$269+ 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 10/1. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MSN
Sep 28 — Oct 51
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
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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 29, 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 29, 2026.
This United Airlines deal was found by Cheapflights users on 8/24. 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 10/176:00 am -
2 stops8h 37m
Sat 10/2412:39 pm -
1 stop5h 04m
Deal found 8/24![United Airlines logo]()
$306
This American Airlines deal was found by Cheapflights users on 8/28. 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.
Sat 10/175:38 pm -
2 stops7h 34m
Tue 10/203:28 pm -
2 stops7h 31m
Deal found 8/28![American Airlines logo]()
$311
This American Airlines deal was found by Cheapflights users on 8/28. 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.
Sat 9/265:06 pm -
1 stop5h 09m
Sat 10/33:06 pm -
1 stop5h 50m
Deal found 8/28![American Airlines logo]()
$315
This American Airlines deal was found by Cheapflights users on 8/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/225:45 pm -
1 stop7h 27m
Mon 10/2610:13 am -
1 stop5h 51m
Deal found 8/26![American Airlines logo]()
$329
This United Airlines deal was found by Cheapflights users on 8/27. 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.
Mon 9/216:00 am -
1 stop4h 40m
Tue 9/294:10 pm -
1 stop4h 44m
Deal found 8/27![United Airlines logo]()
$336
This American Airlines deal was found by Cheapflights users on 8/27. 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.
Fri 9/116:00 am -
1 stop6h 43m
Tue 9/153:25 pm -
1 stop7h 22m
Deal found 8/27![American Airlines logo]()
$340
This American Airlines deal was found by Cheapflights users on 8/25. 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.
Wed 9/94:41 pm -
2 stops8h 36m
Sun 9/135:00 am -
1 stop7h 05m
Deal found 8/25![American Airlines logo]()
$345
This Delta deal was found by Cheapflights users on 8/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1112:55 pm -
2 stops10h 46m
Tue 9/151:30 pm -
2 stops9h 26m
Deal found 8/27![Delta logo]()
$350
This American Airlines deal was found by Cheapflights users on 8/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/175:38 pm -
2 stops7h 34m
Sat 10/246:46 am -
2 stops7h 57m
Deal found 8/24![American Airlines logo]()
$361
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 29, 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 29, 2026.
This United Airlines deal was found by Cheapflights users on 8/24. 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 10/176:00 am -
2 stops8h 37m
Sat 10/2412:39 pm -
1 stop5h 04m
Deal found 8/24![United Airlines logo]()
$306
This American Airlines deal was found by Cheapflights users on 8/28. 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.
Sat 10/175:38 pm -
2 stops7h 34m
Tue 10/203:28 pm -
2 stops7h 31m
Deal found 8/28![American Airlines logo]()
$311
This Delta deal was found by Cheapflights users on 8/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/114:45 pm -
1 stop5h 34m
Tue 9/151:30 pm -
2 stops8h 58m
Deal found 8/27![Delta logo]()
$345
This American Airlines deal was found by Cheapflights users on 8/28. 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.
Sat 9/265:06 pm -
1 stop5h 09m
Sat 10/33:06 pm -
1 stop5h 50m
Deal found 8/28![American Airlines logo]()
$315
This United Airlines deal was found by Cheapflights users on 8/27. 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.
Mon 9/216:00 am -
1 stop4h 40m
Tue 9/294:10 pm -
1 stop4h 44m
Deal found 8/27![United Airlines logo]()
$336
This American Airlines deal was found by Cheapflights users on 8/27. 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.
Fri 9/116:00 am -
1 stop6h 43m
Tue 9/153:25 pm -
1 stop7h 22m
Deal found 8/27![American Airlines logo]()
$340
This United Airlines deal was found by Cheapflights users on 8/27. 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.
