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$165+ Cheap flights from Madison to Portland, ME (MSN - PWM)

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 7/23. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — PWM
Jul 21 — Jul 281
Mon 7/21
Mon 7/28
1 adult, Economy
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Cheapflights Tip: The best prices from Madison Truax Field to Portland are usually found in February or March, booked 57 days in advance, depart on a Sunday or Saturday and return on a Friday

Cheap flight deals from Madison to Portland

Discover tips and strategies to find the most affordable flight options for your journey from Madison (MSN) to Portland (PWM). 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 16, 2025.

Round-trip from

$259
(United Airlines)

One-way from

$165
(Delta)

Popular in

December

Cheapest in

February

Average price

$447
From Madison Truax Field to Portland
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One-way flight from Madison Truax Field to Portland
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Highest demand for flights based on searches. 6% potential increase in price ($30 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($14 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 Madison to Portland

Cheapest flights from Madison to Portland
Explore the most affordable flight options available from Madison to Portland. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 16, 2025.

This United Airlines deal was found by Cheapflights users on 7/15. 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 9/136:30 amMSN - PWM
1 stop6h 56mUnited Airlines
Wed 9/176:23 pmPWM - MSN
1 stop5h 00mUnited Airlines
Deal found 7/15$259
This Delta deal was found by Cheapflights users on 7/15. 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.
Sat 9/131:20 pmMSN - PWM
1 stop7h 40mDelta
Sat 9/207:00 amPWM - MSN
1 stop6h 41mDelta
Deal found 7/15$269
This American Airlines deal was found by Cheapflights users on 7/15. 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 11/611:30 amMSN - PWM
1 stop4h 09mAmerican Airlines
Sun 11/95:50 amPWM - MSN
1 stop5h 03mAmerican Airlines
Deal found 7/15$284

Cheapflights Fare Finder

Customize your flight search to find flights from Madison to Portland 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 16, 2025.
Use the filters below to find and compare flights from Madison to Portland that are best for you.

Fly from

Madison

Fly to

Portland

Route

Depart

Return

Price

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Sat 9/13

1:20 pm-10:00 pm

1 stop7h 40m

Portland

Sat 9/20

7:00 am-12:41 pm

1 stop6h 41m

$259

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Sat 9/13

10:51 am-7:29 pm

2 stops7h 38m

Portland

Wed 9/17

4:56 pm-10:23 pm

1 stop6h 27m

$264

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Thu 11/6

11:30 am-4:39 pm

1 stop4h 09m

Portland

Sun 11/9

5:50 am-9:53 am

1 stop5h 03m

$284

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Wed 7/23

5:19 pm-12:38 am

1 stop6h 19m

$165

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Wed 7/23

6:25 pm-8:12 pm

3 stops24h 47m

$576

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Mon 8/4

4:13 pm-10:45 pm

1 stop5h 32m

$655

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Mon 7/28

5:26 pm-11:14 pm

2 stops28h 48m

$688

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/15

Best time to book a flight from Madison to Portland

Have a flexible travel schedule? Discover the best time to fly to Portland from Madison 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 Madison to Portland

How far ahead should I book a flight from Madison to Portland, Maine?

Use this chart to determine the optimal time to book a round-trip flight from Madison to Portland. Price data was last updated on July 11, 2025.

The best time to book flights from Madison to Portland, Maine is 57 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.

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

Currently, January is the cheapest month in which you can book a flight from Madison to Portland, Maine (average of $296). Flying from Madison to Portland, Maine in July is currently the most expensive (average of $394). 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 Portland

Get insights into the airlines that provide service to Portland. 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 Portland. Reviews last updated July 16, 2025.
Get a feel of what it's like to fly with Delta, United Airlines, and American Airlines from Madison to Portland by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
8.0
Very good
7,959 reviews

Food

7.3

Boarding

8.2

Comfort

7.9

Overall

8.0

Entertainment

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,959 reviews
Delta
8.0
Very good
7,959 reviews

Food

7.3

Boarding

8.2

Comfort

7.9

Overall

8.0

Entertainment

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
United Airlines
7.4
Good
8,863 reviews
Delta
8.0
Very good
7,959 reviews

Food

7.3

Boarding

8.2

Comfort

7.9

Overall

8.0

Entertainment

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,959 reviews

Food

7.3

Boarding

8.2

Comfort

7.9

Overall

8.0

Entertainment

7.9

Crew

8.5

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

Related info for your journey

Find useful and relevant information for your journey from Madison to Portland. 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 Madison to Portland, Maine round-trip?

    Our cheapest airline available from Madison to Portland, Maine is United Airlines. Our recent data shows that you can find tickets from as low as $259 on this airline. Additional options worth looking into are Delta and American Airlines, starting at $269 and $284 round-trip. Users have found that United Airlines is 35% cheaper than the other options available to this destination.

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

    One-way options have recently been found by users for as low as $165 on Delta. Other airlines that offer cheap prices include American Airlines from $655 and United Airlines from $688 one-way.

  • Can I find deals for flights from Madison to Portland that include hotel bookings?

    Yes. In addition to deals on Madison to Portland flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Madison to Portland?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Madison to Portland.

  • Can I find deals for business class flights from Madison to Portland?

    Yes. Cheapflights offers flight deals from Madison to Portland 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 Madison to Portland, Maine?

    Currently, January is the cheapest month in which you can book a flight from Madison to Portland, Maine (average of $296). Flying from Madison to Portland, Maine in July is currently the most expensive (average of $394). 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
Brunswick
North Conway
Auburn
Conway
Lewiston

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Top 3 airlines flying from Madison to Portland

Discover the top 3 airlines that operate flights from Madison to Portland. 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 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$258Average$388FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$258Average$387FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$273Average$442FlexibilityNo cancel feeOn-time69%

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