$110+ Cheap flights from Westchester County to Caribbean
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 4/2. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — SJU
Mar 14 — Mar 211
1 adult, Economy
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Find cheap flights from Westchester County to Caribbean 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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Cheapest flights from Westchester County to CaribbeanExplore the most affordable flight options available from Westchester County to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 12, 2026.
Explore the most affordable flight options available from Westchester County to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 12, 2026.
This American Airlines deal was found by Cheapflights users on 2/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/311:28 am
HPN
- SJU
2 stops8h 11m
American Airlines
Thu 3/58:40 am
SJU
- HPN
2 stops12h 28m
American Airlines
Deal found 2/12![American Airlines logo]()
$236
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/225:16 pm
HPN
- STT
2 stops20h 19m
American Airlines
Wed 4/293:29 pm
STT
- HPN
2 stops19h 01m
American Airlines
Deal found 2/9![American Airlines logo]()
$240
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/97:00 am
HPN
- SJU
1 stop15h 58m
American Airlines
Thu 3/125:00 am
SJU
- HPN
2 stops13h 24m
American Airlines
Deal found 2/9![American Airlines logo]()
$246
This American Airlines deal was found by Cheapflights users on 2/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/86:54 pm
HPN
- STT
1 stop16h 12m
American Airlines
Wed 3/181:53 pm
STT
- HPN
1 stop9h 36m
American Airlines
Deal found 2/12![American Airlines logo]()
$250
This American Airlines deal was found by Cheapflights users on 2/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/236:30 am
HPN
- SJU
2 stops8h 50m
American Airlines
Wed 2/257:00 am
SJU
- HPN
2 stops12h 19m
American Airlines
Deal found 2/10![American Airlines logo]()
$251
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/286:54 pm
HPN
- STT
1 stop16h 12m
American Airlines
Wed 3/41:41 pm
STT
- HPN
1 stop10h 18m
American Airlines
Deal found 2/9![American Airlines logo]()
$251
This American Airlines deal was found by Cheapflights users on 2/11. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/17:47 am
HPN
- SJU
1 stop13h 02m
American Airlines
Thu 3/58:40 am
SJU
- HPN
2 stops12h 28m
American Airlines
Deal found 2/11![American Airlines logo]()
$254
This American Airlines deal was found by Cheapflights users on 2/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/2110:05 am
HPN
- SJU
1 stop10h 44m
American Airlines
Wed 2/255:42 pm
SJU
- HPN
1 stop16h 47m
American Airlines
Deal found 2/12![American Airlines logo]()
$256
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/106:00 am
HPN
- SJU
2 stops13h 39m
American Airlines
Wed 3/116:00 am
SJU
- HPN
2 stops12h 24m
American Airlines
Deal found 2/9![American Airlines logo]()
$261
This American Airlines deal was found by Cheapflights users on 2/11. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/911:29 am
HPN
- SJU
2 stops12h 23m
American Airlines
Wed 3/186:00 am
SJU
- HPN
1 stop17h 29m
American Airlines
Deal found 2/11![American Airlines logo]()
$264
This KAYAK 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/258:00 am
HPN
- SJU
Nonstop3h 45m
JetBlue
Fri 5/295:00 pm
SJU
- HPN
Nonstop3h 56m
JetBlue
Deal found 2/8![JetBlue logo]()
$265
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/176:00 am
HPN
- STT
1 stop7h 47m
Delta
Tue 3/2412:49 pm
STT
- HPN
1 stop9h 18m
Delta
Deal found 2/8![Delta logo]()
$270
Best flights from Westchester County to CaribbeanDiscover carefully curated flight deals from Westchester County to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 12, 2026.
Discover carefully curated flight deals from Westchester County to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 12, 2026.