Wed 10/288:32 am -
1 stop7h 35m
Sat 10/318:15 am -
1 stop5h 01m
Deal found 8/27![United Airlines logo]()
$381
Last-minute flights from Portland to MadisonDiscover last-minute flight deals from Portland to Madison. Data last updated August 29, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Madison. Data last updated August 29, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 8/25. 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.
Tue 9/86:46 pm -
1 stop5h 43m
Sun 9/137:00 am -
1 stop7h 41m
Deal found 8/25![American Airlines logo]()
$379
This American Airlines deal was found by Cheapflights users on 8/23. 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 9/86:46 pm -
1 stop5h 43m
Sat 9/127:15 am -
2 stops8h 09m
Deal found 8/23![American Airlines logo]()
$384
This American Airlines deal was found by Cheapflights users on 8/25. 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.
Wed 9/94:41 pm -
2 stops8h 36m
Sun 9/135:00 am -
1 stop7h 05m
Deal found 8/25![American Airlines logo]()
$345
This American Airlines deal was found by Cheapflights users on 8/27. 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.
Fri 9/116:00 am -
1 stop6h 43m
Tue 9/153:25 pm -
1 stop7h 22m
Deal found 8/27![American Airlines logo]()
$340
This Delta deal was found by Cheapflights users on 8/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/1112:55 pm -
2 stops10h 46m
Tue 9/151:30 pm -
2 stops9h 26m
Deal found 8/27![Delta logo]()
$350
This United Airlines deal was found by Cheapflights users on 8/25. 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.
Fri 9/119:49 am -
2 stops12h 04m
Mon 9/143:58 pm -
1 stop4h 25m
Deal found 8/25![United Airlines logo]()
$463
This United Airlines deal was found by Cheapflights users on 8/27. 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.
Mon 9/216:00 am -
1 stop4h 40m
Tue 9/294:10 pm -
1 stop4h 44m
Deal found 8/27![United Airlines logo]()
$336
This United Airlines deal was found by Cheapflights users on 8/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/255:08 pm -
1 stop6h 27m
Fri 10/22:49 pm -
1 stop5h 57m
Deal found 8/28![United Airlines logo]()
$472
This American Airlines deal was found by Cheapflights users on 8/28. 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.
Sat 9/265:06 pm -
1 stop5h 09m
Sat 10/33:06 pm -
1 stop5h 50m
Deal found 8/28![American Airlines logo]()
$315
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 29, 2026.
Search for one-way flight options from Portland to Madison. Find affordable one-way fares based on user searches. Data last updated August 29, 2026.
This American Airlines deal was found by Cheapflights users on 8/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/15:38 pm -
1 stop7h 39m
Deal found 8/26![American Airlines logo]()
$269
This Kiwi.com deal was found by Cheapflights users on 8/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/257:00 am -
3 stops27h 53m
Deal found 8/28![Multiple Airlines logo]()
$274
This American Airlines deal was found by Cheapflights users on 8/27. 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 -
1 stop6h 43m
Deal found 8/27![American Airlines logo]()
$279
This United Airlines deal was found by Cheapflights users on 8/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/225:15 am -
2 stops10h 44m
Deal found 8/28![United Airlines logo]()
$284
This Kiwi.com deal was found by Cheapflights users on 8/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/13:05 pm -
3 stops43h 48m
Deal found 8/26![Breeze Airways logo]()
$295
This Kiwi.com deal was found by Cheapflights users on 8/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/253:53 pm -
2 stops19h 00m
Deal found 8/28![Breeze Airways logo]()
$307
This United Airlines deal was found by Cheapflights users on 8/25. 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.
