$209+ 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 9/22. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MSN
Jul 22 — Jul 291
Round-trip
1 adult, Economy
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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
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Cheapest flights from Portland to MadisonExplore 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 June 22, 2026.
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 June 22, 2026.
This American Airlines deal was found by Cheapflights users on 6/19. 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.
Thu 7/301:25 pm
PWM
- MSN
1 stop7h 14m
American Airlines
Sat 8/81:25 pm
MSN
- PWM
1 stop5h 45m
American Airlines
Deal found 6/19![American Airlines logo]()
$305
This American Airlines deal was found by Cheapflights users on 6/20. 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.
Thu 7/301:25 pm
PWM
- MSN
1 stop7h 14m
American Airlines
Sun 8/26:43 pm
MSN
- PWM
1 stop5h 00m
American Airlines
Deal found 6/20![American Airlines logo]()
$319
This American Airlines deal was found by Cheapflights users on 6/19. 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 7/17:28 pm
PWM
- MSN
1 stop6h 12m
American Airlines
Fri 7/173:51 pm
MSN
- PWM
1 stop7h 08m
American Airlines
Deal found 6/19![American Airlines logo]()
$330
This American Airlines deal was found by Cheapflights users on 6/21. 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.
Fri 7/315:18 pm
PWM
- MSN
1 stop6h 13m
American Airlines
Sat 8/87:10 am
MSN
- PWM
1 stop6h 57m
American Airlines
Deal found 6/21![American Airlines logo]()
$368
This American Airlines deal was found by Cheapflights users on 6/17. 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.
Thu 7/27:39 pm
PWM
- MSN
1 stop5h 34m
American Airlines
Sun 7/55:00 am
MSN
- PWM
1 stop5h 37m
American Airlines
Deal found 6/17![American Airlines logo]()
$369
This American Airlines deal was found by Cheapflights users on 6/20. 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.
Fri 7/315:18 pm
PWM
- MSN
1 stop6h 13m
American Airlines
Sun 8/93:53 pm
MSN
- PWM
1 stop7h 06m
American Airlines
Deal found 6/20![American Airlines logo]()
$382
This United Airlines deal was found by Cheapflights users on 6/20. 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 7/296:00 am
PWM
- MSN
1 stop6h 49m
United Airlines
Sat 8/13:46 pm
MSN
- PWM
1 stop4h 55m
United Airlines
Deal found 6/20![United Airlines logo]()
$390
This Delta deal was found by Cheapflights users on 6/19. 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 6/272:51 pm
PWM
- MSN
1 stop7h 19m
Delta
Tue 6/301:31 pm
MSN
- PWM
2 stops8h 34m
Delta
Deal found 6/19![Delta logo]()
$396
This United Airlines deal was found by Cheapflights users on 6/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/45:00 pm
PWM
- MSN
1 stop6h 32m
United Airlines
Wed 7/83:46 pm
MSN
- PWM
1 stop4h 55m
United Airlines
Deal found 6/18![United Airlines logo]()
$410
Best flights from Portland to MadisonDiscover carefully curated flight deals from Portland to Madison that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 22, 2026.
Discover carefully curated flight deals from Portland to Madison that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 22, 2026.
This American Airlines deal was found by Cheapflights users on 6/17. 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.
