HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Madison

$159+ 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 11/8. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MSN
Oct 16 — Oct 231
Thu 10/16
Thu 10/23
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Portland to Madison with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

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 September 16, 2025.

Round-trip from

$259
(Delta)

One-way from

$159
(Delta)

Popular in

April

Cheapest in

January

Average price

$397
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. 7% potential increase in price ($33 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($11 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 2025
Search Deals

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 September 16, 2025.

This United Airlines deal was found by Cheapflights users on 9/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/113:45 pmPWM - MSN
1 stop8h 18mUnited Airlines
Wed 10/158:15 amMSN - PWM
1 stop5h 18mUnited Airlines
Deal found 9/14$259
This Delta deal was found by Cheapflights users on 9/15. 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.
Mon 11/244:53 pmPWM - MSN
1 stop4h 33mDelta
Wed 12/31:35 pmMSN - PWM
2 stops7h 42mDelta
Deal found 9/15$264
This Delta deal was found by Cheapflights users on 9/15. 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.
Mon 11/244:53 pmPWM - MSN
2 stops7h 06mDelta
Sat 12/66:00 amMSN - PWM
2 stops9h 06mDelta
Deal found 9/15$269
This American Airlines deal was found by Cheapflights users on 9/14. 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.
Wed 10/156:00 amPWM - MSN
1 stop5h 08mAmerican Airlines
Tue 10/211:00 pmMSN - PWM
1 stop6h 18mAmerican Airlines
Deal found 9/14$271
This United Airlines deal was found by Cheapflights users on 9/16. 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.
Wed 10/16:14 amPWM - MSN
1 stop6h 31mUnited Airlines
Sat 10/43:48 pmMSN - PWM
2 stops7h 11mUnited Airlines
Deal found 9/16$294
This American Airlines deal was found by Cheapflights users on 9/15. 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.
Wed 10/156:00 amPWM - MSN
1 stop7h 15mAmerican Airlines
Wed 10/225:10 pmMSN - PWM
1 stop4h 38mAmerican Airlines
Deal found 9/15$304
This United Airlines deal was found by Cheapflights users on 9/16. 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.
Tue 10/216:14 amPWM - MSN
1 stop4h 41mUnited Airlines
Fri 10/242:46 pmMSN - PWM
1 stop5h 58mUnited Airlines
Deal found 9/16$317
This American Airlines deal was found by Cheapflights users on 9/14. 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.
Sat 11/225:21 pmPWM - MSN
1 stop4h 46mAmerican Airlines
Tue 12/26:00 amMSN - PWM
1 stop4h 46mAmerican Airlines
Deal found 9/14$318

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 September 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

Sat 10/11

3:45 pm-11:03 pm

1 stop8h 18m

Madison Truax Field

Wed 10/15

8:15 am-2:33 pm

1 stop5h 18m

$259

PortlandMadison

PWM - MSN

PWMMSN

Portland

Mon 11/24

4:53 pm-10:59 pm

2 stops7h 06m

Madison Truax Field

Sat 12/6

6:00 am-4:06 pm

2 stops9h 06m

$269

PortlandMadison

PWM - MSN

PWMMSN

Portland

Wed 10/1

6:14 am-11:45 am

1 stop6h 31m

Madison Truax Field

Sat 10/4

3:48 pm-11:59 pm

2 stops7h 11m

$294

PortlandMadison

PWM - MSN

PWMMSN

Portland

Mon 11/24

4:53 pm-8:26 pm

1 stop4h 33m

Madison Truax Field

Wed 12/3

9:38 am-4:06 pm

1 stop5h 28m

$299

PortlandMadison

PWM - MSN

PWMMSN

Portland

Thu 11/27

6:00 am-12:32 pm

1 stop7h 32m

Madison Truax Field

Wed 12/3

3:25 pm-11:21 pm

1 stop6h 56m

$299

PortlandMadison

PWM - MSN

PWMMSN

Portland

Tue 10/21

6:14 am-9:55 am

1 stop4h 41m

Madison Truax Field

Fri 10/24

2:46 pm-9:44 pm

1 stop5h 58m

$317

PortlandMadison

PWM - MSN

PWMMSN

Portland

Thu 11/27

12:48 pm-7:26 pm

2 stops7h 38m

Madison Truax Field

Sat 12/6

1:30 pm-11:59 pm

2 stops9h 29m

$318

PortlandMadison

PWM - MSN

PWMMSN

Portland

Mon 11/24

4:54 pm-8:35 pm

1 stop4h 41m

Madison Truax Field

Tue 12/2

2:48 pm-11:09 pm

2 stops7h 21m

$334

PortlandMadison

PWM - MSN

PWMMSN

Portland

Sat 11/8

4:48 pm-8:21 pm

1 stop4h 33m

$159

PortlandMadison

PWM - MSN

PWMMSN

Portland

Mon 11/24

4:53 pm-8:26 pm

1 stop4h 33m

$159

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 17 results
1
2

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 September 12, 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 September 16, 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
7,957 reviews

Comfort

7.9

Overall

8.0

Entertainment

7.9

Food

7.3

Crew

8.5

Boarding

8.2

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
7,957 reviews
Delta
8.0
Very good
7,957 reviews

Comfort

7.9

Overall

8.0

Entertainment

7.9

Food

7.3

Crew

8.5

Boarding

8.2

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
8,924 reviews
Delta
8.0
Very good
7,957 reviews

Comfort

7.9

Overall

8.0

Entertainment

7.9

Food

7.3

Crew

8.5

Boarding

8.2

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
7,957 reviews

Comfort

7.9

Overall

8.0

Entertainment

7.9

Food

7.3

Crew

8.5

Boarding

8.2

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 $269, United Airlines can have you in Madison from Portland, Maine in 7h 06m. 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 $218. Other airlines that can offer you cheap pricing are Delta, from $258, and United Airlines, from $273. American Airlines is priced at 42% 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

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Portland to Madison

See prices for flight routes from nearby airports that may be better suited for you.
Boston to O'Hare Intl flights
Boston to Minneapolis flights
Boston to Milwaukee flights
Portland to O'Hare Intl flights
Boston to Madison flights
Portland to Minneapolis flights
Boston to Appleton flights
Boston to Green Bay flights
Bangor to O'Hare Intl flights
Boston to Duluth flights
Boston to Wausau flights
Portland to Milwaukee flights
Bangor to Minneapolis flights
Portland to Green Bay flights
Boston to La Crosse flights
Bangor to Milwaukee flights
Bangor to Madison flights
Bangor to Green Bay flights
Portland to Appleton flights
Augusta to O'Hare Intl flights
Bangor to Appleton flights
Portland to Duluth flights
Bar Harbor to O'Hare Intl flights
Portland to Wausau flights
Rockland to O'Hare Intl flights
Boston to Escanaba flights
Presque Isle to Minneapolis flights
Boston to Dubuque flights
Bar Harbor to Minneapolis flights
Augusta to Minneapolis flights
Rockland to Minneapolis flights

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 September 16, 2025.
AirlineCheapestAverageFlexibilityOn-time
American AirlinesCheapest$218Average$369FlexibilityNo cancel feeOn-time71%
DeltaCheapest$258Average$383FlexibilityNo cancel feeOn-timeN/A
United AirlinesCheapest$273Average$377FlexibilityNo cancel feeOn-time69%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.