Mon 9/146:06 am -
1 stop5h 07m
Deal found 8/25![United Airlines logo]()
$449
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 29, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $306 (United Airlines) |
One-way from | $269 (American Airlines) |
Popular in | July |
Cheapest in | February |
Average price | $490 |
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 7,457,451 searches. Data last updated August 29, 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 Portland - MSN Madison Truax Field
PWMMSN
Portland
Sat 10/17
6:00 am-1:37 pm
2 stops8h 37m
Madison Truax Field
Sat 10/24
12:39 pm-6:43 pm
1 stop5h 04m
$306
PortlandMadison
PWM Portland - MSN Madison Truax Field
PWMMSN
Portland
Sat 10/17
5:38 pm-12:12 am
2 stops7h 34m
Madison Truax Field
Tue 10/20
3:28 pm-11:59 pm
2 stops7h 31m
$311
PortlandMadison
PWM Portland - MSN Madison Truax Field
PWMMSN
Portland
Sat 9/26
5:06 pm-9:15 pm
1 stop5h 09m
Madison Truax Field
Sat 10/3
3:06 pm-9:56 pm
1 stop5h 50m
$315
Quickest round-trip
PortlandMadison
PWM Portland - MSN Madison Truax Field
PWMMSN
Portland
Mon 9/21
6:00 am-9:40 am
1 stop4h 40m
Madison Truax Field
Tue 9/29
4:10 pm-9:54 pm
1 stop4h 44m
$336
PortlandMadison
PWM Portland - MSN Madison Truax Field
PWMMSN
Portland
Fri 9/11
6:00 am-11:43 am
1 stop6h 43m
Madison Truax Field
Tue 9/15
3:25 pm-11:47 pm
1 stop7h 22m
$340
PortlandMadison
PWM Portland - MSN Madison Truax Field
PWMMSN
Portland
Fri 9/11
4:45 pm-9:19 pm
1 stop5h 34m
Madison Truax Field
Tue 9/15
1:30 pm-11:28 pm
2 stops8h 58m
$345
PortlandMadison
PWM Portland - MSN Madison Truax Field
PWMMSN
Portland
Wed 10/28
8:32 am-3:07 pm
1 stop7h 35m
Madison Truax Field
Sat 10/31
8:15 am-2:16 pm
1 stop5h 01m
$381
Cheapest one-way
PortlandMadison
PWM Portland - MSN Madison Truax Field
PWMMSN
Portland
Tue 9/22
6:00 am-11:43 am
1 stop6h 43m
$279
PortlandMadison
PWM Portland - MSN Madison Truax Field
PWMMSN
Portland
Fri 9/25
7:32 am-12:56 pm
1 stop6h 24m
$279
PortlandMadison
PWM Portland - MSN Madison Truax Field
PWMMSN
Portland
Tue 9/22
5:15 am-2:59 pm
2 stops10h 44m
$284
Showing 1-10 of 12 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 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 below average for this route at the moment.
Portland, Maine to Madison flights typically cost between $328 and $388 in October.The cheapest round-trip price found within the last 5 days was $306 on United Airlines (Oct 17-Oct 24).
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 29, 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.
Overall
7.8
Food
7.2
Comfort
7.8
Entertainment
7.8
Boarding
8.1
Crew
8.5
Reviews
1 / 20
8.0
ExcellentJorge,Aug 2026
TPA - ATL
Overall
7.8
Food
7.2
Comfort
7.8
Entertainment
7.8
Boarding
8.1
Crew
8.5
Reviews
1 / 20
8.0
ExcellentJorge,Aug 2026
TPA - ATL
Overall
7.8
Food
7.2
Comfort
7.8
Entertainment
7.8
Boarding
8.1
Crew
8.5
Reviews
1 / 20
8.0
ExcellentJorge,Aug 2026
TPA - ATL
Overall
7.8
Food
7.2
Comfort
7.8
Entertainment
7.8
Boarding
8.1
Crew
8.5
Reviews
1 / 20
8.0
ExcellentJorge,Aug 2026
TPA - ATL
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
Fitchburg
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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 29, 2026.
Portland and Madison flights
Browse other Portland and Madison flight options. Last updated on August 29, 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 29, 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 7,457,451 searches. Data last updated August 29, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$258 | Average$362 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$273 | Average$384 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$278 | Average$386 | FlexibilityNo cancel fee | On-time69% |