$167+ 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
Jul 3 — Jul 101
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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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 June 3, 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 June 3, 2026.
This Delta deal was found by Cheapflights users on 5/31. 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.
Tue 7/284:52 pm
PWM
- MSN
1 stop5h 07m
Delta
Tue 8/43:05 pm
MSN
- PWM
1 stop7h 25m
Delta
Deal found 5/31![Delta logo]()
$291
This Delta deal was found by Cheapflights users on 5/31. 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.
Tue 7/284:52 pm
PWM
- MSN
1 stop5h 07m
Delta
Thu 8/63:05 pm
MSN
- PWM
1 stop7h 25m
Delta
Deal found 5/31![Delta logo]()
$305
This Delta deal was found by Cheapflights users on 6/1. 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 7/612:40 pm
PWM
- MSN
1 stop5h 59m
Delta
Tue 7/216:00 am
MSN
- PWM
2 stops9h 01m
Delta
Deal found 6/1![Delta logo]()
$310
This American Airlines deal was found by Cheapflights users on 6/2. 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 7/25:18 pm
PWM
- MSN
1 stop7h 01m
American Airlines
Sun 7/56:00 am
MSN
- PWM
1 stop7h 16m
American Airlines
Deal found 6/2![American Airlines logo]()
$319
This American Airlines deal was found by Cheapflights users on 5/31. 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 7/171:25 pm
PWM
- MSN
1 stop7h 14m
American Airlines
Sun 7/196:43 pm
MSN
- PWM
1 stop5h 00m
American Airlines
Deal found 5/31![American Airlines logo]()
$326
This American Airlines deal was found by Cheapflights users on 5/31. 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 6/197:28 pm
PWM
- MSN
1 stop6h 12m
American Airlines
Tue 6/234:34 pm
MSN
- PWM
1 stop6h 25m
American Airlines
Deal found 5/31![American Airlines logo]()
$344
This American Airlines deal was found by Cheapflights users on 5/29. 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 6/177:28 pm
PWM
- MSN
1 stop6h 12m
American Airlines
Mon 6/226:42 pm
MSN
- PWM
1 stop5h 00m
American Airlines
Deal found 5/29![American Airlines logo]()
$351
This American Airlines deal was found by Cheapflights users on 6/3. 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 6/277:58 am
PWM
- MSN
1 stop5h 05m
American Airlines
Tue 6/306:42 pm
MSN
- PWM
1 stop5h 00m
American Airlines
Deal found 6/3![American Airlines logo]()
$355
This United Airlines deal was found by Cheapflights users on 5/31. 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 7/45:15 am
PWM
- MSN
2 stops9h 36m
United Airlines
Sat 7/43:46 pm
MSN
- PWM
1 stop4h 55m
United Airlines
Deal found 5/31![United Airlines logo]()
$357
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 June 3, 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 June 3, 2026.
This American Airlines deal was found by Cheapflights users on 5/31. 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 8/41:28 pm
PWM
- MSN
1 stop7h 11m
American Airlines
Mon 8/103:54 pm
MSN
- PWM
1 stop7h 05m
American Airlines
Deal found 5/31![American Airlines logo]()
$355
This United Airlines deal was found by Cheapflights users on 5/31. 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 7/45:15 am
PWM
- MSN
2 stops9h 36m
United Airlines
Sat 7/43:46 pm
MSN
- PWM
1 stop4h 55m
United Airlines
Deal found 5/31![United Airlines logo]()
$357
This Delta deal was found by Cheapflights users on 5/31. 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 6/276:14 am
PWM
- MSN
1 stop7h 44m
Delta
Tue 6/306:00 am
MSN
- PWM
2 stops8h 55m
Delta
Deal found 5/31![Delta logo]()
$608
This United Airlines deal was found by Cheapflights users on 5/29. 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 7/19:55 am
PWM
- MSN
2 stops10h 02m
United Airlines
Sat 7/43:46 pm
MSN
- PWM
1 stop4h 55m
United Airlines
Deal found 5/29![United Airlines logo]()
$468
This United Airlines deal was found by Cheapflights users on 6/1. 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 10/25:15 am
PWM
- MSN
2 stops9h 22m
United Airlines
Mon 10/56:49 am
MSN
- PWM
1 stop6h 49m
United Airlines
Deal found 6/1![United Airlines logo]()
$507
This Delta deal was found by Cheapflights users on 5/31. 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 6/151:12 pm
PWM
- MSN
1 stop7h 31m
Delta
Fri 6/192:45 pm
MSN
- PWM
2 stops9h 07m
Delta
Deal found 5/31![Delta logo]()
$625
This Delta deal was found by Cheapflights users on 5/30. 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.
