$120+ Cheap flights from New Windsor (SWF) to San Juan
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/10. Fares are subject to change and may not be available on all flights or dates of travel.
SWF — SJU
Nov 29 — Dec 61
Round-trip
1 adult, Economy
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Find cheap flights from Stewart to San Juan with Cheapflights
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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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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 October 30, 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 October 30, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 12/106:49 pm -
1 stop24h 48m
Wed 12/166:25 am -
1 stop29h 52m
Deal found 10/30![Multiple Airlines logo]()
$274
This Kiwi.com deal was found by Cheapflights users on 10/25. 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 12/912:39 pm -
2 stops30h 58m
Wed 12/166:25 am -
1 stop29h 52m
Deal found 10/25![Multiple Airlines logo]()
$282
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 11/226:48 pm -
1 stop18h 11m
Thu 12/36:25 am -
1 stop12h 34m
Deal found 10/27![Multiple Airlines logo]()
$302
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 11/226:48 pm -
1 stop18h 11m
Tue 12/16:25 am -
2 stops30h 14m
Deal found 10/27![Multiple Airlines logo]()
$324
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 11/196:48 pm -
1 stop18h 11m
Tue 12/16:25 am -
2 stops30h 14m
Deal found 10/27![Multiple Airlines logo]()
$346
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 12/106:49 pm -
1 stop24h 48m
Sun 12/136:25 am -
1 stop12h 34m
Deal found 10/28![Multiple Airlines logo]()
$354
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 October 30, 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 October 30, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 12/106:49 pm -
1 stop24h 48m
Wed 12/166:25 am -
1 stop29h 52m
Deal found 10/30![Multiple Airlines logo]()
$274
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 1/2812:25 pm -
1 stop23h 12m
Sun 1/3110:53 pm -
2 stops13h 04m
Deal found 10/28![Multiple Airlines logo]()
$395
This Kiwi.com deal was found by Cheapflights users on 10/29. 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 12/1712:07 pm -
1 stop11h 07m
Sat 12/194:50 pm -
1 stop19h 27m
Deal found 10/29![Multiple Airlines logo]()
$401
This Kiwi.com deal was found by Cheapflights users on 10/28. 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.
Mon 11/167:04 pm -
1 stop14h 11m
Thu 11/191:56 pm -
2 stops21h 43m
Deal found 10/28![Multiple Airlines logo]()
$426
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Mon 11/97:04 pm -
1 stop14h 11m
Wed 11/113:55 pm -
2 stops19h 15m
Deal found 10/29![Multiple Airlines logo]()
$448
This Kiwi.com deal was found by Cheapflights users on 10/26. 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 11/1812:39 pm -
2 stops20h 36m
Sun 11/227:31 am -
1 stop11h 27m
Deal found 10/26![Multiple Airlines logo]()
$503
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 12/1912:39 pm -
2 stops34h 35m
Wed 12/2310:51 pm -
1 stop12h 35m
Deal found 10/28![Multiple Airlines logo]()
$541
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 1/2110:56 am -
1 stop9h 52m
Sun 1/2410:53 pm -
2 stops13h 04m
Deal found 10/27![Multiple Airlines logo]()
$541
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 12/1912:39 pm -
1 stop10h 53m
Thu 12/246:00 am -
2 stops13h 05m
Deal found 10/28![Multiple Airlines logo]()
$569
This Kiwi.com deal was found by Cheapflights users on 10/26. 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 12/1311:06 am -
1 stop14h 07m
Sat 12/1910:59 pm -
1 stop12h 27m
Deal found 10/26![Multiple Airlines logo]()
$601
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Sat 12/1912:39 pm -
1 stop10h 53m
Sun 1/106:27 am -
1 stop13h 44m
Deal found 10/29![Multiple Airlines logo]()
$602
This Kiwi.com deal was found by Cheapflights users on 10/25. 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 12/2312:39 pm -
2 stops22h 58m
Wed 12/306:00 am -
1 stop30h 17m
Deal found 10/25![Multiple Airlines logo]()
$603
Last-minute flights from Stewart to San JuanDiscover last-minute flight deals from Stewart to San Juan. Data last updated October 30, 2026 and is based on user searches.
Discover last-minute flight deals from Stewart to San Juan. Data last updated October 30, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 11/712:39 pm -
2 stops21h 16m
Wed 11/118:45 am -
1 stop26h 25m
Deal found 10/28![Multiple Airlines logo]()
$396
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 11/812:00 pm -
1 stop24h 25m
Fri 11/137:00 am -
2 stops29h 39m
Deal found 10/28![Multiple Airlines logo]()
$389
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Sun 11/812:00 pm -
1 stop24h 25m
Wed 11/118:45 am -
1 stop26h 25m
Deal found 10/29![Multiple Airlines logo]()
$401
This Kiwi.com deal was found by Cheapflights users on 10/25. 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 11/1512:00 pm -
1 stop24h 25m
Fri 11/207:31 am -
2 stops29h 08m
Deal found 10/25![Multiple Airlines logo]()
$380
This Kiwi.com deal was found by Cheapflights users on 10/29. 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.
