$189+ 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 6/16. Fares are subject to change and may not be available on all flights or dates of travel.
PWM — MSN
Jun 7 — Jun 141
Round-trip
1 adult, Economy
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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 May 8, 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 May 8, 2026.
This American Airlines deal was found by Cheapflights users on 5/7. 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.
Wed 6/101:36 pm
PWM
- MSN
1 stop7h 00m
American Airlines
Tue 6/166:42 pm
MSN
- PWM
1 stop5h 00m
American Airlines
Deal found 5/7![American Airlines logo]()
$291
This American Airlines deal was found by Cheapflights users on 5/6. 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.
Thu 6/185:58 pm
PWM
- MSN
1 stop7h 01m
American Airlines
Tue 6/236:42 pm
MSN
- PWM
1 stop5h 00m
American Airlines
Deal found 5/6![American Airlines logo]()
$315
This Delta deal was found by Cheapflights users on 5/7. 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.
Wed 6/106:00 am
PWM
- MSN
2 stops7h 43m
Delta
Tue 6/162:59 pm
MSN
- PWM
1 stop7h 30m
Delta
Deal found 5/7![Delta logo]()
$318
This American Airlines deal was found by Cheapflights users on 5/6. 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.
Wed 9/97:49 am
PWM
- MSN
1 stop5h 33m
American Airlines
Mon 9/146:35 pm
MSN
- PWM
1 stop4h 38m
American Airlines
Deal found 5/6![American Airlines logo]()
$322
This Delta deal was found by Cheapflights users on 5/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/93:00 pm
PWM
- MSN
1 stop6h 13m
Delta
Tue 9/153:50 pm
MSN
- PWM
1 stop6h 21m
Delta
Deal found 5/6![Delta logo]()
$328
This American Airlines deal was found by Cheapflights users on 5/3. 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.
Mon 6/155:58 pm
PWM
- MSN
1 stop7h 01m
American Airlines
Sun 6/216:42 pm
MSN
- PWM
1 stop5h 00m
American Airlines
Deal found 5/3![American Airlines logo]()
$339
This United Airlines deal was found by Cheapflights users on 5/5. 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.
Fri 9/45:05 pm
PWM
- MSN
1 stop5h 00m
United Airlines
Sun 9/610:49 am
MSN
- PWM
2 stops7h 30m
United Airlines
Deal found 5/5![United Airlines logo]()
$344
This Delta deal was found by Cheapflights users on 5/4. 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 6/121:12 pm
PWM
- MSN
1 stop7h 31m
Delta
Fri 6/193:11 pm
MSN
- PWM
1 stop7h 18m
Delta
Deal found 5/4![Delta logo]()
$353
This American Airlines deal was found by Cheapflights users on 5/4. 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 5/1910:47 am
PWM
- MSN
1 stop5h 55m
American Airlines
Sat 5/231:25 pm
MSN
- PWM
1 stop7h 21m
American Airlines
Deal found 5/4![American Airlines logo]()
$369
This United Airlines deal was found by Cheapflights users on 5/6. 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.
Tue 9/16:00 am
PWM
- MSN
1 stop4h 44m
United Airlines
Sat 9/53:49 pm
MSN
- PWM
1 stop5h 12m
United Airlines
Deal found 5/6![United Airlines logo]()
$371
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 May 8, 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 May 8, 2026.
This United Airlines deal was found by Cheapflights users on 5/5. 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.
Fri 9/45:05 pm
PWM
- MSN
1 stop5h 00m
United Airlines
Sun 9/610:49 am
MSN
- PWM
2 stops7h 30m
United Airlines
Deal found 5/5![United Airlines logo]()
$344
This Delta deal was found by Cheapflights users on 5/4. 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 6/121:12 pm
PWM
- MSN
1 stop7h 31m
Delta
Fri 6/193:11 pm
MSN
- PWM
1 stop7h 18m
Delta
Deal found 5/4![Delta logo]()
$353
This United Airlines deal was found by Cheapflights users on 5/6. 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.
Tue 9/16:00 am
PWM
- MSN
1 stop4h 44m
United Airlines
Sat 9/53:49 pm
MSN
- PWM
1 stop5h 12m
United Airlines
Deal found 5/6![United Airlines logo]()
$371
This Delta deal was found by Cheapflights users on 5/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/42:51 pm
PWM
- MSN
1 stop7h 19m
Delta
Mon 7/66:00 am
MSN
- PWM
2 stops8h 55m
Delta
Deal found 5/6![Delta logo]()
$386
This Delta deal was found by Cheapflights users on 5/4. 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 5/196:02 am
PWM
- MSN
2 stops11h 23m
Delta
Sat 5/2311:48 am
MSN
- PWM
2 stops10h 21m
Delta
Deal found 5/4![Delta logo]()
$395
This United Airlines deal was found by Cheapflights users on 5/6. 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 9/105:05 pm
PWM
- MSN
1 stop6h 37m
United Airlines
Tue 9/1510:57 am
MSN
- PWM
2 stops7h 22m
United Airlines
Deal found 5/6![United Airlines logo]()
$400
This Delta deal was found by Cheapflights users on 5/4. 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 6/1811:48 am
PWM
- MSN
1 stop7h 04m
Delta
Tue 6/231:31 pm
MSN
- PWM
2 stops8h 58m
Delta
Deal found 5/4![Delta logo]()
$410
This United Airlines deal was found by Cheapflights users on 5/6. 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.
