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Stewart

$182+ Cheap flights from Madison to New Windsor (MSN - SWF)

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 5/20. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — SWF
Feb 28 — Mar 71
Sat 2/28
Sat 3/7
1 adult, Economy
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Cheap flight deals from Madison to Stewart

One-way flights from Madison to Stewart
Search for one-way flight options from Madison to Stewart. Find affordable one-way fares based on user searches. Data last updated January 29, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
Wed 5/206:05 pm
MSN
-
SWF
1 stop13h 53m
Breeze Airways
Deal found 1/28$182
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
Wed 5/209:54 am
MSN
-
SWF
2 stops22h 44m
Multiple Airlines
Deal found 1/28$188
This Kiwi.com deal was found by Cheapflights users on 1/26. 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.
Wed 6/179:54 am
MSN
-
SWF
2 stops22h 44m
Multiple Airlines
Deal found 1/26$253
This Kiwi.com deal was found by Cheapflights users on 1/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/256:36 pm
MSN
-
SWF
1 stop15h 32m
Breeze Airways
Deal found 1/29$255
This Kiwi.com deal was found by Cheapflights users on 1/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/246:01 pm
MSN
-
SWF
2 stops38h 38m
Multiple Airlines
Deal found 1/29$259
This Kiwi.com deal was found by Cheapflights users on 1/26. 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.
Wed 6/176:05 pm
MSN
-
SWF
1 stop13h 53m
Breeze Airways
Deal found 1/26$277
This Kiwi.com deal was found by Cheapflights users on 1/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/259:48 am
MSN
-
SWF
2 stops22h 51m
Multiple Airlines
Deal found 1/29$282
This Kiwi.com deal was found by Cheapflights users on 1/26. 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 6/229:10 am
MSN
-
SWF
3 stops49h 15m
Breeze Airways
Deal found 1/26$528
This Kiwi.com deal was found by Cheapflights users on 1/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/216:36 pm
MSN
-
SWF
1 stop15h 32m
Breeze Airways
Deal found 1/29$557
This Kiwi.com deal was found by Cheapflights users on 1/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/219:48 am
MSN
-
SWF
2 stops22h 51m
Multiple Airlines
Deal found 1/29$656
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 2/127:15 pm
MSN
-
SWF
3 stops44h 54m
Multiple Airlines
Deal found 1/27$708

Find flight deals from Madison to Stewart

Discover tips and strategies to find the most affordable flight options for your journey from Madison (MSN) to Stewart (SWF). 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 29, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Popular in

March

Cheapest in

February

Average price

$414
Provider with most accurate pricing for Madison Truax Field-New Windsor Stewart flight deals.
Search Deals
Provider most trusted by Cheapflights users for Madison Truax Field-New Windsor Stewart flights.
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($14 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Madison to Stewart 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 29, 2026.
Use the filters below to find and compare flights from Madison to New Windsor that are best for you.

Fly from

Madison

Fly to

Stewart

Route

Depart

Return

Price

MadisonNew Windsor

MSN - SWF

MSNSWF

Madison Truax Field

Wed 5/20

6:05 pm-8:58 am

1 stop13h 53m

$182

MadisonNew Windsor

MSN - SWF

MSNSWF

Madison Truax Field

Wed 5/20

9:54 am-9:38 am

2 stops22h 44m

$188

MadisonNew Windsor

MSN - SWF

MSNSWF

Madison Truax Field

Wed 6/17

9:54 am-9:38 am

2 stops22h 44m

$253

MadisonNew Windsor

MSN - SWF

MSNSWF

Madison Truax Field

Sat 6/20

7:55 pm-8:58 am

1 stop12h 03m

$255

MadisonNew Windsor

MSN - SWF

MSNSWF

Madison Truax Field

Wed 3/25

6:36 pm-11:08 am

1 stop15h 32m

$255

MadisonNew Windsor

MSN - SWF

MSNSWF

Madison Truax Field

Tue 3/24

6:01 pm-9:39 am

2 stops38h 38m

$259

MadisonNew Windsor

MSN - SWF

MSNSWF

Madison Truax Field

Wed 6/17

6:05 pm-8:58 am

1 stop13h 53m

$277

MadisonNew Windsor

MSN - SWF

MSNSWF

Madison Truax Field

Wed 3/25

9:48 am-9:39 am

2 stops22h 51m

$282

MadisonNew Windsor

MSN - SWF

MSNSWF

Madison Truax Field

Mon 6/22

9:10 am-11:25 am

3 stops49h 15m

$528

MadisonNew Windsor

MSN - SWF

MSNSWF

Madison Truax Field

Sat 3/21

6:36 pm-11:08 am

1 stop15h 32m

$557

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/28

Showing 1-10 of 12 results
1
2
  • Most accurate provider: When it comes to deals on Madison-New Windsor flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Madison-New Windsor flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Madison-New Windsor flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Madison-New Windsor 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 Madison-New Windsor 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 Madison to Stewart

Have a flexible travel schedule? Discover the best time to fly to Stewart from Madison 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 Madison to New Windsor

What is the cheapest month to book a flight from Madison to New Windsor?

Currently, April is the cheapest month in which you can book a flight from Madison to New Windsor (average of $76). Flying from Madison to New Windsor in September is currently the most expensive (average of $228). 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.

Related info for your journey

Find useful and relevant information for your journey from Madison to Stewart. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • Can I find deals for flights from Madison to Stewart that include hotel bookings?

    Yes. In addition to deals on Madison to Stewart flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Madison to Stewart?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Madison to Stewart.

  • Can I find deals for business class flights from Madison to Stewart?

    Yes. Cheapflights offers flight deals from Madison to Stewart by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Madison to New Windsor?

    Currently, April is the cheapest month in which you can book a flight from Madison to New Windsor (average of $76). Flying from Madison to New Windsor in September is currently the most expensive (average of $228). 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.

See more FAQs

Traveling to a place near New Windsor?

Book flights to New Windsor if you plan to visit one of these locations
Kingston

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