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Stewart

$171+ 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 10/1. Fares are subject to change and may not be available on all flights or dates of travel.
MSN — SWF
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
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Cheap 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 September 17, 2025.

Round-trip from

$339
(Kiwi.com)

One-way from

$171
(Kiwi.com)

Popular in

March

Cheapest in

November

Average price

$399
From Madison Truax Field to New Windsor Stewart
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One-way flight from Madison Truax Field to New Windsor Stewart
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Highest demand for flights based on searches. 6% potential increase in price ($31 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find flight deals from Madison to Stewart

Cheapest flights from Madison to Stewart
Explore the most affordable flight options available from Madison to Stewart. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 17, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/15. 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 10/86:08 pmMSN - SWF
1 stop15h 55mMultiple Airlines
Mon 10/1311:01 amSWF - MSN
2 stops47h 07mMultiple Airlines
Deal found 9/15$339
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 10/86:08 pmMSN - SWF
1 stop15h 55mMultiple Airlines
Fri 10/1711:31 amSWF - MSN
2 stops22h 37mMultiple Airlines
Deal found 9/15$350
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 12/136:08 pmMSN - SWF
1 stop15h 55mBreeze Airways
Fri 12/1912:24 pmSWF - MSN
2 stops21h 44mBreeze Airways
Deal found 9/15$543
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 12/106:08 pmMSN - SWF
1 stop15h 55mMultiple Airlines
Fri 12/127:30 pmSWF - MSN
1 stop22h 58mMultiple Airlines
Deal found 9/16$550
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 12/136:08 pmMSN - SWF
1 stop15h 55mMultiple Airlines
Fri 12/198:11 pmSWF - MSN
1 stop22h 17mMultiple Airlines
Deal found 9/15$562
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 10/86:08 pmMSN - SWF
1 stop15h 55mMultiple Airlines
Sun 10/1211:43 amSWF - MSN
2 stops32h 31mMultiple Airlines
Deal found 9/15$582
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 11/266:08 pmMSN - SWF
1 stop15h 55mMultiple Airlines
Mon 12/15:49 pmSWF - MSN
2 stops48h 39mMultiple Airlines
Deal found 9/16$603
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 10/86:08 pmMSN - SWF
1 stop15h 55mMultiple Airlines
Thu 10/1611:43 amSWF - MSN
2 stops32h 31mMultiple Airlines
Deal found 9/15$629
This KAYAK deal was found by Cheapflights users on 9/15. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/16:08 pmMSN - SWF
1 stop16h 55mBreeze Airways
Fri 11/712:24 pmSWF - MSN
2 stops30h 04mBreeze Airways
Deal found 9/15$701
This Booking.com deal was found by Cheapflights users on 9/16. 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.
Wed 12/316:08 pmMSN - SWF
1 stop15h 55mBreeze Airways
Fri 1/212:24 pmSWF - MSN
2 stops30h 04mBreeze Airways
Deal found 9/16$1,399

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 September 17, 2025.
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 10/8

6:08 pm-11:03 am

1 stop15h 55m

New Windsor Stewart

Mon 10/13

11:01 am-9:08 am

2 stops47h 07m

$339

MadisonNew Windsor

MSN - SWF

MSNSWF

Madison Truax Field

Sat 10/11

6:08 pm-11:03 am

1 stop15h 55m

New Windsor Stewart

Fri 10/17

11:31 am-9:08 am

2 stops22h 37m

$350

MadisonNew Windsor

MSN - SWF

MSNSWF

Madison Truax Field

Wed 10/8

6:08 pm-11:03 am

1 stop15h 55m

New Windsor Stewart

Fri 10/17

11:31 am-9:08 am

2 stops22h 37m

$350

MadisonNew Windsor

MSN - SWF

MSNSWF

Madison Truax Field

Sat 12/13

6:08 pm-11:03 am

1 stop15h 55m

New Windsor Stewart

Fri 12/19

12:24 pm-9:08 am

2 stops21h 44m

$543

MadisonNew Windsor

MSN - SWF

MSNSWF

Madison Truax Field

Wed 12/10

6:08 pm-11:03 am

1 stop15h 55m

New Windsor Stewart

Fri 12/12

7:30 pm-5:28 pm

1 stop22h 58m

$550

MadisonNew Windsor

MSN - SWF

MSNSWF

Madison Truax Field

Sat 12/13

6:08 pm-11:03 am

1 stop15h 55m

New Windsor Stewart

Fri 12/19

8:11 pm-5:28 pm

1 stop22h 17m

$562

MadisonNew Windsor

MSN - SWF

MSNSWF

Madison Truax Field

Wed 11/26

6:08 pm-11:03 am

1 stop15h 55m

New Windsor Stewart

Mon 12/1

5:49 pm-5:28 pm

2 stops48h 39m

$603

MadisonNew Windsor

MSN - SWF

MSNSWF

Madison Truax Field

Sat 10/11

6:08 pm-11:03 am

1 stop15h 55m

New Windsor Stewart

Thu 10/16

11:43 am-7:14 pm

2 stops32h 31m

$629

MadisonNew Windsor

MSN - SWF

MSNSWF

Madison Truax Field

Wed 10/8

6:08 pm-11:03 am

1 stop15h 55m

New Windsor Stewart

Thu 10/16

11:43 am-7:14 pm

2 stops32h 31m

$629

MadisonNew Windsor

MSN - SWF

MSNSWF

Madison Truax Field

Sat 11/1

6:08 pm-12:03 pm

1 stop16h 55m

New Windsor Stewart

Fri 11/7

12:24 pm-5:28 pm

2 stops30h 04m

$701

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

Showing 1-10 of 20 results
1
2

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, October is the cheapest month in which you can book a flight from Madison to New Windsor (average of $109). Flying from Madison to New Windsor in December is currently the most expensive (average of $202). 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.

  • How long is the flight from Madison to New Windsor?

    Airlines like Breeze Airways fly from Madison to New Windsor in about 15h 55m. The time it takes to get you to your destination can typically vary by up to . Airlines will cover a distance of 785 mi.

  • 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, October is the cheapest month in which you can book a flight from Madison to New Windsor (average of $109). Flying from Madison to New Windsor in December is currently the most expensive (average of $202). 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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