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$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 2/26. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — BOS
Feb 20 — Feb 271
Fri 2/20
Fri 2/27
1 adult, Economy
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Cheap 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 January 21, 2026.

This Kiwi.com deal was found by Cheapflights users on 1/19. 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.
Thu 3/1911:48 am
SWF
-
BOS
1 stop9h 45m
Multiple Airlines
Sat 3/215:49 pm
BOS
-
SWF
1 stop15h 50m
Multiple Airlines
Deal found 1/19$320
This Kiwi.com deal was found by Cheapflights users on 1/19. 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.
Sun 2/16:49 pm
SWF
-
BOS
1 stop22h 55m
Multiple Airlines
Sun 3/19:57 am
BOS
-
SWF
1 stop7h 10m
Multiple Airlines
Deal found 1/19$340
This Kiwi.com deal was found by Cheapflights users on 1/20. 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.
Thu 2/1211:42 am
SWF
-
BOS
1 stop12h 02m
Multiple Airlines
Thu 2/199:57 am
BOS
-
SWF
1 stop7h 15m
Multiple Airlines
Deal found 1/20$353
This Kiwi.com deal was found by Cheapflights users on 1/20. 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 3/612:11 pm
SWF
-
BOS
2 stops9h 50m
Multiple Airlines
Sun 3/89:57 am
BOS
-
SWF
1 stop7h 09m
Multiple Airlines
Deal found 1/20$376
This Kiwi.com deal was found by Cheapflights users on 1/20. 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.
Thu 1/226:49 pm
SWF
-
BOS
1 stop22h 55m
Multiple Airlines
Thu 1/295:27 pm
BOS
-
SWF
1 stop16h 52m
Multiple Airlines
Deal found 1/20$466
This Kiwi.com deal was found by Cheapflights users on 1/21. 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.
Thu 1/226:49 pm
SWF
-
BOS
1 stop22h 55m
Multiple Airlines
Sat 1/246:39 pm
BOS
-
SWF
1 stop23h 20m
Multiple Airlines
Deal found 1/21$541
This Kiwi.com deal was found by Cheapflights users on 1/21. 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 1/237:33 pm
SWF
-
BOS
1 stop19h 05m
Multiple Airlines
Sun 1/255:27 pm
BOS
-
SWF
1 stop16h 52m
Multiple Airlines
Deal found 1/21$548
This Kiwi.com deal was found by Cheapflights users on 1/20. 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 2/1311:04 am
SWF
-
BOS
1 stop10h 57m
Multiple Airlines
Sun 3/19:57 am
BOS
-
SWF
1 stop7h 10m
Multiple Airlines
Deal found 1/20$568

Find 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 January 21, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Round-trip from

$320
(Kiwi.com)

One-way from

$111
(Kiwi.com)

Popular in

April

Cheapest in

November

Average price

$257
Provider with most accurate pricing for New Windsor Stewart-Boston Logan Intl flight deals.
Search Deals
Provider most trusted by Cheapflights users for New Windsor Stewart-Boston Logan Intl flights.
Search Deals
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. 3% potential increase in price ($8 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 0% potential price decrease ($2 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

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 January 21, 2026.
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

Thu 3/19

11:48 am-9:33 pm

1 stop9h 45m

Boston Logan Intl

Sat 3/21

5:49 pm-9:39 am

1 stop15h 50m

$320

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Sun 2/1

6:49 pm-5:44 pm

1 stop22h 55m

Boston Logan Intl

Sun 3/1

9:57 am-5:07 pm

1 stop7h 10m

$340

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Thu 2/12

11:42 am-11:44 pm

1 stop12h 02m

Boston Logan Intl

Thu 2/19

9:57 am-5:12 pm

1 stop7h 15m

$353

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Fri 3/6

12:11 pm-10:01 pm

2 stops9h 50m

Boston Logan Intl

Sun 3/8

9:57 am-5:06 pm

1 stop7h 09m

$376

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Fri 2/13

11:04 am-10:01 pm

1 stop10h 57m

Boston Logan Intl

Sun 3/1

9:57 am-5:07 pm

1 stop7h 10m

$568

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Fri 2/20

12:11 pm-10:01 pm

2 stops9h 50m

Boston Logan Intl

Sun 2/22

9:57 am-5:12 pm

1 stop7h 15m

$644

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Thu 2/26

11:52 am-11:44 pm

1 stop11h 52m

$111

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Thu 3/5

10:09 am-11:44 pm

1 stop13h 35m

$113

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Thu 3/12

10:09 am-11:59 pm

1 stop13h 50m

$141

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Mon 2/9

12:11 pm-11:19 pm

2 stops11h 08m

$146

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/20

Showing 1-10 of 13 results
1
2

Compare providers for flights from Stewart to Boston

Provider information is updated monthly. Please note that these providers often have deals for this flight, but the availability may vary on a day-by-day basis on Cheapflights.
Use the table below to compare price accuracy, trust ratings, and cancellation policies for each provider offering flight deals from Stewart to Boston in January.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy2 starsTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*1 star

*The Trust Score is based on feedback from users after their booking experience. It measures overall satisfaction, helping us identify issues like hidden fees, problems during the ticketing process, and the quality of customer service. This score is our best indicator of the provider's quality and reliability.

  • Most accurate provider: When it comes to deals on New Windsor-Boston flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on New Windsor-Boston flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from New Windsor-Boston flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on New Windsor-Boston 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 New Windsor-Boston 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 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, July is the cheapest month in which you can book a flight from New Windsor to Boston (average of $77). Flying from New Windsor to Boston in May is currently the most expensive (average of $136). 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, July is the cheapest month in which you can book a flight from New Windsor to Boston (average of $77). Flying from New Windsor to Boston in May is currently the most expensive (average of $136). 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
Seekonk
Brockton
Warwick
Seabrook
Cranston
Lincoln
Smithfield
Peabody
Quincy
York Beach
Londonderry
Swansea
Old Orchard Beach
Waltham
Lowell
Chelsea

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