HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Boston

$84+ 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 10/6. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — BOS
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

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

Discover tips and strategies to find the most affordable flight options for your journey from Stewart (SWF) to Boston (BOS). 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

$230
(Kiwi.com)

One-way from

$84
(Kiwi.com)

Popular in

April

Cheapest in

October

Average price

$157
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. 12% potential increase in price ($28 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($5 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in September 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 September 11, 2025.

This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
Fri 10/3111:31 amSWF - BOS
1 stop23h 45mMultiple Airlines
Sun 11/28:24 pmBOS - SWF
1 stop14h 47mMultiple Airlines
Deal found 9/9$227
This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
Fri 10/312:11 pmSWF - BOS
1 stop11h 46mMultiple Airlines
Sun 11/28:24 pmBOS - SWF
1 stop14h 47mMultiple Airlines
Deal found 9/9$230
This Kiwi.com deal was found by Cheapflights users on 9/11. 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.
Fri 10/1011:41 amSWF - BOS
1 stop23h 45mMultiple Airlines
Thu 10/168:24 pmBOS - SWF
1 stop14h 17mMultiple Airlines
Deal found 9/11$239
This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
Fri 10/1711:31 amSWF - BOS
1 stop23h 55mMultiple Airlines
Sun 10/198:24 pmBOS - SWF
1 stop13h 47mMultiple Airlines
Deal found 9/9$243
This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
Fri 10/312:11 pmSWF - BOS
1 stop23h 02mMultiple Airlines
Sun 10/59:55 amBOS - SWF
1 stop7h 00mMultiple Airlines
Deal found 9/9$252
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.
Fri 10/1011:41 amSWF - BOS
1 stop12h 18mMultiple Airlines
Sun 10/128:24 pmBOS - SWF
1 stop13h 47mMultiple Airlines
Deal found 9/10$257
This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
Fri 11/1411:01 amSWF - BOS
1 stop13h 39mMultiple Airlines
Sun 11/166:57 pmBOS - SWF
2 stops16h 14mMultiple Airlines
Deal found 9/9$268
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.
Fri 12/512:27 pmSWF - BOS
1 stop12h 13mMultiple Airlines
Sun 12/76:57 pmBOS - SWF
2 stops16h 40mMultiple Airlines
Deal found 9/10$271
This Kiwi.com deal was found by Cheapflights users on 9/9. 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.
Fri 10/2411:31 amSWF - BOS
1 stop23h 55mMultiple Airlines
Sun 10/269:55 amBOS - SWF
1 stop7h 00mMultiple Airlines
Deal found 9/9$275

Cheapflights Fare Finder

 
Customize your flight search to find flights from Stewart to Boston 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 New Windsor to Boston that are best for you.

Fly from

Stewart

Fly to

Boston

Route

Depart

Return

Price

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Fri 10/31

11:31 am-11:16 am

1 stop23h 45m

Boston Logan Intl

Sun 11/2

8:24 pm-11:11 am

1 stop14h 47m

$227

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Fri 10/3

12:11 pm-11:57 pm

1 stop11h 46m

Boston Logan Intl

Sun 11/2

8:24 pm-11:11 am

1 stop14h 47m

$230

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Fri 10/10

11:41 am-11:26 am

1 stop23h 45m

Boston Logan Intl

Thu 10/16

8:24 pm-10:41 am

1 stop14h 17m

$239

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Fri 10/17

11:31 am-11:26 am

1 stop23h 55m

Boston Logan Intl

Sun 10/19

8:24 pm-10:11 am

1 stop13h 47m

$243

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Fri 10/10

11:41 am-11:59 pm

1 stop12h 18m

Boston Logan Intl

Sun 10/12

8:24 pm-10:11 am

1 stop13h 47m

$257

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Fri 10/24

11:31 am-11:26 am

1 stop23h 55m

Boston Logan Intl

Sun 10/26

9:55 am-4:55 pm

1 stop7h 00m

$275

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Fri 10/3

12:11 pm-11:13 am

1 stop23h 02m

Boston Logan Intl

Sun 10/5

9:55 am-4:55 pm

1 stop7h 00m

$276

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Mon 10/6

11:01 am-11:26 am

1 stop24h 25m

$84

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Fri 10/3

12:11 pm-11:13 am

1 stop23h 02m

$89

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Fri 10/17

11:31 am-11:26 am

1 stop23h 55m

$92

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/10

Showing 1-10 of 13 results
1
2

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.

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?

    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

Traveling to a place near Boston?

Book flights to Boston if you plan to visit one of these locations
Cambridge
Medford
Hampton Beach
Watertown
Seabrook
Seekonk
Lincoln
Lowell
Smithfield
Cranston
Chestnut Hill
Chelsea
Warwick
Peabody
Quincy
York Beach
Swansea
Waltham
Saugus
Burlington

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.
Newark to Boston flights
LaGuardia to Boston flights
John F Kennedy Intl to Boston flights
Islip to Boston flights
Rochester to Boston flights
John F Kennedy Intl to Nantucket flights
White Plains to Boston flights
Syracuse to Boston flights
Newark to Nantucket flights
Buffalo to Boston flights
John F Kennedy Intl to West Tisbury flights
LaGuardia to Nantucket flights
John F Kennedy Intl to Albany flights
Newark to West Tisbury flights
LaGuardia to Albany flights
Newark to Albany flights
John F Kennedy Intl to Hyannis flights
White Plains to Nantucket flights
White Plains to West Tisbury flights
Newark to Hyannis flights
Rochester to Hartford flights
John F Kennedy Intl to Hartford flights
Ithaca to Boston flights
LaGuardia to Worcester flights
Newark to Hartford flights
John F Kennedy Intl to Worcester flights
Buffalo to Albany flights
Albany to Boston flights
Buffalo to Hartford flights
LaGuardia to Hartford flights
Rutland to Boston flights
Islip to West Tisbury flights
White Plains to Hyannis flights
White Plains to Albany flights
Watertown to Boston flights
Islip to Albany flights
White Plains to Hartford flights
LaGuardia to West Tisbury flights
John F Kennedy Intl to Provincetown flights
Binghamton to Boston flights
Elmira to Boston flights
White Plains to Provincetown flights
Buffalo to Hyannis flights
Buffalo to Worcester flights
Syracuse to Hyannis flights
Saranac Lake to Boston flights
Buffalo to Nantucket flights
LaGuardia to Hyannis flights
Syracuse to West Tisbury flights

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.