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Stewart

$155+ 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 12/4. Fares are subject to change and may not be available on all flights or dates of travel.
SAN — SWF
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
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 September 17, 2025.

Round-trip from

$1,310
(KAYAK)

One-way from

$155
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$327
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. 1% potential increase in price ($5 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 September 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 September 17, 2025.

This KAYAK deal was found by Cheapflights users on 9/15. 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.
Wed 9/241:12 pmSAN - SWF
3 stops43h 32mBreeze Airways
Sun 10/511:43 amSWF - SAN
2 stops51h 53mBreeze Airways
Deal found 9/15$1,310

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 September 17, 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

Wed 9/24

1:12 pm-11:44 am

3 stops43h 32m

New Windsor Stewart

Sun 10/5

11:43 am-12:36 pm

2 stops51h 53m

$1,310

San DiegoNew Windsor

SAN - SWF

SANSWF

San Diego

Thu 12/4

4:52 pm-6:40 pm

2 stops22h 48m

$155

San DiegoNew Windsor

SAN - SWF

SANSWF

San Diego

Wed 10/22

2:11 pm-10:41 am

2 stops41h 30m

$167

San DiegoNew Windsor

SAN - SWF

SANSWF

San Diego

Wed 10/29

9:00 am-10:41 am

2 stops46h 41m

$167

San DiegoNew Windsor

SAN - SWF

SANSWF

San Diego

Thu 10/23

8:11 am-10:41 am

2 stops23h 30m

$168

San DiegoNew Windsor

SAN - SWF

SANSWF

San Diego

Thu 10/2

8:25 am-11:21 am

2 stops23h 56m

$172

San DiegoNew Windsor

SAN - SWF

SANSWF

San Diego

Wed 10/8

2:11 pm-10:51 am

2 stops41h 40m

$174

San DiegoNew Windsor

SAN - SWF

SANSWF

San Diego

Thu 10/30

3:59 pm-10:41 am

2 stops15h 42m

$178

San DiegoNew Windsor

SAN - SWF

SANSWF

San Diego

Wed 11/19

2:24 pm-10:22 am

3 stops40h 58m

$185

San DiegoNew Windsor

SAN - SWF

SANSWF

San Diego

Sun 11/2

5:41 am-10:44 am

3 stops26h 03m

$185

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

Showing 1-10 of 11 results
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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.

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

    Breeze Airways can get you from San Diego to New Windsor in just under 43h 32m. Your travel time can differ by up to . Airlines will cover a distance of 2422 mi.

  • 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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