$192+ Cheap flights from Madison to Portland, ME (MSN - PWM)
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 12/16. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — PWM
Nov 26 — Dec 31
Round-trip
1 adult, Economy
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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.Cheap flight deals from Madison to Portland
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Cheapest flights from Madison to PortlandExplore 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 October 27, 2026.
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 October 27, 2026.
This United Airlines deal was found by Cheapflights users on 10/22. 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 12/58:15 am -
1 stop6h 23m
Sat 12/124:47 pm -
1 stop6h 36m
Deal found 10/22![United Airlines logo]()
$341
This American Airlines deal was found by Cheapflights users on 10/23. 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 12/15:25 pm -
1 stop4h 31m
Sun 12/65:00 am -
1 stop7h 50m
Deal found 10/23![American Airlines logo]()
$345
This Delta deal was found by Cheapflights users on 10/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/159:59 am -
1 stop5h 11m
Sun 11/224:50 pm -
1 stop5h 23m
Deal found 10/25![Delta logo]()
$349
This American Airlines deal was found by Cheapflights users on 10/22. 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 12/23:12 pm -
2 stops7h 07m
Sun 12/612:44 pm -
1 stop6h 46m
Deal found 10/22![American Airlines logo]()
$350
This American Airlines deal was found by Cheapflights users on 10/22. 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 12/55:00 am -
2 stops8h 35m
Sat 12/126:00 am -
2 stops9h 42m
Deal found 10/22![American Airlines logo]()
$351
This Delta deal was found by Cheapflights users on 10/26. 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 11/197:00 am -
1 stop3h 58m
Mon 11/236:27 am -
2 stops7h 23m
Deal found 10/26![Delta logo]()
$354
This American Airlines deal was found by Cheapflights users on 10/23. 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 11/75:18 pm -
1 stop4h 39m
Wed 11/1111:07 am -
1 stop6h 46m
Deal found 10/23![American Airlines logo]()
$399
This United Airlines deal was found by Cheapflights users on 10/26. 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 11/118:15 am -
1 stop5h 01m
Sat 11/1410:50 am -
2 stops9h 17m
Deal found 10/26![United Airlines logo]()
$404
Best flights from Madison to PortlandDiscover carefully curated flight deals from Madison to Portland that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 27, 2026.
Discover carefully curated flight deals from Madison to Portland that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 27, 2026.
This United Airlines deal was found by Cheapflights users on 10/22. 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 12/58:15 am -
1 stop6h 23m
Sat 12/124:47 pm -
1 stop6h 36m
Deal found 10/22![United Airlines logo]()
$341
This American Airlines deal was found by Cheapflights users on 10/23. 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 12/15:25 pm -
1 stop4h 31m
Sun 12/65:00 am -
1 stop7h 50m
Deal found 10/23![American Airlines logo]()
$345
This Delta deal was found by Cheapflights users on 10/26. 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 11/197:00 am -
1 stop3h 58m
Mon 11/236:27 am -
2 stops7h 23m
Deal found 10/26![Delta logo]()
$354
This American Airlines deal was found by Cheapflights users on 10/25. 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.
Sat 12/51:55 pm -
1 stop7h 51m
Sat 12/1212:34 pm -
1 stop7h 04m
Deal found 10/25![American Airlines logo]()
$391
This United Airlines deal was found by Cheapflights users on 10/26. 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 1/308:15 am -
1 stop5h 36m
Tue 2/24:25 pm -
1 stop7h 50m
Deal found 10/26![United Airlines logo]()
$441
Last-minute flights from Madison to PortlandDiscover last-minute flight deals from Madison to Portland. Data last updated October 27, 2026 and is based on user searches.
Discover last-minute flight deals from Madison to Portland. Data last updated October 27, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 10/26. 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 10/316:25 am -
1 stop6h 51m
Wed 11/45:08 pm -
1 stop6h 59m
Deal found 10/26![United Airlines logo]()
$441
This Delta deal was found by Cheapflights users on 10/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/35:51 am -
1 stop6h 11m
Sun 11/811:55 am -
1 stop8h 11m
Deal found 10/25![Delta logo]()
$420
This Delta deal was found by Cheapflights users on 10/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/45:51 am -
2 stops8h 44m
Sun 11/811:55 am -
1 stop8h 11m
Deal found 10/25![Delta logo]()
$425
This United Airlines deal was found by Cheapflights users on 10/25. 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.
Wed 11/46:10 am -
2 stops7h 17m
Sun 11/85:30 am -
2 stops7h 29m
Deal found 10/25![United Airlines logo]()
$430
This American Airlines deal was found by Cheapflights users on 10/23. 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 11/75:18 pm -
1 stop4h 39m
Wed 11/1111:07 am -
1 stop6h 46m
Deal found 10/23![American Airlines logo]()
$399
This United Airlines deal was found by Cheapflights users on 10/26. 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 11/118:15 am -
1 stop5h 01m
Sat 11/1410:50 am -
2 stops9h 17m
Deal found 10/26![United Airlines logo]()
$404
This Delta deal was found by Cheapflights users on 10/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/159:59 am -
1 stop5h 11m
Sun 11/224:50 pm -
1 stop5h 23m
Deal found 10/25![Delta logo]()
$349
This American Airlines deal was found by Cheapflights users on 10/25. 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.
