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San Jose

$295+ Cheap flights from New Windsor to San Jose, CA (SWF - SJC)

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 3/1. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — SJC
Mar 26 — Apr 21
Thu 3/26
Thu 4/2
1 adult, Economy
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Cheap flight deals from Stewart to San Jose

One-way flights from Stewart to San Jose
Search for one-way flight options from Stewart to San Jose. Find affordable one-way fares based on user searches. Data last updated February 24, 2026.

This Kiwi.com deal was found by Cheapflights users on 2/22. 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.
Sun 3/111:52 am
SWF
-
SJC
3 stops23h 48m
Multiple Airlines
Deal found 2/22$295
This Kiwi.com deal was found by Cheapflights users on 2/20. 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 8/99:38 am
SWF
-
SJC
2 stops31h 04m
Multiple Airlines
Deal found 2/20$318
This Kiwi.com deal was found by Cheapflights users on 2/22. 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.
Sun 6/1410:28 am
SWF
-
SJC
2 stops29h 46m
Multiple Airlines
Deal found 2/22$338
This Kiwi.com deal was found by Cheapflights users on 2/23. 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.
Sun 8/29:38 am
SWF
-
SJC
2 stops31h 04m
Multiple Airlines
Deal found 2/23$409

Find flight deals from Stewart to San Jose

Discover tips and strategies to find the most affordable flight options for your journey from Stewart (SWF) to San Jose (SJC). 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 February 24, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Popular in

November

Cheapest in

January

Average price

$416
Provider with most accurate pricing for New Windsor Stewart-San Jose flight deals.
Search Deals
Provider most trusted by Cheapflights users for New Windsor Stewart-San Jose flights.
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($37 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in February 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Stewart to San Jose 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 February 24, 2026.
Use the filters below to find and compare flights from New Windsor to San Jose that are best for you.

Fly from

Stewart

Fly to

San Jose

Route

Depart

Return

Price

New WindsorSan Jose

SWF - SJC

SWFSJC

New Windsor Stewart

Sun 3/1

11:52 am-8:40 am

3 stops23h 48m

$295

New WindsorSan Jose

SWF - SJC

SWFSJC

New Windsor Stewart

Sun 8/9

9:38 am-1:42 pm

2 stops31h 04m

$318

New WindsorSan Jose

SWF - SJC

SWFSJC

New Windsor Stewart

Sun 6/14

10:28 am-1:14 pm

2 stops29h 46m

$338

New WindsorSan Jose

SWF - SJC

SWFSJC

New Windsor Stewart

Sun 8/2

9:38 am-1:42 pm

2 stops31h 04m

$409

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/22

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

Have a flexible travel schedule? Discover the best time to fly to San Jose 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 San Jose

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

Currently, December is the cheapest month in which you can book a flight from New Windsor to San Jose, California (average of $113). Flying from New Windsor to San Jose, California in July is currently the most expensive (average of $190). 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 San Jose. 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 San Jose that include hotel bookings?

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

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

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

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

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

    Currently, December is the cheapest month in which you can book a flight from New Windsor to San Jose, California (average of $113). Flying from New Windsor to San Jose, California in July is currently the most expensive (average of $190). 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

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