$181+ 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 11/8. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — PWM
Oct 10 — Oct 171
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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Best
Last-minute
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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 September 10, 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 September 10, 2026.
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/136:17 pm -
1 stop4h 42m
Wed 10/215:37 pm -
1 stop6h 48m
Deal found 9/9![American Airlines logo]()
$301
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.
Tue 10/1311:14 am -
2 stops11h 56m
Wed 10/2112:42 pm -
2 stops11h 21m
Deal found 9/9![Delta logo]()
$311
This American Airlines deal was found by Cheapflights users on 9/7. 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 10/75:31 pm -
1 stop5h 05m
Fri 10/165:37 pm -
1 stop5h 54m
Deal found 9/7![American Airlines logo]()
$315
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 10/74:10 pm -
2 stops6h 49m
Wed 10/146:00 am -
1 stop5h 29m
Deal found 9/9![United Airlines logo]()
$320
This Delta deal was found by Cheapflights users on 9/7. 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 10/178:45 am -
1 stop6h 10m
Sat 10/2412:43 pm -
1 stop5h 05m
Deal found 9/7![Delta logo]()
$321
This American Airlines deal was found by Cheapflights users on 9/5. 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 9/267:00 am -
1 stop6h 20m
Sat 10/35:06 pm -
1 stop5h 09m
Deal found 9/5![American Airlines logo]()
$329
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/66:17 pm -
1 stop4h 42m
Thu 10/156:00 am -
1 stop6h 54m
Deal found 9/9![American Airlines logo]()
$346
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 September 10, 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 September 10, 2026.
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 10/74:10 pm -
2 stops6h 49m
Wed 10/146:00 am -
1 stop5h 29m
Deal found 9/9![United Airlines logo]()
$320
This Delta deal was found by Cheapflights users on 9/5. 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 9/291:30 pm -
2 stops8h 47m
Sat 10/312:55 pm -
2 stops10h 46m
Deal found 9/5![Delta logo]()
$429
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.
Sat 10/248:10 am -
1 stop5h 28m
Wed 10/285:08 pm -
1 stop6h 59m
Deal found 9/9![United Airlines logo]()
$381
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.
Tue 9/222:47 pm -
1 stop5h 36m
Sat 9/267:58 am -
1 stop8h 06m
Deal found 9/9![United Airlines logo]()
$390
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.
Fri 11/138:15 am -
1 stop5h 01m
Sun 11/155:08 pm -
1 stop6h 59m
Deal found 9/10![United Airlines logo]()
$409
This United Airlines deal was found by Cheapflights users on 9/6. 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 9/292:49 pm -
1 stop6h 05m
Tue 10/66:00 am -
1 stop5h 29m
Deal found 9/6![United Airlines logo]()
$415
This United Airlines deal was found by Cheapflights users on 9/5. 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 9/268:10 am -
2 stops10h 14m
Wed 9/308:03 am -
2 stops6h 34m
Deal found 9/5![United Airlines logo]()
$439
Last-minute flights from Madison to PortlandDiscover last-minute flight deals from Madison to Portland. Data last updated September 10, 2026 and is based on user searches.
Discover last-minute flight deals from Madison to Portland. Data last updated September 10, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 9/5. 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 9/267:00 am -
1 stop6h 20m
Sat 10/35:06 pm -
1 stop5h 09m
Deal found 9/5![American Airlines logo]()
$329
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/66:17 pm -
1 stop4h 42m
Thu 10/156:00 am -
1 stop6h 54m
Deal found 9/9![American Airlines logo]()
$346
This American Airlines deal was found by Cheapflights users on 9/7. 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 10/75:31 pm -
1 stop5h 05m
Fri 10/165:37 pm -
1 stop5h 54m
Deal found 9/7![American Airlines logo]()
$315
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 10/74:10 pm -
2 stops6h 49m
Wed 10/146:00 am -
1 stop5h 29m
Deal found 9/9![United Airlines logo]()
$320
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/136:17 pm -
1 stop4h 42m
Wed 10/215:37 pm -
1 stop6h 48m
Deal found 9/9![American Airlines logo]()
$301
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.
Tue 10/1311:14 am -
2 stops11h 56m
Wed 10/2112:42 pm -
2 stops11h 21m
Deal found 9/9![Delta logo]()
$311
This Delta deal was found by Cheapflights users on 9/7. 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 10/178:45 am -
1 stop6h 10m
Sat 10/2412:43 pm -
1 stop5h 05m
Deal found 9/7![Delta logo]()
$321
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 September 10, 2026.
