$246+ 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
Aug 31 — Sep 71
Round-trip
1 adult, Economy
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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
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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 Portland to Madison
Cheapest
Best
Last-minute
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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 August 1, 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 August 1, 2026.
This American Airlines deal was found by Cheapflights users on 7/29. 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 10/135:09 pm
PWM
- MSN
2 stops8h 03m
American Airlines
Sat 10/173:28 pm
MSN
- PWM
1 stop7h 15m
American Airlines
Deal found 7/29![American Airlines logo]()
$306
This Delta deal was found by Cheapflights users on 7/31. 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 9/912:55 pm
PWM
- MSN
1 stop5h 22m
Delta
Mon 9/143:35 pm
MSN
- PWM
1 stop6h 42m
Delta
Deal found 7/31![Delta logo]()
$315
This American Airlines deal was found by Cheapflights users on 7/28. 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 9/175:38 pm
PWM
- MSN
1 stop7h 39m
American Airlines
Sun 9/205:00 am
MSN
- PWM
1 stop7h 05m
American Airlines
Deal found 7/28![American Airlines logo]()
$329
This American Airlines deal was found by Cheapflights users on 7/31. 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 8/311:30 pm
PWM
- MSN
1 stop7h 00m
American Airlines
Sun 9/62:35 pm
MSN
- PWM
1 stop7h 13m
American Airlines
Deal found 7/31![American Airlines logo]()
$349
This Delta deal was found by Cheapflights users on 7/31. 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 9/171:59 pm
PWM
- MSN
1 stop6h 07m
Delta
Sun 9/205:50 am
MSN
- PWM
2 stops8h 49m
Delta
Deal found 7/31![Delta logo]()
$369
This American Airlines deal was found by Cheapflights users on 7/30. 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 8/146:46 pm
PWM
- MSN
1 stop5h 43m
American Airlines
Tue 8/189:48 am
MSN
- PWM
1 stop6h 44m
American Airlines
Deal found 7/30![American Airlines logo]()
$379
This United Airlines deal was found by Cheapflights users on 7/31. 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 9/56:02 am
PWM
- MSN
1 stop5h 02m
United Airlines
Wed 9/91:00 pm
MSN
- PWM
1 stop7h 44m
United Airlines
Deal found 7/31![United Airlines logo]()
$381
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 August 1, 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 August 1, 2026.
This Delta deal was found by Cheapflights users on 7/31. 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 9/912:55 pm
PWM
- MSN
1 stop5h 22m
Delta
Mon 9/143:35 pm
MSN
- PWM
1 stop6h 42m
Delta
Deal found 7/31![Delta logo]()
$315
This American Airlines deal was found by Cheapflights users on 7/31. 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 8/311:30 pm
PWM
- MSN
1 stop7h 00m
American Airlines
Sun 9/62:35 pm
MSN
- PWM
1 stop7h 13m
American Airlines
Deal found 7/31![American Airlines logo]()
$349
This United Airlines deal was found by Cheapflights users on 7/30. 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 9/55:03 pm
PWM
- MSN
1 stop6h 48m
United Airlines
Wed 9/98:05 am
MSN
- PWM
2 stops9h 24m
United Airlines
Deal found 7/30![United Airlines logo]()
$386
This Delta deal was found by Cheapflights users on 7/31. 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 9/171:59 pm
PWM
- MSN
1 stop6h 07m
Delta
Sun 9/205:50 am
MSN
- PWM
2 stops8h 49m
Delta
Deal found 7/31![Delta logo]()
$369
This American Airlines deal was found by Cheapflights users on 7/27. 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 8/116:46 pm
