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$112+ 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 9/11. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — BOS
Aug 25 — Sep 11
Tue 8/25
Tue 9/1
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 July 26, 2026.

This Kiwi.com deal was found by Cheapflights users on 7/23. 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.
Sat 9/512:05 pm
SWF
-
BOS
1 stop23h 45m
Multiple Airlines
Thu 9/1011:05 am
BOS
-
SWF
2 stops24h 31m
Multiple Airlines
Deal found 7/23$387
This Kiwi.com deal was found by Cheapflights users on 7/24. 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.
Sat 7/2512:05 pm
SWF
-
BOS
2 stops21h 04m
Multiple Airlines
Sat 8/110:04 am
BOS
-
SWF
1 stop23h 49m
Multiple Airlines
Deal found 7/24$749
This Kiwi.com deal was found by Cheapflights users on 7/23. 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 8/610:33 am
SWF
-
BOS
1 stop22h 36m
Multiple Airlines
Sun 8/910:04 am
BOS
-
SWF
2 stops25h 33m
Multiple Airlines
Deal found 7/23$774
This Kiwi.com deal was found by Cheapflights users on 7/23. 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 7/247:41 pm
SWF
-
BOS
2 stops38h 09m
Multiple Airlines
Fri 7/318:41 am
BOS
-
SWF
1 stop26h 44m
Multiple Airlines
Deal found 7/23$945

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 July 26, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$387
(Kiwi.com)

One-way from

$112
(Kiwi.com)

Popular in

April

Cheapest in

November

Average price

$234
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. 10% potential increase in price ($30 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 3% potential price decrease ($8 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 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 July 26, 2026.
Use the filters below to find and compare flights from New Windsor to Boston that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Sat 9/5

12:05 pm-11:50 am

1 stop23h 45m

Boston Logan Intl

Thu 9/10

11:05 am-11:36 am

2 stops24h 31m

$387
Quickest round-trip

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Thu 8/6

10:33 am-9:09 am

1 stop22h 36m

Boston Logan Intl

Sun 8/9

10:04 am-11:37 am

2 stops25h 33m

$774
Cheapest one-way

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Fri 9/11

12:16 pm-10:51 am

2 stops22h 35m

$128

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Sat 8/29

12:05 pm-11:50 am

1 stop23h 45m

$158

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Sat 9/26

12:39 pm-10:32 am

1 stop21h 53m

$176

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Thu 9/10

10:56 am-10:09 am

1 stop23h 13m

$192
Quickest one-way

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Wed 10/7

12:39 pm-8:20 am

2 stops19h 41m

$194

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Wed 9/2

12:05 pm-9:09 am

2 stops21h 04m

$198

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Fri 11/6

11:09 am-8:19 am

2 stops21h 10m

$200

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Fri 8/14

7:35 pm-9:50 am

2 stops38h 15m

$226

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/26

Showing 1-10 of 12 resultsSorted by cheapest first
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 July.
ProviderPrice AccuracyTrust Score*
ExpediaPrice Accuracy1 starTrust Score*3 stars
FlightHubPrice Accuracy3 starsTrust Score*3 stars

*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 FlightHub the most. FlightHub 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.

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.

Traveling to a place near Boston?

Book flights to Boston if you plan to visit one of these locations
Waltham
Cambridge
Concord
Randolph
Brockton
Seekonk
Hampton Beach
Cranston
Warwick
Peabody
Dedham
Auburn
York Beach
Chelsea
Londonderry
Swansea
Fitchburg
North Falmouth
Braintree
Revere

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