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/86:54 pm
HPN
- STT
1 stop16h 12m
American Airlines
Wed 3/183:40 pm
STT
- HPN
1 stop7h 49m
American Airlines
Deal found 2/9![American Airlines logo]()
$240
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/176:00 am
HPN
- STT
1 stop7h 47m
Delta
Tue 3/2412:49 pm
STT
- HPN
1 stop9h 18m
Delta
Deal found 2/8![Delta logo]()
$270
This Cheapflightsfares deal was found by Cheapflights users on 2/11. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/228:30 am
HPN
- SJU
Nonstop3h 47m
JetBlue
Wed 3/255:01 am
SJU
- HPN
1 stop6h 58m
JetBlue
Deal found 2/11![JetBlue logo]()
$309
This American Airlines deal was found by Cheapflights users on 2/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/226:00 am
HPN
- STT
1 stop10h 15m
American Airlines
Wed 4/291:15 pm
STT
- HPN
2 stops21h 15m
American Airlines
Deal found 2/10![American Airlines logo]()
$250
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/186:00 am
HPN
- STT
1 stop8h 45m
Delta
Tue 3/2412:49 pm
STT
- HPN
1 stop9h 18m
Delta
Deal found 2/8![Delta logo]()
$270
This American Airlines deal was found by Cheapflights users on 2/11. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/185:30 pm
HPN
- STT
2 stops19h 33m
American Airlines
Tue 3/241:53 pm
STT
- HPN
1 stop9h 36m
American Airlines
Deal found 2/11![American Airlines logo]()
$250
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/2112:48 pm
HPN
- SJU
1 stop10h 24m
Delta
Tue 4/282:34 pm
SJU
- HPN
1 stop7h 27m
Delta
Deal found 2/9![Delta logo]()
$274
This Mytrip deal was found by Cheapflights users on 2/10. 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.
Fri 3/279:23 am
HPN
- SDQ
2 stops17h 17m
Multiple Airlines
Thu 4/23:55 am
SDQ
- HPN
2 stops12h 51m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$631
This American Airlines deal was found by Cheapflights users on 2/11. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/1611:29 am
HPN
- SJU
2 stops12h 23m
American Airlines
Thu 3/196:00 am
SJU
- HPN
1 stop17h 29m
American Airlines
Deal found 2/11![American Airlines logo]()
$264
This Delta deal was found by Cheapflights users on 2/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/186:00 am
HPN
- STT
1 stop8h 45m
Delta
Wed 3/251:55 pm
STT
- HPN
1 stop8h 12m
Delta
Deal found 2/11![Delta logo]()
$280
This American Airlines deal was found by Cheapflights users on 2/11. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/126:00 am
HPN
- MBJ
1 stop6h 51m
American Airlines
Wed 4/1512:56 pm
MBJ
- HPN
1 stop8h 56m
American Airlines
Deal found 2/11![American Airlines logo]()
$302
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/1812:48 pm
HPN
- SJU
1 stop10h 24m
Delta
Sat 4/256:15 am
SJU
- HPN
1 stop8h 14m
Delta
Deal found 2/9![Delta logo]()
$304
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/195:30 pm
HPN
- MBJ
2 stops19h 57m
American Airlines
Tue 3/241:27 pm
MBJ
- HPN
1 stop9h 02m
American Airlines
Deal found 2/8![American Airlines logo]()
$305
This Delta deal was found by Cheapflights users on 2/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/16:00 am
HPN
- SJU
1 stop10h 27m
Delta
Wed 3/47:30 am
SJU
- HPN
1 stop7h 58m
Delta
Deal found 2/11![Delta logo]()
$314
This KAYAK deal was found by Cheapflights users on 2/10. 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 3/208:35 pm
HPN
- SDQ
1 stop10h 56m
JetBlue
Wed 3/259:45 am
SDQ
- HPN
1 stop8h 50m
JetBlue
Deal found 2/10![JetBlue logo]()
$494
This American Airlines deal was found by Cheapflights users on 2/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/175:16 pm
HPN
- PUJ
2 stops19h 26m
American Airlines
Wed 4/221:39 pm
PUJ
- HPN
1 stop9h 13m
American Airlines
Deal found 2/12![American Airlines logo]()
$313
This Delta deal was found by Cheapflights users on 2/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/266:00 am
HPN
- SJU
1 stop10h 27m
Delta
Wed 3/46:15 am
SJU
- HPN
1 stop9h 13m
Delta
Deal found 2/11![Delta logo]()
$314
This American Airlines deal was found by Cheapflights users on 2/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/146:57 pm
HPN
- PUJ
2 stops18h 05m
American Airlines
Sat 4/181:39 pm
PUJ
- HPN
2 stops19h 50m
American Airlines
Deal found 2/10![American Airlines logo]()
$313
This Delta deal was found by Cheapflights users on 2/10. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/256:00 am
HPN
- SJU
1 stop10h 27m
Delta
Tue 3/36:15 am
SJU
- HPN
1 stop9h 13m
Delta
Deal found 2/10![Delta logo]()
$314
This KAYAK deal was found by Cheapflights users on 2/10. 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.
