$334+ Cheap flights from New Windsor to Madison (SWF - 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 4/10. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — MSN
Feb 19 — Feb 261
1 adult, Economy
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Find cheap flights from Stewart 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 Stewart to Madison
One-way flights from Stewart to MadisonSearch for one-way flight options from Stewart to Madison. Find affordable one-way fares based on user searches. Data last updated January 20, 2026.
Search for one-way flight options from Stewart to Madison. Find affordable one-way fares based on user searches. Data last updated January 20, 2026.
This Kiwi.com deal was found by Cheapflights users on 1/19. 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 4/1012:11 pm
SWF
- MSN
2 stops21h 57m
Breeze Airways
Deal found 1/19![Breeze Airways logo]()
$334
This Kiwi.com deal was found by Cheapflights users on 1/18. 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.
Thu 2/1211:48 am
SWF
- MSN
3 stops46h 20m
Breeze Airways
Deal found 1/18![Breeze Airways logo]()
$842
This Booking.com deal was found by Cheapflights users on 1/19. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/312:11 pm
SWF
- MSN
2 stops30h 45m
Breeze Airways
Deal found 1/19![Breeze Airways logo]()
$1,175
Find flight deals from Stewart to Madison
Discover tips and strategies to find the most affordable flight options for your journey from Stewart (SWF) 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 January 20, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 1 star |
Popular in | August |
Cheapest in | February |
Average price | $442 |
Cheapflights Fare Finder
Customize your flight search to find flights from Stewart 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 January 20, 2026.
Use the filters below to find and compare flights from New Windsor to Madison that are best for you.
Fly from
Stewart
Fly to
Madison
Route
Depart
Return
Price
New WindsorMadison
SWF - MSN
SWFMSN
New Windsor Stewart
Fri 4/10
12:11 pm-9:08 am
2 stops21h 57m
$334
New WindsorMadison
SWF - MSN
SWFMSN
New Windsor Stewart
Thu 2/12
11:48 am-9:08 am
3 stops46h 20m
$842
New WindsorMadison
SWF - MSN
SWFMSN
New Windsor Stewart
Fri 4/3
12:11 pm-5:56 pm
2 stops30h 45m
$1,175
- Most accurate provider: When it comes to deals on New Windsor-Madison flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on New Windsor-Madison flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from New Windsor-Madison flight searches over the past month and is updated monthly.
- Most trusted provider: When it comes to deals on New Windsor-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 New Windsor-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 Stewart to Madison
Have a flexible travel schedule? Discover the best time to fly to Madison from Stewart with our price prediction graph.
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 New Windsor to Madison
Related info for your journey
Find useful and relevant information for your journey from Stewart 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
Middleton
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Fitchburg