$113+ Cheap flights from New Windsor (SWF) to San Juan
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 8/26. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — SJU
Aug 1 — Aug 81
Round-trip
1 adult, Economy
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Find cheap flights from Stewart to San Juan with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Stewart to San Juan
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Best
Last-minute
One-way
Cheapest flights from Stewart to San JuanExplore the most affordable flight options available from Stewart to San Juan. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 2, 2026.
Explore the most affordable flight options available from Stewart to San Juan. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 2, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/27. 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 10/2511:58 am
SWF
- SJU
1 stop11h 40m
Multiple Airlines
Sat 10/315:12 pm
SJU
- SWF
1 stop18h 56m
Multiple Airlines
Deal found 6/27![Multiple Airlines logo]()
$250
This Kiwi.com deal was found by Cheapflights users on 6/27. 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.
Wed 8/2612:05 pm
SWF
- SJU
2 stops12h 51m
Multiple Airlines
Thu 9/36:35 am
SJU
- SWF
1 stop12h 05m
Multiple Airlines
Deal found 6/27![Multiple Airlines logo]()
$254
This Kiwi.com deal was found by Cheapflights users on 6/30. 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.
Wed 8/2612:05 pm
SWF
- SJU
2 stops12h 51m
Multiple Airlines
Sun 8/306:35 am
SJU
- SWF
1 stop12h 06m
Multiple Airlines
Deal found 6/30![Multiple Airlines logo]()
$255
This Kiwi.com deal was found by Cheapflights users on 6/30. 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.
Thu 8/277:31 pm
SWF
- SJU
1 stop20h 40m
Multiple Airlines
Tue 9/15:37 pm
SJU
- SWF
2 stops17h 48m
Multiple Airlines
Deal found 6/30![Multiple Airlines logo]()
$266
This Kiwi.com deal was found by Cheapflights users on 6/27. 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.
Thu 8/201:00 pm
SWF
- SJU
1 stop27h 11m
Multiple Airlines
Tue 9/15:37 pm
SJU
- SWF
2 stops17h 48m
Multiple Airlines
Deal found 6/27![Multiple Airlines logo]()
$268
Best flights from Stewart to San JuanDiscover carefully curated flight deals from Stewart to San Juan that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 2, 2026.
Discover carefully curated flight deals from Stewart to San Juan that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 2, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/1. 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.
Wed 8/2612:05 pm
SWF
- SJU
2 stops12h 51m
Multiple Airlines
Sun 8/306:35 am
SJU
- SWF
1 stop12h 06m
Multiple Airlines
Deal found 7/1![Multiple Airlines logo]()
$270
This Kiwi.com deal was found by Cheapflights users on 6/28. 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.
Sat 8/2212:05 pm
SWF
- SJU
2 stops12h 51m
Multiple Airlines
Sun 8/306:35 am
SJU
- SWF
1 stop12h 06m
Multiple Airlines
Deal found 6/28![Multiple Airlines logo]()
$318
This Kiwi.com deal was found by Cheapflights users on 6/27. 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.
Wed 9/1612:39 pm
SWF
- SJU
2 stops11h 18m
Multiple Airlines
Sun 9/206:42 pm
SJU
- SWF
1 stop15h 49m
Multiple Airlines
Deal found 6/27![Multiple Airlines logo]()
$391
This Kiwi.com deal was found by Cheapflights users on 6/28. 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 7/1210:28 am
SWF
- SJU
1 stop29h 37m
Multiple Airlines
Wed 7/156:00 am
SJU
- SWF
1 stop27h 38m
Multiple Airlines
Deal found 6/28![Multiple Airlines logo]()
$431
This Kiwi.com deal was found by Cheapflights users on 6/27. 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.
Thu 7/1611:45 am
SWF
- SJU
1 stop12h 56m
Multiple Airlines
Wed 7/225:15 pm
SJU
- SWF
2 stops16h 23m
Multiple Airlines
Deal found 6/27![Multiple Airlines logo]()
$447
This Kiwi.com deal was found by Cheapflights users on 6/27. 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.
Wed 7/157:46 pm
SWF
- SJU
1 stop12h 11m
Multiple Airlines
Tue 7/213:10 am
SJU
- SWF
1 stop15h 46m
Multiple Airlines
Deal found 6/27![Multiple Airlines logo]()
$478
This Kiwi.com deal was found by Cheapflights users on 7/1. 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 7/2811:48 am
SWF
- SJU
1 stop14h 27m
Multiple Airlines
Mon 8/33:10 am
SJU
- SWF
1 stop7h 58m
Multiple Airlines
Deal found 7/1![Multiple Airlines logo]()
$523
This Kiwi.com deal was found by Cheapflights users on 6/28. 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 7/1411:48 am
SWF
- SJU
1 stop7h 54m
Multiple Airlines
Mon 7/203:10 am
SJU
- SWF
1 stop7h 58m
Multiple Airlines
Deal found 6/28![Multiple Airlines logo]()
$535
This Kiwi.com deal was found by Cheapflights users on 6/27. 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 7/1411:48 am
SWF
- SJU
1 stop7h 54m
Multiple Airlines
Tue 7/213:10 am
SJU
- SWF
1 stop15h 46m
Multiple Airlines
Deal found 6/27![Multiple Airlines logo]()
$537
This Kiwi.com deal was found by Cheapflights users on 6/28. 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 7/711:48 am
SWF
- SJU
1 stop14h 27m
Multiple Airlines
Fri 7/1010:48 pm
SJU
- SWF
1 stop19h 06m
Multiple Airlines
Deal found 6/28![Multiple Airlines logo]()
$541
This Kiwi.com deal was found by Cheapflights users on 6/28. 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 7/511:45 am
SWF
- SJU
1 stop12h 56m
Multiple Airlines
Wed 7/88:37 pm
SJU
- SWF
1 stop13h 16m
Multiple Airlines
Deal found 6/28![Multiple Airlines logo]()
$608
This Kiwi.com deal was found by Cheapflights users on 7/1. 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.
