$138+ 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 4/8. Fares are subject to change and may not be available on all flights or dates of travel.
HPN — SJU
May 1 — May 81
Round-trip
1 adult, Economy
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Find cheap flights from Westchester County to Caribbean 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 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 April 1, 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 April 1, 2026.
This American Airlines deal was found by Cheapflights users on 3/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/176:00 am
HPN
- STT
1 stop10h 15m
American Airlines
Thu 5/214:48 pm
STT
- HPN
2 stops17h 42m
American Airlines
Deal found 3/30![American Airlines logo]()
$280
This American Airlines deal was found by Cheapflights users on 3/31. 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 5/146:00 am
HPN
- STT
1 stop10h 15m
American Airlines
Mon 5/1812:25 pm
STT
- HPN
2 stops22h 05m
American Airlines
Deal found 3/31![American Airlines logo]()
$281
This American Airlines deal was found by Cheapflights users on 3/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/45:16 pm
HPN
- STT
2 stops22h 59m
American Airlines
Wed 5/63:29 pm
STT
- HPN
2 stops19h 01m
American Airlines
Deal found 3/28![American Airlines logo]()
$300
This American Airlines deal was found by Cheapflights users on 3/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/295:16 pm
HPN
- STT
2 stops18h 19m
American Airlines
Wed 5/63:29 pm
STT
- HPN
2 stops19h 01m
American Airlines
Deal found 3/28![American Airlines logo]()
$305
This American Airlines deal was found by Cheapflights users on 3/31. 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 4/145:16 pm
HPN
- SJU
2 stops15h 57m
American Airlines
Tue 4/215:45 am
SJU
- HPN
2 stops12h 42m
American Airlines
Deal found 3/31![American Airlines logo]()
$316
This American Airlines deal was found by Cheapflights users on 3/31. 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 4/157:49 am
HPN
- SJU
1 stop13h 02m
American Airlines
Tue 4/2111:43 am
SJU
- HPN
1 stop11h 09m
American Airlines
Deal found 3/31![American Airlines logo]()
$321
This Cheapflightsfares deal was found by Cheapflights users on 3/31. 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.
Wed 4/228:30 am
HPN
- SJU
Nonstop3h 50m
JetBlue
Mon 4/274:55 pm
SJU
- HPN
Nonstop4h 05m
JetBlue
Deal found 3/31![JetBlue logo]()
$330
This American Airlines deal was found by Cheapflights users on 3/31. 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 5/76:00 am
HPN
- STT
1 stop10h 15m
American Airlines
Mon 5/1112:25 pm
STT
- HPN
1 stop10h 27m
American Airlines
Deal found 3/31![American Airlines logo]()
$332
This American Airlines deal was found by Cheapflights users on 3/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/256:57 pm
HPN
- MBJ
2 stops21h 40m
American Airlines
Sat 5/212:56 pm
MBJ
- HPN
2 stops19h 33m
American Airlines
Deal found 3/28![American Airlines logo]()
$337
This KAYAK deal was found by Cheapflights users on 3/27. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/2510:48 am
HPN
- SJU
1 stop10h 01m
JetBlue
Mon 4/274:55 pm
SJU
- HPN
Nonstop4h 05m
JetBlue
Deal found 3/27![JetBlue logo]()
$340
This American Airlines deal was found by Cheapflights users on 4/1. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/66:30 am
HPN
- SJU
2 stops16h 26m
American Airlines
Tue 9/83:50 pm
SJU
- HPN
1 stop17h 23m
American Airlines
Deal found 4/1![American Airlines logo]()
$341
This American Airlines deal was found by Cheapflights users on 3/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/196:59 pm
HPN
- MBJ
2 stops17h 52m
American Airlines
Sun 5/312:56 pm
MBJ
- HPN
2 stops19h 33m
American Airlines
Deal found 3/28![American Airlines logo]()
$342
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 April 1, 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 April 1, 2026.
