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 37 days before your planned departure. Booking around this time can save you about 119% on the cost of this flight compared to booking a flight leaving this week. We have found prices from $136 if you need a flight within two weeks. For flights within the next 72 hours, you can find tickets from as low as $256.

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 $156. You can even find prices in October for less than $156, as users have found deals to New Windsor from as low as $47. The month of April 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 32%.

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.

Most accurate provider : When it comes to deals on Boston-New Windsor flights, users find the pricing of Expedia to be most consistent on Cheapflights vs. Expedia Users can find the same prices on Boston-New Windsor flight deals on Cheapflights vs. Expedia <90% of the time. Price accuracy is based on data collected from Boston-New Windsor flight searches over the past month and is updated monthly.

Most trusted provider : When it comes to deals on Boston-New Windsor flights, Cheapflights users trust Expedia the most. Expedia 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 Boston-New Windsor flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

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.

$81+ Flights from Boston to New Windsor

Q: 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 $226). 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.

Q: E

Most trusted provider : When it comes to deals on Boston-New Windsor flights, Cheapflights users trust Expedia the most. Expedia 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 Boston-New Windsor flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Q: 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.

Q: 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.

Q: 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.

Home Search by date Vacation packages Hotels Flight deals Car rental Travel tips & news

Find cheap flights from Boston to Stewart with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Boston to Stewart

Most accurate provider	Expedia 1 star
Most trusted provider	Expedia 3 stars
Round-trip from	$234 (Mytrip)
One-way from	$81 (Mytrip)
Popular in	April
Cheapest in	October
Average price	$186

Provider with most accurate pricing for Boston Logan Intl-New Windsor Stewart flight deals.

Search Deals

Provider most trusted by Cheapflights users for Boston Logan Intl-New Windsor Stewart flights.

Search Deals

From Boston Logan Intl to New Windsor Stewart

Search Deals

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

Search Deals

Highest demand for flights based on searches. 8% potential increase in price ($13 potential increase over avg. RT price).

Search Deals

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

Search Deals

Average for round-trip flights in February 2025

Search Deals

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 February 4, 2025.

Thu 2/275:45 amBOS - SWF

1 stop11h 52mMultiple Airlines

Sun 3/26:27 pmSWF - BOS

1 stop5h 12mMultiple Airlines

Deal found 2/4

$234

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 February 4, 2025.

Thu 2/275:45 amBOS - SWF

1 stop11h 52mMultiple Airlines

Sun 3/26:27 pmSWF - BOS

1 stop5h 12mMultiple Airlines

Deal found 2/4

$234

Last-minute flights from Boston to Stewart
Discover last-minute flight deals from Boston to Stewart. Data last updated February 4, 2025 and is based on user searches.

Sun 2/96:25 amBOS - SWF

1 stop12h 49mMultiple Airlines

Sun 2/167:54 pmSWF - BOS

1 stop17h 35mMultiple Airlines

Deal found 2/4

$318

Thu 2/275:45 amBOS - SWF

1 stop11h 52mMultiple Airlines

Sun 3/26:27 pmSWF - BOS

1 stop5h 12mMultiple Airlines

Deal found 2/4

$234

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 February 4, 2025.

