HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Portland

$239+ 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 11/28. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — PWM
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Madison to Portland 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 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 September 11, 2025.

Round-trip from

$259
(Delta)

One-way from

$239
(American Airlines)

Popular in

December

Cheapest in

February

Average price

$358
From Madison Truax Field to Portland
Search Deals
One-way flight from Madison Truax Field to Portland
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($35 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 September 2025
Search Deals

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 September 11, 2025.

This United Airlines deal was found by Cheapflights users on 9/10. 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 10/16:17 amMSN - PWM
1 stop6h 36mUnited Airlines
Sun 10/56:14 amPWM - MSN
1 stop4h 41mUnited Airlines
Deal found 9/10$259
This Delta deal was found by Cheapflights users on 9/11. 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 11/81:25 pmMSN - PWM
2 stops9h 40mDelta
Tue 11/116:35 amPWM - MSN
2 stops10h 49mDelta
Deal found 9/11$269
This American Airlines deal was found by Cheapflights users on 9/11. 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 10/48:10 amMSN - PWM
1 stop7h 40mAmerican Airlines
Wed 10/86:00 amPWM - MSN
1 stop5h 08mAmerican Airlines
Deal found 9/11$274
This Delta deal was found by Cheapflights users on 9/11. 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.
Tue 10/287:05 amMSN - PWM
1 stop5h 01mDelta
Sat 11/12:38 pmPWM - MSN
2 stops6h 43mDelta
Deal found 9/11$303
This United Airlines deal was found by Cheapflights users on 9/11. 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 10/43:48 pmMSN - PWM
2 stops7h 11mUnited Airlines
Wed 10/86:00 amPWM - MSN
2 stops8h 50mUnited Airlines
Deal found 9/11$304
This United Airlines deal was found by Cheapflights users on 9/9. 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 10/82:46 pmMSN - PWM
1 stop5h 58mUnited Airlines
Mon 10/136:14 amPWM - MSN
1 stop4h 41mUnited Airlines
Deal found 9/9$329
This Delta deal was found by Cheapflights users on 9/9. 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 10/205:30 amMSN - PWM
1 stop5h 52mDelta
Tue 10/286:00 amPWM - MSN
2 stops12h 12mDelta
Deal found 9/9$342
This Delta deal was found by Cheapflights users on 9/11. 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 9/1310:00 amMSN - PWM
1 stop6h 16mDelta
Sat 9/206:33 pmPWM - MSN
1 stop4h 41mDelta
Deal found 9/11$349

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 September 11, 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 11/8

1:25 pm-10:19 pm

1 stop7h 54m

Portland

Tue 11/11

12:48 pm-5:22 pm

1 stop5h 34m

$259

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Wed 10/29

7:00 am-12:00 pm

1 stop4h 00m

Portland

Sat 11/1

4:48 pm-8:21 pm

1 stop4h 33m

$259

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Sat 10/4

8:10 am-4:50 pm

1 stop7h 40m

Portland

Wed 10/8

6:00 am-10:08 am

1 stop5h 08m

$274

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Mon 10/20

5:10 pm-10:48 pm

1 stop4h 38m

Portland

Tue 10/28

7:44 am-12:15 pm

1 stop5h 31m

$274

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Wed 2/18

3:50 pm-11:05 pm

1 stop6h 15m

Portland

Sat 2/21

12:50 pm-10:08 pm

2 stops10h 18m

$322

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Wed 10/8

2:46 pm-9:44 pm

1 stop5h 58m

Portland

Mon 10/13

6:14 am-9:55 am

1 stop4h 41m

$329

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Wed 10/15

2:46 pm-9:44 pm

1 stop5h 58m

Portland

Mon 10/20

6:14 am-9:55 am

1 stop4h 41m

$329

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Wed 2/18

3:52 pm-11:44 pm

1 stop6h 52m

Portland

Sat 2/21

5:47 am-10:10 am

1 stop5h 23m

$329

MadisonPortland

MSN - PWM

MSNPWM

Madison Truax Field

Fri 11/28

10:20 am-6:10 pm

1 stop6h 50m

$239

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

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 August 29, 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 September 11, 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
7,960 reviews

Entertainment

7.9

Crew

8.5

Boarding

8.2

Comfort

7.9

Overall

8.0

Food

7.3

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
7,960 reviews
Delta
8.0
Very good
7,960 reviews

Entertainment

7.9

Crew

8.5

Boarding

8.2

Comfort

7.9

Overall

8.0

Food

7.3

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
8,937 reviews
Delta
8.0
Very good
7,960 reviews

Entertainment

7.9

Crew

8.5

Boarding

8.2

Comfort

7.9

Overall

8.0

Food

7.3

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
7,960 reviews

Entertainment

7.9

Crew

8.5

Boarding

8.2

Comfort

7.9

Overall

8.0

Food

7.3

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.

  • How long is the flight from Madison to Portland, Maine?

    Airlines like Delta and American Airlines fly from Madison to Portland, Maine in about 7h 40m. The time it takes to get you to your destination can typically vary by up to 14m. There are 953 mi between Madison and Portland, Maine. This flight may include one or multiple stops.

  • What are the cheapest airlines flying from Madison to Portland, Maine round-trip?

    Our cheapest airline available from Madison to Portland, Maine is American Airlines. Our recent data shows that you can find tickets from as low as $258 on this airline. Additional options worth looking into are Delta and United Airlines, starting at $258 and $273 round-trip. Users have found that American Airlines is 34% cheaper than the other options available to this destination.

  • 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

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 Madison to Portland

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

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 September 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$258Average$388FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$258Average$398FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$273Average$459FlexibilityNo 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.