$126+ Cheap flights from New Windsor to Boston (SWF - BOS)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/9. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — BOS
Nov 21 — Nov 281
Round-trip
1 adult, Economy
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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
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Best
Last-minute
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Cheapest flights from Stewart to BostonExplore 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 October 22, 2026.
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 October 22, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/17. 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.
Wed 12/212:39 pm -
2 stops21h 00m
Sun 1/1010:29 am -
1 stop8h 42m
Deal found 10/17![Multiple Airlines logo]()
$301
This Kiwi.com deal was found by Cheapflights users on 10/21. 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 12/411:03 am -
1 stop23h 10m
Sun 12/611:08 am -
1 stop23h 05m
Deal found 10/21![Multiple Airlines logo]()
$328
This Kiwi.com deal was found by Cheapflights users on 10/17. 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.
Wed 12/212:39 pm -
2 stops21h 00m
Sat 1/1612:49 pm -
1 stop22h 46m
Deal found 10/17![Multiple Airlines logo]()
$356
This Kiwi.com deal was found by Cheapflights users on 10/18. 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.
Wed 12/912:39 pm -
2 stops21h 00m
Sun 12/1311:08 am -
1 stop23h 05m
Deal found 10/18![Multiple Airlines logo]()
$375
This Kiwi.com deal was found by Cheapflights users on 10/21. 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 12/610:38 am -
2 stops24h 01m
Sun 12/1311:08 am -
1 stop23h 05m
Deal found 10/21![Multiple Airlines logo]()
$455
This Kiwi.com deal was found by Cheapflights users on 10/20. 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.
Sun 11/111:58 am -
1 stop22h 11m
Tue 11/312:15 pm -
2 stops23h 24m
Deal found 10/20![Multiple Airlines logo]()
$571
This Kiwi.com deal was found by Cheapflights users on 10/20. 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 10/2910:56 am -
2 stops22h 15m
Sat 10/3110:19 am -
1 stop25h 49m
Deal found 10/20![Multiple Airlines logo]()
$574
This Kiwi.com deal was found by Cheapflights users on 10/17. 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 11/111:58 am -
1 stop22h 11m
Tue 11/1012:15 pm -
2 stops23h 24m
Deal found 10/17![Multiple Airlines logo]()
$590
This Kiwi.com deal was found by Cheapflights users on 10/17. 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 11/111:58 am -
2 stops20h 58m
Sat 11/710:19 am -
1 stop24h 51m
Deal found 10/17![Allegiant Air logo]()
$614
This Kiwi.com deal was found by Cheapflights users on 10/20. 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 11/1910:56 am -
1 stop23h 15m
Sun 11/2211:06 am -
1 stop23h 33m
Deal found 10/20![Multiple Airlines logo]()
$617
Best flights from Stewart to BostonDiscover carefully curated flight deals from Stewart to Boston that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 22, 2026.
Discover carefully curated flight deals from Stewart to Boston that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 22, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/17. 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.
Wed 12/212:39 pm -
2 stops21h 00m
Sun 1/1010:29 am -
1 stop8h 42m
Deal found 10/17![Multiple Airlines logo]()
$301
This Kiwi.com deal was found by Cheapflights users on 10/17. 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 11/111:58 am -
2 stops20h 58m
Sat 11/710:19 am -
1 stop24h 51m
Deal found 10/17![Allegiant Air logo]()
$614
This Kiwi.com deal was found by Cheapflights users on 10/21. 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 12/411:03 am -
1 stop23h 10m
Sun 12/611:08 am -
1 stop23h 05m
Deal found 10/21![Multiple Airlines logo]()
$328
This Kiwi.com deal was found by Cheapflights users on 10/18. 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.
Wed 12/912:39 pm -
2 stops21h 00m
Sun 12/1311:08 am -
1 stop23h 05m
Deal found 10/18![Multiple Airlines logo]()
$375
This Kiwi.com deal was found by Cheapflights users on 10/21. 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 12/610:38 am -
2 stops24h 01m
Sun 12/1311:08 am -
1 stop23h 05m
Deal found 10/21![Multiple Airlines logo]()
$455
This Kiwi.com deal was found by Cheapflights users on 10/17. 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 11/111:58 am -
1 stop22h 11m
Tue 11/1012:15 pm -
2 stops23h 24m
Deal found 10/17![Multiple Airlines logo]()
$590
This Kiwi.com deal was found by Cheapflights users on 10/18. 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.
