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$117+ 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 4/9. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — BOS
Apr 9 — Apr 161
Thu 4/9
Thu 4/16
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 March 10, 2026.

This Kiwi.com deal was found by Cheapflights users on 3/9. 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 5/295:53 pm
SWF
-
BOS
1 stop13h 54m
Multiple Airlines
Tue 6/210:12 am
BOS
-
SWF
1 stop25h 13m
Multiple Airlines
Deal found 3/9$283
This Kiwi.com deal was found by Cheapflights users on 3/7. 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 5/2810:28 am
SWF
-
BOS
1 stop13h 29m
Multiple Airlines
Sun 5/3112:22 pm
BOS
-
SWF
1 stop5h 39m
Multiple Airlines
Deal found 3/7$311
This Kiwi.com deal was found by Cheapflights users on 3/7. 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 4/2311:45 am
SWF
-
BOS
2 stops20h 13m
Multiple Airlines
Sat 4/258:16 pm
BOS
-
SWF
1 stop14h 39m
Multiple Airlines
Deal found 3/7$322
This Kiwi.com deal was found by Cheapflights users on 3/7. 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 5/295:53 pm
SWF
-
BOS
1 stop13h 54m
Multiple Airlines
Sun 5/3112:22 pm
BOS
-
SWF
1 stop5h 39m
Multiple Airlines
Deal found 3/7$360
This Kiwi.com deal was found by Cheapflights users on 3/10. 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.
Thu 7/3010:28 am
SWF
-
BOS
1 stop13h 26m
Multiple Airlines
Mon 8/39:15 am
BOS
-
SWF
1 stop7h 44m
Multiple Airlines
Deal found 3/10$421
This Kiwi.com deal was found by Cheapflights users on 3/8. 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 5/711:45 am
SWF
-
BOS
1 stop12h 12m
Multiple Airlines
Sun 5/109:36 am
BOS
-
SWF
2 stops9h 21m
Multiple Airlines
Deal found 3/8$426
This Kiwi.com deal was found by Cheapflights users on 3/6. 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 3/2610:29 am
SWF
-
BOS
1 stop13h 30m
Multiple Airlines
Sun 3/294:23 pm
BOS
-
SWF
1 stop16h 34m
Multiple Airlines
Deal found 3/6$447
This Kiwi.com deal was found by Cheapflights users on 3/7. 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 4/306:15 pm
SWF
-
BOS
1 stop13h 32m
Multiple Airlines
Sun 5/38:42 am
BOS
-
SWF
1 stop8h 43m
Multiple Airlines
Deal found 3/7$456
This Kiwi.com deal was found by Cheapflights users on 3/8. 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 5/1011:45 am
SWF
-
BOS
1 stop12h 12m
Multiple Airlines
Sun 5/178:42 am
BOS
-
SWF
1 stop8h 43m
Multiple Airlines
Deal found 3/8$466

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 March 10, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$283
(Kiwi.com)

One-way from

$117
(Kiwi.com)

Popular in

February

Cheapest in

November

Average price

$254
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. 6% potential increase in price ($16 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($4 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in March 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 March 10, 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 5/29

5:53 pm-7:47 am

1 stop13h 54m

Boston Logan Intl

Tue 6/2

10:12 am-11:25 am

1 stop25h 13m

$283

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Thu 5/28

10:28 am-11:57 pm

1 stop13h 29m

Boston Logan Intl

Sun 5/31

12:22 pm-6:01 pm

1 stop5h 39m

$311

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Fri 6/12

5:55 pm-7:47 am

1 stop13h 52m

Boston Logan Intl

Sun 6/14

12:22 pm-5:43 pm

1 stop5h 21m

$322

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Thu 5/7

11:45 am-11:57 pm

1 stop12h 12m

Boston Logan Intl

Sun 5/10

9:36 am-6:57 pm

2 stops9h 21m

$426

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Thu 4/30

6:15 pm-7:47 am

1 stop13h 32m

Boston Logan Intl

Sun 5/3

8:42 am-5:25 pm

1 stop8h 43m

$456

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Sun 5/10

11:45 am-11:57 pm

1 stop12h 12m

Boston Logan Intl

Sun 5/17

8:42 am-5:25 pm

1 stop8h 43m

$466

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Fri 3/27

9:47 am-9:54 am

1 stop24h 07m

Boston Logan Intl

Sun 3/29

4:23 pm-8:57 am

1 stop16h 34m

$525
Quickest round-trip

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Thu 7/16

9:38 am-7:35 pm

2 stops9h 57m

Boston Logan Intl

Mon 7/20

9:15 am-4:59 pm

1 stop7h 44m

$529

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Thu 6/18

6:33 pm-8:20 am

1 stop13h 47m

Boston Logan Intl

Mon 6/22

9:15 am-5:00 pm

1 stop7h 45m

$551
Cheapest one-way
Quickest one-way

New WindsorBoston

SWF - BOS

SWFBOS

New Windsor Stewart

Thu 4/9

11:45 am-11:59 pm

1 stop12h 14m

$117

Flights are sorted by cheapest round-trip flights first.

Deals found on 3/6

Showing 1-10 of 17 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 March.
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.

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 March is currently the most expensive (average of $121). 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 March is currently the most expensive (average of $121). 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
Medford
Cambridge
Concord
Hampton Beach
Watertown
Seekonk
Brockton
Seabrook
Cranston
Chelsea
Smithfield
Lincoln
Warwick
Peabody
Waltham
York Beach
Londonderry
Swansea
Old Orchard Beach
Quincy

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