This American Airlines deal was found by Cheapflights users on 3/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/146:00 am
HPN
- STT
1 stop10h 15m
American Airlines
Mon 5/1812:25 pm
STT
- HPN
2 stops22h 05m
American Airlines
Deal found 3/30![American Airlines logo]()
$281
This JetBlue deal was found by Cheapflights users on 3/26. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/38:30 am
HPN
- SJU
Nonstop3h 50m
JetBlue
Thu 5/74:55 pm
SJU
- HPN
Nonstop4h 05m
JetBlue
Deal found 3/26![JetBlue logo]()
$335
This Delta deal was found by Cheapflights users on 3/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/2212:48 pm
HPN
- SJU
1 stop7h 36m
Delta
Wed 4/296:15 am
SJU
- HPN
1 stop12h 01m
Delta
Deal found 3/28![Delta logo]()
$344
This American Airlines deal was found by Cheapflights users on 3/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/76:00 am
HPN
- STT
1 stop10h 15m
American Airlines
Mon 5/1112:25 pm
STT
- HPN
1 stop10h 27m
American Airlines
Deal found 3/29![American Airlines logo]()
$332
This JetBlue deal was found by Cheapflights users on 3/27. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/58:30 am
HPN
- SJU
Nonstop3h 50m
JetBlue
Wed 5/64:55 pm
SJU
- HPN
Nonstop4h 05m
JetBlue
Deal found 3/27![JetBlue logo]()
$355
This Delta deal was found by Cheapflights users on 3/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/266:00 am
HPN
- STT
1 stop8h 48m
Delta
Fri 5/11:22 pm
STT
- HPN
1 stop8h 41m
Delta
Deal found 3/28![Delta logo]()
$359
This American Airlines deal was found by Cheapflights users on 3/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/256:00 am
HPN
- MBJ
1 stop10h 37m
American Airlines
Sat 5/212:56 pm
MBJ
- HPN
2 stops19h 33m
American Airlines
Deal found 3/28![American Airlines logo]()
$337
This Delta deal was found by Cheapflights users on 3/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/276:00 am
HPN
- STT
1 stop8h 48m
Delta
Fri 5/11:22 pm
STT
- HPN
1 stop8h 41m
Delta
Deal found 3/28![Delta logo]()
$359
This KAYAK deal was found by Cheapflights users on 3/28. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/268:59 pm
HPN
- STI
1 stop11h 03m
JetBlue
Wed 4/297:30 am
STI
- HPN
1 stop7h 04m
JetBlue
Deal found 3/28![JetBlue logo]()
$363
This American Airlines deal was found by Cheapflights users on 3/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/196:00 am
HPN
- MBJ
1 stop10h 37m
American Airlines
Sun 5/312:56 pm
MBJ
- HPN
2 stops19h 33m
American Airlines
Deal found 3/28![American Airlines logo]()
$342
This KAYAK deal was found by Cheapflights users on 3/28. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/107:55 pm
HPN
- STI
1 stop11h 52m
JetBlue
Fri 5/298:52 am
STI
- HPN
1 stop11h 07m
JetBlue
Deal found 3/28![JetBlue logo]()
$363
This Delta deal was found by Cheapflights users on 3/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/196:00 am
HPN
- NAS
1 stop8h 03m
Delta
Thu 4/233:28 pm
NAS
- HPN
1 stop6h 35m
Delta
Deal found 3/27![Delta logo]()
$396
This KAYAK deal was found by Cheapflights users on 3/31. 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 4/207:55 pm
HPN
- STI
1 stop11h 25m
JetBlue
Thu 4/307:30 am
STI
- HPN
1 stop7h 04m
JetBlue
Deal found 3/31![JetBlue logo]()
$364
This American Airlines deal was found by Cheapflights users on 3/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/126:00 am
HPN
- NAS
1 stop8h 46m
American Airlines
Tue 5/195:28 pm
NAS
- HPN
1 stop16h 01m
American Airlines
Deal found 3/28![American Airlines logo]()
$366
This Delta deal was found by Cheapflights users on 3/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/176:00 am
HPN
- NAS
1 stop8h 03m
Delta
Mon 4/203:28 pm
NAS
- HPN
1 stop6h 35m
Delta
Deal found 3/27![Delta logo]()
$396
This JetBlue deal was found by Cheapflights users on 3/27. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/278:59 pm