Sun 11/1512:00 pm -
1 stop24h 25m
Thu 11/194:52 pm -
2 stops43h 47m
Deal found 10/29![Multiple Airlines logo]()
$383
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 11/1512:00 pm -
1 stop24h 25m
Sun 11/227:31 am -
1 stop11h 27m
Deal found 10/27![Multiple Airlines logo]()
$405
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 11/196:48 pm -
1 stop18h 11m
Tue 12/16:25 am -
2 stops30h 14m
Deal found 10/27![Multiple Airlines logo]()
$346
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 11/226:48 pm -
1 stop18h 11m
Thu 12/36:25 am -
1 stop12h 34m
Deal found 10/27![Multiple Airlines logo]()
$302
This Kiwi.com deal was found by Cheapflights users on 10/27. 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 11/226:48 pm -
1 stop18h 11m
Tue 12/16:25 am -
2 stops30h 14m
Deal found 10/27![Multiple Airlines logo]()
$324
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 October 30, 2026.
Search for one-way flight options from Stewart to San Juan. Find affordable one-way fares based on user searches. Data last updated October 30, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 1/108:01 pm -
1 stop27h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Multiple Airlines logo]()
$120
This Trip.com deal was found by Cheapflights users on 10/29. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/226:48 pm -
1 stop18h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![Multiple Airlines logo]()
$126
This Trip.com deal was found by Cheapflights users on 10/29. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/66:49 pm -
1 stop24h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/29![Multiple Airlines logo]()
$135
This Kiwi.com deal was found by Cheapflights users on 10/28. 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 12/106:49 pm -
1 stop24h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/28![Multiple Airlines logo]()
$141
This Kiwi.com deal was found by Cheapflights users on 10/26. 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 1/612:39 pm -
2 stops34h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/26![Multiple Airlines logo]()
$144
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 October 30, 2026.
Round-trip from | $256 (Kiwi.com) |
|---|---|
One-way from | $120 (Kiwi.com) |
Popular in | July |
Cheapest in | January |
Average price | $354 |
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 7,457,451 searches. Data last updated October 30, 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 New Windsor Stewart - SJU San Juan Luis Munoz Marin Intl
SWFSJU
New Windsor Stewart
Wed 1/6
12:39 pm-8:30 pm
2 stops30h 51m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$139
New WindsorSan Juan
SWF New Windsor Stewart - SJU San Juan Luis Munoz Marin Intl
SWFSJU
New Windsor Stewart
Sat 1/9
12:39 pm-12:38 am
2 stops34h 59m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$146
New WindsorSan Juan
SWF New Windsor Stewart - SJU San Juan Luis Munoz Marin Intl
SWFSJU
New Windsor Stewart
Thu 1/21
12:25 pm-12:37 pm
1 stop23h 12m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$159
New WindsorSan Juan
SWF New Windsor Stewart - SJU San Juan Luis Munoz Marin Intl
SWFSJU
New Windsor Stewart
Sat 12/5
12:39 pm-1:19 am
2 stops35h 40m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$162
Quickest round-trip
New WindsorSan Juan
SWF New Windsor Stewart - SJU San Juan Luis Munoz Marin Intl
SWFSJU
New Windsor Stewart
Sat 11/14
12:39 pm-10:55 am
2 stops21h 16m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$196
New WindsorSan Juan
SWF New Windsor Stewart - SJU San Juan Luis Munoz Marin Intl
SWFSJU
New Windsor Stewart
Mon 11/16
12:16 pm-3:19 pm
2 stops26h 03m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$201
New WindsorSan Juan
SWF New Windsor Stewart - SJU San Juan Luis Munoz Marin Intl
SWFSJU
New Windsor Stewart
Wed 12/2
12:39 pm-1:07 am
2 stops35h 28m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$203
New WindsorSan Juan
SWF New Windsor Stewart - SJU San Juan Luis Munoz Marin Intl
SWFSJU
New Windsor Stewart
Wed 11/11
12:39 pm-11:38 pm
3 stops33h 59m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$221
New WindsorSan Juan
SWF New Windsor Stewart - SJU San Juan Luis Munoz Marin Intl
SWFSJU
New Windsor Stewart
Sat 11/7
12:39 pm-10:55 am
2 stops21h 16m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$223
New WindsorSan Juan
SWF New Windsor Stewart - SJU San Juan Luis Munoz Marin Intl
SWFSJU
New Windsor Stewart
Thu 12/10
6:49 pm-8:37 pm
1 stop24h 48m
San Juan Luis Munoz Marin Intl
Wed 12/16
6:25 am-11:17 am
1 stop29h 52m
$274
Showing 1-10 of 21 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 October 30, 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.
Boarding
7.3
Food
6.6
Entertainment
7.2
Comfort
7.4
Overall
7.1
Crew
7.9
Reviews
1 / 20
6.0
GoodAnonymous,Jul 2026
ISP - FLL
Boarding
7.3
Food
6.6
Entertainment
7.2
Comfort
7.4
Overall
7.1
Crew
7.9
Reviews
1 / 20
6.0
GoodAnonymous,Jul 2026
ISP - FLL
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.
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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 October 30, 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 7,457,451 searches. Data last updated October 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$227 | Average$365 | FlexibilityNo cancel fee | On-time62% |