$256+ 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
Sep 22 — Sep 291
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
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 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 23, 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 23, 2026.
This American Airlines deal was found by Cheapflights users on 8/19. 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.
Fri 9/117:32 am -
1 stop6h 24m
Mon 9/141:26 pm -
1 stop7h 29m
Deal found 8/19![American Airlines logo]()
$315
This United Airlines deal was found by Cheapflights users on 8/19. 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 9/116:06 am -
2 stops8h 36m
Mon 9/143:58 pm -
1 stop4h 25m
Deal found 8/19![United Airlines logo]()
$320
This United Airlines deal was found by Cheapflights users on 8/21. 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 10/25:08 pm -
1 stop4h 52m
Mon 10/54:10 pm -
1 stop4h 36m
Deal found 8/21![United Airlines logo]()
$329
This American Airlines deal was found by Cheapflights users on 8/19. 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.
Fri 11/64:10 pm -
1 stop7h 15m
Sun 11/85:00 am -
1 stop5h 59m
Deal found 8/19![American Airlines logo]()
$346
This American Airlines deal was found by Cheapflights users on 8/21. 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 9/86:46 pm -
1 stop5h 43m
Tue 9/153:06 pm -
1 stop5h 50m
Deal found 8/21![American Airlines logo]()
$354
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/167:58 am -
1 stop6h 39m
Sun 10/188:17 am -
1 stop5h 21m
Deal found 8/23![United Airlines logo]()
$380
This United Airlines deal was found by Cheapflights users on 8/18. 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.
Tue 10/275:08 pm -
1 stop4h 57m
Sat 10/313:49 pm -
1 stop5h 02m
Deal found 8/18![United Airlines logo]()
$381
This United Airlines deal was found by Cheapflights users on 8/19. 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 11/65:08 pm -
1 stop6h 59m
Sun 11/86:25 am -
2 stops7h 02m
Deal found 8/19![United Airlines logo]()
$393
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 23, 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 23, 2026.
This American Airlines deal was found by Cheapflights users on 8/19. 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 10/226:00 am -
1 stop7h 16m
Mon 10/2610:13 am -
1 stop5h 51m
Deal found 8/19![American Airlines logo]()
$329
This United Airlines deal was found by Cheapflights users on 8/19. 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 9/116:06 am -
2 stops8h 36m
Sun 9/133:58 pm -
1 stop4h 25m
Deal found 8/19![United Airlines logo]()
$354
This American Airlines deal was found by Cheapflights users on 8/21. 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 9/86:46 pm -
1 stop5h 43m
Tue 9/153:06 pm -
1 stop5h 50m
Deal found 8/21![American Airlines logo]()
$354
This United Airlines deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/112:38 pm -
2 stops7h 15m
Mon 9/143:58 pm -
1 stop4h 25m
Deal found 8/22![United Airlines logo]()
$359
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/167:58 am -
1 stop6h 39m
Sun 10/188:17 am -
1 stop5h 21m
Deal found 8/23![United Airlines logo]()
$380
This United Airlines deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/275:08 pm -
1 stop4h 57m
Sat 10/313:49 pm -
1 stop5h 02m
Deal found 8/22![United Airlines logo]()
$381
This United Airlines deal was found by Cheapflights users on 8/19. 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 11/65:08 pm -
1 stop6h 59m
Sun 11/86:25 am -
2 stops7h 02m
Deal found 8/19![United Airlines logo]()
$393
This United Airlines deal was found by Cheapflights users on 8/21. 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.
Sat 9/53:45 pm -
2 stops8h 06m
Wed 9/94:14 pm -
1 stop4h 30m
Deal found 8/21![United Airlines logo]()
$425
Last-minute flights from Portland to MadisonDiscover last-minute flight deals from Portland to Madison. Data last updated August 23, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Madison. Data last updated August 23, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 8/21. 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.
Sat 9/53:45 pm -
1 stop5h 29m
Wed 9/92:47 pm -
1 stop5h 57m
Deal found 8/21![United Airlines logo]()
$420
This American Airlines deal was found by Cheapflights users on 8/21. 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 9/86:46 pm -
1 stop5h 43m
Tue 9/153:06 pm -
1 stop5h 50m
Deal found 8/21![American Airlines logo]()
$354
This United Airlines deal was found by Cheapflights users on 8/21. 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 9/89:49 am -
2 stops10h 11m
Tue 9/155:00 am -
2 stops8h 38m
Deal found 8/21![United Airlines logo]()
$503
This American Airlines deal was found by Cheapflights users on 8/19. 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.
Fri 9/117:32 am -
1 stop6h 24m
Mon 9/141:26 pm -
1 stop7h 29m
Deal found 8/19![American Airlines logo]()
$315
This United Airlines deal was found by Cheapflights users on 8/19. 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 9/116:06 am -
2 stops8h 36m
Mon 9/143:58 pm -
1 stop4h 25m
Deal found 8/19![United Airlines logo]()
$320
This United Airlines deal was found by Cheapflights users on 8/19. 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 9/119:49 am -
2 stops10h 17m
Sun 9/136:30 am -
2 stops7h 08m
Deal found 8/19![United Airlines logo]()
$545
This United Airlines deal was found by Cheapflights users on 8/20. 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.
Sun 9/136:00 am -
1 stop4h 40m
Mon 9/146:30 am -
1 stop7h 04m
Deal found 8/20![United Airlines logo]()
$584
This American Airlines deal was found by Cheapflights users on 8/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/146:00 am -
1 stop6h 43m
Thu 9/175:50 pm -
1 stop4h 46m
Deal found 8/22![American Airlines logo]()
$587
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 23, 2026.
