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$246+ 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 9/22. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MSN
Aug 28 — Sep 41
Fri 8/28
Fri 9/4
1 adult, Economy
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Cheap 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 July 29, 2026.

This American Airlines deal was found by Cheapflights users on 7/25. 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 10/136:00 am
PWM
-
MSN
1 stop6h 54m
American Airlines
Sat 10/175:26 pm
MSN
-
PWM
1 stop5h 15m
American Airlines
Deal found 7/25$301
This American Airlines deal was found by Cheapflights users on 7/28. 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 9/175:38 pm
PWM
-
MSN
1 stop7h 39m
American Airlines
Sun 9/205:00 am
MSN
-
PWM
1 stop7h 05m
American Airlines
Deal found 7/28$329
This Delta deal was found by Cheapflights users on 7/28. 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 9/171:59 pm
PWM
-
MSN
1 stop6h 07m
Delta
Sun 9/205:50 am
MSN
-
PWM
2 stops8h 49m
Delta
Deal found 7/28$377
This United Airlines deal was found by Cheapflights users on 7/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/56:02 am
PWM
-
MSN
1 stop5h 02m
United Airlines
Wed 9/91:00 pm
MSN
-
PWM
1 stop7h 44m
United Airlines
Deal found 7/27$381
This American Airlines deal was found by Cheapflights users on 7/27. 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.
Tue 8/42:56 pm
PWM
-
MSN
1 stop7h 45m
American Airlines
Tue 8/115:47 pm
MSN
-
PWM
1 stop4h 54m
American Airlines
Deal found 7/27$390
This United Airlines deal was found by Cheapflights users on 7/25. 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.
Mon 8/245:03 pm
PWM
-
MSN
1 stop4h 50m
United Airlines
Mon 8/316:30 am
MSN
-
PWM
2 stops7h 08m
United Airlines
Deal found 7/25$394

Find 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 July 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$301
(American Airlines)

One-way from

$246
(American Airlines)

Popular in

July

Cheapest in

February

Average price

$586
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.
Search Deals
From Portland to Madison Truax Field
Search Deals
One-way flight from Portland to Madison Truax Field
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($40 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 4% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals

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 July 29, 2026.
Use the filters below to find and compare flights from Portland to Madison that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

PortlandMadison

PWM - MSN

PWMMSN

Portland

Tue 10/13

5:09 pm-12:12 am

2 stops8h 03m

Madison Truax Field

Sat 10/17

9:53 am-5:04 pm

1 stop6h 11m

$306

PortlandMadison

PWM - MSN

PWMMSN

Portland

Sat 9/5

6:02 am-10:04 am

1 stop5h 02m

Madison Truax Field

Wed 9/9

1:00 pm-9:44 pm

1 stop7h 44m

$381

PortlandMadison

PWM - MSN

PWMMSN

Portland

Thu 9/17

5:15 am-1:42 pm

2 stops9h 27m

Madison Truax Field

Sun 9/20

12:41 pm-9:23 pm

1 stop7h 42m

$414

PortlandMadison

PWM - MSN

PWMMSN

Portland

Tue 10/13

12:42 pm-11:02 pm

2 stops11h 20m

Madison Truax Field

Sun 10/18

5:51 am-1:02 pm

1 stop6h 11m

$434

PortlandMadison

PWM - MSN

PWMMSN

Portland

Thu 9/17

6:30 am-4:20 pm

2 stops10h 50m

Madison Truax Field

Sun 9/20

5:50 am-3:39 pm

2 stops8h 49m

$462

PortlandMadison

PWM - MSN

PWMMSN

Portland

Wed 8/12

6:00 am-10:13 am

1 stop5h 13m

Madison Truax Field

Fri 8/14

2:44 pm-9:23 pm

1 stop5h 39m

$597
Quickest round-trip

PortlandMadison

PWM - MSN

PWMMSN

Portland

Sun 8/9

6:00 am-9:47 am

1 stop4h 47m

Madison Truax Field

Thu 8/13

2:44 pm-9:23 pm

1 stop5h 39m

$597

PortlandMadison

PWM - MSN

PWMMSN

Portland

Wed 8/12

6:30 am-12:47 pm

2 stops7h 17m

Madison Truax Field

Fri 8/14

1:35 pm-12:59 am

2 stops10h 24m

$607
Cheapest one-way

PortlandMadison

PWM - MSN

PWMMSN

Portland

Tue 9/22

7:32 am-2:27 pm

1 stop7h 55m

$246

PortlandMadison

PWM - MSN

PWMMSN

Portland

Tue 8/4

1:28 pm-7:39 pm

1 stop7h 11m

$291

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/25

Showing 1-10 of 12 resultsSorted by cheapest first
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 July.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice 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

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

Currently, February is the cheapest month in which you can book a flight from Portland, Maine to Madison (average of $278). Flying from Portland, Maine to Madison in July is currently the most expensive (average of $586). 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.

How much does it cost to fly round-trip from Portland, Maine to Madison?

Airfare is typical for this route at the moment.

Portland, Maine to Madison flights typically cost between $290 and $490 in October.
The cheapest round-trip price found within the last 5 days was $301 on American Airlines (Oct 13-Oct 17).

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 July 29, 2026.
Get a feel of what it's like to fly with Delta,United Airlines, andAmerican 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
7.8
Good
8,486 reviews

Overall

7.8

Comfort

7.8

Crew

8.5

Entertainment

7.8

Food

7.2

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

The snacks were not very good, not everyone was very friendly and professional
Delta
7.8
Good
8,486 reviews
Delta
7.8
Good
8,486 reviews

Overall

7.8

Comfort

7.8

Crew

8.5

Entertainment

7.8

Food

7.2

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

The snacks were not very good, not everyone was very friendly and professional
United Airlines
7.4
Good
10,052 reviews
Delta
7.8
Good
8,486 reviews

Overall

7.8

Comfort

7.8

Crew

8.5

Entertainment

7.8

Food

7.2

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

The snacks were not very good, not everyone was very friendly and professional
American Airlines
7.1
Good
11,839 reviews
Delta
7.8
Good
8,486 reviews

Overall

7.8

Comfort

7.8

Crew

8.5

Entertainment

7.8

Food

7.2

Boarding

8.1

Reviews

1 / 20
10.0
Excellent

Anonymous,May 2026

SEA - KOA

The snacks were not very good, not everyone was very friendly and professional

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 $381, American Airlines can have you in Madison from Portland, Maine in 5h 02m. 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 United Airlines, from $273, and American Airlines, from $273. Delta is priced at 37% 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, February is the cheapest month in which you can book a flight from Portland, Maine to Madison (average of $278). Flying from Portland, Maine to Madison in July is currently the most expensive (average of $586). 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
Sun Prairie
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 July 29, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$258Average$383FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$273Average$382FlexibilityNo cancel feeOn-time69%
American AirlinesCheapest$273Average$376FlexibilityNo cancel feeOn-time71%

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