Wed 3/125:45 amBOS - SWF

1 stop11h 13mMultiple Airlines

Deal found 2/3

$81

Fri 7/119:01 amBOS - SWF

2 stops25h 12mAllegiant Air

Deal found 2/3

$253

Find flights from Boston to Stewart within your budget

Fly from

Fly to

Route

Depart

Return

Price

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Thu 2/27

5:45 am-5:37 pm

1 stop11h 52m

New Windsor Stewart

Sun 3/2

6:27 pm-11:39 pm

1 stop5h 12m

$234

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Wed 3/12

5:45 am-4:58 pm

1 stop11h 13m

$81

BostonNew Windsor

BOS - SWF

BOSSWF

Boston Logan Intl

Fri 7/11

9:01 am-10:13 am

2 stops25h 12m

$253

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/3

Most accurate provider: When it comes to deals on Boston-New Windsor flights, users find the pricing of Expedia to be most consistent on Cheapflights vs. Expedia Users can find the same prices on Boston-New Windsor flight deals on Cheapflights vs. Expedia <90% of the time. Price accuracy is based on data collected from Boston-New Windsor flight searches over the past month and is updated monthly.
Most trusted provider: When it comes to deals on Boston-New Windsor flights, Cheapflights users trust Expedia the most. Expedia 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 Boston-New Windsor 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 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.

Travel insights for flights from Boston to Stewart

Get recent, data-driven insights about flights from Boston to Stewart including ideal travel times, pricing trends, and more.

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 $226). 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.

Reviews of airlines servicing Stewart

Allegiant Air

7.3

Good

782 reviews

Reviews

1 / 20

10.0

Excellent

Joellen,Aug 2024

LAS - GEG

Boarding was a hassle. I’ve had the same guy before. Never enjoy seeing him.

Allegiant Air

7.3

Good

782 reviews

Allegiant Air

7.3

Good

782 reviews

Reviews

1 / 20

10.0

Excellent

Joellen,Aug 2024

LAS - GEG

Boarding was a hassle. I’ve had the same guy before. Never enjoy seeing him.

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 $226). 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

Kingston

Browse thousands of different options on Cheapflights for your next trip

Alternative routes for Boston to Stewart

Boston to Newark flights

Boston to LaGuardia flights

Boston to John F Kennedy Intl flights

Boston to Buffalo flights

Boston to Rochester flights

Boston to Syracuse flights

Boston to White Plains flights

Hartford to Newark flights

Hartford to John F Kennedy Intl flights

Albany to John F Kennedy Intl flights

Hartford to LaGuardia flights

Hartford to Buffalo flights

Albany to Buffalo flights

Worcester to Newark flights

Hartford to Rochester flights

Worcester to John F Kennedy Intl flights

Boston to Islip flights

Albany to Newark flights

Albany to LaGuardia flights

Boston to Ithaca flights

Boston to Albany flights

West Tisbury to LaGuardia flights

Albany to Rochester flights

West Tisbury to John F Kennedy Intl flights

Worcester to Buffalo flights

Hartford to Syracuse flights

Hyannis to LaGuardia flights

Boston to Massena flights

Hartford to White Plains flights

Boston to Saranac Lake flights

Hyannis to John F Kennedy Intl flights

Boston to Niagara Falls flights

Nantucket to John F Kennedy Intl flights

Nantucket to LaGuardia flights

Albany to White Plains flights

Boston to Rutland flights

West Tisbury to Newark flights

Albany to Plattsburgh flights

Boston to Binghamton flights

Hartford to Stewart flights

Albany to Stewart flights

Hyannis to Newark flights

Nantucket to Newark flights

Albany to Islip flights

Boston to Plattsburgh flights

Albany to Ogdensburg flights

Boston to Watertown flights

West Tisbury to Buffalo flights

Boston to Elmira flights

Complete your trip

New York John F Kennedy Intl Airport car rentals

Newark Airport car rentals

New York LaGuardia Airport car rentals

New Windsor Stewart Airport car rentals

New York car rentals

Rochester car rentals

Binghamton car rentals

Utica car rentals

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.

$81+ 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 3/12. 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

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheap flight deals from Boston to Stewart

Most accurate provider

Most trusted provider

Round-trip from

One-way from

Popular in

Cheapest in

Average price

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 February 4, 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 February 4, 2025.

Find flights from Boston to Stewart within your budget

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.

Travel insights for flights from Boston to Stewart

Get recent, data-driven insights about flights from Boston to Stewart including ideal travel times, pricing trends, and more.

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

Reviews of airlines servicing Stewart

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 Boston?

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 Boston 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 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 February 4, 2025.