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Stewart

$146+ Cheap flights from San Diego to New Windsor (SAN - 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 9/6. Fares are subject to change and may not be available on all flights or dates of travel.
SAN — SWF
Aug 21 — Aug 281
Thu 8/21
Thu 8/28
1 adult, Economy
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Cheap flight deals from San Diego to Stewart

Discover tips and strategies to find the most affordable flight options for your journey from San Diego (SAN) 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 August 16, 2025.

Round-trip from

$979
(KAYAK)

One-way from

$146
(Mytrip)

Popular in

December

Cheapest in

January

Average price

$332
From San Diego to New Windsor Stewart
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One-way flight from San Diego to New Windsor Stewart
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Highest demand for flights based on searches. 2% potential increase in price ($9 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($9 potential savings vs. average RT price).
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Average for round-trip flights in August 2025
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Find flight deals from San Diego to Stewart

Cheapest flights from San Diego to Stewart
Explore the most affordable flight options available from San Diego to Stewart. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 16, 2025.

This KAYAK deal was found by Cheapflights users on 8/15. 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.
Tue 9/212:48 pmSAN - SWF
2 stops43h 15mBreeze Airways
Fri 9/512:24 pmSWF - SAN
3 stops27h 03mBreeze Airways
Deal found 8/15$979
This KAYAK deal was found by Cheapflights users on 8/15. 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 8/3112:48 pmSAN - SWF
2 stops44h 08mBreeze Airways
Fri 9/512:24 pmSWF - SAN
3 stops27h 03mBreeze Airways
Deal found 8/15$989
This KAYAK deal was found by Cheapflights users on 8/15. 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 8/3112:48 pmSAN - SWF
2 stops44h 08mBreeze Airways
Thu 9/411:43 amSWF - SAN
3 stops51h 44mBreeze Airways
Deal found 8/15$1,026
This KAYAK deal was found by Cheapflights users on 8/14. 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.
Wed 8/2712:21 pmSAN - SWF
3 stops45h 27mBreeze Airways
Mon 9/11:28 pmSWF - SAN
2 stops49h 59mBreeze Airways
Deal found 8/14$1,059
This KAYAK deal was found by Cheapflights users on 8/14. 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 8/2812:48 pmSAN - SWF
2 stops51h 01mBreeze Airways
Mon 9/11:28 pmSWF - SAN
2 stops49h 59mBreeze Airways
Deal found 8/14$1,118
This KAYAK deal was found by Cheapflights users on 8/14. 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 8/2912:58 pmSAN - SWF
3 stops26h 51mBreeze Airways
Mon 9/11:28 pmSWF - SAN
2 stops49h 59mBreeze Airways
Deal found 8/14$1,255

Cheapflights Fare Finder

 
Customize your flight search to find flights from San Diego 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 August 16, 2025.
Use the filters below to find and compare flights from San Diego to New Windsor that are best for you.

Fly from

San Diego

Fly to

Stewart

Route

Depart

Return

Price

San DiegoNew Windsor

SAN - SWF

SANSWF

San Diego

Tue 9/2

12:48 pm-11:03 am

2 stops43h 15m

New Windsor Stewart

Fri 9/5

12:24 pm-12:27 pm

3 stops27h 03m

$979

San DiegoNew Windsor

SAN - SWF

SANSWF

San Diego

Tue 9/16

1:21 pm-11:03 am

2 stops42h 42m

New Windsor Stewart

Fri 9/19

12:24 pm-12:27 pm

3 stops27h 03m

$989

San DiegoNew Windsor

SAN - SWF

SANSWF

San Diego

Sun 8/31

12:48 pm-11:56 am

2 stops44h 08m

New Windsor Stewart

Fri 9/5

12:24 pm-12:27 pm

3 stops27h 03m

$989

San DiegoNew Windsor

SAN - SWF

SANSWF

San Diego

Sun 8/31

12:48 pm-11:56 am

2 stops44h 08m

New Windsor Stewart

Thu 9/4

11:43 am-12:27 pm

3 stops51h 44m

$1,026

San DiegoNew Windsor

SAN - SWF

SANSWF

San Diego

Wed 8/27

12:21 pm-12:48 pm

3 stops45h 27m

New Windsor Stewart

Mon 9/1

1:28 pm-12:27 pm

2 stops49h 59m

$1,059

San DiegoNew Windsor

SAN - SWF

SANSWF

San Diego

Thu 8/28

12:48 pm-6:49 pm

2 stops51h 01m

New Windsor Stewart

Mon 9/1

1:28 pm-12:27 pm

2 stops49h 59m

$1,118

San DiegoNew Windsor

SAN - SWF

SANSWF

San Diego

Fri 8/29

12:58 pm-6:49 pm

3 stops26h 51m

New Windsor Stewart

Mon 9/1

1:28 pm-12:27 pm

2 stops49h 59m

$1,255

San DiegoNew Windsor

SAN - SWF

SANSWF

San Diego

Sat 9/6

7:47 pm-6:22 pm

2 stops19h 35m

$146

San DiegoNew Windsor

SAN - SWF

SANSWF

San Diego

Wed 10/22

2:11 pm-10:41 am

2 stops41h 30m

$172

San DiegoNew Windsor

SAN - SWF

SANSWF

San Diego

Wed 9/10

7:47 pm-6:22 pm

3 stops19h 35m

$175

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/14

Showing 1-10 of 15 results
1
2

Best time to book a flight from San Diego to Stewart

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

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

Currently, October is the cheapest month in which you can book a flight from San Diego to New Windsor (average of $109). Flying from San Diego to New Windsor in December 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 Diego 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 Diego to Stewart that include hotel bookings?

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

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

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

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

    Yes. Cheapflights offers flight deals from San Diego 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 Diego to New Windsor?

    Currently, October is the cheapest month in which you can book a flight from San Diego to New Windsor (average of $109). Flying from San Diego to New Windsor in December 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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