Thu 7/27:39 pm
PWM
- MSN
1 stop5h 34m
American Airlines
Sun 7/55:00 am
MSN
- PWM
1 stop5h 37m
American Airlines
Deal found 6/17![American Airlines logo]()
$369
This United Airlines deal was found by Cheapflights users on 6/20. 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 7/296:00 am
PWM
- MSN
1 stop6h 49m
United Airlines
Sat 8/13:46 pm
MSN
- PWM
1 stop4h 55m
United Airlines
Deal found 6/20![United Airlines logo]()
$390
This Delta deal was found by Cheapflights users on 6/20. 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 7/212:40 pm
PWM
- MSN
2 stops9h 50m
Delta
Sun 7/56:00 am
MSN
- PWM
2 stops10h 52m
Delta
Deal found 6/20![Delta logo]()
$662
This United Airlines deal was found by Cheapflights users on 6/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/45:00 pm
PWM
- MSN
1 stop6h 32m
United Airlines
Wed 7/812:30 pm
MSN
- PWM
2 stops10h 21m
United Airlines
Deal found 6/18![United Airlines logo]()
$415
This deal was found by Cheapflights users on 6/17. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/186:00 am
PWM
- MSN
1 stop4h 40m
United Airlines
Sun 9/203:58 pm
MSN
- PWM
1 stop4h 25m
United Airlines
Deal found 6/17![United Airlines logo]()
$483
This United Airlines deal was found by Cheapflights users on 6/21. 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 8/46:00 am
PWM
- MSN
1 stop4h 47m
United Airlines
Tue 8/412:30 pm
MSN
- PWM
2 stops10h 00m
United Airlines
Deal found 6/21![United Airlines logo]()
$555
This United Airlines deal was found by Cheapflights users on 6/19. 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 7/76:00 am
PWM
- MSN
1 stop4h 47m
United Airlines
Thu 7/95:00 am
MSN
- PWM
2 stops8h 34m
United Airlines
Deal found 6/19![United Airlines logo]()
$592
This United Airlines deal was found by Cheapflights users on 6/19. 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 7/315:00 pm
PWM
- MSN
1 stop7h 12m
United Airlines
Sat 8/88:10 am
MSN
- PWM
2 stops14h 20m
United Airlines
Deal found 6/19![United Airlines logo]()
$605
This United Airlines deal was found by Cheapflights users on 6/19. 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.
Thu 7/306:00 am
PWM
- MSN
1 stop5h 04m
United Airlines
Sat 8/86:41 am
MSN
- PWM
2 stops15h 49m
United Airlines
Deal found 6/19![United Airlines logo]()
$605
This United Airlines deal was found by Cheapflights users on 6/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/25:15 am
PWM
- MSN
3 stops10h 50m
United Airlines
Sun 7/56:41 am
MSN
- PWM
1 stop6h 49m
United Airlines
Deal found 6/18![United Airlines logo]()
$715
Last-minute flights from Portland to MadisonDiscover last-minute flight deals from Portland to Madison. Data last updated June 22, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Madison. Data last updated June 22, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 6/19. 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 6/272:51 pm
PWM
- MSN
1 stop7h 19m
Delta
Tue 6/301:31 pm
MSN
- PWM
2 stops8h 34m
Delta
Deal found 6/19![Delta logo]()
$396
This American Airlines deal was found by Cheapflights users on 6/19. 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 7/17:28 pm
PWM
- MSN
1 stop6h 12m
American Airlines
Fri 7/173:51 pm
MSN
- PWM
1 stop7h 08m
American Airlines
Deal found 6/19![American Airlines logo]()
$330
This American Airlines deal was found by Cheapflights users on 6/17. 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.
Thu 7/27:39 pm
PWM
- MSN
1 stop5h 34m
American Airlines
Sun 7/55:00 am
MSN
- PWM
1 stop5h 37m
American Airlines
Deal found 6/17![American Airlines logo]()
$369
This United Airlines deal was found by Cheapflights users on 6/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/45:00 pm
PWM
- MSN
1 stop6h 32m
United Airlines
Wed 7/83:46 pm
MSN
- PWM
1 stop4h 55m
United Airlines
Deal found 6/18![United Airlines logo]()
$410
This United Airlines deal was found by Cheapflights users on 6/20. 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 7/296:00 am
PWM
- MSN
1 stop6h 49m
United Airlines
Sat 8/13:46 pm
MSN
- PWM
1 stop4h 55m
United Airlines
Deal found 6/20![United Airlines logo]()
$390
This American Airlines deal was found by Cheapflights users on 6/19. 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.
