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Stewart

$138+ 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 3/16. Fares are subject to change and may not be available on all flights or dates of travel.
SAN — SWF
Mar 12 — Mar 191
Thu 3/12
Thu 3/19
1 adult, Economy
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Cheap 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 February 10, 2026.

This Kiwi.com deal was found by Cheapflights users on 2/9. 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 6/2312:54 pm
SAN
-
SWF
1 stop19h 31m
Breeze Airways
Sat 7/2512:05 pm
SWF
-
SAN
1 stop26h 19m
Breeze Airways
Deal found 2/9$404
This Kiwi.com deal was found by Cheapflights users on 2/9. 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 6/212:54 pm
SAN
-
SWF
1 stop19h 31m
Multiple Airlines
Mon 6/85:55 pm
SWF
-
SAN
2 stops20h 49m
Multiple Airlines
Deal found 2/9$460
This Kiwi.com deal was found by Cheapflights users on 2/8. 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 5/1912:54 pm
SAN
-
SWF
1 stop19h 31m
Multiple Airlines
Mon 5/255:53 pm
SWF
-
SAN
2 stops20h 51m
Multiple Airlines
Deal found 2/8$511
This eDestinos deal was found by Cheapflights users on 2/8. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/2612:54 pm
SAN
-
SWF
1 stop19h 31m
Breeze Airways
Sat 5/3012:05 pm
SWF
-
SAN
1 stop26h 19m
Breeze Airways
Deal found 2/8$555

Find 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 February 10, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$404
(Kiwi.com)

One-way from

$138
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$307
Provider with most accurate pricing for San Diego-New Windsor Stewart flight deals.
Search Deals
Provider most trusted by Cheapflights users for San Diego-New Windsor Stewart flights.
Search Deals
From San Diego to New Windsor Stewart
Search Deals
One-way flight from San Diego to New Windsor Stewart
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($11 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($7 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 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 February 10, 2026.
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 6/23

12:54 pm-11:25 am

1 stop19h 31m

New Windsor Stewart

Sat 7/25

12:05 pm-11:24 am

1 stop26h 19m

$404

San DiegoNew Windsor

SAN - SWF

SANSWF

San Diego

Tue 6/2

12:54 pm-11:25 am

1 stop19h 31m

New Windsor Stewart

Mon 6/8

5:55 pm-11:44 am

2 stops20h 49m

$460

San DiegoNew Windsor

SAN - SWF

SANSWF

San Diego

Tue 5/19

12:54 pm-11:25 am

1 stop19h 31m

New Windsor Stewart

Mon 5/25

5:53 pm-11:44 am

2 stops20h 51m

$511

San DiegoNew Windsor

SAN - SWF

SANSWF

San Diego

Tue 5/26

12:54 pm-11:25 am

1 stop19h 31m

New Windsor Stewart

Sat 5/30

12:05 pm-11:24 am

1 stop26h 19m

$555

San DiegoNew Windsor

SAN - SWF

SANSWF

San Diego

Mon 3/16

9:08 pm-9:39 am

3 stops57h 31m

$138

San DiegoNew Windsor

SAN - SWF

SANSWF

San Diego

Tue 3/24

6:25 am-9:39 am

3 stops48h 14m

$138

San DiegoNew Windsor

SAN - SWF

SANSWF

San Diego

Wed 5/20

10:00 am-8:51 am

2 stops43h 51m

$141

San DiegoNew Windsor

SAN - SWF

SANSWF

San Diego

Tue 3/10

8:25 am-9:19 am

3 stops45h 54m

$152

San DiegoNew Windsor

SAN - SWF

SANSWF

San Diego

Tue 5/5

11:42 am-11:25 am

3 stops20h 43m

$155

San DiegoNew Windsor

SAN - SWF

SANSWF

San Diego

Tue 5/19

12:54 pm-11:25 am

1 stop19h 31m

$160

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/8

Showing 1-10 of 13 results
1
2
  • Most accurate provider: When it comes to deals on San Diego-New Windsor flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on San Diego-New Windsor flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from San Diego-New Windsor flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on San Diego-New Windsor 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 San Diego-New Windsor 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 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, June is the cheapest month in which you can book a flight from San Diego to New Windsor (average of $78). Flying from San Diego to New Windsor in December is currently the most expensive (average of $179). 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 19h 31m. 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, June is the cheapest month in which you can book a flight from San Diego to New Windsor (average of $78). Flying from San Diego to New Windsor in December is currently the most expensive (average of $179). 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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