$289+ 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 1/18. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MSN
Dec 10 — Dec 171
Round-trip
1 adult, Economy
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Find cheap flights from Portland to Madison with Cheapflights
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Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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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 November 10, 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 November 10, 2026.
This United Airlines deal was found by Cheapflights users on 11/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/44:47 pm -
1 stop5h 28m
Tue 12/89:12 am -
1 stop5h 26m
Deal found 11/9![United Airlines logo]()
$359
This United Airlines deal was found by Cheapflights users on 11/6. 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 12/315:15 am -
2 stops10h 49m
Tue 1/58:10 am -
1 stop5h 34m
Deal found 11/6![United Airlines logo]()
$360
This American Airlines deal was found by Cheapflights users on 11/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/310:55 am -
1 stop6h 59m
Mon 12/75:00 am -
2 stops9h 32m
Deal found 11/9![American Airlines logo]()
$364
This United Airlines deal was found by Cheapflights users on 11/5. 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 11/245:08 pm -
1 stop4h 57m
Tue 12/16:00 am -
1 stop6h 38m
Deal found 11/5![United Airlines logo]()
$397
This United Airlines deal was found by Cheapflights users on 11/8. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/238:29 am -
1 stop7h 42m
Fri 11/278:15 am -
1 stop5h 01m
Deal found 11/8![United Airlines logo]()
$409
This American Airlines deal was found by Cheapflights users on 11/6. 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 11/176:17 am -
1 stop6h 36m
Sun 11/225:00 am -
1 stop5h 56m
Deal found 11/6![American Airlines logo]()
$430
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 November 10, 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 November 10, 2026.
This United Airlines deal was found by Cheapflights users on 11/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/54:47 pm -
1 stop5h 28m
Tue 12/86:00 am -
1 stop6h 38m
Deal found 11/9![United Airlines logo]()
$359
This American Airlines deal was found by Cheapflights users on 11/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/53:18 pm -
2 stops9h 50m
Tue 12/85:00 am -
2 stops9h 32m
Deal found 11/9![American Airlines logo]()
$369
This United Airlines deal was found by Cheapflights users on 11/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/44:47 pm -
1 stop5h 28m
Tue 12/89:12 am -
1 stop5h 26m
Deal found 11/9![United Airlines logo]()
$359
This American Airlines deal was found by Cheapflights users on 11/7. 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 1/155:00 am -
2 stops11h 28m
Mon 1/1811:30 am -
2 stops9h 13m
Deal found 11/7![American Airlines logo]()
$369
This United Airlines deal was found by Cheapflights users on 11/6. 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 1/87:30 am -
2 stops8h 36m
Tue 1/126:05 am -
1 stop7h 39m
Deal found 11/6![United Airlines logo]()
$360
This United Airlines deal was found by Cheapflights users on 11/6. 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 12/313:38 pm -
2 stops8h 21m
Tue 1/510:45 am -
2 stops7h 08m
Deal found 11/6![United Airlines logo]()
$365
This United Airlines deal was found by Cheapflights users on 11/8. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/238:29 am -
1 stop7h 42m
Fri 11/278:15 am -
1 stop5h 01m
Deal found 11/8![United Airlines logo]()
$409
This United Airlines deal was found by Cheapflights users on 11/5. 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 11/2410:50 am -
2 stops7h 12m
Tue 12/16:30 am -
2 stops7h 07m
Deal found 11/5![United Airlines logo]()
$433
This United Airlines deal was found by Cheapflights users on 11/7. 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 12/23:20 pm -
1 stop6h 26m
Sat 12/53:52 pm -
1 stop4h 37m
Deal found 11/7![United Airlines logo]()
$459
Last-minute flights from Portland to MadisonDiscover last-minute flight deals from Portland to Madison. Data last updated November 10, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Madison. Data last updated November 10, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 11/6. 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 11/176:17 am -
1 stop6h 36m
Sun 11/225:00 am -
1 stop5h 56m
Deal found 11/6![American Airlines logo]()
$430
This United Airlines deal was found by Cheapflights users on 11/8. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/238:29 am -
1 stop7h 42m
Fri 11/278:15 am -
1 stop5h 01m
Deal found 11/8![United Airlines logo]()
$409
This United Airlines deal was found by Cheapflights users on 11/5. 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 11/245:08 pm -
1 stop4h 57m
Tue 12/16:00 am -
1 stop6h 38m
Deal found 11/5![United Airlines logo]()
$397
This American Airlines deal was found by Cheapflights users on 11/9. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/310:55 am -
1 stop6h 59m
Mon 12/75:00 am -
2 stops9h 32m
Deal found 11/9![American Airlines logo]()
$364
This United Airlines deal was found by Cheapflights users on 11/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/44:47 pm -
1 stop5h 28m
Tue 12/89:12 am -
1 stop5h 26m
Deal found 11/9![United Airlines logo]()
$359
This United Airlines deal was found by Cheapflights users on 11/6. 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 12/315:15 am -
2 stops10h 49m
Tue 1/58:10 am -
1 stop5h 34m
Deal found 11/6![United Airlines logo]()
$360
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 November 10, 2026.
Search for one-way flight options from Portland to Madison. Find affordable one-way fares based on user searches. Data last updated November 10, 2026.
