In terms of precipitation, rainfall in Boston ranges from 3.1 - 4.0 inches per month. March is typically the wettest month, when rainfall can reach 4.0 in. July is typically the driest time to visit Boston when rainfall is around 3.1 in.

If weather is an important factor for your trip to Boston, use this chart to help with planning. For those seeking warmer temperatures, July is the ideal time of year to visit, when temperatures reach an average of 73.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 30.2 F).

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

Find a great deal and save up to 242% by booking at least 54 days prior to your desired departure date, rather than waiting until the week of travel. According to our data, there are a number of flights available from New Windsor to Boston within the next two weeks, with the cheapest ticket starting at $177.

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

Due to multiple factors, expect to potentially pay more when booking in April. For low rates, September can be a great choice for travel to Boston. Flights to Boston from New Windsor in September are about $200 on average during September, but can be found for as low as $52.

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

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from New Windsor to Boston as you normally would.

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

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

How can I find direct flights from Stewart to Boston?

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

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

Yes. Cheapflights offers flight deals from Stewart to Boston 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 New Windsor to Boston

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

Find cheap flights from Stewart to Boston 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 Stewart to Boston

Round-trip from	$229 (Mytrip)
One-way from	$111 (Mytrip)
Popular in	April
Cheapest in	September
Average price	$197

From New Windsor Stewart to Boston Logan Intl

Search Deals

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

Search Deals

Highest demand for flights based on searches. 16% potential increase in price ($40 potential increase over avg. RT price).

Search Deals

Cheapest flight prices on average. 3% potential price decrease ($6 potential savings vs. average RT price).

Search Deals

Average for round-trip flights in July 2025

Search Deals

Find flight deals from Stewart to Boston

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

vie. 8/225:36 pmSWF - BOS

1 stop17h 42mMultiple Airlines

lun. 8/256:05 amBOS - SWF

1 stop10h 41mMultiple Airlines

Deal found 7/27

$229

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

vie. 8/225:36 pmSWF - BOS

1 stop17h 42mMultiple Airlines

lun. 8/256:05 amBOS - SWF

1 stop10h 41mMultiple Airlines

Deal found 7/27

$229

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

vie. 8/86:36 pmSWF - BOS

2 stops23h 45mMultiple Airlines

lun. 8/116:00 amBOS - SWF

2 stops13h 06mMultiple Airlines

Deal found 7/27

$441

vie. 8/225:36 pmSWF - BOS

1 stop17h 42mMultiple Airlines

lun. 8/256:05 amBOS - SWF

1 stop10h 41mMultiple Airlines

Deal found 7/27

$229

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

vie. 8/225:36 pmSWF - BOS

1 stop17h 42mMultiple Airlines

Deal found 7/28

$111

dom. 8/3112:13 pmSWF - BOS

2 stops21h 36mAllegiant Air

Deal found 7/28

$205

Fly from

Fly to

Route

Depart

Return

Price

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

vie. 8/22

5:36 pm-11:18 am

1 stop17h 42m

Boston Logan Intl

lun. 8/25

6:05 am-4:46 pm

1 stop10h 41m

$229

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

vie. 8/22

5:36 pm-11:18 am

1 stop17h 42m

$111

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

dom. 8/31

12:13 pm-9:49 am

2 stops21h 36m

$205

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/28

Best time to book a flight from Stewart to Boston

Have a flexible travel schedule? Discover the best time to fly to Boston 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 Boston

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

Currently, January is the cheapest month in which you can book a flight from New Windsor to Boston (average of $218). Flying from New Windsor to Boston in July is currently the most expensive (average of $311). 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 Boston

Read reviews from past customers who have flown Allegiant Air from New Windsor to Boston. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.

Allegiant Air

7.2

Good

702 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

7.2

Good

702 reviews

Allegiant Air

7.2

Good

702 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 Stewart to Boston that include hotel bookings?
Yes. In addition to deals on Stewart to Boston flights, Cheapflights offers vacation packages that include both flights and hotel.
How can I find direct flights from Stewart to Boston?
After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Stewart to Boston.
Can I find deals for business class flights from Stewart to Boston?
Yes. Cheapflights offers flight deals from Stewart to Boston 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 Boston?
Currently, January is the cheapest month in which you can book a flight from New Windsor to Boston (average of $218). Flying from New Windsor to Boston in July is currently the most expensive (average of $311). 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

Cambridge

Medford

Watertown

Warwick

Seabrook

Waltham

Framingham

Lowell

Randolph

Smithfield

Cranston

Chestnut Hill

York Beach

Chelsea

Saco

Burlington

Hampton Beach

Swansea

Lincoln

Quincy

Browse thousands of different options on Cheapflights for your next trip

Alternative routes for Stewart to Boston

Newark to Boston flights

LaGuardia to Boston flights

John F Kennedy Intl to Boston flights

John F Kennedy Intl to Nantucket flights

LaGuardia to West Tisbury flights

John F Kennedy Intl to West Tisbury flights

LaGuardia to Nantucket flights

Newark to Nantucket flights

Islip to Boston flights

Buffalo to Boston flights

John F Kennedy Intl to Hyannis flights

Rochester to Boston flights

Newark to West Tisbury flights

White Plains to Nantucket flights

White Plains to Boston flights

Syracuse to Boston flights

White Plains to West Tisbury flights

LaGuardia to Hyannis flights

Rochester to Hartford flights

Newark to Hyannis flights

LaGuardia to Albany flights

John F Kennedy Intl to Hartford flights

LaGuardia to Hartford flights

Newark to Hartford flights

John F Kennedy Intl to Albany flights

Newark to Albany flights

John F Kennedy Intl to Provincetown flights

John F Kennedy Intl to Worcester flights

White Plains to Hyannis flights

Albany to Boston flights

Newark to Provincetown flights

LaGuardia to Worcester flights

Buffalo to Hartford flights

Buffalo to Nantucket flights

Rochester to Nantucket flights

Islip to West Tisbury flights

Ithaca to Boston flights

Syracuse to Nantucket flights

Binghamton to Boston flights

White Plains to Provincetown flights

Rochester to West Tisbury flights

Saranac Lake to Boston flights

Buffalo to Albany flights

Rutland to Boston flights

LaGuardia to Provincetown flights

White Plains to Albany flights

Islip to Albany flights

White Plains to Hartford flights

Syracuse to West Tisbury flights

Other flights to Boston

Complete your trip

Boston car rentals

Boston Logan Intl Airport car rentals

Providence-TFGreen Airport car rentals

Manchester Airport car rentals

Bedford Hanscom Field Airport car rentals

Worcester car rentals

Springfield car rentals

Hyannis car rentals

Downtown car rentals

Back Bay car rentals

Seaport District car rentals

North End 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.

$111+ Cheap flights from New Windsor to Boston (SWF - BOS)

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 8/22. Fares are subject to change and may not be available on all flights or dates of travel.

Find cheap flights from Stewart to Boston with Cheapflights

1. Tell us where you want to go

2. Select your favorite providers

3. Compare prices and book

Cheap flight deals from Stewart to Boston

Round-trip from

One-way from

Popular in

Cheapest in

Average price

Find flight deals from Stewart to Boston

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

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

Cheapflights Fare Finder

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

Best time to book a flight from Stewart to Boston

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

Cheapflights Insights

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

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

Reviews of airlines servicing Boston

Read reviews from past customers who have flown Allegiant Air from New Windsor to Boston. Users can see the overall rating for each airline as well as how each is rated 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 Stewart to Boston. 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 Stewart to Boston that include hotel bookings?

How can I find direct flights from Stewart to Boston?

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

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

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 Stewart to Boston

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