Search for one-way flight options from Portland to Madison. Find affordable one-way fares based on user searches. Data last updated August 23, 2026.
This American Airlines deal was found by Cheapflights users on 8/19. 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.
Tue 9/226:00 am -
1 stop6h 43m
Deal found 8/19![American Airlines logo]()
$256
This Kiwi.com deal was found by Cheapflights users on 8/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/511:07 am -
1 stop9h 08m
Deal found 8/21![Breeze Airways logo]()
$257
This United Airlines deal was found by Cheapflights users on 8/21. 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.
Sun 9/206:06 am -
1 stop5h 08m
Deal found 8/21![United Airlines logo]()
$269
This Kiwi.com deal was found by Cheapflights users on 8/20. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/88:00 am -
3 stops26h 53m
Deal found 8/20![Breeze Airways logo]()
$297
This American Airlines deal was found by Cheapflights users on 8/20. 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.
Tue 9/86:46 pm -
1 stop5h 43m
Deal found 8/20![American Airlines logo]()
$309
This Delta deal was found by Cheapflights users on 8/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/51:02 pm -
2 stops10h 36m
Deal found 8/21![Delta logo]()
$314
This Kiwi.com deal was found by Cheapflights users on 8/21. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/55:01 pm -
3 stops27h 09m
Deal found 8/21![Multiple Airlines logo]()
$418
This United Airlines deal was found by Cheapflights users on 8/19. 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 9/229:49 am -
3 stops11h 24m
Deal found 8/19![United Airlines logo]()
$757
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 23, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $315 (American Airlines) |
One-way from | $256 (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 23, 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
Thu 10/22
6:00 am-12:16 pm
1 stop7h 16m
Madison Truax Field
Mon 10/26
10:13 am-5:04 pm
1 stop5h 51m
$329
PortlandMadison
PWM Portland - MSN Madison Truax Field
PWMMSN
Portland
Fri 9/11
6:06 am-1:42 pm
2 stops8h 36m
Madison Truax Field
Sun 9/13
3:58 pm-9:23 pm
1 stop4h 25m
$354
PortlandMadison
PWM Portland - MSN Madison Truax Field
PWMMSN
Portland
Tue 9/8
6:46 pm-11:29 pm
1 stop5h 43m
Madison Truax Field
Tue 9/15
3:06 pm-9:56 pm
1 stop5h 50m
$354
PortlandMadison
PWM Portland - MSN Madison Truax Field
PWMMSN
Portland
Fri 9/11
2:38 pm-8:53 pm
2 stops7h 15m
Madison Truax Field
Mon 9/14
3:58 pm-9:23 pm
1 stop4h 25m
$359
PortlandMadison
PWM Portland - MSN Madison Truax Field
PWMMSN
Portland
Fri 10/16
7:58 am-1:37 pm
1 stop6h 39m
Madison Truax Field
Sun 10/18
8:17 am-2:38 pm
1 stop5h 21m
$380
Quickest round-trip
PortlandMadison
PWM Portland - MSN Madison Truax Field
PWMMSN
Portland
Tue 10/27
5:08 pm-9:05 pm
1 stop4h 57m
Madison Truax Field
Sat 10/31
3:49 pm-9:51 pm
1 stop5h 02m
$381
PortlandMadison
PWM Portland - MSN Madison Truax Field
PWMMSN
Portland
Fri 11/6
5:08 pm-11:07 pm
1 stop6h 59m
Madison Truax Field
Sun 11/8
6:25 am-2:27 pm
2 stops7h 02m
$393
PortlandMadison
PWM Portland - MSN Madison Truax Field
PWMMSN
Portland
Sat 9/5
3:45 pm-10:51 pm
2 stops8h 06m
Madison Truax Field
Wed 9/9
4:14 pm-9:44 pm
1 stop4h 30m
$425
Cheapest one-way
PortlandMadison
PWM Portland - MSN Madison Truax Field
PWMMSN
Portland
Tue 9/22
6:00 am-11:43 am
1 stop6h 43m
$256
PortlandMadison
PWM Portland - MSN Madison Truax Field
PWMMSN
Portland
Sat 9/5
11:07 am-7:15 pm
1 stop9h 08m
$257
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 typical for this route at the moment.
Portland, Maine to Madison flights typically cost between $309 and $539 in September.The cheapest round-trip price found within the last 5 days was $315 on American Airlines (Sep 11-Sep 14).
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 23, 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.
Entertainment
7.8
Crew
8.5
Boarding
8.1
Overall
7.8
Food
7.2
Comfort
7.8
Reviews
1 / 20
10.0
ExcellentSalvador,Aug 2026
PHL - DTW
Entertainment
7.8
Crew
8.5
Boarding
8.1
Overall
7.8
Food
7.2
Comfort
7.8
Reviews
1 / 20
10.0
ExcellentSalvador,Aug 2026
PHL - DTW
Entertainment
7.8
Crew
8.5
Boarding
8.1
Overall
7.8
Food
7.2
Comfort
7.8
Reviews
1 / 20
10.0
ExcellentSalvador,Aug 2026
PHL - DTW
Entertainment
7.8
Crew
8.5
Boarding
8.1
Overall
7.8
Food
7.2
Comfort
7.8
Reviews
1 / 20
10.0
ExcellentSalvador,Aug 2026
PHL - DTW
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 23, 2026.
Portland and Madison flights
Browse other Portland and Madison flight options. Last updated on August 23, 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 23, 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 23, 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% |