Thu 7/301:25 pm
PWM
- MSN
1 stop7h 14m
American Airlines
Sat 8/81:25 pm
MSN
- PWM
1 stop5h 45m
American Airlines
Deal found 6/19![American Airlines logo]()
$305
This American Airlines deal was found by Cheapflights users on 6/20. 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.
Thu 7/301:25 pm
PWM
- MSN
1 stop7h 14m
American Airlines
Sun 8/26:43 pm
MSN
- PWM
1 stop5h 00m
American Airlines
Deal found 6/20![American Airlines logo]()
$319
This American Airlines deal was found by Cheapflights users on 6/21. 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.
Fri 7/315:18 pm
PWM
- MSN
1 stop6h 13m
American Airlines
Sat 8/87:10 am
MSN
- PWM
1 stop6h 57m
American Airlines
Deal found 6/21![American Airlines logo]()
$368
This American Airlines deal was found by Cheapflights users on 6/20. 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.
Fri 7/315:18 pm
PWM
- MSN
1 stop6h 13m
American Airlines
Sun 8/93:53 pm
MSN
- PWM
1 stop7h 06m
American Airlines
Deal found 6/20![American Airlines logo]()
$382
One-way flights from Portland to MadisonSearch for one-way flight options from Portland to Madison. Find affordable one-way fares based on user searches. Data last updated June 22, 2026.
Search for one-way flight options from Portland to Madison. Find affordable one-way fares based on user searches. Data last updated June 22, 2026.
This American Airlines deal was found by Cheapflights users on 6/21. 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 9/227:32 am
PWM
- MSN
1 stop7h 55m
American Airlines
Deal found 6/21![American Airlines logo]()
$209
This Delta deal was found by Cheapflights users on 6/19. 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 9/226:02 am
PWM
- MSN
2 stops11h 16m
Delta
Deal found 6/19![Delta logo]()
$214
This American Airlines deal was found by Cheapflights users on 6/19. 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 8/106:46 pm
PWM
- MSN
1 stop5h 43m
American Airlines
Deal found 6/19![American Airlines logo]()
$221
This American Airlines deal was found by Cheapflights users on 6/21. 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.
Thu 7/305:45 am
PWM
- MSN
1 stop7h 28m
American Airlines
Deal found 6/21![American Airlines logo]()
$254
This Delta deal was found by Cheapflights users on 6/19. 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.
Fri 7/101:12 pm
PWM
- MSN
1 stop7h 33m
Delta
Deal found 6/19![Delta logo]()
$264
This United Airlines deal was found by Cheapflights users on 6/21. 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 7/103:16 pm
PWM
- MSN
1 stop6h 23m
United Airlines
Deal found 6/21![United Airlines logo]()
$289
This United Airlines deal was found by Cheapflights users on 6/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/306:00 am
PWM
- MSN
1 stop5h 04m
United Airlines
Deal found 6/18![United Airlines logo]()
$298
This Kiwi.com deal was found by Cheapflights users on 6/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/106:29 pm
PWM
- MSN
3 stops40h 18m
Breeze Airways
Deal found 6/18![Breeze Airways logo]()
$315
This United Airlines deal was found by Cheapflights users on 6/19. 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 7/196:00 am
PWM
- MSN
1 stop4h 47m
United Airlines
Deal found 6/19![United Airlines logo]()
$318
This Kiwi.com deal was found by Cheapflights users on 6/19. 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 7/197:00 am
PWM
- MSN
2 stops26h 25m
Breeze Airways
Deal found 6/19![Breeze Airways logo]()
$337
Find 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 June 22, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $305 (American Airlines) |
One-way from | $209 (American Airlines) |
Popular in | December |
Cheapest in | February |
Average price | $557 |
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 June 22, 2026.