This Kiwi.com deal was found by Cheapflights users on 11/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/185:00 pm -
3 stops41h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/6![Breeze Airways logo]()
$289
This United Airlines deal was found by Cheapflights users on 11/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/305:08 pm -
1 stop6h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/9![United Airlines logo]()
$428
This KAYAK deal was found by Cheapflights users on 11/9. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/303:53 pm -
3 stops43h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/9![Breeze Airways logo]()
$636
This United Airlines deal was found by Cheapflights users on 11/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/295:08 pm -
1 stop4h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/9![United Airlines logo]()
$683
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 November 10, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $355 (United Airlines) |
One-way from | $289 (Kiwi.com) |
Popular in | December |
Cheapest in | February |
Average price | $521 |
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 November 10, 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
Mon 1/18
5:00 pm-9:58 am
3 stops41h 58m
Madison Truax Field
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$289
PortlandMadison
PWM Portland - MSN Madison Truax Field
PWMMSN
Portland
Sat 12/5
4:47 pm-9:15 pm
1 stop5h 28m
Madison Truax Field
Tue 12/8
6:00 am-1:38 pm
1 stop6h 38m
$359
PortlandMadison
PWM Portland - MSN Madison Truax Field
PWMMSN
Portland
Fri 12/4
4:47 pm-9:15 pm
1 stop5h 28m
Madison Truax Field
Tue 12/8
9:12 am-3:38 pm
1 stop5h 26m
$359
PortlandMadison
PWM Portland - MSN Madison Truax Field
PWMMSN
Portland
Fri 1/8
7:30 am-3:06 pm
2 stops8h 36m
Madison Truax Field
Tue 1/12
6:05 am-2:44 pm
1 stop7h 39m
$360
PortlandMadison
PWM Portland - MSN Madison Truax Field
PWMMSN
Portland
Thu 12/31
3:38 pm-10:59 pm
2 stops8h 21m
Madison Truax Field
Tue 1/5
10:45 am-6:53 pm
2 stops7h 08m
$365
PortlandMadison
PWM Portland - MSN Madison Truax Field
PWMMSN
Portland
Sat 12/5
3:18 pm-12:08 am
2 stops9h 50m
Madison Truax Field
Tue 12/8
5:00 am-3:32 pm
2 stops9h 32m
$369
PortlandMadison
PWM Portland - MSN Madison Truax Field
PWMMSN
Portland
Fri 1/15
5:00 am-3:28 pm
2 stops11h 28m
Madison Truax Field
Mon 1/18
11:30 am-9:43 pm
2 stops9h 13m
$369
PortlandMadison
PWM Portland - MSN Madison Truax Field
PWMMSN
Portland
Mon 11/23
8:29 am-3:11 pm
1 stop7h 42m
Madison Truax Field
Fri 11/27
8:15 am-2:16 pm
1 stop5h 01m
$409
PortlandMadison
PWM Portland - MSN Madison Truax Field
PWMMSN
Portland
Mon 11/30
5:08 pm-11:07 pm
1 stop6h 59m
Madison Truax Field
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$428
PortlandMadison
PWM Portland - MSN Madison Truax Field
PWMMSN
Portland
Tue 11/24
10:50 am-5:02 pm
2 stops7h 12m
Madison Truax Field
Tue 12/1
6:30 am-2:37 pm
2 stops7h 07m
$433
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 November.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- Most accurate provider: When it comes to deals on Portland, Maine-Madison flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Portland, Maine-Madison flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Portland, Maine-Madison flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on Portland, Maine-Madison flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Portland, Maine-Madison flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.
Best time to book a flight from Portland to Madison
Have a flexible travel schedule? Discover the best time to fly to Madison from Portland with our price prediction graph.
PWM-MSN
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Portland to Madison
What is the cheapest month to book a flight from Portland, Maine to Madison?
Currently, February is the cheapest month in which you can book a flight from Portland, Maine to Madison (average of $278). Flying from Portland, Maine to Madison in December is currently the most expensive (average of $602). 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 $467 and $629 in January.The cheapest round-trip price found within the last 5 days was $355 on United Airlines (Jan 8-Jan 12).
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 November 10, 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
Comfort
7.8
Food
7.2
Boarding
8.1
Crew
8.5
Overall
7.8
Reviews
1 / 20
6.0
GoodEllen,Oct 2026
GRR - ATL
Entertainment
7.8
Comfort
7.8
Food
7.2
Boarding
8.1
Crew
8.5
Overall
7.8
Reviews
1 / 20
6.0
GoodEllen,Oct 2026
GRR - ATL
Entertainment
7.8
Comfort
7.8
Food
7.2
Boarding
8.1
Crew
8.5
Overall
7.8
Reviews
1 / 20
6.0
GoodEllen,Oct 2026
GRR - ATL
Entertainment
7.8
Comfort
7.8
Food
7.2
Boarding
8.1
Crew
8.5
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 November 10, 2026.
Portland and Madison flights
Browse other Portland and Madison flight options. Last updated on November 10, 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 November 10, 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 November 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$278 | Average$426 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$290 | Average$470 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$300 | Average$448 | FlexibilityNo cancel fee | On-timeN/A |