Tue 9/85:05 pm
PWM
- MSN
1 stop6h 37m
United Airlines
Sun 9/133:49 pm
MSN
- PWM
1 stop5h 12m
United Airlines
Deal found 5/6![United Airlines logo]()
$419
This United Airlines deal was found by Cheapflights users on 5/5. 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.
Sat 5/236:25 pm
PWM
- MSN
1 stop5h 17m
United Airlines
Wed 5/273:53 pm
MSN
- PWM
1 stop4h 58m
United Airlines
Deal found 5/5![United Airlines logo]()
$434
Last-minute flights from Portland to MadisonDiscover last-minute flight deals from Portland to Madison. Data last updated May 8, 2026 and is based on user searches.
Discover last-minute flight deals from Portland to Madison. Data last updated May 8, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 5/4. 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 5/1910:47 am
PWM
- MSN
1 stop5h 55m
American Airlines
Sat 5/231:25 pm
MSN
- PWM
1 stop7h 21m
American Airlines
Deal found 5/4![American Airlines logo]()
$369
This Delta deal was found by Cheapflights users on 5/4. 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 5/191:18 pm
PWM
- MSN
1 stop7h 54m
Delta
Sat 5/2311:48 am
MSN
- PWM
2 stops10h 21m
Delta
Deal found 5/4![Delta logo]()
$390
This Delta deal was found by Cheapflights users on 5/4. 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 5/286:02 am
PWM
- MSN
2 stops7h 39m
Delta
Sun 5/317:00 am
MSN
- PWM
1 stop3h 55m
Delta
Deal found 5/4![Delta logo]()
$387
This American Airlines deal was found by Cheapflights users on 5/7. 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.
Wed 6/101:36 pm
PWM
- MSN
1 stop7h 00m
American Airlines
Tue 6/166:42 pm
MSN
- PWM
1 stop5h 00m
American Airlines
Deal found 5/7![American Airlines logo]()
$291
This Delta deal was found by Cheapflights users on 5/7. 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.
Wed 6/106:00 am
PWM
- MSN
2 stops7h 43m
Delta
Tue 6/162:59 pm
MSN
- PWM
1 stop7h 30m
Delta
Deal found 5/7![Delta logo]()
$318
This Delta deal was found by Cheapflights users on 5/4. 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 6/121:12 pm
PWM
- MSN
1 stop7h 31m
Delta
Fri 6/193:11 pm
MSN
- PWM
1 stop7h 18m
Delta
Deal found 5/4![Delta logo]()
$353
This American Airlines deal was found by Cheapflights users on 5/3. 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.
Mon 6/155:58 pm
PWM
- MSN
1 stop7h 01m
American Airlines
Sun 6/216:42 pm
MSN
- PWM
1 stop5h 00m
American Airlines
Deal found 5/3![American Airlines logo]()
$339
This American Airlines deal was found by Cheapflights users on 5/6. 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.
Thu 6/185:58 pm
PWM
- MSN
1 stop7h 01m
American Airlines
Tue 6/236:42 pm
MSN
- PWM
1 stop5h 00m
American Airlines
Deal found 5/6![American Airlines logo]()
$315
This Delta deal was found by Cheapflights users on 5/5. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/1811:48 am
PWM
- MSN
1 stop7h 04m
Delta
Tue 6/231:31 pm
MSN
- PWM
2 stops8h 58m
Delta
Deal found 5/5![Delta logo]()
$386
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 May 8, 2026.
Search for one-way flight options from Portland to Madison. Find affordable one-way fares based on user searches. Data last updated May 8, 2026.
This American Airlines deal was found by Cheapflights users on 5/6. 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 6/161:34 pm
PWM
- MSN
1 stop7h 09m
American Airlines
Deal found 5/6![American Airlines logo]()
$189
This American Airlines deal was found by Cheapflights users on 5/7. 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.
Tue 9/225:30 pm
PWM
- MSN
1 stop5h 01m
American Airlines
Deal found 5/7![American Airlines logo]()
$194
This Delta deal was found by Cheapflights users on 5/6. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/223:00 pm
PWM
- MSN
2 stops7h 57m
Delta
Deal found 5/6![Delta logo]()
$202
This Delta deal was found by Cheapflights users on 5/7. 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.
Tue 6/1611:02 am
PWM
- MSN
2 stops12h 41m
Delta
Deal found 5/7![Delta logo]()
$207
This American Airlines deal was found by Cheapflights users on 5/5. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/31:25 pm
PWM
- MSN
1 stop7h 14m
American Airlines
Deal found 5/5![American Airlines logo]()
$229
This American Airlines deal was found by Cheapflights users on 5/7. 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.
