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$169+ 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 8/30. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MSN
Jun 21 — Jun 281
Sat 6/21
Sat 6/28
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 June 16, 2025.

Round-trip from

$258
(American Airlines)

One-way from

$169
(Delta)

Popular in

July

Cheapest in

January

Average price

$403
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. 17% potential increase in price ($86 potential increase over avg. RT price).
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Cheapest flight prices on average. 7% potential price decrease ($30 potential savings vs. average RT price).
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Average for round-trip flights in June 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 June 16, 2025.

This American Airlines deal was found by Cheapflights users on 6/14. 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 7/296:01 pmPWM - MSN
1 stop6h 49mAmerican Airlines
Tue 8/56:00 amMSN - PWM
1 stop4h 46mAmerican Airlines
Deal found 6/14$258
This Delta deal was found by Cheapflights users on 6/14. 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.
Tue 7/296:05 amPWM - MSN
2 stops7h 35mDelta
Tue 8/55:19 pmMSN - PWM
1 stop6h 19mDelta
Deal found 6/14$264
This United Airlines deal was found by Cheapflights users on 6/16. 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 7/106:10 amPWM - MSN
1 stop5h 03mUnited Airlines
Tue 7/156:30 amMSN - PWM
1 stop5h 50mUnited Airlines
Deal found 6/16$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 June 16, 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

Tue 7/29

6:01 pm-11:50 pm

1 stop6h 49m

Madison Truax Field

Tue 8/5

6:00 am-11:46 am

1 stop4h 46m

$258

PortlandMadison

PWM - MSN

PWMMSN

Portland

Tue 7/29

6:05 am-12:40 pm

2 stops7h 35m

Madison Truax Field

Tue 8/5

5:19 pm-12:38 am

1 stop6h 19m

$264

PortlandMadison

PWM - MSN

PWMMSN

Portland

Thu 7/10

6:10 am-10:13 am

1 stop5h 03m

Madison Truax Field

Tue 7/15

6:30 am-1:20 pm

1 stop5h 50m

$329

PortlandMadison

PWM - MSN

PWMMSN

Portland

Sat 8/30

11:28 am-4:54 pm

1 stop6h 26m

$169

PortlandMadison

PWM - MSN

PWMMSN

Portland

Sat 8/23

5:57 pm-11:59 pm

1 stop7h 02m

$184

PortlandMadison

PWM - MSN

PWMMSN

Portland

Sat 8/30

2:14 pm-10:23 pm

2 stops9h 09m

$219

PortlandMadison

PWM - MSN

PWMMSN

Portland

Fri 8/8

6:16 pm-8:01 am

2 stops14h 45m

$458

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/15

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 June 13, 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 March is currently the most expensive (average of $422). 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 June 16, 2025.
Breeze Airways
8.1
Very good
181 reviews

Food

6.7

Crew

8.8

Overall

8.1

Entertainment

6.6

Boarding

8.3

Comfort

8.2

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
181 reviews
Breeze Airways
8.1
Very good
181 reviews

Food

6.7

Crew

8.8

Overall

8.1

Entertainment

6.6

Boarding

8.3

Comfort

8.2

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
7,963 reviews
Breeze Airways
8.1
Very good
181 reviews

Food

6.7

Crew

8.8

Overall

8.1

Entertainment

6.6

Boarding

8.3

Comfort

8.2

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
8,801 reviews
Breeze Airways
8.1
Very good
181 reviews

Food

6.7

Crew

8.8

Overall

8.1

Entertainment

6.6

Boarding

8.3

Comfort

8.2

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
181 reviews

Food

6.7

Crew

8.8

Overall

8.1

Entertainment

6.6

Boarding

8.3

Comfort

8.2

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 $258. Other airlines that can offer you cheap pricing are Delta, from $264, and United Airlines, from $329. American Airlines is priced at 36% 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 Delta ($169), American Airlines ($184), and United Airlines ($219).

  • 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 March is currently the most expensive (average of $422). 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
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 June 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$218Average$364FlexibilityNo cancel feeOn-time71%
DeltaCheapest$258Average$378FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$283Average$438FlexibilityNo cancel feeOn-time69%

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