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Stewart

$236+ Cheap flights from San Jose, CA to New Windsor (SJC - SWF)

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 11/24. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — SWF
Nov 28 — Dec 51
Fri 11/28
Fri 12/5
1 adult, Economy
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Find flight deals from San Jose to Stewart

One-way flights from San Jose to Stewart
Search for one-way flight options from San Jose to Stewart. Find affordable one-way fares based on user searches. Data last updated October 29, 2025.

This Kiwi.com deal was found by Cheapflights users on 10/28. 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 11/244:40 pmSJC - SWF
3 stops39h 47mMultiple Airlines
Deal found 10/28$236
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 12/73:27 pmSJC - SWF
2 stops17h 10mMultiple Airlines
Deal found 10/29$277
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 11/234:20 pmSJC - SWF
3 stops37h 33mMultiple Airlines
Deal found 10/27$282
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 11/2212:42 pmSJC - SWF
3 stops42h 25mMultiple Airlines
Deal found 10/28$284
This Kiwi.com deal was found by Cheapflights users on 10/27. 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.
Tue 11/2512:42 pmSJC - SWF
2 stops43h 21mMultiple Airlines
Deal found 10/27$288
This Kiwi.com deal was found by Cheapflights users on 10/26. 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 12/253:27 pmSJC - SWF
2 stops16h 40mMultiple Airlines
Deal found 10/26$290
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 11/146:19 pmSJC - SWF
3 stops37h 44mMultiple Airlines
Deal found 10/29$313

Cheap flight deals from San Jose to Stewart

Discover tips and strategies to find the most affordable flight options for your journey from San Jose (SJC) to Stewart (SWF). 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 29, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

Expedia
3 stars

Popular in

December

Cheapest in

February

Average price

$364
Provider with most accurate pricing for San Jose-New Windsor Stewart flight deals.
Search Deals
Provider most trusted by Cheapflights users for San Jose-New Windsor Stewart flights.
Search Deals
Highest demand for flights based on searches. 8% potential increase in price ($31 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in October 2025
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from San Jose to Stewart 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 October 29, 2025.
Use the filters below to find and compare flights from San Jose to New Windsor that are best for you.

Fly from

San Jose

Fly to

Stewart

Route

Depart

Return

Price

San JoseNew Windsor

SJC - SWF

SJCSWF

San Jose

Mon 11/24

4:40 pm-11:27 am

3 stops39h 47m

$262

San JoseNew Windsor

SJC - SWF

SJCSWF

San Jose

Sun 12/7

3:27 pm-11:37 am

2 stops17h 10m

$277

San JoseNew Windsor

SJC - SWF

SJCSWF

San Jose

Sun 11/23

4:20 pm-8:53 am

3 stops37h 33m

$282

San JoseNew Windsor

SJC - SWF

SJCSWF

San Jose

Thu 12/25

3:27 pm-11:07 am

2 stops16h 40m

$282

San JoseNew Windsor

SJC - SWF

SJCSWF

San Jose

Sat 11/22

12:42 pm-10:07 am

3 stops42h 25m

$309

San JoseNew Windsor

SJC - SWF

SJCSWF

San Jose

Fri 11/14

6:19 pm-11:03 am

3 stops37h 44m

$313

San JoseNew Windsor

SJC - SWF

SJCSWF

San Jose

Mon 2/9

6:02 pm-4:56 pm

3 stops43h 54m

$366

San JoseNew Windsor

SJC - SWF

SJCSWF

San Jose

Sun 1/4

3:27 pm-11:44 am

3 stops17h 17m

$389

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/26

Compare providers for flights from San Jose to Stewart

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 San Jose to Stewart in October.
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 San Jose, California-New Windsor flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on San Jose, California-New Windsor flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from San Jose, California-New Windsor flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on San Jose, California-New Windsor 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 San Jose, California-New Windsor 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 San Jose to Stewart

Have a flexible travel schedule? Discover the best time to fly to Stewart from San Jose 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 San Jose to New Windsor

What is the cheapest month to book a flight from San Jose, California to New Windsor?

Currently, January is the cheapest month in which you can book a flight from San Jose, California to New Windsor (average of $64). Flying from San Jose, California to New Windsor in June is currently the most expensive (average of $202). 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 San Jose to Stewart. 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 San Jose to Stewart that include hotel bookings?

    Yes. In addition to deals on San Jose to Stewart flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from San Jose to Stewart?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from San Jose to Stewart.

  • Can I find deals for business class flights from San Jose to Stewart?

    Yes. Cheapflights offers flight deals from San Jose to Stewart 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 San Jose, California to New Windsor?

    Currently, January is the cheapest month in which you can book a flight from San Jose, California to New Windsor (average of $64). Flying from San Jose, California to New Windsor in June is currently the most expensive (average of $202). 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 New Windsor?

Book flights to New Windsor if you plan to visit one of these locations
Kingston

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