Thu 7/301:25 pm
PWM
- MSN
1 stop7h 14m
American Airlines
Deal found 5/7![American Airlines logo]()
$230
This Delta deal was found by Cheapflights users on 5/4. 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 6/51:18 pm
PWM
- MSN
2 stops10h 26m
Delta
Deal found 5/4![Delta logo]()
$235
This Kiwi.com deal was found by Cheapflights users on 5/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/48:00 am
PWM
- MSN
2 stops34h 25m
Breeze Airways
Deal found 5/3![Breeze Airways logo]()
$251
This American Airlines deal was found by Cheapflights users on 5/5. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/187:23 pm
PWM
- MSN
1 stop5h 05m
American Airlines
Deal found 5/5![American Airlines logo]()
$259
This Kiwi.com deal was found by Cheapflights users on 5/5. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/186:13 pm
PWM
- MSN
2 stops48h 12m
Breeze Airways
Deal found 5/5![Breeze Airways logo]()
$260
This United Airlines deal was found by Cheapflights users on 5/5. 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 8/45:00 pm
PWM
- MSN
1 stop7h 12m
United Airlines
Deal found 5/5![United Airlines logo]()
$268
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 May 8, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $291 (American Airlines) |
One-way from | $189 (American Airlines) |
Popular in | December |
Cheapest in | February |
Average price | $382 |
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 May 8, 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
Fri 9/4
5:05 pm-9:05 pm
1 stop5h 00m
Madison Truax Field
Sun 9/6
10:49 am-7:19 pm
2 stops7h 30m
$344
PortlandMadison
PWM - MSN
PWMMSN
Portland
Fri 6/12
1:12 pm-7:43 pm
1 stop7h 31m
Madison Truax Field
Fri 6/19
3:11 pm-11:29 pm
1 stop7h 18m
$353
Quickest round-trip
PortlandMadison
PWM - MSN
PWMMSN
Portland
Tue 9/1
6:00 am-9:44 am
1 stop4h 44m
Madison Truax Field
Sat 9/5
3:49 pm-10:01 pm
1 stop5h 12m
$371
PortlandMadison
PWM - MSN
PWMMSN
Portland
Sat 7/4
2:51 pm-9:10 pm
1 stop7h 19m
Madison Truax Field
Mon 7/6
6:00 am-3:55 pm
2 stops8h 55m
$386
PortlandMadison
PWM - MSN
PWMMSN
Portland
Tue 5/19
6:02 am-4:25 pm
2 stops11h 23m
Madison Truax Field
Sat 5/23
11:48 am-11:09 pm
2 stops10h 21m
$395
PortlandMadison
PWM - MSN
PWMMSN
Portland
Thu 9/10
5:05 pm-10:42 pm
1 stop6h 37m
Madison Truax Field
Tue 9/15
10:57 am-7:19 pm
2 stops7h 22m
$400
PortlandMadison
PWM - MSN
PWMMSN
Portland
Thu 6/18
11:48 am-5:52 pm
1 stop7h 04m
Madison Truax Field
Tue 6/23
1:31 pm-11:29 pm
2 stops8h 58m
$410
PortlandMadison
PWM - MSN
PWMMSN
Portland
Tue 9/8
5:05 pm-10:42 pm
1 stop6h 37m
Madison Truax Field
Sun 9/13
3:49 pm-10:01 pm
1 stop5h 12m
$419
PortlandMadison
PWM - MSN
PWMMSN
Portland
Sat 5/23
6:25 pm-10:42 pm
1 stop5h 17m
Madison Truax Field
Wed 5/27
3:53 pm-9:51 pm
1 stop4h 58m
$434
Cheapest one-way
PortlandMadison
PWM - MSN
PWMMSN
Portland
Tue 9/22
6:30 am-4:35 pm
2 stops11h 05m
$202
Showing 1-10 of 15 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 May.
| 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
Prices
Airlines
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 May 8, 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
7.9
Overall
7.9
Boarding
8.1
Food
7.2
Crew
8.5
Reviews
1 / 20
4.0
OkayJoel,May 2026
ATL - JAX
Entertainment
7.8
Comfort
7.9
Overall
7.9
Boarding
8.1
Food
7.2
Crew
8.5
Reviews
1 / 20
4.0
OkayJoel,May 2026
ATL - JAX
Entertainment
7.8
Comfort
7.9
Overall
7.9
Boarding
8.1
Food
7.2
Crew
8.5
Reviews
1 / 20
4.0
OkayJoel,May 2026
ATL - JAX
Entertainment
7.8
Comfort
7.9
Overall
7.9
Boarding
8.1
Food
7.2
Crew
8.5
Reviews
1 / 20
4.0
OkayJoel,May 2026
ATL - JAX
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.
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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 May 8, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$258 | Average$370 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$258 | Average$408 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$273 | Average$378 | FlexibilityNo cancel fee | On-time69% |