Sat 3/218:35 pm
HPN
- SDQ
1 stop10h 56m
JetBlue
Wed 3/259:45 am
SDQ
- HPN
1 stop8h 50m
JetBlue
Deal found 2/10![JetBlue logo]()
$521
This American Airlines deal was found by Cheapflights users on 2/11. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/26:57 pm
HPN
- PUJ
2 stops19h 37m
American Airlines
Fri 5/84:23 pm
PUJ
- HPN
2 stops19h 04m
American Airlines
Deal found 2/11![American Airlines logo]()
$313
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/256:00 am
HPN
- SJU
1 stop10h 27m
Delta
Wed 3/47:30 am
SJU
- HPN
1 stop7h 58m
Delta
Deal found 2/9![Delta logo]()
$314
This KAYAK deal was found by Cheapflights users on 2/10. 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.
Mon 4/136:30 am
HPN
- SDQ
1 stop12h 01m
JetBlue
Sat 4/181:40 pm
SDQ
- HPN
1 stop8h 56m
JetBlue
Deal found 2/10![JetBlue logo]()
$524
This American Airlines deal was found by Cheapflights users on 2/11. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/305:30 pm
HPN
- AUA
2 stops22h 20m
American Airlines
Mon 4/64:50 pm
AUA
- HPN
2 stops20h 10m
American Airlines
Deal found 2/11![American Airlines logo]()
$314
This Delta deal was found by Cheapflights users on 2/12. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/1612:48 pm
HPN
- SJU
1 stop10h 24m
Delta
Tue 4/216:15 am
SJU
- HPN
1 stop8h 14m
Delta
Deal found 2/12![Delta logo]()
$324
This American Airlines deal was found by Cheapflights users on 2/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/226:00 am
HPN
- AUA
1 stop10h 25m
American Airlines
Mon 4/272:30 pm
AUA
- HPN
2 stops20h 57m
American Airlines
Deal found 2/12![American Airlines logo]()
$314
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/246:00 am
HPN
- AUA
1 stop8h 20m
Delta
Tue 3/313:35 pm
AUA
- HPN
1 stop18h 09m
Delta
Deal found 2/9![Delta logo]()
$325
This KAYAK deal was found by Cheapflights users on 2/10. 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 5/159:00 pm
HPN
- SDQ
1 stop10h 40m
JetBlue
Mon 5/1810:00 am
SDQ
- HPN
1 stop8h 55m
JetBlue
Deal found 2/10![JetBlue logo]()
$608
This American Airlines deal was found by Cheapflights users on 2/11. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/146:57 pm
HPN
- AUA
2 stops21h 28m
American Airlines
Sat 4/182:30 pm
AUA
- HPN
2 stops18h 59m
American Airlines
Deal found 2/11![American Airlines logo]()
$314
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/303:13 pm
HPN
- AUA
2 stops23h 07m
Delta
Wed 4/13:35 pm
AUA
- HPN
1 stop18h 09m
Delta
Deal found 2/9![Delta logo]()
$330
Last-minute flights from Westchester County to CaribbeanDiscover last-minute flight deals from Westchester County to Caribbean. Data last updated February 12, 2026 and is based on user searches.
