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$142+ 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
jul. 8 — jul. 151
mar. 7/8
mar. 7/15
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 julio 3, 2025.

Round-trip from

$259
(American Airlines)

One-way from

$142
(Delta)

Popular in

July

Cheapest in

January

Average price

$700
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. 16% potential increase in price ($76 potential increase over avg. RT price).
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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 July 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 julio 3, 2025.

This American Airlines deal was found by Cheapflights users on 7/2. 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.
mié. 7/236:01 pmPWM - MSN
1 stop6h 49mAmerican Airlines
mié. 7/305:06 pmMSN - PWM
1 stop5h 13mAmerican Airlines
Deal found 7/2$259
This Delta deal was found by Cheapflights users on 7/2. 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.
mié. 7/236:05 amPWM - MSN
2 stops7h 35mDelta
mié. 7/305:19 pmMSN - PWM
1 stop6h 19mDelta
Deal found 7/2$384
This United Airlines deal was found by Cheapflights users on 7/1. 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.
dom. 9/76:14 amPWM - MSN
1 stop4h 31mUnited Airlines
jue. 9/116:30 amMSN - PWM
2 stops6h 55mUnited Airlines
Deal found 7/1$514

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 julio 3, 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

mié. 7/23

6:01 pm-11:50 pm

1 stop6h 49m

Madison Truax Field

mié. 7/30

5:06 pm-11:19 pm

1 stop5h 13m

$259

PortlandMadison

PWM - MSN

PWMMSN

Portland

mié. 7/23

6:05 am-12:40 pm

2 stops7h 35m

Madison Truax Field

mié. 7/30

5:19 pm-12:38 am

1 stop6h 19m

$384

PortlandMadison

PWM - MSN

PWMMSN

Portland

dom. 9/7

6:14 am-9:45 am

1 stop4h 31m

Madison Truax Field

jue. 9/11

6:30 am-2:25 pm

2 stops6h 55m

$514

PortlandMadison

PWM - MSN

PWMMSN

Portland

sáb. 8/30

5:30 pm-11:02 pm

1 stop6h 32m

$142

PortlandMadison

PWM - MSN

PWMMSN

Portland

sáb. 8/23

5:57 pm-11:59 pm

1 stop7h 02m

$184

PortlandMadison

PWM - MSN

PWMMSN

Portland

jue. 10/23

2:25 pm-10:28 pm

2 stops9h 03m

$212

PortlandMadison

PWM - MSN

PWMMSN

Portland

jue. 7/24

3:17 pm-9:39 am

3 stops43h 22m

$613

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/3

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 27, 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.

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 julio 3, 2025.
Get a feel of what it's like to fly with Breeze Airways, Delta, and United 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.
Breeze Airways
8.1
Very good
183 reviews

Entertainment

6.6

Crew

8.8

Food

6.8

Comfort

8.2

Boarding

8.3

Overall

8.1

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
183 reviews
Breeze Airways
8.1
Very good
183 reviews

Entertainment

6.6

Crew

8.8

Food

6.8

Comfort

8.2

Boarding

8.3

Overall

8.1

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
7,982 reviews
Breeze Airways
8.1
Very good
183 reviews

Entertainment

6.6

Crew

8.8

Food

6.8

Comfort

8.2

Boarding

8.3

Overall

8.1

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
8,861 reviews
Breeze Airways
8.1
Very good
183 reviews

Entertainment

6.6

Crew

8.8

Food

6.8

Comfort

8.2

Boarding

8.3

Overall

8.1

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
183 reviews

Entertainment

6.6

Crew

8.8

Food

6.8

Comfort

8.2

Boarding

8.3

Overall

8.1

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 Delta, from $384, and United Airlines, from $514. American Airlines is priced at 35% 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 ($142), American Airlines ($184), and United Airlines ($212).

  • 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 julio 3, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$218Average$366FlexibilityNo cancel feeOn-time71%
DeltaCheapest$258Average$398FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$281Average$378FlexibilityNo cancel feeOn-time69%

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