Search for one-way flight options from Madison to Portland. Find affordable one-way fares based on user searches. Data last updated September 10, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/8. 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.
Sun 11/86:00 pm -
1 stop14h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Breeze Airways logo]()
$181
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/2010:30 am -
1 stop21h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Breeze Airways logo]()
$203
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 10/146:06 am -
1 stop6h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![United Airlines logo]()
$256
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/86:00 pm -
3 stops39h 14m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Multiple Airlines logo]()
$263
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.
Sun 11/86:25 am -
2 stops7h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![United Airlines logo]()
$274
This American Airlines deal was found by Cheapflights users on 9/6. 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.
Mon 10/56:00 am -
1 stop5h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![American Airlines logo]()
$279
This Kiwi.com deal was found by Cheapflights users on 9/5. 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 10/1410:38 am -
3 stops45h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![Multiple Airlines logo]()
$280
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 September 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $301 (American Airlines) |
One-way from | $181 (Kiwi.com) |
Popular in | December |
Cheapest in | May |
Average price | $403 |
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 September 10, 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
Sun 11/8
6:00 pm-9:08 am
1 stop14h 08m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$181
MadisonPortland
MSN Madison Truax Field - PWM Portland
MSNPWM
Madison Truax Field
Tue 10/20
10:30 am-9:08 am
1 stop21h 38m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$203
MadisonPortland
MSN Madison Truax Field - PWM Portland
MSNPWM
Madison Truax Field
Wed 10/14
3:28 pm-11:43 pm
1 stop7h 15m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$256
MadisonPortland
MSN Madison Truax Field - PWM Portland
MSNPWM
Madison Truax Field
Wed 10/14
2:49 pm-11:28 pm
2 stops7h 39m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$261
MadisonPortland
MSN Madison Truax Field - PWM Portland
MSNPWM
Madison Truax Field
Sun 11/8
6:00 pm-10:14 am
3 stops39h 14m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$263
Quickest round-trip
MadisonPortland
MSN Madison Truax Field - PWM Portland
MSNPWM
Madison Truax Field
Sun 11/8
6:25 am-2:27 pm
2 stops7h 02m
Portland
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$274
MadisonPortland
MSN Madison Truax Field - PWM Portland
MSNPWM
Madison Truax Field
Wed 10/7
4:10 pm-11:59 pm
2 stops6h 49m
Portland
Wed 10/14
6:00 am-10:29 am
1 stop5h 29m
$320
MadisonPortland
MSN Madison Truax Field - PWM Portland
MSNPWM
Madison Truax Field
Sat 10/24
8:10 am-2:38 pm
1 stop5h 28m
Portland
Wed 10/28
5:08 pm-11:07 pm
1 stop6h 59m
$381
MadisonPortland
MSN Madison Truax Field - PWM Portland
MSNPWM
Madison Truax Field
Tue 9/22
2:47 pm-9:23 pm
1 stop5h 36m
Portland
Sat 9/26
7:58 am-3:04 pm
1 stop8h 06m
$390
MadisonPortland
MSN Madison Truax Field - PWM Portland
MSNPWM
Madison Truax Field
Fri 11/13
8:15 am-2:16 pm
1 stop5h 01m
Portland
Sun 11/15
5:08 pm-11:07 pm
1 stop6h 59m
$409
Showing 1-10 of 13 resultsSorted 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 September.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 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 September 10, 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.
Boarding
8.1
Overall
7.8
Crew
8.5
Entertainment
7.8
Comfort
7.8
Food
7.2
Reviews
1 / 20
8.0
ExcellentJorge,Aug 2026
TPA - ATL
Boarding
8.1
Overall
7.8
Crew
8.5
Entertainment
7.8
Comfort
7.8
Food
7.2
Reviews
1 / 20
8.0
ExcellentJorge,Aug 2026
TPA - ATL
Boarding
8.1
Overall
7.8
Crew
8.5
Entertainment
7.8
Comfort
7.8
Food
7.2
Reviews
1 / 20
8.0
ExcellentJorge,Aug 2026
TPA - ATL
Boarding
8.1
Overall
7.8
Crew
8.5
Entertainment
7.8
Comfort
7.8
Food
7.2
Reviews
1 / 20
8.0
ExcellentJorge,Aug 2026
TPA - 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 locationsNorth Conway
Lewiston
Brunswick
Conway
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Madison and Portland flights
Browse other Madison and Portland flight options. Last updated on September 10, 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 September 10, 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 September 10, 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 September 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$258 | Average$323 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$290 | Average$428 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$300 | Average$403 | FlexibilityNo cancel fee | On-time69% |