How far in advance should I book a flight from Boston to New Windsor?

To save on the cost of your flight from Boston to New Windsor, book at least 42 days before your planned departure. Booking around this time can save you about 118% on the cost of this flight compared to booking a flight leaving this week. We have found prices from $157 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as $260.

What is the cheapest month to fly from Boston to New Windsor?

The best pricing can be found in the month of October. Prices to New Windsor from Boston average $187. You can even find prices in October for less than $187, as users have found deals to New Windsor from as low as $47. The month of June appears to be one of the more expensive times to travel to New Windsor from Boston. Flying in the targeted month can save you up to 28%.

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

When flying from Boston 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 Boston to Stewart that include hotel bookings?

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

How can I find direct flights from Boston to Stewart?

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

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

Yes. Cheapflights offers flight deals from Boston 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.

$111+ Flights from Boston to New Windsor

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Cheap flight deals from Boston to Stewart

Round-trip from	$238 (Mytrip)
One-way from	$111 (Mytrip)
Popular in	June
Cheapest in	October
Average price	$193

From Boston Logan Intl to New Windsor Stewart

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One-way flight from Boston Logan Intl to New Windsor Stewart

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Highest demand for flights based on searches. 13% potential increase in price ($30 potential increase over avg. RT price).

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Cheapest flight prices on average. 2% potential price decrease ($5 potential savings vs. average RT price).

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Average for round-trip flights in July 2025

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Find flight deals from Boston to Stewart

Cheapest flights from Boston to Stewart
Explore the most affordable flight options available from Boston to Stewart. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 29, 2025.

Mon 8/256:05 amBOS - SWF

1 stop10h 41mMultiple Airlines

Fri 8/291:55 pmSWF - BOS

1 stop9h 54mMultiple Airlines

Deal found 7/29

$237

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

Thu 8/286:55 pmBOS - SWF

1 stop18h 10mMultiple Airlines

Thu 9/42:04 pmSWF - BOS

1 stop9h 06mMultiple Airlines

Deal found 7/29

$238

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

Thu 8/710:08 amBOS - SWF

1 stop7h 44mMultiple Airlines

Sun 8/106:42 pmSWF - BOS

1 stop14h 21mMultiple Airlines

Deal found 7/29

$349

Mon 8/256:05 amBOS - SWF

1 stop10h 41mMultiple Airlines

Fri 8/291:55 pmSWF - BOS

1 stop9h 54mMultiple Airlines

Deal found 7/28

$256

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

Thu 10/98:03 pmBOS - SWF

1 stop14h 48mMultiple Airlines

Deal found 7/28

$111

Fly from

Fly to

Route

Depart

Return

Price

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Thu 8/28

6:55 pm-1:05 pm

1 stop18h 10m

New Windsor Stewart

Thu 9/4

2:04 pm-11:10 pm

1 stop9h 06m

$238

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Thu 10/9

8:03 pm-10:51 am

1 stop14h 48m

$111

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/28

Best time to book a flight from Boston to Stewart

Have a flexible travel schedule? Discover the best time to fly to Stewart from Boston 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 Boston to New Windsor

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

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

Related info for your journey

Can I find deals for flights from Boston to Stewart that include hotel bookings?
Yes. In addition to deals on Boston to Stewart flights, Cheapflights offers vacation packages that include both flights and hotel.
How can I find direct flights from Boston to Stewart?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Boston to Stewart.
Can I find deals for business class flights from Boston to Stewart?
Yes. Cheapflights offers flight deals from Boston 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 Boston to New Windsor?
Currently, October is the cheapest month in which you can book a flight from Boston to New Windsor (average of $109). Flying from Boston 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.

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$111+ Cheap flights from Boston to New Windsor (BOS - 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 10/9. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Boston to Stewart with Cheapflights

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2. Select your favorite providers

3. Compare prices and book

Cheap flight deals from Boston to Stewart

Round-trip from

One-way from

Popular in

Cheapest in

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Find flight deals from Boston to Stewart

Cheapest flights from Boston to StewartExplore the most affordable flight options available from Boston to Stewart. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 29, 2025.

Explore the most affordable flight options available from Boston to Stewart. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 29, 2025.

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

Best time to book a flight from Boston to Stewart

Have a flexible travel schedule? Discover the best time to fly to Stewart from Boston with our price prediction graph.

Cheapflights Insights

Everything you need to know about your flight from Boston to New Windsor

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

Related info for your journey

Find useful and relevant information for your journey from Boston 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 Boston to Stewart that include hotel bookings?

How can I find direct flights from Boston to Stewart?

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

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

Traveling to a place near New Windsor?

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Cheapest flights from Boston to Stewart
Explore the most affordable flight options available from Boston to Stewart. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 29, 2025.