Wed 10/76:00 am
PWM
- MSN
2 stops8h 55m
Delta
Sun 10/115:45 am
MSN
- PWM
2 stops10h 14m
Delta
Deal found 5/30![Delta logo]()
$680
This United Airlines deal was found by Cheapflights users on 5/30. 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 6/145:50 am
PWM
- MSN
1 stop5h 19m
United Airlines
Thu 6/186:24 am
MSN
- PWM
1 stop6h 01m
United Airlines
Deal found 5/30![United Airlines logo]()
$620
This Delta deal was found by Cheapflights users on 6/2. 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 7/26:20 am
PWM
- MSN
2 stops10h 30m
Delta
Sun 7/55:48 am
MSN
- PWM
2 stops10h 12m
Delta
Deal found 6/2![Delta logo]()
$689
This United Airlines deal was found by Cheapflights users on 6/1. 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 6/275:00 pm
PWM
- MSN
1 stop7h 12m
United Airlines
Tue 6/308:10 am
MSN
- PWM
2 stops10h 17m
United Airlines
Deal found 6/1![United Airlines logo]()
$640
Last-minute flights from Portland to MadisonDiscover last-minute flight deals from Portland to Madison. Data last updated June 3, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Madison. Data last updated June 3, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 5/29. 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 6/177:28 pm
PWM
- MSN
1 stop6h 12m
American Airlines
Mon 6/226:42 pm
MSN
- PWM
1 stop5h 00m
American Airlines
Deal found 5/29![American Airlines logo]()
$351
This American Airlines deal was found by Cheapflights users on 5/31. 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 6/197:28 pm
PWM
- MSN
1 stop6h 12m
American Airlines
Tue 6/234:34 pm
MSN
- PWM
1 stop6h 25m
American Airlines
Deal found 5/31![American Airlines logo]()
$344
This American Airlines deal was found by Cheapflights users on 6/3. 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 6/277:58 am
PWM
- MSN
1 stop5h 05m
American Airlines
Tue 6/306:42 pm
MSN
- PWM
1 stop5h 00m
American Airlines
Deal found 6/3![American Airlines logo]()
$355
This American Airlines deal was found by Cheapflights users on 6/3. 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 7/25:18 pm
PWM
- MSN
1 stop7h 01m
American Airlines
Sun 7/56:00 am
MSN
- PWM
1 stop7h 16m
American Airlines
Deal found 6/3![American Airlines logo]()
$319
This United Airlines deal was found by Cheapflights users on 5/31. 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 7/45:15 am
PWM
- MSN
2 stops9h 36m
United Airlines
Sat 7/43:46 pm
MSN
- PWM
1 stop4h 55m
United Airlines
Deal found 5/31![United Airlines logo]()
$357
This Delta deal was found by Cheapflights users on 6/1. 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 7/612:40 pm
PWM
- MSN
1 stop5h 59m
Delta
Tue 7/216:00 am
MSN
- PWM
2 stops9h 01m
Delta
Deal found 6/1![Delta logo]()
$310
This American Airlines deal was found by Cheapflights users on 5/31. 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 7/171:25 pm
PWM
- MSN
1 stop7h 14m
American Airlines
Sun 7/196:43 pm
MSN
- PWM
1 stop5h 00m
American Airlines
Deal found 5/31![American Airlines logo]()
$326
This Delta deal was found by Cheapflights users on 5/31. 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.
Tue 7/284:52 pm
PWM
- MSN
1 stop5h 07m
Delta
Tue 8/43:05 pm
MSN
- PWM
1 stop7h 25m
Delta
Deal found 5/31![Delta logo]()
$291
This Delta deal was found by Cheapflights users on 5/31. 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.
Tue 7/284:52 pm
PWM
- MSN
1 stop5h 07m
Delta
Wed 8/51:35 pm
MSN
- PWM
2 stops8h 55m
Delta
Deal found 5/31![Delta logo]()
$296
This Delta deal was found by Cheapflights users on 5/31. 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.
Tue 7/284:52 pm
PWM
- MSN
1 stop5h 07m
Delta
Fri 8/73:05 pm
MSN
- PWM
1 stop7h 25m
Delta
Deal found 5/31![Delta logo]()
$305
This Delta deal was found by Cheapflights users on 5/31. 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.
Tue 7/284:52 pm
PWM
- MSN
1 stop5h 07m
Delta
Thu 8/61:35 pm
MSN
- PWM
2 stops10h 24m
Delta
Deal found 5/31![Delta 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 June 3, 2026.
Search for one-way flight options from Portland to Madison. Find affordable one-way fares based on user searches. Data last updated June 3, 2026.
This Delta deal was found by Cheapflights users on 5/31. 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.
Tue 9/2211:50 am
PWM
- MSN
1 stop7h 05m
Delta
Deal found 5/31![Delta logo]()
$167
This Kiwi.com deal was found by Cheapflights users on 5/31. 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 7/411:07 am
PWM
- MSN
1 stop9h 08m
Breeze Airways
Deal found 5/31![Breeze Airways logo]()
$181
This Delta deal was found by Cheapflights users on 6/1. 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.
