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$344+ 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 12/23. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — MSN
Jan 8 — Jan 151
Thu 1/8
Thu 1/15
1 adult, Economy
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Cheap 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 December 9, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/8. 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 12/198:11 pmSWF - MSN
1 stop22h 17mMultiple Airlines
Wed 12/316:08 pmMSN - SWF
1 stop15h 55mMultiple Airlines
Deal found 12/8$458
This Kiwi.com deal was found by Cheapflights users on 12/8. 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 12/1912:24 pmSWF - MSN
2 stops30h 04mBreeze Airways
Wed 12/316:08 pmMSN - SWF
1 stop15h 55mBreeze Airways
Deal found 12/8$543
This Kiwi.com deal was found by Cheapflights users on 12/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/198:11 pmSWF - MSN
1 stop22h 17mMultiple Airlines
Sat 1/36:08 pmMSN - SWF
1 stop15h 55mMultiple Airlines
Deal found 12/7$570
This Kiwi.com deal was found by Cheapflights users on 12/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/2311:43 amSWF - MSN
1 stop30h 45mBreeze Airways
Wed 12/316:08 pmMSN - SWF
1 stop15h 55mBreeze Airways
Deal found 12/7$577
This Kiwi.com deal was found by Cheapflights users on 12/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/2311:43 amSWF - MSN
1 stop30h 45mBreeze Airways
Sat 1/36:08 pmMSN - SWF
1 stop15h 55mBreeze Airways
Deal found 12/7$633
This Kiwi.com deal was found by Cheapflights users on 12/8. 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 12/1912:24 pmSWF - MSN
2 stops30h 04mBreeze Airways
Sat 1/36:08 pmMSN - SWF
1 stop15h 55mBreeze Airways
Deal found 12/8$666
This Kiwi.com deal was found by Cheapflights users on 12/8. 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 12/1912:24 pmSWF - MSN
2 stops21h 44mBreeze Airways
Sat 12/206:08 pmMSN - SWF
1 stop15h 55mBreeze Airways
Deal found 12/8$901
This Kiwi.com deal was found by Cheapflights users on 12/8. 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 12/2612:24 pmSWF - MSN
2 stops30h 04mBreeze Airways
Wed 12/316:08 pmMSN - SWF
1 stop15h 55mBreeze Airways
Deal found 12/8$1,336

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 December 9, 2025.

Most accurate provider

eDreams
3 stars

Most trusted provider

eDreams
3 stars

Round-trip from

$453
(Kiwi.com)

One-way from

$344
(Kiwi.com)

Popular in

August

Cheapest in

September

Average price

$467
Provider with most accurate pricing for New Windsor Stewart-Madison Truax Field flight deals.
Search Deals
Provider most trusted by Cheapflights users for New Windsor Stewart-Madison Truax Field flights.
Search Deals
From New Windsor Stewart to Madison Truax Field
Search Deals
One-way flight from New Windsor Stewart to Madison Truax Field
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. 1% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
Search Deals

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 December 9, 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 12/19

8:11 pm-5:28 pm

1 stop22h 17m

Madison Truax Field

Wed 12/31

6:08 pm-11:03 am

1 stop15h 55m

$458

New WindsorMadison

SWF - MSN

SWFMSN

New Windsor Stewart

Fri 12/19

12:24 pm-5:28 pm

2 stops30h 04m

Madison Truax Field

Wed 12/31

6:08 pm-11:03 am

1 stop15h 55m

$543

New WindsorMadison

SWF - MSN

SWFMSN

New Windsor Stewart

Fri 12/19

8:11 pm-5:28 pm

1 stop22h 17m

Madison Truax Field

Sat 1/3

6:08 pm-11:03 am

1 stop15h 55m

$570

New WindsorMadison

SWF - MSN

SWFMSN

New Windsor Stewart

Tue 12/23

11:43 am-5:28 pm

1 stop30h 45m

Madison Truax Field

Wed 12/31

6:08 pm-11:03 am

1 stop15h 55m

$577

New WindsorMadison

SWF - MSN

SWFMSN

New Windsor Stewart

Tue 12/23

11:43 am-5:28 pm

1 stop30h 45m

Madison Truax Field

Sat 1/3

6:08 pm-11:03 am

1 stop15h 55m

$633

New WindsorMadison

SWF - MSN

SWFMSN

New Windsor Stewart

Fri 12/19

12:24 pm-5:28 pm

2 stops30h 04m

Madison Truax Field

Sat 1/3

6:08 pm-11:03 am

1 stop15h 55m

$666

New WindsorMadison

SWF - MSN

SWFMSN

New Windsor Stewart

Fri 12/26

12:24 pm-5:28 pm

2 stops30h 04m

Madison Truax Field

Wed 12/31

6:08 pm-11:03 am

1 stop15h 55m

$1,336

New WindsorMadison

SWF - MSN

SWFMSN

New Windsor Stewart

Tue 12/23

11:43 am-5:28 pm

1 stop30h 45m

$344

New WindsorMadison

SWF - MSN

SWFMSN

New Windsor Stewart

Fri 12/19

12:24 pm-5:28 pm

2 stops30h 04m

$347

New WindsorMadison

SWF - MSN

SWFMSN

New Windsor Stewart

Mon 12/22

7:10 pm-9:08 am

3 stops38h 58m

$363

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/8

Showing 1-10 of 13 results
1
2

Compare providers for flights from Stewart 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 Stewart to Madison in December.
ProviderPrice AccuracyTrust Score*
FlightHubPrice Accuracy3 starsTrust Score*1 star
eDreamsPrice Accuracy3 starsTrust Score*3 stars

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on New Windsor-Madison flights, users find the pricing of eDreams to be most consistent on Cheapflights vs. eDreams Users can find the same prices on New Windsor-Madison flight deals on Cheapflights vs. eDreams >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 eDreams the most. eDreams 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

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

Currently, May is the cheapest month in which you can book a flight from New Windsor to Madison (average of $55). Flying from New Windsor to Madison in April is currently the most expensive (average of $236). 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.

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

    A quick flight from New Windsor to Madison can take about 30h 04m. Breeze Airways provides one of the quickest options available for as low as $543. Airlines will cover a distance of 785 mi.

  • 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, May is the cheapest month in which you can book a flight from New Windsor to Madison (average of $55). Flying from New Windsor to Madison in April is currently the most expensive (average of $236). 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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