PWM
- MSN
1 stop5h 43m
American Airlines
Sat 8/152:45 pm
MSN
- PWM
2 stops7h 52m
American Airlines
Deal found 7/27![American Airlines logo]()
$395
This United Airlines deal was found by Cheapflights users on 7/29. 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 10/135:08 pm
PWM
- MSN
1 stop6h 27m
United Airlines
Sun 10/182:49 pm
MSN
- PWM
1 stop5h 57m
United Airlines
Deal found 7/29![United Airlines logo]()
$400
This American Airlines deal was found by Cheapflights users on 7/29. 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 10/125:37 pm
PWM
- MSN
1 stop6h 48m
American Airlines
Sat 10/173:28 pm
MSN
- PWM
2 stops7h 13m
American Airlines
Deal found 7/29![American Airlines logo]()
$414
Last-minute flights from Portland to MadisonDiscover last-minute flight deals from Portland to Madison. Data last updated August 1, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Madison. Data last updated August 1, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 7/27. 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 8/42:56 pm
PWM
- MSN
1 stop7h 45m
American Airlines
Tue 8/115:47 pm
MSN
- PWM
1 stop4h 54m
American Airlines
Deal found 7/27![American Airlines logo]()
$390
This Delta deal was found by Cheapflights users on 8/1. 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 8/512:47 pm
PWM
- MSN
1 stop5h 48m
Delta
Sun 8/163:00 pm
MSN
- PWM
1 stop7h 30m
Delta
Deal found 8/1![Delta logo]()
$400
This American Airlines deal was found by Cheapflights users on 7/30. 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 8/136:02 am
PWM
- MSN
1 stop7h 06m
American Airlines
Wed 8/193:54 pm
MSN
- PWM
1 stop6h 53m
American Airlines
Deal found 7/30![American Airlines logo]()
$399
This American Airlines deal was found by Cheapflights users on 7/30. 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 8/146:46 pm
PWM
- MSN
1 stop5h 43m
American Airlines
Tue 8/189:48 am
MSN
- PWM
1 stop6h 44m
American Airlines
Deal found 7/30![American Airlines logo]()
$379
This American Airlines deal was found by Cheapflights users on 7/31. 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 8/311:30 pm
PWM
- MSN
1 stop7h 00m
American Airlines
Sun 9/62:35 pm
MSN
- PWM
1 stop7h 13m
American Airlines
Deal found 7/31![American Airlines logo]()
$349
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 August 1, 2026.
Search for one-way flight options from Portland to Madison. Find affordable one-way fares based on user searches. Data last updated August 1, 2026.
This American Airlines deal was found by Cheapflights users on 7/27. 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 9/226:00 am
PWM
- MSN
1 stop6h 43m
American Airlines
Deal found 7/27![American Airlines logo]()
$246
This Delta deal was found by Cheapflights users on 7/30. 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 9/226:00 am
PWM
- MSN
1 stop5h 38m
Delta
Deal found 7/30![Delta logo]()
$256
This Kiwi.com deal was found by Cheapflights users on 7/30. 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.
Sat 8/157:00 am
PWM
- MSN
3 stops50h 25m
Multiple Airlines
Deal found 7/30![Multiple Airlines logo]()
$340
This American Airlines deal was found by Cheapflights users on 7/30. 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 8/157:28 am
PWM
- MSN
1 stop6h 21m
American Airlines
Deal found 7/30![American Airlines logo]()
$371
This United Airlines deal was found by Cheapflights users on 7/31. 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 8/156:00 am
PWM
- MSN
2 stops9h 51m
United Airlines
Deal found 7/31![United Airlines logo]()
$376
This Kiwi.com deal was found by Cheapflights users on 7/30. 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.
