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$165+ 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 10/13. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — SAN
Oct 11 — Oct 181
Sat 10/11
Sat 10/18
1 adult, Economy
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Cheap 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 September 11, 2025.

Round-trip from

$1,287
(KAYAK)

One-way from

$165
(Kiwi.com)

Popular in

December

Cheapest in

October

Average price

$328
From New Windsor Stewart to San Diego
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One-way flight from New Windsor Stewart to San Diego
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Highest demand for flights based on searches. 6% potential increase in price ($27 potential increase over avg. RT price).
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Cheapest flight prices on average. 3% potential price decrease ($13 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find 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 September 11, 2025.

This KAYAK deal was found by Cheapflights users on 9/11. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/1211:43 amSWF - SAN
2 stops51h 53mBreeze Airways
Fri 10/171:12 pmSAN - SWF
3 stops42h 51mBreeze Airways
Deal found 9/11$1,287
This KAYAK deal was found by Cheapflights users on 9/10. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/2811:43 amSWF - SAN
2 stops51h 53mBreeze Airways
Sat 1/31:12 pmSAN - SWF
2 stops43h 32mBreeze Airways
Deal found 9/10$1,466
This KAYAK deal was found by Cheapflights users on 9/11. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/2511:43 amSWF - SAN
3 stops51h 44mBreeze Airways
Sat 1/31:12 pmSAN - SWF
2 stops43h 32mBreeze Airways
Deal found 9/11$1,528
This KAYAK deal was found by Cheapflights users on 9/11. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/2612:24 pmSWF - SAN
3 stops27h 03mBreeze Airways
Sat 1/31:12 pmSAN - SWF
2 stops43h 32mBreeze Airways
Deal found 9/11$1,565
This KAYAK deal was found by Cheapflights users on 9/10. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/2811:43 amSWF - SAN
2 stops51h 53mBreeze Airways
Fri 1/21:12 pmSAN - SWF
2 stops42h 51mBreeze Airways
Deal found 9/10$1,821
This KAYAK deal was found by Cheapflights users on 9/11. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/2511:43 amSWF - SAN
3 stops51h 44mBreeze Airways
Fri 1/21:12 pmSAN - SWF
2 stops42h 51mBreeze Airways
Deal found 9/11$1,883

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 September 11, 2025.
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

Sun 10/12

11:43 am-12:36 pm

2 stops51h 53m

San Diego

Fri 10/17

1:12 pm-11:03 am

3 stops42h 51m

$1,287

New WindsorSan Diego

SWF - SAN

SWFSAN

New Windsor Stewart

Sun 12/28

11:43 am-12:36 pm

2 stops51h 53m

San Diego

Sat 1/3

1:12 pm-11:44 am

2 stops43h 32m

$1,466

New WindsorSan Diego

SWF - SAN

SWFSAN

New Windsor Stewart

Thu 12/25

11:43 am-12:27 pm

3 stops51h 44m

San Diego

Sat 1/3

1:12 pm-11:44 am

2 stops43h 32m

$1,528

New WindsorSan Diego

SWF - SAN

SWFSAN

New Windsor Stewart

Fri 12/26

12:24 pm-12:27 pm

3 stops27h 03m

San Diego

Sat 1/3

1:12 pm-11:44 am

2 stops43h 32m

$1,565

New WindsorSan Diego

SWF - SAN

SWFSAN

New Windsor Stewart

Sun 12/28

11:43 am-12:36 pm

2 stops51h 53m

San Diego

Fri 1/2

1:12 pm-11:03 am

2 stops42h 51m

$1,821

New WindsorSan Diego

SWF - SAN

SWFSAN

New Windsor Stewart

Thu 12/25

11:43 am-12:27 pm

3 stops51h 44m

San Diego

Fri 1/2

1:12 pm-11:03 am

2 stops42h 51m

$1,883

New WindsorSan Diego

SWF - SAN

SWFSAN

New Windsor Stewart

Mon 10/13

11:01 am-9:20 pm

2 stops37h 19m

$165

New WindsorSan Diego

SWF - SAN

SWFSAN

New Windsor Stewart

Sun 10/5

7:11 pm-11:09 am

2 stops18h 58m

$202

New WindsorSan Diego

SWF - SAN

SWFSAN

New Windsor Stewart

Fri 10/10

11:41 am-8:51 pm

2 stops36h 10m

$208

New WindsorSan Diego

SWF - SAN

SWFSAN

New Windsor Stewart

Sat 12/20

7:50 pm-12:13 pm

3 stops43h 23m

$402

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/9

Showing 1-10 of 14 results
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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, August is the cheapest month in which you can book a flight from New Windsor to San Diego (average of $286). Flying from New Windsor to San Diego in March is currently the most expensive (average of $366). 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 51h 53m. 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, August is the cheapest month in which you can book a flight from New Windsor to San Diego (average of $286). Flying from New Windsor to San Diego in March is currently the most expensive (average of $366). 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
La Mesa
Poway
Lemon Grove
Coronado
Imperial Beach
National City
Alpine

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