$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 10/27. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MSN
Oct 25 — Nov 11
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 September 25, 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 September 25, 2026.
This American Airlines deal was found by Cheapflights users on 9/21. 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 10/275:45 pm -
1 stop6h 27m
Tue 11/35:00 am -
1 stop5h 28m
Deal found 9/21![American Airlines logo]()
$321
This American Airlines deal was found by Cheapflights users on 9/23. 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.
Thu 10/226:00 am -
1 stop6h 54m
Tue 10/275:00 am -
1 stop6h 31m
Deal found 9/23![American Airlines logo]()
$335
This American Airlines deal was found by Cheapflights users on 9/23. 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.
Fri 10/165:37 pm -
1 stop5h 54m
Mon 10/195:31 pm -
1 stop5h 05m
Deal found 9/23![American Airlines logo]()
$349
This American Airlines deal was found by Cheapflights users on 9/24. 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.
Wed 10/215:37 pm -
2 stops7h 35m
Mon 10/265:00 am -
1 stop6h 31m
Deal found 9/24![American Airlines logo]()
$354
This Delta deal was found by Cheapflights users on 9/24. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/106:12 am -
2 stops7h 26m
Sun 12/135:30 am -
2 stops9h 41m
Deal found 9/24![Delta logo]()
$359
This United Airlines deal was found by Cheapflights users on 9/23. 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.
Thu 11/195:08 pm -
1 stop6h 59m
Mon 11/236:25 am -
1 stop6h 51m
Deal found 9/23![United Airlines logo]()
$362
This American Airlines deal was found by Cheapflights users on 9/24. 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.
Fri 12/115:25 am -
1 stop7h 22m
Sun 12/136:02 am -
2 stops8h 31m
Deal found 9/24![American Airlines logo]()
$371
This United Airlines deal was found by Cheapflights users on 9/22. 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.
Wed 10/76:00 am -
1 stop5h 29m
Tue 10/134:10 pm -
1 stop4h 44m
Deal found 9/22![United Airlines logo]()
$374
This Delta deal was found by Cheapflights users on 9/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/196:27 am -
2 stops10h 58m
Mon 11/237:00 am -
2 stops7h 16m
Deal found 9/23![Delta logo]()
$376
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 September 25, 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 September 25, 2026.
This United Airlines deal was found by Cheapflights users on 9/23. 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 11/65:08 pm -
1 stop6h 59m
Sun 11/86:25 am -
2 stops7h 02m
Deal found 9/23![United Airlines logo]()
$354
This American Airlines deal was found by Cheapflights users on 9/24. 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.
Thu 10/226:00 am -
1 stop6h 54m
Sun 10/255:00 am -
1 stop6h 31m
Deal found 9/24![American Airlines logo]()
$550
This United Airlines deal was found by Cheapflights users on 9/22. 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.
Wed 10/76:00 am -
1 stop5h 29m
Tue 10/134:10 pm -
1 stop4h 44m
Deal found 9/22![United Airlines logo]()
$374
This United Airlines deal was found by Cheapflights users on 9/23. 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.
Wed 10/288:32 am -
1 stop7h 35m
Sat 10/318:15 am -
1 stop5h 01m
Deal found 9/23![United Airlines logo]()
$421
This United Airlines deal was found by Cheapflights users on 9/22. 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.
Wed 10/75:15 am -
2 stops7h 38m
Sun 10/118:17 am -
1 stop5h 21m
Deal found 9/22![United Airlines logo]()
$426
This United Airlines deal was found by Cheapflights users on 9/23. 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.
Thu 10/225:15 am -
2 stops9h 22m
Tue 10/2712:32 pm -
2 stops9h 49m
Deal found 9/23![United Airlines logo]()
$445
Last-minute flights from Portland to MadisonDiscover last-minute flight deals from Portland to Madison. Data last updated September 25, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Madison. Data last updated September 25, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 9/22. 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.
Wed 10/76:00 am -
1 stop5h 29m
Tue 10/134:10 pm -
1 stop4h 44m
Deal found 9/22![United Airlines logo]()
$374
This United Airlines deal was found by Cheapflights users on 9/22. 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.
Wed 10/76:00 am -
1 stop5h 29m
Sun 10/116:49 am -
1 stop6h 49m
Deal found 9/22![United Airlines logo]()
$399
This American Airlines deal was found by Cheapflights users on 9/23. 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.
Thu 10/156:00 am -
1 stop6h 54m
Mon 10/195:31 pm -
1 stop5h 05m
Deal found 9/23![American Airlines logo]()
$412
This American Airlines deal was found by Cheapflights users on 9/23. 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.
Fri 10/165:37 pm -
1 stop5h 54m
Mon 10/195:31 pm -
1 stop5h 05m
Deal found 9/23![American Airlines logo]()
$349
This American Airlines deal was found by Cheapflights users on 9/24. 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.
Wed 10/215:37 pm -
2 stops7h 35m
Mon 10/265:00 am -
1 stop6h 31m
Deal found 9/24![American Airlines logo]()
$354
This American Airlines deal was found by Cheapflights users on 9/23. 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.
