What is the cheapest month to book a flight from Islip, New York to New Windsor?

Currently, October is the cheapest month in which you can book a flight from Islip, New York to New Windsor (average of $109). Flying from Islip, New York to New Windsor in August is currently the most expensive (average of $206). 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.

What is the cheapest time of day to fly from ISP to SWF?

When flying from Islip, New York to New Windsor, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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.

$307+ Flights from Islip, NY to New Windsor

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Cheap flight deals from Islip to Stewart

Round-trip from	$948 (Mytrip)
One-way from	$307 (FlightHub)

From Islip Long Island to New Windsor Stewart

Search Deals

One-way flight from Islip Long Island to New Windsor Stewart

Search Deals

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 julho 29, 2025.

seg 8/114:33 pmISP - SWF

2 stops19h 23mMultiple Airlines

sex 8/157:37 pmSWF - ISP

2 stops24h 24mMultiple Airlines

Deal found 7/27

$948

Best flights from Islip to Stewart
Discover carefully curated flight deals from Islip to Stewart that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated julho 29, 2025.

seg 8/114:33 pmISP - SWF

2 stops19h 23mMultiple Airlines

sex 8/157:37 pmSWF - ISP

2 stops24h 24mMultiple Airlines

Deal found 7/27

$948

qua 8/132:55 pmISP - SWF

2 stops28h 17mBreeze Airways

dom 8/177:52 pmSWF - ISP

2 stops19h 27mBreeze Airways

Deal found 7/29

$1,040

Last-minute flights from Islip to Stewart
Discover last-minute flight deals from Islip to Stewart. Data last updated julho 29, 2025 and is based on user searches.

seg 8/114:33 pmISP - SWF

2 stops19h 23mMultiple Airlines

sex 8/157:37 pmSWF - ISP

2 stops24h 24mMultiple Airlines

Deal found 7/27

$948

One-way flights from Islip to Stewart
Search for one-way flight options from Islip to Stewart. Find affordable one-way fares based on user searches. Data last updated julho 29, 2025.

dom 8/317:39 pmISP - SWF

2 stops17h 09mBreeze Airways

Deal found 7/27

$307

dom 8/317:30 amISP - SWF

2 stops10h 30mMultiple Airlines

Deal found 7/27

$431

Fly from

Fly to

Route

Depart

Return

Price

IslipNew Windsor

ISP - SWF

ISPSWF

Islip Long Island

seg 8/11

4:33 pm-11:56 am

2 stops19h 23m

New Windsor Stewart

sex 8/15

7:37 pm-8:01 pm

2 stops24h 24m

$948

IslipNew Windsor

ISP - SWF

ISPSWF

Islip Long Island

qua 8/13

2:55 pm-7:12 pm

2 stops28h 17m

New Windsor Stewart

dom 8/17

7:52 pm-3:19 pm

2 stops19h 27m

$1,040

IslipNew Windsor

ISP - SWF

ISPSWF

Islip Long Island

dom 8/31

7:39 pm-12:48 pm

2 stops17h 09m

$307

IslipNew Windsor

ISP - SWF

ISPSWF

Islip Long Island

dom 8/31

7:30 am-6:00 pm

2 stops10h 30m

$431

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/27

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.

Reviews of airlines servicing Stewart

Get a feel of what it's like to fly with Breeze Airways from Islip to New Windsor by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.

Breeze Airways

8.0

Very good

190 reviews

Reviews

1 / 13

8.0

Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!

Breeze Airways

8.0

Very good

190 reviews

Breeze Airways

8.0

Very good

190 reviews

Reviews

1 / 13

8.0

Excellent

Anonymous,Jul 2025

RIC - BDL

All went smoothly but the announcements from the crew were way to fast--approaching inaudible. Pilot announcements were perfect!

Related info for your journey

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, New York to New Windsor?
Currently, October is the cheapest month in which you can book a flight from Islip, New York to New Windsor (average of $109). Flying from Islip, New York to New Windsor in August is currently the most expensive (average of $206). 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

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Complete your trip

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$307+ Cheap flights from Islip, NY 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 8/31. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Islip to Stewart with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheap flight deals from Islip to Stewart

Round-trip from

One-way from

Find flight deals from Islip to Stewart

Cheapest flights from Islip to StewartExplore 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 julho 29, 2025.

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 julho 29, 2025.

Cheapflights Fare Finder

Use the filters below to find and compare flights from Islip to New Windsor that are best for you.

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.

Reviews of airlines servicing Stewart

Get a feel of what it's like to fly with Breeze Airways from Islip to New Windsor by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.

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.

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

How can I find direct flights from Islip to Stewart?

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

What is the cheapest month to book a flight from Islip, New York to New Windsor?

Traveling to a place near New Windsor?

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Islip to Stewart

See prices for flight routes from nearby airports that may be better suited for you.

100% Free

Book with Flexibility

Travel Smart

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 julho 29, 2025.