Thu 7/3010:33 am
SWF
- SJU
1 stop8h 59m
Multiple Airlines
Wed 8/58:37 pm
SJU
- SWF
1 stop13h 16m
Multiple Airlines
Deal found 7/1![Multiple Airlines logo]()
$666
Last-minute flights from Stewart to San JuanDiscover last-minute flight deals from Stewart to San Juan. Data last updated July 2, 2026 and is based on user searches.
Discover last-minute flight deals from Stewart to San Juan. Data last updated July 2, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 6/27. 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.
Thu 8/201:00 pm
SWF
- SJU
1 stop27h 11m
Multiple Airlines
Tue 9/15:37 pm
SJU
- SWF
2 stops17h 48m
Multiple Airlines
Deal found 6/27![Multiple Airlines logo]()
$268
This Kiwi.com deal was found by Cheapflights users on 6/27. 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.
Thu 8/201:00 pm
SWF
- SJU
1 stop27h 11m
Multiple Airlines
Thu 9/36:35 am
SJU
- SWF
1 stop12h 05m
Multiple Airlines
Deal found 6/27![Multiple Airlines logo]()
$271
This Kiwi.com deal was found by Cheapflights users on 6/27. 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.
Wed 8/2612:05 pm
SWF
- SJU
2 stops12h 51m
Multiple Airlines
Thu 9/36:35 am
SJU
- SWF
1 stop12h 05m
Multiple Airlines
Deal found 6/27![Multiple Airlines logo]()
$254
This Kiwi.com deal was found by Cheapflights users on 6/30. 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.
Wed 8/2612:05 pm
SWF
- SJU
2 stops12h 51m
Multiple Airlines
Sun 8/306:35 am
SJU
- SWF
1 stop12h 06m
Multiple Airlines
Deal found 6/30![Multiple Airlines logo]()
$255
This Kiwi.com deal was found by Cheapflights users on 6/30. 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.
Thu 8/277:31 pm
SWF
- SJU
1 stop20h 40m
Multiple Airlines
Tue 9/15:37 pm
SJU
- SWF
2 stops17h 48m
Multiple Airlines
Deal found 6/30![Multiple Airlines logo]()
$266
One-way flights from Stewart to San JuanSearch for one-way flight options from Stewart to San Juan. Find affordable one-way fares based on user searches. Data last updated July 2, 2026.
Search for one-way flight options from Stewart to San Juan. Find affordable one-way fares based on user searches. Data last updated July 2, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/30. 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.
Wed 8/2612:05 pm
SWF
- SJU
2 stops12h 51m
Multiple Airlines
Deal found 6/30![Multiple Airlines logo]()
$113
This Kiwi.com deal was found by Cheapflights users on 6/27. 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.
Thu 8/1310:28 am
SWF
- SJU
1 stop29h 43m
Multiple Airlines
Deal found 6/27![Multiple Airlines logo]()
$128
This Kiwi.com deal was found by Cheapflights users on 6/29. 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.
Thu 8/277:31 pm
SWF
- SJU
1 stop20h 40m
Multiple Airlines
Deal found 6/29![Multiple Airlines logo]()
$131
This Kiwi.com deal was found by Cheapflights users on 6/30. 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.
Wed 8/1912:05 pm
SWF
- SJU
2 stops12h 51m
Multiple Airlines
Deal found 6/30![Multiple Airlines logo]()
$133
This Kiwi.com deal was found by Cheapflights users on 6/28. 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.
Thu 9/37:30 pm
SWF
- SJU
1 stop20h 41m
Multiple Airlines
Deal found 6/28![Multiple Airlines logo]()
$139
This Kiwi.com deal was found by Cheapflights users on 6/30. 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 8/231:00 pm
SWF
- SJU
1 stop27h 11m
Multiple Airlines
Deal found 6/30![Multiple Airlines logo]()
$140
This Kiwi.com deal was found by Cheapflights users on 6/28. 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 9/67:30 pm
SWF
- SJU
1 stop20h 41m
Multiple Airlines
Deal found 6/28![Multiple Airlines logo]()
$145
Find flight deals from Stewart to San Juan
Discover tips and strategies to find the most affordable flight options for your journey from Stewart (SWF) to San Juan (PR1). 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 July 2, 2026.