Discover last-minute flight deals from Westchester County to Caribbean. Data last updated February 12, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 2/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/211:37 pm
HPN
- SJU
1 stop7h 12m
American Airlines
Wed 2/257:00 am
SJU
- HPN
2 stops12h 19m
American Airlines
Deal found 2/12![American Airlines logo]()
$256
This American Airlines deal was found by Cheapflights users on 2/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/236:30 am
HPN
- SJU
2 stops8h 50m
American Airlines
Wed 2/257:00 am
SJU
- HPN
2 stops12h 19m
American Airlines
Deal found 2/10![American Airlines logo]()
$251
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/286:54 pm
HPN
- STT
1 stop16h 12m
American Airlines
Wed 3/41:41 pm
STT
- HPN
1 stop10h 18m
American Airlines
Deal found 2/9![American Airlines logo]()
$251
This American Airlines deal was found by Cheapflights users on 2/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/17:47 am
HPN
- SJU
1 stop13h 02m
American Airlines
Thu 3/58:40 am
SJU
- HPN
2 stops12h 28m
American Airlines
Deal found 2/12![American Airlines logo]()
$236
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/86:54 pm
HPN
- STT
1 stop16h 12m
American Airlines
Wed 3/184:42 pm
STT
- HPN
2 stops18h 17m
American Airlines
Deal found 2/9![American Airlines logo]()
$240
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/97:00 am
HPN
- SJU
1 stop15h 58m
American Airlines
Thu 3/125:00 am
SJU
- HPN
2 stops13h 24m
American Airlines
Deal found 2/9![American Airlines logo]()
$246
This American Airlines deal was found by Cheapflights users on 2/11. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/911:29 am
HPN
- SJU
2 stops12h 23m
American Airlines
Wed 3/186:00 am
SJU
- HPN
1 stop17h 29m
American Airlines
Deal found 2/11![American Airlines logo]()
$264
This American Airlines deal was found by Cheapflights users on 2/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/97:00 am
HPN
- SJU
1 stop13h 50m
American Airlines
Tue 3/107:11 am
SJU
- HPN
1 stop16h 18m
American Airlines
Deal found 2/10![American Airlines logo]()
$271
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/93:05 pm
HPN
- SJU
1 stop8h 54m
JetBlue
Thu 3/125:01 am
SJU
- HPN
1 stop6h 58m
JetBlue
Deal found 2/9![JetBlue logo]()
$274
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/106:00 am
HPN
- SJU
2 stops13h 39m
American Airlines
Wed 3/116:00 am
SJU
- HPN
2 stops12h 24m
American Airlines
Deal found 2/9![American Airlines logo]()
$261
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/176:00 am
HPN
- STT
1 stop7h 47m
Delta
Tue 3/2412:49 pm
STT
- HPN
1 stop9h 18m
Delta
Deal found 2/8![Delta logo]()
$270
This KAYAK deal was found by Cheapflights users on 2/10. 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.
Sun 3/228:30 am
HPN
- SJU
Nonstop3h 47m
JetBlue
Thu 3/262:20 pm
SJU
- HPN
Nonstop4h 15m
JetBlue
Deal found 2/10![JetBlue logo]()
$275
One-way flights from Westchester County to CaribbeanSearch for one-way flight options from Westchester County to Caribbean. Find affordable one-way fares based on user searches. Data last updated February 12, 2026.
Search for one-way flight options from Westchester County to Caribbean. Find affordable one-way fares based on user searches. Data last updated February 12, 2026.
