$321+ Cheap flights from Portland, ME to Madison (PWM - MSN)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/10. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MSN
Nov 11 — Nov 181
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 October 12, 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 October 12, 2026.
This American Airlines deal was found by Cheapflights users on 10/11. 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 11/106:17 am -
1 stop6h 36m
Tue 11/176:00 am -
1 stop4h 28m
Deal found 10/11![American Airlines logo]()
$321
This Delta deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/611:55 am -
1 stop8h 11m
Tue 11/104:01 pm -
1 stop6h 20m
Deal found 10/7![Delta logo]()
$335
This American Airlines deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2911:28 am -
1 stop6h 33m
Mon 11/25:00 am -
1 stop5h 53m
Deal found 10/8![American Airlines logo]()
$349
This Delta deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/296:28 am -
2 stops10h 59m
Mon 11/25:51 am -
1 stop6h 11m
Deal found 10/8![Delta logo]()
$354
This United Airlines deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/195:08 pm -
1 stop6h 59m
Mon 11/236:25 am -
1 stop6h 51m
Deal found 10/7![United Airlines logo]()
$362
This Delta deal was found by Cheapflights users on 10/11. 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.
Mon 10/2611:55 am -
1 stop8h 11m
Wed 11/47:00 am -
1 stop3h 57m
Deal found 10/11![Delta logo]()
$374
This United Airlines deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/65:08 pm -
1 stop4h 57m
Tue 11/108:15 am -
2 stops9h 47m
Deal found 10/7![United Airlines logo]()
$378
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 October 12, 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 October 12, 2026.
This Delta deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/611:55 am -
1 stop8h 11m
Tue 11/104:01 pm -
1 stop6h 20m
Deal found 10/7![Delta logo]()
$335
This American Airlines deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/235:45 pm -
1 stop7h 27m
Tue 10/273:45 pm -
1 stop4h 51m
Deal found 10/7![American Airlines logo]()
$399
This United Airlines deal was found by Cheapflights users on 10/11. 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 10/226:00 am -
1 stop6h 53m
Mon 10/266:25 am -
1 stop6h 51m
Deal found 10/11![United Airlines logo]()
$437
This Delta deal was found by Cheapflights users on 10/11. 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 12/34:53 pm -
1 stop5h 31m
Mon 12/711:45 am -
2 stops10h 35m
Deal found 10/11![Delta logo]()
$354
This Delta deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/296:28 am -
2 stops10h 59m
Mon 11/25:51 am -
1 stop6h 11m
Deal found 10/8![Delta logo]()
$354
This American Airlines deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/226:00 am -
1 stop6h 54m
Mon 10/263:28 pm -
2 stops7h 00m
Deal found 10/8![American Airlines logo]()
$442
This United Airlines deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/285:08 pm -
1 stop4h 57m
Sat 10/316:25 am -
1 stop6h 51m
Deal found 10/7![United Airlines logo]()
$449
This Delta deal was found by Cheapflights users on 10/11. 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 11/511:55 am -
1 stop8h 11m
Mon 11/95:30 am -
1 stop6h 31m
Deal found 10/11![Delta logo]()
$402
This Delta deal was found by Cheapflights users on 10/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/241:10 pm -
2 stops6h 56m
Wed 10/281:29 pm -
2 stops8h 32m
Deal found 10/9![Delta logo]()
$409
This Delta deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/61:52 pm -
2 stops10h 11m
Fri 11/132:30 pm -
2 stops8h 01m
Deal found 10/7![Delta logo]()
$464
Last-minute flights from Portland to MadisonDiscover last-minute flight deals from Portland to Madison. Data last updated October 12, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Madison. Data last updated October 12, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 10/11. 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.
