average temperature totals by month.

If weather is an important factor for your trip to Madison, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 71.6 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 19.4 F).

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 April 24, 2025.
Breeze Airways
8.1
Very good
159 reviews

Comfort

8.2

Crew

8.8

Overall

8.1

Entertainment

6.7

Boarding

8.3

Food

6.7

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Breeze Airways
8.1
Very good
159 reviews
Breeze Airways
8.1
Very good
159 reviews

Comfort

8.2

Crew

8.8

Overall

8.1

Entertainment

6.7

Boarding

8.3

Food

6.7

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
Delta
8.0
Very good
7,920 reviews
Breeze Airways
8.1
Very good
159 reviews

Comfort

8.2

Crew

8.8

Overall

8.1

Entertainment

6.7

Boarding

8.3

Food

6.7

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
United Airlines
7.4
Good
8,685 reviews
Breeze Airways
8.1
Very good
159 reviews

Comfort

8.2

Crew

8.8

Overall

8.1

Entertainment

6.7

Boarding

8.3

Food

6.7

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!
American Airlines
7.2
Good
10,000 reviews
Breeze Airways
8.1
Very good
159 reviews

Comfort

8.2

Crew

8.8

Overall

8.1

Entertainment

6.7

Boarding

8.3

Food

6.7

Reviews

1 / 11
10.0
Excellent

Dena,Dec 2024

LAS - BDL

It was comfortable and the crew was great! A few free snacks offered would be nice!

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.

  • 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 $259. Other airlines that can offer you cheap pricing are American Airlines, from $309, and United Airlines, from $494. Delta is priced at 41% lower than the current average price of a flight leaving 3 months from now.

  • What are the cheapest airlines to fly from Portland, Maine to Madison one-way?

    The cheapest airlines for a one-way flight from Portland, Maine to Madison are American Airlines ($100), Delta ($124), and United Airlines ($205).

  • 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, January is the cheapest month in which you can book a flight from Portland, Maine to Madison (average of $338). Flying from Portland, Maine to Madison in June is currently the most expensive (average of $423). 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 Portland?

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

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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 April 24, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$218Average$376FlexibilityNo cancel feeOn-time71%
DeltaCheapest$258Average$392FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$283Average$466FlexibilityNo cancel feeOn-time69%

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