This American Airlines deal was found by Cheapflights users on 2/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/26:30 am
HPN
- GCM
1 stop8h 14m
American Airlines
Deal found 2/12![American Airlines logo]()
$110
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/66:00 am
HPN
- NAS
1 stop7h 00m
American Airlines
Deal found 2/8![American Airlines logo]()
$111
This American Airlines deal was found by Cheapflights users on 2/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/126:00 am
HPN
- NAS
1 stop7h 17m
American Airlines
Deal found 2/12![American Airlines logo]()
$116
This American Airlines deal was found by Cheapflights users on 2/11. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/177:00 am
HPN
- MBJ
1 stop6h 27m
American Airlines
Deal found 2/11![American Airlines logo]()
$122
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/216:54 pm
HPN
- SJU
1 stop15h 46m
American Airlines
Deal found 2/9![American Airlines logo]()
$123
This American Airlines deal was found by Cheapflights users on 2/11. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/107:00 am
HPN
- STT
1 stop7h 46m
American Airlines
Deal found 2/11![American Airlines logo]()
$123
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/124:30 pm
HPN
- MBJ
2 stops17h 37m
American Airlines
Deal found 2/8![American Airlines logo]()
$127
This American Airlines deal was found by Cheapflights users on 2/12. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/195:30 pm
HPN
- MBJ
2 stops18h 54m
American Airlines
Deal found 2/12![American Airlines logo]()
$128
This American Airlines deal was found by Cheapflights users on 2/10. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/256:30 am
HPN
- SJU
2 stops9h 22m
American Airlines
Deal found 2/10![American Airlines logo]()
$128
This American Airlines deal was found by Cheapflights users on 2/11. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/305:29 pm
HPN
- AUA
2 stops20h 01m
American Airlines
Deal found 2/11![American Airlines logo]()
$130
This American Airlines deal was found by Cheapflights users on 2/11. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/117:00 am
HPN
- MBJ
1 stop6h 27m
American Airlines
Deal found 2/11![American Airlines logo]()
$132
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/285:29 pm
HPN
- MBJ
2 stops18h 50m
American Airlines
Deal found 2/9![American Airlines logo]()
$133
Find flight deals from Westchester County to Caribbean
Keep the following information in mind while searching for Westchester County to Caribbean flight deals. Data was last updated February 12, 2026.
Round-trip from | $236 (American Airlines) |
|---|---|
One-way from | $110 (American Airlines) |
Popular in | December |
Cheapest in | May |
Average price | $299 |
Cheapflights Fare Finder
Customize your flight search to find flights from Westchester County to Caribbean 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 12, 2026.
Use the filters below to find and compare flights from Westchester County to Caribbean that are best for you.
Fly from
Westchester County
Fly to
Caribbean
Route
Depart
Return
Price
White PlainsSaint Thomas Island
HPN - STT
HPNSTT
White Plains Westchester County
Sun 3/8
6:54 pm-11:06 am
1 stop16h 12m
Saint Thomas Island Cyril E King
Wed 3/18
3:40 pm-11:29 pm
1 stop7h 49m
$240
White PlainsSaint Thomas Island
HPN - STT
HPNSTT
White Plains Westchester County
Wed 4/22
6:00 am-4:15 pm
1 stop10h 15m
Saint Thomas Island Cyril E King
Wed 4/29
1:15 pm-10:30 am
2 stops21h 15m
$250
White PlainsSaint Thomas Island
HPN - STT
HPNSTT
White Plains Westchester County
Wed 3/18
5:30 pm-1:03 pm
2 stops19h 33m
Saint Thomas Island Cyril E King
Tue 3/24
1:53 pm-11:29 pm
1 stop9h 36m
$250
White PlainsSan Juan
HPN - SJU
HPNSJU
White Plains Westchester County
Mon 3/16
11:29 am-11:52 pm
2 stops12h 23m
San Juan Luis Munoz Marin Intl
Thu 3/19
6:00 am-11:29 pm
1 stop17h 29m
$264
White PlainsSaint Thomas Island
HPN - STT
HPNSTT
White Plains Westchester County
Tue 3/17
6:00 am-1:47 pm
1 stop7h 47m
Saint Thomas Island Cyril E King
Tue 3/24
12:49 pm-10:07 pm
1 stop9h 18m
$270
White PlainsSaint Thomas Island
HPN - STT
HPNSTT
White Plains Westchester County
Wed 3/18
6:00 am-2:45 pm
1 stop8h 45m
Saint Thomas Island Cyril E King
Tue 3/24
12:49 pm-10:07 pm
1 stop9h 18m
$270
White PlainsSan Juan
HPN - SJU
HPNSJU
White Plains Westchester County
Tue 4/21
12:48 pm-11:12 pm
1 stop10h 24m
San Juan Luis Munoz Marin Intl
Tue 4/28
2:34 pm-10:01 pm
1 stop7h 27m
$274
White PlainsSaint Thomas Island
HPN - STT
HPNSTT
White Plains Westchester County
Wed 3/18
6:00 am-2:45 pm
1 stop8h 45m
Saint Thomas Island Cyril E King
Wed 3/25
1:55 pm-10:07 pm
1 stop8h 12m
$280
White PlainsMontego Bay
HPN - MBJ
HPNMBJ
White Plains Westchester County
Sun 4/12
6:00 am-11:51 am
1 stop6h 51m
Montego Bay Sangster Intl
Wed 4/15
12:56 pm-10:52 pm
1 stop8h 56m
$302
White PlainsSan Juan
HPN - SJU
HPNSJU
White Plains Westchester County
Sat 4/18
12:48 pm-11:12 pm
1 stop10h 24m
San Juan Luis Munoz Marin Intl
Sat 4/25
6:15 am-2:29 pm
1 stop8h 14m
$304
Showing 1-10 of 60 results
Best time to book a flight from Westchester County to Caribbean
Have a flexible travel schedule? Discover the best time to fly to Caribbean from Westchester County with our price prediction graph.