Use the filters below to find and compare flights from Portland to Madison that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
PortlandMadison
PWM - MSN
PWMMSN
Portland
Thu 7/2
7:39 pm-12:13 am
1 stop5h 34m
Madison Truax Field
Sun 7/5
5:00 am-11:37 am
1 stop5h 37m
$369
PortlandMadison
PWM - MSN
PWMMSN
Portland
Wed 7/29
6:00 am-11:49 am
1 stop6h 49m
Madison Truax Field
Sat 8/1
3:46 pm-9:41 pm
1 stop4h 55m
$390
PortlandMadison
PWM - MSN
PWMMSN
Portland
Sat 7/4
5:00 pm-10:32 pm
1 stop6h 32m
Madison Truax Field
Wed 7/8
12:30 pm-11:51 pm
2 stops10h 21m
$415
Quickest round-trip
PortlandMadison
PWM - MSN
PWMMSN
Portland
Fri 9/18
6:00 am-9:40 am
1 stop4h 40m
Madison Truax Field
Sun 9/20
3:58 pm-9:23 pm
1 stop4h 25m
$483
PortlandMadison
PWM - MSN
PWMMSN
Portland
Tue 8/4
6:00 am-9:47 am
1 stop4h 47m
Madison Truax Field
Tue 8/4
12:30 pm-11:30 pm
2 stops10h 00m
$555
PortlandMadison
PWM - MSN
PWMMSN
Portland
Tue 7/7
6:00 am-9:47 am
1 stop4h 47m
Madison Truax Field
Thu 7/9
5:00 am-2:34 pm
2 stops8h 34m
$592
PortlandMadison
PWM - MSN
PWMMSN
Portland
Fri 7/31
5:00 pm-11:12 pm
1 stop7h 12m
Madison Truax Field
Sat 8/8
8:10 am-11:30 pm
2 stops14h 20m
$605
PortlandMadison
PWM - MSN
PWMMSN
Portland
Thu 7/30
6:00 am-10:04 am
1 stop5h 04m
Madison Truax Field
Sat 8/8
6:41 am-11:30 pm
2 stops15h 49m
$605
PortlandMadison
PWM - MSN
PWMMSN
Portland
Thu 7/2
12:40 pm-9:30 pm
2 stops9h 50m
Madison Truax Field
Sun 7/5
6:00 am-5:52 pm
2 stops10h 52m
$662
PortlandMadison
PWM - MSN
PWMMSN
Portland
Thu 7/2
5:15 am-3:05 pm
3 stops10h 50m
Madison Truax Field
Sun 7/5
6:41 am-2:30 pm
1 stop6h 49m
$715
Showing 1-10 of 18 resultsSorted by cheapest first
Compare providers for flights from Portland to Madison
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 Portland to Madison in June.
| 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 Portland, Maine-Madison flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Portland, Maine-Madison flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Portland, Maine-Madison flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Portland, Maine-Madison 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 Portland, Maine-Madison 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 Portland to Madison
Have a flexible travel schedule? Discover the best time to fly to Madison from Portland with our price prediction graph.
PWM-MSN
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, February is the cheapest month in which you can book a flight from Portland, Maine to Madison (average of $278). Flying from Portland, Maine to Madison in December is currently the most expensive (average of $583). 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.
How much does it cost to fly round-trip from Portland, Maine to Madison?
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 June 22, 2026.
Get a feel of what it's like to fly with Delta,United Airlines, andAmerican 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.
Crew
8.5
Comfort
7.8
Entertainment
7.8
Overall
7.8
Boarding
8.1
Food
7.2
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Crew
8.5
Comfort
7.8
Entertainment
7.8
Overall
7.8
Boarding
8.1
Food
7.2
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Crew
8.5
Comfort
7.8
Entertainment
7.8
Overall
7.8
Boarding
8.1
Food
7.2
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Crew
8.5
Comfort
7.8
Entertainment
7.8
Overall
7.8
Boarding
8.1
Food
7.2
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
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Top 3 airlines flying from Portland to Madison
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| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$258 | Average$428 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$270 | Average$369 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$273 | Average$377 | FlexibilityNo cancel fee | On-time69% |