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Madison

$259+ Cheap flights from Portland, ME to Madison (PWM - MSN)

This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/23. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MSN
ago. 25 — sep. 11
lun. 8/25
lun. 9/1
1 adult, Economy
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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 agosto 20, 2025.

Round-trip from

$259
(Delta)

Popular in

April

Cheapest in

January

Average price

$373
From Portland to Madison Truax Field
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($41 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in August 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 agosto 20, 2025.

This Delta deal was found by Cheapflights users on 8/18. 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.
dom. 11/234:55 pmPWM - MSN
1 stop4h 49mDelta
mar. 12/29:25 amMSN - PWM
1 stop5h 45mDelta
Deal found 8/18$259
This Delta deal was found by Cheapflights users on 8/18. 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.
lun. 11/242:35 pmPWM - MSN
2 stops7h 09mDelta
sáb. 12/67:00 amMSN - PWM
1 stop3h 51mDelta
Deal found 8/18$264
This American Airlines deal was found by Cheapflights users on 8/18. 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.
jue. 10/165:59 pmPWM - MSN
1 stop6h 52mAmerican Airlines
mar. 10/216:00 amMSN - PWM
1 stop4h 28mAmerican Airlines
Deal found 8/18$274
This Delta deal was found by Cheapflights users on 8/18. 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.
sáb. 11/226:30 pmPWM - MSN
1 stop4h 24mDelta
mar. 12/29:25 amMSN - PWM
1 stop5h 45mDelta
Deal found 8/18$288
This Delta deal was found by Cheapflights users on 8/18. 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.
vie. 9/56:33 pmPWM - MSN
1 stop4h 41mDelta
dom. 9/75:40 amMSN - PWM
1 stop5h 49mDelta
Deal found 8/18$289
This Delta deal was found by Cheapflights users on 8/18. 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.
sáb. 11/226:30 pmPWM - MSN
1 stop4h 24mDelta
sáb. 12/69:25 amMSN - PWM
2 stops11h 34mDelta
Deal found 8/18$293
This Delta deal was found by Cheapflights users on 8/18. 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.
lun. 11/242:35 pmPWM - MSN
2 stops7h 09mDelta
mié. 12/311:11 amMSN - PWM
2 stops11h 40mDelta
Deal found 8/18$298
This American Airlines deal was found by Cheapflights users on 8/18. 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.
mar. 11/255:41 amPWM - MSN
1 stop5h 43mAmerican Airlines
mié. 12/33:52 pmMSN - PWM
1 stop6h 48mAmerican Airlines
Deal found 8/18$304
This Delta deal was found by Cheapflights users on 8/18. 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.
vie. 8/2911:48 amPWM - MSN
1 stop7h 09mDelta
sáb. 8/302:44 pmMSN - PWM
2 stops8h 19mDelta
Deal found 8/18$305
This American Airlines deal was found by Cheapflights users on 8/18. 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.
vie. 8/295:57 pmPWM - MSN
1 stop6h 51mAmerican Airlines
sáb. 8/301:12 pmMSN - PWM
1 stop7h 33mAmerican Airlines
Deal found 8/18$317

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 agosto 20, 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

dom. 11/23

4:55 pm-8:44 pm

1 stop4h 49m

Madison Truax Field

mié. 12/3

7:00 am-11:51 am

1 stop3h 51m

$259

PortlandMadison

PWM - MSN

PWMMSN

Portland

jue. 10/16

6:00 am-10:08 am

1 stop5h 08m

Madison Truax Field

mar. 10/21

8:09 am-2:38 pm

1 stop5h 29m

$259

PortlandMadison

PWM - MSN

PWMMSN

Portland

lun. 11/24

4:55 pm-8:44 pm

1 stop4h 49m

Madison Truax Field

mié. 12/3

7:00 am-11:51 am

1 stop3h 51m

$259

PortlandMadison

PWM - MSN

PWMMSN

Portland

vie. 9/26

3:56 pm-10:57 pm

1 stop8h 01m

Madison Truax Field

lun. 9/29

6:20 am-12:29 pm

1 stop5h 09m

$259

PortlandMadison

PWM - MSN

PWMMSN

Portland

lun. 11/24

4:55 pm-8:44 pm

1 stop4h 49m

Madison Truax Field

sáb. 12/6

7:00 am-11:51 am

1 stop3h 51m

$259

PortlandMadison

PWM - MSN

PWMMSN

Portland

dom. 11/23

4:55 pm-8:44 pm

1 stop4h 49m

Madison Truax Field

sáb. 12/6

7:00 am-11:51 am

1 stop3h 51m

$259

PortlandMadison

PWM - MSN

PWMMSN

Portland

dom. 11/23

4:55 pm-8:44 pm

1 stop4h 49m

Madison Truax Field

mar. 12/2

9:25 am-4:10 pm

1 stop5h 45m

$259

PortlandMadison

PWM - MSN

PWMMSN

Portland

lun. 11/24

4:55 pm-8:44 pm

1 stop4h 49m

Madison Truax Field

mar. 12/2

9:25 am-4:10 pm

1 stop5h 45m

$259

PortlandMadison

PWM - MSN

PWMMSN

Portland

jue. 11/27

6:00 am-4:37 pm

2 stops11h 37m

Madison Truax Field

sáb. 12/6

7:00 am-11:51 am

1 stop3h 51m

$264

PortlandMadison

PWM - MSN

PWMMSN

Portland

jue. 11/27

6:00 am-4:37 pm

2 stops11h 37m

Madison Truax Field

mié. 12/3

9:25 am-4:10 pm

1 stop5h 45m

$264

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/19

Showing 1-10 of 12 results
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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, 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 agosto 20, 2025.
Get a feel of what it's like to fly with Delta, United Airlines, and American 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
8.0
Very good
7,982 reviews

Food

7.3

Boarding

8.2

Crew

8.5

Comfort

7.9

Entertainment

7.9

Overall

8.0

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
7,982 reviews
Delta
8.0
Very good
7,982 reviews

Food

7.3

Boarding

8.2

Crew

8.5

Comfort

7.9

Entertainment

7.9

Overall

8.0

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
8,928 reviews
Delta
8.0
Very good
7,982 reviews

Food

7.3

Boarding

8.2

Crew

8.5

Comfort

7.9

Entertainment

7.9

Overall

8.0

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
7,982 reviews

Food

7.3

Boarding

8.2

Crew

8.5

Comfort

7.9

Entertainment

7.9

Overall

8.0

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 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 $259, Delta can have you in Madison from Portland, Maine in 4h 49m. Airlines will cover a distance of 953 mi.

  • 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 $218. Other airlines that can offer you cheap pricing are Delta, from $258, and United Airlines, from $273. American Airlines is priced at 41% 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, 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 Madison?

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

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Alternative routes for Portland to Madison

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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 agosto 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$218Average$370FlexibilityNo cancel feeOn-time71%
DeltaCheapest$258Average$396FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$273Average$378FlexibilityNo cancel feeOn-time69%

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