HPN-GCM
HPN-NAS
HPN-MBJ
HPN-SJU
HPN-STT
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 Westchester County to Caribbean
zzREU-0CB
HPN-GCM
HPN-NAS
HPN-MBJ
HPN-SJU
What is the cheapest month to book a flight from Westchester County to Caribbean?
Currently, March is the cheapest month in which you can book a flight from Westchester County to Caribbean (average of $151). Flying from Westchester County to Caribbean in August is currently the most expensive (average of $321). 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.
What is the cheapest time of day to fly from REU to CB?
Find hourly flight availability from Westchester County to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 12, 2026.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Westchester County to Caribbean as you normally would.
Weekly flight availability from Westchester County to Caribbean
Explore weekly flight availability from Westchester County to Caribbean. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated February 12, 2026.
The most flights from zzREU to 0CB are scheduled on a Monday (1 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (1 on average).
Reviews of airlines servicing Caribbean
Get insights into the airlines that provide service to Caribbean. 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 Caribbean. Reviews last updated February 12, 2026.
Read reviews from past customers who have flown Delta, American Airlines, and JetBlue from Westchester County to Caribbean. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
7.9
Food
7.2
Crew
8.5
Overall
7.9
Boarding
8.1
Entertainment
7.8
Reviews
1 / 20
10.0
ExcellentKymberlee,Oct 2024
JFK - ATL
Comfort
7.9
Food
7.2
Crew
8.5
Overall
7.9
Boarding
8.1
Entertainment
7.8
Reviews
1 / 20
10.0
ExcellentKymberlee,Oct 2024
JFK - ATL
Comfort
7.9
Food
7.2
Crew
8.5
Overall
7.9
Boarding
8.1
Entertainment
7.8
Reviews
1 / 20
10.0
ExcellentKymberlee,Oct 2024
JFK - ATL
Comfort
7.9
Food
7.2
Crew
8.5
Overall
7.9
Boarding
8.1
Entertainment
7.8
Reviews
1 / 20
10.0
ExcellentKymberlee,Oct 2024
JFK - ATL
Comfort
7.9
Food
7.2
Crew
8.5
Overall
7.9
Boarding
8.1
Entertainment
7.8
Reviews
1 / 20
10.0
ExcellentKymberlee,Oct 2024
JFK - ATL
Related info for your journey
Find useful and relevant information for your journey from Westchester County to Caribbean. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
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Alternative routes for Westchester County to Caribbean
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Caribbean by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Westchester County to Caribbean by cabin class
Find flights from Westchester County to Caribbean, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Westchester County and Caribbean flights
Browse other Westchester County and Caribbean flight options. Last updated on February 12, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Find a return flight route from Caribbean
Find the right flight back to Westchester County after your stay in Caribbean
Fly to Caribbean countries
Consider these flights traveling to countries located in Caribbean.
Westchester County to Caribbean flights
Consider these flights traveling from Westchester County to Caribbean.
Top 4 airlines flying from Westchester County to Caribbean
Discover the top 4 airlines that operate flights from Westchester County to Caribbean. 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 February 12, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$64 | Average$214 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$118 | Average$298 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$204 | Average$564 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$220 | Average$521 | FlexibilityNo cancel fee | On-time71% |