Sun 11/156:02 am -
1 stop4h 33m
Sun 11/225:26 am -
2 stops10h 33m
Deal found 10/25![American Airlines logo]()
$427
This Delta deal was found by Cheapflights users on 10/26. 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 11/197:00 am -
1 stop3h 58m
Mon 11/236:27 am -
2 stops7h 23m
Deal found 10/26![Delta logo]()
$354
One-way flights from Madison to PortlandSearch for one-way flight options from Madison to Portland. Find affordable one-way fares based on user searches. Data last updated October 27, 2026.
Search for one-way flight options from Madison to Portland. Find affordable one-way fares based on user searches. Data last updated October 27, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/166:04 pm -
1 stop14h 47m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Breeze Airways logo]()
$192
This Delta deal was found by Cheapflights users on 10/23. 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.
Wed 12/1611:45 am -
2 stops10h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Delta logo]()
$281
This Kiwi.com deal was found by Cheapflights users on 10/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/1610:38 am -
3 stops45h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Multiple Airlines logo]()
$318
This United Airlines deal was found by Cheapflights users on 10/23. 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 12/237:00 am -
1 stop7h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![United Airlines logo]()
$595
Find 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 October 27, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $341 (United Airlines) |
One-way from | $192 (Kiwi.com) |
Popular in | December |
Cheapest in | May |
Average price | $397 |
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 7,457,451 searches. Data last updated October 27, 2026.
Use the filters below to find and compare flights from Madison to Portland that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
MadisonPortland
MSN Madison Truax Field - PWM Portland
MSNPWM
Madison Truax Field
Wed 12/16
11:45 am-11:20 pm
2 stops10h 35m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$281
MadisonPortland
MSN Madison Truax Field - PWM Portland
MSNPWM
Madison Truax Field
Sat 12/5
8:15 am-3:38 pm
1 stop6h 23m
Portland
Sat 12/12
4:47 pm-10:23 pm
1 stop6h 36m
$341
MadisonPortland
MSN Madison Truax Field - PWM Portland
MSNPWM
Madison Truax Field
Tue 12/1
5:25 pm-10:56 pm
1 stop4h 31m
Portland
Sun 12/6
5:00 am-11:50 am
1 stop7h 50m
$345
MadisonPortland
MSN Madison Truax Field - PWM Portland
MSNPWM
Madison Truax Field
Thu 11/19
7:00 am-11:58 am
1 stop3h 58m
Portland
Mon 11/23
6:27 am-12:50 pm
2 stops7h 23m
$354
MadisonPortland
MSN Madison Truax Field - PWM Portland
MSNPWM
Madison Truax Field
Sat 12/5
1:55 pm-10:46 pm
1 stop7h 51m
Portland
Sat 12/12
12:34 pm-6:38 pm
1 stop7h 04m
$391
MadisonPortland
MSN Madison Truax Field - PWM Portland
MSNPWM
Madison Truax Field
Sat 1/30
8:15 am-2:51 pm
1 stop5h 36m
Portland
Tue 2/2
4:25 pm-11:15 pm
1 stop7h 50m
$441
Quickest round-trip
MadisonPortland
MSN Madison Truax Field - PWM Portland
MSNPWM
Madison Truax Field
Wed 12/23
7:00 am-3:31 pm
1 stop7h 31m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$595
Sorted by cheapest first
Compare providers for flights from Madison to Portland
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 Madison to Portland in October.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars | |
| Price Accuracy2 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Madison-Portland, Maine flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Madison-Portland, Maine flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Madison-Portland, Maine flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Madison-Portland, Maine 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 Madison-Portland, Maine 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 Madison to Portland
Have a flexible travel schedule? Discover the best time to fly to Portland from Madison with our price prediction graph.
MSN-PWM
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
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 October 27, 2026.
Get a feel of what it's like to fly with Delta,United Airlines, andAmerican 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.
Comfort
7.8
Crew
8.5
Entertainment
7.8
Food
7.2
Boarding
8.1
Overall
7.8
Reviews
1 / 20
6.0
GoodEllen,Oct 2026
GRR - ATL
Comfort
7.8
Crew
8.5
Entertainment
7.8
Food
7.2
Boarding
8.1
Overall
7.8
Reviews
1 / 20
6.0
GoodEllen,Oct 2026
GRR - ATL
Comfort
7.8
Crew
8.5
Entertainment
7.8
Food
7.2
Boarding
8.1
Overall
7.8
Reviews
1 / 20
6.0
GoodEllen,Oct 2026
GRR - ATL
Comfort
7.8
Crew
8.5
Entertainment
7.8
Food
7.2
Boarding
8.1
Overall
7.8
Reviews
1 / 20
6.0
GoodEllen,Oct 2026
GRR - ATL
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.
Traveling to a place near Portland?
Book flights to Portland if you plan to visit one of these locationsLewiston
North Conway
Brunswick
Conway
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Complete your trip
Complete your trip to Portland by adding a car rental and/or hotel reservation to your travel itinerary.
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Find flights from Madison to Portland, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Madison and Portland flights
Browse other Madison and Portland flight options. Last updated on October 27, 2026.
Other flights from Madison
Browse through other flights departing from Madison. Flights are based on user searches made on Cheapflights and were last updated on October 27, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Other flights to Portland
Explore flights to Portland departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on October 27, 2026.
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 7,457,451 searches. Data last updated October 27, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$258 | Average$513 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$290 | Average$428 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$300 | Average$457 | FlexibilityNo cancel fee | On-time69% |