Round-trip from | $250 (Kiwi.com) |
|---|---|
One-way from | $113 (Kiwi.com) |
Popular in | May |
Cheapest in | October |
Average price | $351 |
Cheapflights Fare Finder
Customize your flight search to find flights from Stewart to San Juan 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 July 2, 2026.
Use the filters below to find and compare flights from New Windsor to San Juan that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
New WindsorSan Juan
SWF - SJU
SWFSJU
New Windsor Stewart
Wed 8/26
12:05 pm-12:56 am
2 stops12h 51m
San Juan Luis Munoz Marin Intl
Sun 8/30
6:35 am-6:41 pm
1 stop12h 06m
$270
New WindsorSan Juan
SWF - SJU
SWFSJU
New Windsor Stewart
Sat 8/22
12:05 pm-12:56 am
2 stops12h 51m
San Juan Luis Munoz Marin Intl
Sun 8/30
6:35 am-6:41 pm
1 stop12h 06m
$318
New WindsorSan Juan
SWF - SJU
SWFSJU
New Windsor Stewart
Wed 9/16
12:39 pm-11:57 pm
2 stops11h 18m
San Juan Luis Munoz Marin Intl
Sun 9/20
6:42 pm-10:31 am
1 stop15h 49m
$391
New WindsorSan Juan
SWF - SJU
SWFSJU
New Windsor Stewart
Sun 7/12
10:28 am-4:05 pm
1 stop29h 37m
San Juan Luis Munoz Marin Intl
Wed 7/15
6:00 am-9:38 am
1 stop27h 38m
$431
New WindsorSan Juan
SWF - SJU
SWFSJU
New Windsor Stewart
Thu 7/16
11:45 am-12:41 am
1 stop12h 56m
San Juan Luis Munoz Marin Intl
Wed 7/22
5:15 pm-9:38 am
2 stops16h 23m
$447
New WindsorSan Juan
SWF - SJU
SWFSJU
New Windsor Stewart
Wed 7/15
7:46 pm-7:57 am
1 stop12h 11m
San Juan Luis Munoz Marin Intl
Tue 7/21
3:10 am-6:56 pm
1 stop15h 46m
$478
New WindsorSan Juan
SWF - SJU
SWFSJU
New Windsor Stewart
Tue 7/28
11:48 am-2:15 am
1 stop14h 27m
San Juan Luis Munoz Marin Intl
Mon 8/3
3:10 am-11:08 am
1 stop7h 58m
$523
Quickest round-trip
New WindsorSan Juan
SWF - SJU
SWFSJU
New Windsor Stewart
Tue 7/14
11:48 am-7:42 pm
1 stop7h 54m
San Juan Luis Munoz Marin Intl
Mon 7/20
3:10 am-11:08 am
1 stop7h 58m
$535
New WindsorSan Juan
SWF - SJU
SWFSJU
New Windsor Stewart
Tue 7/14
11:48 am-7:42 pm
1 stop7h 54m
San Juan Luis Munoz Marin Intl
Tue 7/21
3:10 am-6:56 pm
1 stop15h 46m
$537
New WindsorSan Juan
SWF - SJU
SWFSJU
New Windsor Stewart
Tue 7/7
11:48 am-2:15 am
1 stop14h 27m
San Juan Luis Munoz Marin Intl
Fri 7/10
10:48 pm-5:54 pm
1 stop19h 06m
$541
Showing 1-10 of 22 resultsSorted by cheapest first
Best time to book a flight from Stewart to San Juan
Have a flexible travel schedule? Discover the best time to fly to San Juan from Stewart with our price prediction graph.
SWF-PR1
SWF-SJU
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 Juan
SWF-PR1
SWF-SJU
No data available for this route at this time. Please check back soon.
Reviews of airlines servicing San Juan
Get insights into the airlines that provide service to San Juan. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to San Juan. Reviews last updated July 2, 2026.
Peruse reviews from past customers who have flown with JetBlue from New Windsor to San Juan to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
7.9
Boarding
7.3
Overall
7.1
Entertainment
7.2
Food
6.6
Comfort
7.5
Reviews
1 / 20
8.0
ExcellentWei,Feb 2026
JFK - BOS
Crew
7.9
Boarding
7.3
Overall
7.1
Entertainment
7.2
Food
6.6
Comfort
7.5
Reviews
1 / 20
8.0
ExcellentWei,Feb 2026
JFK - BOS
Related info for your journey
Find useful and relevant information for your journey from Stewart to San Juan. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Stewart to San Juan
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Complete your trip
Complete your trip to San Juan by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Stewart to San Juan by cabin class
Find flights from Stewart to San Juan, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Stewart and San Juan flights
Browse other Stewart and San Juan flight options. Last updated on July 2, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Top airline flying from Stewart to San Juan
Discover the top airline that operate flights from Stewart to San Juan. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated July 2, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$227 | Average$365 | FlexibilityNo cancel fee | On-time62% |