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Stewart

$170+ 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 9/1. Fares are subject to change and may not be available on all flights or dates of travel.
SAN — SWF
Jul 9 — Jul 161
Thu 7/9
Thu 7/16
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 June 9, 2026.

This Kiwi.com deal was found by Cheapflights users on 6/7. 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 6/912:54 pm
SAN
-
SWF
1 stop19h 31m
Breeze Airways
Sat 6/1312:05 pm
SWF
-
SAN
1 stop26h 19m
Breeze Airways
Deal found 6/7$556
This Booking.com deal was found by Cheapflights users on 6/4. 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.
Tue 11/31:22 pm
SAN
-
SWF
1 stop19h 17m
Breeze Airways
Sat 11/712:39 pm
SWF
-
SAN
1 stop26h 13m
Breeze Airways
Deal found 6/4$688
This KAYAK deal was found by Cheapflights users on 6/4. 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 9/112:54 pm
SAN
-
SWF
1 stop19h 31m
Breeze Airways
Wed 9/912:39 pm
SWF
-
SAN
1 stop26h 13m
Breeze Airways
Deal found 6/4$738
This Booking.com deal was found by Cheapflights users on 6/8. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/2112:54 pm
SAN
-
SWF
1 stop19h 31m
Breeze Airways
Sat 7/2512:05 pm
SWF
-
SAN
1 stop26h 19m
Breeze Airways
Deal found 6/8$748
This Booking.com deal was found by Cheapflights users on 6/5. 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.
Tue 8/1112:54 pm
SAN
-
SWF
1 stop19h 31m
Breeze Airways
Wed 8/1912:05 pm
SWF
-
SAN
1 stop26h 19m
Breeze Airways
Deal found 6/5$758
This Kiwi.com deal was found by Cheapflights users on 6/5. 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.
Sun 6/1412:09 pm
SAN
-
SWF
2 stops17h 40m
Multiple Airlines
Wed 6/1712:05 pm
SWF
-
SAN
1 stop26h 19m
Multiple Airlines
Deal found 6/5$774
This KAYAK deal was found by Cheapflights users on 6/6. 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 6/3012:54 pm
SAN
-
SWF
1 stop19h 31m
Breeze Airways
Sat 7/412:05 pm
SWF
-
SAN
1 stop26h 19m
Breeze Airways
Deal found 6/6$878
This Mytrip deal was found by Cheapflights users on 6/8. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/2812:54 pm
SAN
-
SWF
1 stop19h 31m
Breeze Airways
Sat 8/812:05 pm
SWF
-
SAN
1 stop26h 19m
Breeze Airways
Deal found 6/8$888
This Booking.com deal was found by Cheapflights users on 6/4. 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.
Tue 6/3012:54 pm
SAN
-
SWF
1 stop19h 31m
Breeze Airways
Wed 7/812:05 pm
SWF
-
SAN
1 stop26h 19m
Breeze Airways
Deal found 6/4$908
This KAYAK deal was found by Cheapflights users on 6/4. 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 10/112:37 pm
SAN
-
SWF
3 stops19h 59m
Breeze Airways
Wed 10/712:39 pm
SWF
-
SAN
1 stop26h 13m
Breeze Airways
Deal found 6/4$923
This KAYAK deal was found by Cheapflights users on 6/4. 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 10/212:45 pm
SAN
-
SWF
3 stops19h 54m
Breeze Airways
Wed 10/712:39 pm
SWF
-
SAN
1 stop26h 13m
Breeze Airways
Deal found 6/4$998

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 June 9, 2026.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$688
(Booking.com)

One-way from

$170
(Kiwi.com)

Popular in

June

Cheapest in

September

Average price

$421
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. 5% potential increase in price ($20 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 June 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 June 9, 2026.
Use the filters below to find and compare flights from San Diego to New Windsor that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

Cheapest round-trip

San DiegoNew Windsor

SAN - SWF

SANSWF

San Diego

Tue 8/11

12:54 pm-11:25 am

1 stop19h 31m

New Windsor Stewart

Wed 8/19

12:05 pm-11:24 am

1 stop26h 19m

$758
Quickest round-trip

San DiegoNew Windsor

SAN - SWF

SANSWF

San Diego

Sun 6/14

12:09 pm-8:49 am

2 stops17h 40m

New Windsor Stewart

Wed 6/17

12:05 pm-11:24 am

1 stop26h 19m

$774

San DiegoNew Windsor

SAN - SWF

SANSWF

San Diego

Tue 6/30

12:54 pm-11:25 am

1 stop19h 31m

New Windsor Stewart

Sat 7/4

12:05 pm-11:24 am

1 stop26h 19m

$878

San DiegoNew Windsor

SAN - SWF

SANSWF

San Diego

Tue 6/30

12:54 pm-11:25 am

1 stop19h 31m

New Windsor Stewart

Wed 7/8

12:05 pm-11:24 am

1 stop26h 19m

$908

San DiegoNew Windsor

SAN - SWF

SANSWF

San Diego

Tue 6/23

12:54 pm-11:25 am

1 stop19h 31m

New Windsor Stewart

Sat 6/27

12:05 pm-11:24 am

1 stop26h 19m

$1,027

San DiegoNew Windsor

SAN - SWF

SANSWF

San Diego

Tue 6/23

12:54 pm-11:25 am

1 stop19h 31m

New Windsor Stewart

Tue 6/30

11:48 am-11:24 am

2 stops50h 36m

$1,228

San DiegoNew Windsor

SAN - SWF

SANSWF

San Diego

Tue 6/23

12:54 pm-11:25 am

1 stop19h 31m

New Windsor Stewart

Mon 6/29

12:17 pm-12:09 pm

3 stops26h 52m

$1,278

San DiegoNew Windsor

SAN - SWF

SANSWF

San Diego

Wed 6/24

12:29 pm-11:37 am

3 stops44h 08m

New Windsor Stewart

Tue 6/30

11:48 am-11:24 am

2 stops50h 36m

$1,694

San DiegoNew Windsor

SAN - SWF

SANSWF

San Diego

Wed 7/1

12:29 pm-11:37 am

3 stops44h 08m

New Windsor Stewart

Mon 7/6

12:17 pm-12:09 pm

3 stops26h 52m

$1,720
Cheapest one-way

San DiegoNew Windsor

SAN - SWF

SANSWF

San Diego

Tue 8/18

6:25 am-12:10 pm

2 stops50h 45m

$171

Flights are sorted by cheapest round-trip flights first.

Deals found on 6/4

Showing 1-10 of 21 resultsSorted by cheapest first
1
2
3
  • 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.

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.

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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