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$124+ 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 6/5. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — BOS
May 23 — May 301
Sat 5/23
Sat 5/30
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 April 23, 2026.

This Kiwi.com deal was found by Cheapflights users on 4/19. 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.
Fri 6/125:55 pm
SWF
-
BOS
1 stop18h 16m
Multiple Airlines
Sat 6/278:41 pm
BOS
-
SWF
1 stop21h 02m
Multiple Airlines
Deal found 4/19$389
This Kiwi.com deal was found by Cheapflights users on 4/19. 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.
Fri 7/105:49 pm
SWF
-
BOS
1 stop25h 49m
Multiple Airlines
Tue 9/88:41 pm
BOS
-
SWF
2 stops14h 58m
Multiple Airlines
Deal found 4/19$393
This Kiwi.com deal was found by Cheapflights users on 4/18. 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 6/216:33 pm
SWF
-
BOS
1 stop20h 10m
Multiple Airlines
Fri 6/269:12 pm
BOS
-
SWF
2 stops21h 58m
Multiple Airlines
Deal found 4/18$397
This Kiwi.com deal was found by Cheapflights users on 4/20. 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 5/289:38 am
SWF
-
BOS
1 stop12h 04m
Multiple Airlines
Sun 5/316:29 pm
BOS
-
SWF
1 stop22h 34m
Multiple Airlines
Deal found 4/20$401
This Kiwi.com deal was found by Cheapflights users on 4/21. 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.
Sun 6/79:38 am
SWF
-
BOS
1 stop12h 04m
Multiple Airlines
Sun 6/1410:38 am
BOS
-
SWF
2 stops22h 11m
Multiple Airlines
Deal found 4/21$414
This Kiwi.com deal was found by Cheapflights users on 4/21. 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.
Sun 6/79:38 am
SWF
-
BOS
1 stop12h 04m
Multiple Airlines
Fri 6/1212:01 pm
BOS
-
SWF
2 stops23h 24m
Multiple Airlines
Deal found 4/21$426
This Kiwi.com deal was found by Cheapflights users on 4/21. 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.
Sat 6/276:45 pm
SWF
-
BOS
1 stop19h 58m
Multiple Airlines
Sat 7/412:04 pm
BOS
-
SWF
2 stops21h 34m
Multiple Airlines
Deal found 4/21$464
This Kiwi.com deal was found by Cheapflights users on 4/22. 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 5/1612:05 pm
SWF
-
BOS
2 stops21h 07m
Multiple Airlines
Thu 5/216:29 pm
BOS
-
SWF
1 stop22h 34m
Multiple Airlines
Deal found 4/22$478
This Kiwi.com deal was found by Cheapflights users on 4/21. 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 6/265:55 pm
SWF
-
BOS
1 stop25h 43m
Multiple Airlines
Sat 7/412:04 pm
BOS
-
SWF
2 stops21h 34m
Multiple Airlines
Deal found 4/21$480
This Kiwi.com deal was found by Cheapflights users on 4/18. 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 5/311:48 am
SWF
-
BOS
1 stop22h 43m
Multiple Airlines
Thu 5/77:00 am
BOS
-
SWF
2 stops28h 37m
Multiple Airlines
Deal found 4/18$498
This Kiwi.com deal was found by Cheapflights users on 4/22. 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 5/2212:17 pm
SWF
-
BOS
2 stops9h 25m
Multiple Airlines
Sun 5/247:00 am
BOS
-
SWF
1 stop25h 51m
Multiple Airlines
Deal found 4/22$544

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 April 23, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$389
(Kiwi.com)

One-way from

$124
(Kiwi.com)

Popular in

April

Cheapest in

November

Average price

$319
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 ($28 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($7 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in April 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 April 23, 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

Fri 6/12

5:55 pm-12:11 pm

1 stop18h 16m

Boston Logan Intl

Sat 6/27

8:41 pm-5:43 pm

1 stop21h 02m

$389

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Fri 7/10

5:49 pm-7:38 pm

1 stop25h 49m

Boston Logan Intl

Tue 9/8

8:41 pm-11:39 am

2 stops14h 58m

$393

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Sun 6/21

6:33 pm-2:43 pm

1 stop20h 10m

Boston Logan Intl

Fri 6/26

9:12 pm-7:10 pm

2 stops21h 58m

$397

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Thu 5/28

9:38 am-1:24 am

2 stops15h 46m

Boston Logan Intl

Sun 5/31

6:29 pm-5:03 pm

1 stop22h 34m

$421

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Sat 6/27

6:45 pm-2:43 pm

1 stop19h 58m

Boston Logan Intl

Sat 7/4

12:04 pm-9:38 am

2 stops21h 34m

$464

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Sat 5/16

12:05 pm-9:12 am

2 stops21h 07m

Boston Logan Intl

Thu 5/21

6:29 pm-5:03 pm

1 stop22h 34m

$478

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Fri 6/26

5:55 pm-7:38 pm

1 stop25h 43m

Boston Logan Intl

Sat 7/4

12:04 pm-9:38 am

2 stops21h 34m

$480

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Sun 5/3

11:48 am-10:31 am

1 stop22h 43m

Boston Logan Intl

Thu 5/7

7:00 am-11:37 am

2 stops28h 37m

$498

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Mon 5/18

12:17 pm-9:42 pm

2 stops9h 25m

Boston Logan Intl

Wed 5/20

10:07 am-8:58 am

1 stop22h 51m

$546

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Thu 5/7

9:38 am-9:42 pm

1 stop12h 04m

Boston Logan Intl

Sun 5/10

9:36 am-6:57 pm

2 stops9h 21m

$588

Flights are sorted by cheapest round-trip flights first.

Deals found on 4/22

Showing 1-10 of 21 resultsSorted by cheapest first
1
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3

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 April.
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
Medford
Cambridge
Concord
Hampton Beach
Watertown
Brockton
Seekonk
Cranston
Chelsea
Warwick
Peabody
Seabrook
York Beach
Londonderry
Swansea
Old Orchard Beach
Quincy
Waltham
Lowell
Braintree

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