HPN
- STI
1 stop11h 03m
JetBlue
Thu 4/307:30 am
STI
- HPN
1 stop7h 04m
JetBlue
Deal found 3/27![JetBlue logo]()
$365
This American Airlines deal was found by Cheapflights users on 3/31. 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 5/25:59 pm
HPN
- AUA
2 stops19h 23m
American Airlines
Sat 5/95:25 pm
AUA
- HPN
2 stops17h 05m
American Airlines
Deal found 3/31![American Airlines logo]()
$374
This Delta deal was found by Cheapflights users on 3/31. 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 9/146:00 am
HPN
- NAS
1 stop5h 50m
Delta
Fri 9/181:15 pm
NAS
- HPN
1 stop8h 27m
Delta
Deal found 3/31![Delta logo]()
$396
This JetBlue deal was found by Cheapflights users on 3/29. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/187:00 am
HPN
- PUJ
1 stop10h 16m
JetBlue
Wed 4/223:24 pm
PUJ
- HPN
1 stop7h 35m
JetBlue
Deal found 3/29![JetBlue logo]()
$369
This American Airlines deal was found by Cheapflights users on 3/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/106:59 pm
HPN
- PUJ
2 stops16h 01m
American Airlines
Fri 7/175:56 pm
PUJ
- HPN
2 stops19h 17m
American Airlines
Deal found 3/30![American Airlines logo]()
$398
This Delta deal was found by Cheapflights users on 3/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/134:29 pm
HPN
- SJU
1 stop6h 43m
Delta
Thu 4/166:15 am
SJU
- HPN
1 stop8h 14m
Delta
Deal found 3/30![Delta logo]()
$404
This JetBlue deal was found by Cheapflights users on 3/29. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/118:59 pm
HPN
- MBJ
1 stop11h 42m
JetBlue
Fri 5/1511:35 am
MBJ
- HPN
1 stop10h 24m
JetBlue
Deal found 3/29![JetBlue logo]()
$382
This American Airlines deal was found by Cheapflights users on 3/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/166:00 am
HPN
- AUA
1 stop10h 25m
American Airlines
Sun 4/192:30 pm
AUA
- HPN
2 stops18h 59m
American Airlines
Deal found 3/29![American Airlines logo]()
$401
This Delta deal was found by Cheapflights users on 3/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/256:00 am
HPN
- NAS
1 stop5h 48m
Delta
Sun 8/301:13 pm
NAS
- HPN
1 stop8h 29m
Delta
Deal found 3/27![Delta logo]()
$434
This American Airlines deal was found by Cheapflights users on 3/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/166:59 pm
HPN
- PLS
1 stop17h 01m
American Airlines
Tue 4/211:25 pm
PLS
- HPN
1 stop9h 27m
American Airlines
Deal found 3/27![American Airlines logo]()
$405
This JetBlue deal was found by Cheapflights users on 3/30. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/18:30 pm
HPN
- STI
1 stop11h 10m
JetBlue
Thu 6/48:52 am
STI
- HPN
1 stop11h 07m
JetBlue
Deal found 3/30![JetBlue logo]()
$410
This Delta deal was found by Cheapflights users on 3/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/266:00 am
HPN
- NAS
1 stop5h 48m
Delta
Sun 8/301:13 pm
NAS
- HPN
1 stop8h 29m
Delta
Deal found 3/27![Delta logo]()
$434
This American Airlines deal was found by Cheapflights users on 3/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/145:16 pm
HPN
- PLS
2 stops18h 44m
American Airlines
Thu 5/212:55 pm
PLS
- HPN
2 stops18h 33m
American Airlines
Deal found 3/30![American Airlines logo]()
$410
This JetBlue deal was found by Cheapflights users on 3/28. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/268:05 am
HPN
- SJU
1 stop6h 24m
JetBlue
Wed 4/295:01 am
SJU
- HPN
1 stop9h 33m
JetBlue
Deal found 3/28![JetBlue logo]()
$419
This Delta deal was found by Cheapflights users on 3/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/186:00 am
HPN
- NAS
1 stop8h 03m
Delta
Sat 4/251:13 pm
NAS
- HPN
1 stop8h 50m
Delta
Deal found 3/29![Delta logo]()
$434
Last-minute flights from Westchester County to CaribbeanDiscover last-minute flight deals from Westchester County to Caribbean. Data last updated April 1, 2026 and is based on user searches.