Thu 10/226:00 am -
1 stop6h 54m
Tue 10/275:00 am -
1 stop6h 31m
Deal found 9/23![American Airlines logo]()
$335
This American Airlines deal was found by Cheapflights users on 9/23. 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.
Thu 10/226:00 am -
1 stop6h 54m
Mon 10/263:28 pm -
2 stops7h 08m
Deal found 9/23![American Airlines logo]()
$417
This American Airlines deal was found by Cheapflights users on 9/21. 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 10/275:45 pm -
1 stop6h 27m
Tue 11/35:00 am -
1 stop5h 28m
Deal found 9/21![American Airlines logo]()
$321
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 September 25, 2026.
Search for one-way flight options from Portland to Madison. Find affordable one-way fares based on user searches. Data last updated September 25, 2026.
This United Airlines deal was found by Cheapflights users on 9/21. 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 10/96:00 am -
1 stop6h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![United Airlines logo]()
$374
This Kiwi.com deal was found by Cheapflights users on 9/20. 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.
Fri 10/93:53 pm -
2 stops19h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Breeze Airways logo]()
$411
This Kiwi.com deal was found by Cheapflights users on 9/20. 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.
Fri 10/93:53 pm -
3 stops50h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/20![Multiple Airlines logo]()
$417
This United Airlines deal was found by Cheapflights users on 9/21. 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 12/123:41 pm -
1 stop6h 05m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/21![United Airlines logo]()
$419
This Delta deal was found by Cheapflights users on 9/23. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/46:00 am -
1 stop5h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Delta logo]()
$436
This United Airlines deal was found by Cheapflights users on 9/23. 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.
Sun 10/46:00 am -
2 stops10h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![United Airlines logo]()
$441
This Kiwi.com deal was found by Cheapflights users on 9/23. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/410:01 am -
3 stops53h 04m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/23![Breeze Airways logo]()
$474
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 September 25, 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 | $378 |
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 September 25, 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
5:08 pm-11:07 pm
1 stop6h 59m
Madison Truax Field
Sun 11/8
6:25 am-2:27 pm
2 stops7h 02m
$354
PortlandMadison
PWM Portland - MSN Madison Truax Field
PWMMSN
Portland
Fri 10/9
6:00 am-11:53 am
1 stop6h 53m
Madison Truax Field
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$374
PortlandMadison
PWM Portland - MSN Madison Truax Field
PWMMSN
Portland
Wed 10/7
6:00 am-10:29 am
1 stop5h 29m
Madison Truax Field
Tue 10/13
4:10 pm-9:54 pm
1 stop4h 44m
$374
PortlandMadison
PWM Portland - MSN Madison Truax Field
PWMMSN
Portland
Fri 10/9
3:53 pm-9:58 am
2 stops19h 05m
Madison Truax Field
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$411
PortlandMadison
PWM Portland - MSN Madison Truax Field
PWMMSN
Portland
Sat 12/12
3:41 pm-8:46 pm
1 stop6h 05m
Madison Truax Field
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$419
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
$421
PortlandMadison
PWM Portland - MSN Madison Truax Field
PWMMSN
Portland
Wed 10/7
5:15 am-11:53 am
2 stops7h 38m
Madison Truax Field
Sun 10/11
8:17 am-2:38 pm
1 stop5h 21m
$426
Quickest round-trip
PortlandMadison
PWM Portland - MSN Madison Truax Field
PWMMSN
Portland
Sun 10/4
6:00 am-10:38 am
1 stop5h 38m
Madison Truax Field
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$436
PortlandMadison
PWM Portland - MSN Madison Truax Field
PWMMSN
Portland
Sun 10/4
6:00 am-3:04 pm
2 stops10h 04m
Madison Truax Field
Wed 12/31
12:00 am-1:00 am
Nonstop0h 00m
$441
PortlandMadison
PWM Portland - MSN Madison Truax Field
PWMMSN
Portland
Thu 10/22
5:15 am-1:37 pm
2 stops9h 22m
Madison Truax Field
Tue 10/27
12:32 pm-11:21 pm
2 stops9h 49m
$445
Showing 1-10 of 11 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 September.
| 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
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 September 25, 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.
Crew
8.5
Boarding
8.1
Overall
7.8
Entertainment
7.8
Food
7.2
Comfort
7.8
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Crew
8.5
Boarding
8.1
Overall
7.8
Entertainment
7.8
Food
7.2
Comfort
7.8
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Crew
8.5
Boarding
8.1
Overall
7.8
Entertainment
7.8
Food
7.2
Comfort
7.8
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
Crew
8.5
Boarding
8.1
Overall
7.8
Entertainment
7.8
Food
7.2
Comfort
7.8
Reviews
1 / 20
4.0
OkayJennifer,Sep 2026
ORD - LGA
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 September 25, 2026.
Portland and Madison flights
Browse other Portland and Madison flight options. Last updated on September 25, 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 September 25, 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 September 25, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$258 | Average$448 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$273 | Average$396 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$278 | Average$401 | FlexibilityNo cancel fee | On-time69% |