Mon 10/2611:55 am -
1 stop8h 11m
Wed 11/47:00 am -
1 stop3h 57m
Deal found 10/11![Delta logo]()
$374
This American Airlines deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2911:28 am -
1 stop6h 33m
Mon 11/25:00 am -
1 stop5h 53m
Deal found 10/8![American Airlines logo]()
$349
This Delta deal was found by Cheapflights users on 10/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/296:28 am -
2 stops10h 59m
Mon 11/25:51 am -
1 stop6h 11m
Deal found 10/8![Delta logo]()
$354
This Delta deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/611:55 am -
1 stop8h 11m
Tue 11/104:01 pm -
1 stop6h 20m
Deal found 10/7![Delta logo]()
$335
This United Airlines deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/65:08 pm -
1 stop4h 57m
Tue 11/108:15 am -
2 stops9h 47m
Deal found 10/7![United Airlines logo]()
$378
This American Airlines deal was found by Cheapflights users on 10/11. 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 11/106:17 am -
1 stop6h 36m
Tue 11/176:00 am -
1 stop4h 28m
Deal found 10/11![American Airlines logo]()
$321
This United Airlines deal was found by Cheapflights users on 10/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/195:08 pm -
1 stop6h 59m
Mon 11/236:25 am -
1 stop6h 51m
Deal found 10/7![United Airlines logo]()
$362
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 October 12, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $321 (American Airlines) |
Popular in | July |
Cheapest in | February |
Average price | $394 |
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 October 12, 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
Fri 11/6
11:55 am-7:06 pm
1 stop8h 11m
Madison Truax Field
Tue 11/10
4:01 pm-11:21 pm
1 stop6h 20m
$335
PortlandMadison
PWM Portland - MSN Madison Truax Field
PWMMSN
Portland
Thu 12/3
4:53 pm-9:24 pm
1 stop5h 31m
Madison Truax Field
Mon 12/7
11:45 am-11:20 pm
2 stops10h 35m
$354
PortlandMadison
PWM Portland - MSN Madison Truax Field
PWMMSN
Portland
Thu 10/29
6:28 am-4:27 pm
2 stops10h 59m
Madison Truax Field
Mon 11/2
5:51 am-1:02 pm
1 stop6h 11m
$354
PortlandMadison
PWM Portland - MSN Madison Truax Field
PWMMSN
Portland
Fri 10/23
5:45 pm-12:12 am
1 stop7h 27m
Madison Truax Field
Tue 10/27
3:45 pm-9:36 pm
1 stop4h 51m
$399
PortlandMadison
PWM Portland - MSN Madison Truax Field
PWMMSN
Portland
Thu 11/5
11:55 am-7:06 pm
1 stop8h 11m
Madison Truax Field
Mon 11/9
5:30 am-1:01 pm
1 stop6h 31m
$402
PortlandMadison
PWM Portland - MSN Madison Truax Field
PWMMSN
Portland
Sat 10/24
1:10 pm-7:06 pm
2 stops6h 56m
Madison Truax Field
Wed 10/28
1:29 pm-11:01 pm
2 stops8h 32m
$409
PortlandMadison
PWM Portland - MSN Madison Truax Field
PWMMSN
Portland
Thu 10/22
6:00 am-11:53 am
1 stop6h 53m
Madison Truax Field
Mon 10/26
6:25 am-2:16 pm
1 stop6h 51m
$437
PortlandMadison
PWM Portland - MSN Madison Truax Field
PWMMSN
Portland
Thu 10/22
6:00 am-11:54 am
1 stop6h 54m
Madison Truax Field
Mon 10/26
3:28 pm-11:28 pm
2 stops7h 00m
$442
Quickest round-trip
PortlandMadison
PWM Portland - MSN Madison Truax Field
PWMMSN
Portland
Wed 10/28
5:08 pm-9:05 pm
1 stop4h 57m
Madison Truax Field
Sat 10/31
6:25 am-2:16 pm
1 stop6h 51m
$449
PortlandMadison
PWM Portland - MSN Madison Truax Field
PWMMSN
Portland
Fri 11/6
1:52 pm-11:03 pm
2 stops10h 11m
Madison Truax Field
Fri 11/13
2:30 pm-11:31 pm
2 stops8h 01m
$464
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 October.
| 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 $371 and $474 in November.The cheapest round-trip price found within the last 5 days was $321 on American Airlines (Nov 10-Nov 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 October 12, 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
Entertainment
7.8
Crew
8.5
Comfort
7.8
Food
7.2
Overall
7.8
Reviews
1 / 20
6.0
GoodEllen,Oct 2026
GRR - ATL
Boarding
8.1
Entertainment
7.8
Crew
8.5
Comfort
7.8
Food
7.2
Overall
7.8
Reviews
1 / 20
6.0
GoodEllen,Oct 2026
GRR - ATL
Boarding
8.1
Entertainment
7.8
Crew
8.5
Comfort
7.8
Food
7.2
Overall
7.8
Reviews
1 / 20
6.0
GoodEllen,Oct 2026
GRR - ATL
Boarding
8.1
Entertainment
7.8
Crew
8.5
Comfort
7.8
Food
7.2
Overall
7.8
Reviews
1 / 20
6.0
GoodEllen,Oct 2026
GRR - 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 October 12, 2026.
Portland and Madison flights
Browse other Portland and Madison flight options. Last updated on October 12, 2026.
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Browse through other flights departing from Portland. Flights are based on user searches made on Cheapflights and were last updated on October 12, 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 October 12, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$258 | Average$448 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$273 | Average$386 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$278 | Average$401 | FlexibilityNo cancel fee | On-time69% |