Sat 11/2112:39 pm -
2 stops21h 32m
Sat 11/2811:06 am -
1 stop20h 50m
Deal found 10/18![Multiple Airlines logo]()
$716
This Kiwi.com deal was found by Cheapflights users on 10/20. 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.
Mon 11/2311:29 am -
1 stop22h 42m
Sat 11/2811:06 am -
1 stop20h 50m
Deal found 10/20![Multiple Airlines logo]()
$761
Last-minute flights from Stewart to BostonDiscover last-minute flight deals from Stewart to Boston. Data last updated October 22, 2026 and is based on user searches.
Discover last-minute flight deals from Stewart to Boston. Data last updated October 22, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 10/20. 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 10/2910:56 am -
2 stops22h 15m
Sat 10/3110:19 am -
1 stop25h 49m
Deal found 10/20![Multiple Airlines logo]()
$574
This Kiwi.com deal was found by Cheapflights users on 10/20. 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.
Sun 11/111:58 am -
1 stop22h 11m
Tue 11/312:15 pm -
2 stops23h 24m
Deal found 10/20![Multiple Airlines logo]()
$571
This Kiwi.com deal was found by Cheapflights users on 10/17. 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 11/111:58 am -
1 stop22h 11m
Tue 11/1012:15 pm -
2 stops23h 24m
Deal found 10/17![Multiple Airlines logo]()
$590
This Kiwi.com deal was found by Cheapflights users on 10/17. 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 11/111:58 am -
2 stops20h 58m
Sat 11/710:19 am -
1 stop24h 51m
Deal found 10/17![Allegiant Air logo]()
$614
This Kiwi.com deal was found by Cheapflights users on 10/18. 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 11/111:58 am -
1 stop22h 11m
Wed 11/412:39 pm -
2 stops21h 37m
Deal found 10/18![Multiple Airlines logo]()
$626
This Kiwi.com deal was found by Cheapflights users on 10/20. 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 11/1910:56 am -
1 stop23h 15m
Sun 11/2211:06 am -
1 stop23h 33m
Deal found 10/20![Multiple Airlines logo]()
$617
This Kiwi.com deal was found by Cheapflights users on 10/18. 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.
Sat 11/2112:39 pm -
2 stops21h 32m
Sat 11/2811:06 am -
1 stop20h 50m
Deal found 10/18![Multiple Airlines logo]()
$716
One-way flights from Stewart to BostonSearch for one-way flight options from Stewart to Boston. Find affordable one-way fares based on user searches. Data last updated October 22, 2026.
Search for one-way flight options from Stewart to Boston. Find affordable one-way fares based on user searches. Data last updated October 22, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/20. 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.
Wed 12/912:39 pm -
2 stops21h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![Multiple Airlines logo]()
$126
This Kiwi.com deal was found by Cheapflights users on 10/17. 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.
Wed 12/212:39 pm -
2 stops21h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/17![Multiple Airlines logo]()
$149
This Kiwi.com deal was found by Cheapflights users on 10/17. 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 12/512:39 pm -
2 stops21h 02m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/17![Multiple Airlines logo]()
$156
This Kiwi.com deal was found by Cheapflights users on 10/20. 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 12/1112:16 pm -
2 stops21h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![Multiple Airlines logo]()
$181
This Kiwi.com deal was found by Cheapflights users on 10/22. 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.
Wed 12/1612:39 pm -
2 stops23h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Multiple Airlines logo]()
$182
This Kiwi.com deal was found by Cheapflights users on 10/19. 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.
Mon 1/1111:58 am -
2 stops21h 31m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Multiple Airlines logo]()
$186
This Kiwi.com deal was found by Cheapflights users on 10/17. 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.
