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Stewart

$271+ Cheap flights from Islip to New Windsor (ISP - 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 3/8. Fares are subject to change and may not be available on all flights or dates of travel.
ISP — SWF
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheap flight deals from Islip to Stewart

Discover tips and strategies to find the most affordable flight options for your journey from Islip (ISP) 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 11, 2025.

Round-trip from

$656
(Kiwi.com)

One-way from

$271
(Kiwi.com)
From Islip Long Island to New Windsor Stewart
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One-way flight from Islip Long Island to New Windsor Stewart
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Find flight deals from Islip to Stewart

Cheapest flights from Islip to Stewart
Explore the most affordable flight options available from Islip to Stewart. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 11, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/10. 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 9/257:36 pmISP - SWF
2 stops16h 08mBreeze Airways
Mon 9/2912:24 pmSWF - ISP
1 stop7h 43mBreeze Airways
Deal found 9/10$656

Cheapflights Fare Finder

 
Customize your flight search to find flights from Islip 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 11, 2025.
Use the filters below to find and compare flights from Islip to New Windsor that are best for you.

Fly from

Islip

Fly to

Stewart

Route

Depart

Return

Price

IslipNew Windsor

ISP - SWF

ISPSWF

Islip Long Island

Thu 9/25

7:36 pm-11:44 am

2 stops16h 08m

New Windsor Stewart

Mon 9/29

12:24 pm-8:07 pm

1 stop7h 43m

$656

IslipNew Windsor

ISP - SWF

ISPSWF

Islip Long Island

Sun 3/8

7:26 pm-11:31 am

2 stops16h 05m

$271

IslipNew Windsor

ISP - SWF

ISPSWF

Islip Long Island

Sun 9/21

7:36 pm-11:44 am

2 stops16h 08m

$368

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/11

Best time to book a flight from Islip to Stewart

Have a flexible travel schedule? Discover the best time to fly to Stewart from Islip 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.

Related info for your journey

Find useful and relevant information for your journey from Islip 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 Islip to New Windsor?

    For as low as $656, Breeze Airways can have you in New Windsor from Islip in 16h 08m. The distance between Islip and New Windsor is about 72 mi.

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

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

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

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

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

    Yes. Cheapflights offers flight deals from Islip 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 Islip to New Windsor?

    Currently, October is the cheapest month in which you can book a flight from Islip to New Windsor (average of $109). Flying from Islip 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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