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$300+ 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 9/26. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — MSN
Aug 21 — Aug 281
Thu 8/21
Thu 8/28
1 adult, Economy
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Cheap 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 August 16, 2025.

Round-trip from

$595
(Booking.com)

One-way from

$300
(Booking.com)

Popular in

August

Cheapest in

February

Average price

$533
From New Windsor Stewart to Madison Truax Field
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One-way flight from New Windsor Stewart to Madison Truax Field
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Highest demand for flights based on searches. 9% potential increase in price ($46 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Find flight deals from Stewart to Madison

Cheapest flights from Stewart to Madison
Explore the most affordable flight options available from Stewart to Madison. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 16, 2025.

This Booking.com deal was found by Cheapflights users on 8/14. 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 9/1912:24 pmSWF - MSN
2 stops30h 04mBreeze Airways
Wed 9/246:08 pmMSN - SWF
1 stop15h 55mBreeze Airways
Deal found 8/14$595
This FlightHub deal was found by Cheapflights users on 8/15. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/291:28 pmSWF - MSN
2 stops21h 11mBreeze Airways
Wed 9/36:08 pmMSN - SWF
1 stop15h 55mBreeze Airways
Deal found 8/15$627
This KAYAK deal was found by Cheapflights users on 8/15. 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.
Fri 9/1212:24 pmSWF - MSN
2 stops30h 04mBreeze Airways
Wed 9/176:08 pmMSN - SWF
1 stop15h 55mBreeze Airways
Deal found 8/15$645
This Gotogate deal was found by Cheapflights users on 8/14. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/2612:36 pmSWF - MSN
1 stop22h 03mBreeze Airways
Sat 8/3010:19 amMSN - SWF
1 stop7h 30mBreeze Airways
Deal found 8/14$715
This KAYAK deal was found by Cheapflights users on 8/15. 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.
Tue 8/1912:36 pmSWF - MSN
1 stop22h 03mBreeze Airways
Sat 8/2310:19 amMSN - SWF
1 stop7h 30mBreeze Airways
Deal found 8/15$1,063

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 August 16, 2025.
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 9/19

12:24 pm-5:28 pm

2 stops30h 04m

Madison Truax Field

Wed 9/24

6:08 pm-11:03 am

1 stop15h 55m

$595

New WindsorMadison

SWF - MSN

SWFMSN

New Windsor Stewart

Fri 8/29

1:28 pm-9:39 am

2 stops21h 11m

Madison Truax Field

Wed 9/3

6:08 pm-11:03 am

1 stop15h 55m

$627

New WindsorMadison

SWF - MSN

SWFMSN

New Windsor Stewart

Fri 9/12

12:24 pm-5:28 pm

2 stops30h 04m

Madison Truax Field

Wed 9/17

6:08 pm-11:03 am

1 stop15h 55m

$645

New WindsorMadison

SWF - MSN

SWFMSN

New Windsor Stewart

Tue 8/26

12:36 pm-9:39 am

1 stop22h 03m

Madison Truax Field

Sat 8/30

10:19 am-6:49 pm

1 stop7h 30m

$715

New WindsorMadison

SWF - MSN

SWFMSN

New Windsor Stewart

Fri 9/26

12:24 pm-5:28 pm

2 stops30h 04m

$300

New WindsorMadison

SWF - MSN

SWFMSN

New Windsor Stewart

Tue 8/26

12:36 pm-9:39 am

1 stop22h 03m

$334

New WindsorMadison

SWF - MSN

SWFMSN

New Windsor Stewart

Fri 9/12

12:24 pm-5:28 pm

2 stops30h 04m

$350

New WindsorMadison

SWF - MSN

SWFMSN

New Windsor Stewart

Fri 8/22

1:28 pm-9:39 am

2 stops21h 11m

$382

New WindsorMadison

SWF - MSN

SWFMSN

New Windsor Stewart

Fri 9/19

12:24 pm-9:08 am

2 stops21h 44m

$404

New WindsorMadison

SWF - MSN

SWFMSN

New Windsor Stewart

Fri 10/17

12:24 pm-5:28 pm

2 stops30h 04m

$411

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/14

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

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

Currently, January is the cheapest month in which you can book a flight from New Windsor to Madison (average of $338). Flying from New Windsor to Madison in March is currently the most expensive (average of $422). 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 Stewart to Madison. 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 Stewart to Madison that include hotel bookings?

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

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

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

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

    Yes. Cheapflights offers flight deals from Stewart to Madison 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 New Windsor to Madison?

    Currently, January is the cheapest month in which you can book a flight from New Windsor to Madison (average of $338). Flying from New Windsor to Madison in March is currently the most expensive (average of $422). 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 Madison?

Book flights to Madison if you plan to visit one of these locations
Portage
Middleton
Baraboo
Fitchburg

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