Wed 1/1312:39 pm -
2 stops21h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/17![Multiple Airlines logo]()
$189
This Kiwi.com deal was found by Cheapflights users on 10/21. 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 12/412:16 pm -
3 stops45h 25m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Multiple Airlines logo]()
$192
This Kiwi.com deal was found by Cheapflights users on 10/19. 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.
Sat 1/912:39 pm -
2 stops20h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/19![Multiple Airlines logo]()
$199
This Kiwi.com deal was found by Cheapflights users on 10/20. 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.
Sun 11/226:48 pm -
2 stops36h 53m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![Multiple Airlines logo]()
$201
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 October 22, 2026.
Most accurate provider | FlightHub 3 stars |
|---|---|
Most trusted provider | FlightHub 3 stars |
Round-trip from | $301 (Kiwi.com) |
One-way from | $126 (Kiwi.com) |
Popular in | September |
Cheapest in | December |
Average price | $325 |
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 7,457,451 searches. Data last updated October 22, 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
Cheapest round-trip
New WindsorBoston
SWF New Windsor Stewart - BOS Boston Logan Intl
SWFBOS
New Windsor Stewart
Wed 12/9
12:39 pm-9:39 am
2 stops21h 00m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$148
New WindsorBoston
SWF New Windsor Stewart - BOS Boston Logan Intl
SWFBOS
New Windsor Stewart
Fri 12/4
12:16 pm-9:41 am
3 stops45h 25m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$192
New WindsorBoston
SWF New Windsor Stewart - BOS Boston Logan Intl
SWFBOS
New Windsor Stewart
Sat 1/9
12:39 pm-9:06 am
2 stops20h 27m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$199
New WindsorBoston
SWF New Windsor Stewart - BOS Boston Logan Intl
SWFBOS
New Windsor Stewart
Wed 11/11
12:39 pm-11:44 am
3 stops23h 05m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$215
Quickest round-trip
New WindsorBoston
SWF New Windsor Stewart - BOS Boston Logan Intl
SWFBOS
New Windsor Stewart
Sat 12/19
12:39 pm-8:09 am
1 stop19h 30m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$230
New WindsorBoston
SWF New Windsor Stewart - BOS Boston Logan Intl
SWFBOS
New Windsor Stewart
Thu 12/3
11:06 am-10:11 am
1 stop23h 05m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$232
New WindsorBoston
SWF New Windsor Stewart - BOS Boston Logan Intl
SWFBOS
New Windsor Stewart
Fri 11/13
12:16 pm-9:29 am
3 stops21h 13m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$246
New WindsorBoston
SWF New Windsor Stewart - BOS Boston Logan Intl
SWFBOS
New Windsor Stewart
Fri 11/20
11:29 am-8:30 am
2 stops21h 01m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$247
New WindsorBoston
SWF New Windsor Stewart - BOS Boston Logan Intl
SWFBOS
New Windsor Stewart
Mon 11/23
11:29 am-8:30 am
2 stops21h 01m
Boston Logan Intl
Wed 12/31
12:00 am-12:00 am
Nonstop0h 00m
$251
New WindsorBoston
SWF New Windsor Stewart - BOS Boston Logan Intl
SWFBOS
New Windsor Stewart
Wed 12/2
12:39 pm-9:39 am
2 stops21h 00m
Boston Logan Intl
Sun 1/10
10:29 am-7:11 pm
1 stop8h 42m
$301
Showing 1-10 of 17 resultsSorted by cheapest first
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 October.
| Provider | Price Accuracy | Trust Score* |
|---|---|---|
| Price Accuracy1 star | Trust Score*3 stars | |
| Price Accuracy3 stars | Trust Score*3 stars |
- 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.
SWF-BOS
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.
Traveling to a place near Boston?
Book flights to Boston if you plan to visit one of these locationsWaltham
Randolph
Concord
Cambridge
Brockton
Dedham
Cranston
Warwick
Pawtucket
Peabody
Fitchburg
Londonderry
York Beach
Revere
North Falmouth
Chelsea
Swansea
Braintree
Auburn
Sandwich
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