Sat 8/156:38 pm
PWM
- MSN
2 stops38h 47m
Breeze Airways
Deal found 7/30![Breeze Airways logo]()
$431
This United Airlines deal was found by Cheapflights users on 7/27. 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 9/229:49 am
PWM
- MSN
3 stops11h 24m
United Airlines
Deal found 7/27![United Airlines logo]()
$627
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 August 1, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $306 (American Airlines) |
One-way from | $246 (American Airlines) |
Popular in | July |
Cheapest in | February |
Average price | $311 |
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 August 1, 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
Quickest round-trip
PortlandMadison
PWM - MSN
PWMMSN
Portland
Wed 9/9
12:55 pm-5:17 pm
1 stop5h 22m
Madison Truax Field
Mon 9/14
3:35 pm-11:17 pm
1 stop6h 42m
$315
PortlandMadison
PWM - MSN
PWMMSN
Portland
Mon 8/31
1:30 pm-7:30 pm
1 stop7h 00m
Madison Truax Field
Sun 9/6
2:35 pm-10:48 pm
1 stop7h 13m
$349
PortlandMadison
PWM - MSN
PWMMSN
Portland
Thu 9/17
1:59 pm-7:06 pm
1 stop6h 07m
Madison Truax Field
Sun 9/20
5:50 am-3:39 pm
2 stops8h 49m
$369
PortlandMadison
PWM - MSN
PWMMSN
Portland
Sat 9/5
5:03 pm-10:51 pm
1 stop6h 48m
Madison Truax Field
Wed 9/9
8:05 am-6:29 pm
2 stops9h 24m
$386
PortlandMadison
PWM - MSN
PWMMSN
Portland
Tue 8/11
6:46 pm-11:29 pm
1 stop5h 43m
Madison Truax Field
Sat 8/15
2:45 pm-11:37 pm
2 stops7h 52m
$395
PortlandMadison
PWM - MSN
PWMMSN
Portland
Tue 10/13
5:08 pm-10:35 pm
1 stop6h 27m
Madison Truax Field
Sun 10/18
2:49 pm-9:46 pm
1 stop5h 57m
$400
PortlandMadison
PWM - MSN
PWMMSN
Portland
Mon 10/12
5:37 pm-11:25 pm
1 stop6h 48m
Madison Truax Field
Sat 10/17
3:28 pm-11:41 pm
2 stops7h 13m
$414
Cheapest one-way
PortlandMadison
PWM - MSN
PWMMSN
Portland
Tue 9/22
6:00 am-11:43 am
1 stop6h 43m
$246
Quickest one-way
PortlandMadison
PWM - MSN
PWMMSN
Portland
Tue 9/22
6:00 am-10:38 am
1 stop5h 38m
$256
PortlandMadison
PWM - MSN
PWMMSN
Portland
Sat 8/15
7:28 am-12:49 pm
1 stop6h 21m
$371
Sorted 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 August.
| 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 July is currently the most expensive (average of $586). 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?
Airfare is typical for this route at the moment.
Portland, Maine to Madison flights typically cost between $290 and $490 in October.The cheapest round-trip price found within the last 5 days was $306 on American Airlines (Oct 13-Oct 17).
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 August 1, 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.
Boarding
8.1
Crew
8.5
Overall
7.8
Entertainment
7.8
Comfort
7.8
Food
7.2
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Boarding
8.1
Crew
8.5
Overall
7.8
Entertainment
7.8
Comfort
7.8
Food
7.2
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Boarding
8.1
Crew
8.5
Overall
7.8
Entertainment
7.8
Comfort
7.8
Food
7.2
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Boarding
8.1
Crew
8.5
Overall
7.8
Entertainment
7.8
Comfort
7.8
Food
7.2
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
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.
Traveling to a place near Madison?
Book flights to Madison if you plan to visit one of these locationsSun Prairie
Middleton
Baraboo
Fitchburg
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Complete your trip
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Other flights to Madison
Explore flights to Madison departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on August 1, 2026.
Portland and Madison flights
Browse other Portland and Madison flight options. Last updated on August 1, 2026.
Other flights from Portland
Browse through other flights departing from Portland. Flights are based on user searches made on Cheapflights and were last updated on August 1, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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 August 1, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$258 | Average$383 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$273 | Average$382 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$273 | Average$376 | FlexibilityNo cancel fee | On-time71% |