Tue 6/231:12 pm
PWM
- MSN
1 stop7h 31m
Delta
Deal found 6/1![Delta logo]()
$228
This United Airlines deal was found by Cheapflights users on 5/30. 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 6/235:15 am
PWM
- MSN
2 stops10h 42m
United Airlines
Deal found 5/30![United Airlines logo]()
$251
This American Airlines deal was found by Cheapflights users on 6/3. 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 7/305:45 am
PWM
- MSN
1 stop7h 28m
American Airlines
Deal found 6/3![American Airlines logo]()
$254
This United Airlines deal was found by Cheapflights users on 5/31. 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 7/45:15 am
PWM
- MSN
2 stops9h 36m
United Airlines
Deal found 5/31![United Airlines logo]()
$259
This American Airlines deal was found by Cheapflights users on 5/31. 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 6/297:28 pm
PWM
- MSN
1 stop6h 12m
American Airlines
Deal found 5/31![American Airlines logo]()
$264
This American Airlines deal was found by Cheapflights users on 5/30. 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 6/245:04 pm
PWM
- MSN
1 stop7h 15m
American Airlines
Deal found 5/30![American Airlines logo]()
$268
This Delta deal was found by Cheapflights users on 6/1. 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 7/306:25 am
PWM
- MSN
2 stops7h 17m
Delta
Deal found 6/1![Delta logo]()
$269
This United Airlines deal was found by Cheapflights users on 6/2. 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 6/163:16 pm
PWM
- MSN
1 stop6h 23m
United Airlines
Deal found 6/2![United Airlines logo]()
$276
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 June 3, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $291 (Delta) |
One-way from | $167 (Delta) |
Popular in | December |
Cheapest in | February |
Average price | $480 |
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 2,558,603 searches. Data last updated June 3, 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 - MSN
PWMMSN
Portland
Tue 8/4
1:28 pm-7:39 pm
1 stop7h 11m
Madison Truax Field
Mon 8/10
3:54 pm-11:59 pm
1 stop7h 05m
$355
PortlandMadison
PWM - MSN
PWMMSN
Portland
Sat 7/4
5:15 am-1:51 pm
2 stops9h 36m
Madison Truax Field
Sat 7/4
3:46 pm-9:41 pm
1 stop4h 55m
$357
PortlandMadison
PWM - MSN
PWMMSN
Portland
Wed 7/1
9:55 am-6:57 pm
2 stops10h 02m
Madison Truax Field
Sat 7/4
3:46 pm-9:41 pm
1 stop4h 55m
$468
PortlandMadison
PWM - MSN
PWMMSN
Portland
Fri 10/2
5:15 am-1:37 pm
2 stops9h 22m
Madison Truax Field
Mon 10/5
6:49 am-2:38 pm
1 stop6h 49m
$507
PortlandMadison
PWM - MSN
PWMMSN
Portland
Sat 6/27
6:14 am-12:58 pm
1 stop7h 44m
Madison Truax Field
Tue 6/30
6:00 am-3:55 pm
2 stops8h 55m
$608
Quickest round-trip
PortlandMadison
PWM - MSN
PWMMSN
Portland
Sun 6/14
5:50 am-10:09 am
1 stop5h 19m
Madison Truax Field
Thu 6/18
6:24 am-1:25 pm
1 stop6h 01m
$620
PortlandMadison
PWM - MSN
PWMMSN
Portland
Mon 6/15
1:12 pm-7:43 pm
1 stop7h 31m
Madison Truax Field
Fri 6/19
2:45 pm-12:52 am
2 stops9h 07m
$625
PortlandMadison
PWM - MSN
PWMMSN
Portland
Sat 6/27
5:00 pm-11:12 pm
1 stop7h 12m
Madison Truax Field
Tue 6/30
8:10 am-7:27 pm
2 stops10h 17m
$640
PortlandMadison
PWM - MSN
PWMMSN
Portland
Wed 10/7
6:00 am-1:55 pm
2 stops8h 55m
Madison Truax Field
Sun 10/11
5:45 am-4:59 pm
2 stops10h 14m
$680
PortlandMadison
PWM - MSN
PWMMSN
Portland
Thu 7/2
6:20 am-3:50 pm
2 stops10h 30m
Madison Truax Field
Sun 7/5
5:48 am-5:00 pm
2 stops10h 12m
$689
Showing 1-10 of 17 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 June.
| 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 $577). 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?
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 June 3, 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.
Comfort
7.8
Crew
8.5
Boarding
8.1
Entertainment
7.8
Food
7.2
Overall
7.9
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Comfort
7.8
Crew
8.5
Boarding
8.1
Entertainment
7.8
Food
7.2
Overall
7.9
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Comfort
7.8
Crew
8.5
Boarding
8.1
Entertainment
7.8
Food
7.2
Overall
7.9
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Comfort
7.8
Crew
8.5
Boarding
8.1
Entertainment
7.8
Food
7.2
Overall
7.9
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
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 locationsPortage
Sun Prairie
Middleton
Baraboo
Fitchburg
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Portland and Madison flights
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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 2,558,603 searches. Data last updated June 3, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$258 | Average$408 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$270 | Average$369 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$273 | Average$377 | FlexibilityNo cancel fee | On-time69% |