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$161+ Cheap flights from New Windsor to San Diego (SWF - SAN)

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 5/16. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — SAN
Feb 26 — Mar 51
Thu 2/26
Thu 3/5
1 adult, Economy
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Cheap flight deals from Stewart to San Diego

Cheapest flights from Stewart to San Diego
Explore the most affordable flight options available from Stewart to San Diego. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 27, 2026.

This Booking.com deal was found by Cheapflights users on 1/24. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/612:05 pm
SWF
-
SAN
1 stop26h 19m
Breeze Airways
Tue 5/1212:54 pm
SAN
-
SWF
1 stop19h 31m
Breeze Airways
Deal found 1/24$512
This Booking.com deal was found by Cheapflights users on 1/25. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/412:05 pm
SWF
-
SAN
1 stop26h 19m
Breeze Airways
Tue 7/712:54 pm
SAN
-
SWF
1 stop19h 31m
Breeze Airways
Deal found 1/25$609
This Kiwi.com deal was found by Cheapflights users on 1/25. 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 8/1811:48 am
SWF
-
SAN
2 stops27h 45m
Multiple Airlines
Tue 8/2512:54 pm
SAN
-
SWF
1 stop19h 31m
Multiple Airlines
Deal found 1/25$792

Find flight deals from Stewart to San Diego

Discover tips and strategies to find the most affordable flight options for your journey from Stewart (SWF) to San Diego (SAN). 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 January 27, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$512
(Booking.com)

One-way from

$161
(Kiwi.com)

Popular in

December

Cheapest in

September

Average price

$347
Provider with most accurate pricing for New Windsor Stewart-San Diego flight deals.
Search Deals
Provider most trusted by Cheapflights users for New Windsor Stewart-San Diego flights.
Search Deals
From New Windsor Stewart to San Diego
Search Deals
One-way flight from New Windsor Stewart to San Diego
Search Deals
Highest demand for flights based on searches. 9% potential increase in price ($38 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Stewart to San Diego 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 January 27, 2026.
Use the filters below to find and compare flights from New Windsor to San Diego that are best for you.

Fly from

Stewart

Fly to

San Diego

Route

Depart

Return

Price

New WindsorSan Diego

SWF - SAN

SWFSAN

New Windsor Stewart

Wed 5/6

12:05 pm-11:24 am

1 stop26h 19m

San Diego

Tue 5/12

12:54 pm-11:25 am

1 stop19h 31m

$512

New WindsorSan Diego

SWF - SAN

SWFSAN

New Windsor Stewart

Sat 7/4

12:05 pm-11:24 am

1 stop26h 19m

San Diego

Tue 7/7

12:54 pm-11:25 am

1 stop19h 31m

$609

New WindsorSan Diego

SWF - SAN

SWFSAN

New Windsor Stewart

Sat 5/16

12:05 pm-12:01 am

2 stops38h 56m

$161

New WindsorSan Diego

SWF - SAN

SWFSAN

New Windsor Stewart

Sat 5/16

12:05 pm-11:24 am

1 stop26h 19m

$198

New WindsorSan Diego

SWF - SAN

SWFSAN

New Windsor Stewart

Wed 6/17

12:05 pm-11:24 am

1 stop26h 19m

$238

New WindsorSan Diego

SWF - SAN

SWFSAN

New Windsor Stewart

Sat 5/30

12:05 pm-11:24 am

1 stop26h 19m

$254

New WindsorSan Diego

SWF - SAN

SWFSAN

New Windsor Stewart

Sun 5/31

8:10 pm-12:09 pm

2 stops42h 59m

$277

New WindsorSan Diego

SWF - SAN

SWFSAN

New Windsor Stewart

Sat 7/25

12:05 pm-11:24 am

1 stop26h 19m

$300

New WindsorSan Diego

SWF - SAN

SWFSAN

New Windsor Stewart

Mon 5/25

5:53 pm-11:44 am

2 stops20h 51m

$357

New WindsorSan Diego

SWF - SAN

SWFSAN

New Windsor Stewart

Fri 5/29

12:15 pm-12:33 pm

2 stops27h 18m

$477

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/25

Showing 1-10 of 11 results
1
2

Compare providers for flights from Stewart to San Diego

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 San Diego in January.
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-San Diego 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 Diego flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from New Windsor-San Diego flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on New Windsor-San Diego 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 Diego 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 Diego

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

What is the cheapest month to book a flight from New Windsor to San Diego?

Currently, November is the cheapest month in which you can book a flight from New Windsor to San Diego (average of $72). Flying from New Windsor to San Diego in July is currently the most expensive (average of $168). 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 Diego. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • How long is the flight from New Windsor to San Diego?

    Departing from New Windsor to San Diego will take you 26h 19m. New Windsor and San Diego are separated by a distance of 2422 mi.

  • Can I find deals for flights from Stewart to San Diego that include hotel bookings?

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

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

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

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

    Yes. Cheapflights offers flight deals from Stewart to San Diego 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 Diego?

    Currently, November is the cheapest month in which you can book a flight from New Windsor to San Diego (average of $72). Flying from New Windsor to San Diego in July is currently the most expensive (average of $168). 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 San Diego?

Book flights to San Diego if you plan to visit one of these locations
El Cajon
Chula Vista
National City
Coronado
La Mesa
Poway
Julian
Lemon Grove

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