Discover last-minute flight deals from Westchester County to Caribbean. Data last updated April 1, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 3/31. 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 4/511:29 am
HPN
- SJU
2 stops9h 05m
American Airlines
Thu 4/910:03 am
SJU
- HPN
1 stop12h 49m
American Airlines
Deal found 3/31![American Airlines logo]()
$346
This American Airlines deal was found by Cheapflights users on 3/31. 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 4/146:00 am
HPN
- SJU
1 stop8h 52m
American Airlines
Tue 4/2110:03 am
SJU
- HPN
1 stop12h 49m
American Airlines
Deal found 3/31![American Airlines logo]()
$316
This American Airlines deal was found by Cheapflights users on 3/31. 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 4/156:00 am
HPN
- SJU
1 stop12h 10m
American Airlines
Tue 4/215:45 am
SJU
- HPN
2 stops14h 42m
American Airlines
Deal found 3/31![American Airlines logo]()
$321
This American Airlines deal was found by Cheapflights users on 3/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/175:16 pm
HPN
- STT
2 stops17h 31m
American Airlines
Tue 4/2112:25 pm
STT
- HPN
1 stop10h 27m
American Airlines
Deal found 3/30![American Airlines logo]()
$281
This American Airlines deal was found by Cheapflights users on 3/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/196:00 am
HPN
- MBJ
1 stop10h 37m
American Airlines
Sun 5/312:56 pm
MBJ
- HPN
2 stops19h 33m
American Airlines
Deal found 3/28![American Airlines logo]()
$342
This Delta deal was found by Cheapflights users on 3/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/216:00 am
HPN
- SJU
1 stop10h 23m
Delta
Wed 4/296:15 am
SJU
- HPN
1 stop12h 01m
Delta
Deal found 3/28![Delta logo]()
$344
This Cheapflightsfares deal was found by Cheapflights users on 3/31. 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.
Wed 4/228:30 am
HPN
- SJU
Nonstop3h 50m
JetBlue
Mon 4/274:55 pm
SJU
- HPN
Nonstop4h 05m
JetBlue
Deal found 3/31![JetBlue logo]()
$330
This American Airlines deal was found by Cheapflights users on 3/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/256:57 pm
HPN
- MBJ
2 stops21h 40m
American Airlines
Sat 5/212:56 pm
MBJ
- HPN
2 stops19h 33m
American Airlines
Deal found 3/28![American Airlines logo]()
$337
This KAYAK deal was found by Cheapflights users on 3/27. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/2510:48 am
HPN
- SJU
1 stop10h 01m
JetBlue
Mon 4/274:55 pm
SJU
- HPN
Nonstop4h 05m
JetBlue
Deal found 3/27![JetBlue logo]()
$340
This KAYAK deal was found by Cheapflights users on 3/28. 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 KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/2510:48 am
HPN
- SJU
1 stop10h 01m
JetBlue
Wed 4/2912:55 pm
SJU
- HPN
1 stop10h 04m
JetBlue
Deal found 3/28![JetBlue logo]()
$345
This American Airlines deal was found by Cheapflights users on 3/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/275:16 pm
HPN
- STT
2 stops18h 19m
American Airlines
Fri 5/15:05 pm
STT
- HPN
2 stops21h 26m
American Airlines
Deal found 3/28![American Airlines logo]()
$300
This American Airlines deal was found by Cheapflights users on 3/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/295:16 pm
HPN
- STT
2 stops18h 19m
American Airlines
Wed 5/63:29 pm
STT
- HPN
2 stops19h 01m
American Airlines
Deal found 3/28![American Airlines logo]()
$305
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 April 1, 2026.
Search for one-way flight options from Westchester County to Caribbean. Find affordable one-way fares based on user searches. Data last updated April 1, 2026.
This Delta deal was found by Cheapflights users on 3/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/86:00 am
HPN
- STT
1 stop8h 48m
Delta
Deal found 3/27![Delta logo]()
$138
This American Airlines deal was found by Cheapflights users on 3/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/83:01 pm
HPN
- STT
2 stops19h 46m
American Airlines
Deal found 3/27![American Airlines logo]()
$143
This Delta deal was found by Cheapflights users on 3/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/176:00 am
HPN
- NAS
1 stop8h 03m
Delta
Deal found 3/27![Delta logo]()
$144
This American Airlines deal was found by Cheapflights users on 3/31. 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 9/45:29 pm
HPN
- NAS
2 stops16h 11m
American Airlines
Deal found 3/31![American Airlines logo]()
$146
This American Airlines deal was found by Cheapflights users on 3/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/36:59 pm
HPN
- MBJ
2 stops19h 10m
American Airlines
Deal found 3/28![American Airlines logo]()
$148
This American Airlines deal was found by Cheapflights users on 3/31. 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 5/2711:00 am
HPN
- NAS
2 stops8h 30m
American Airlines
Deal found 3/31![American Airlines logo]()
$151
This Delta deal was found by Cheapflights users on 3/31. 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 5/176:00 am
HPN
- MBJ
1 stop10h 34m
Delta
Deal found 3/31![Delta logo]()
$152
This American Airlines deal was found by Cheapflights users on 3/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/286:30 pm
HPN
- MBJ
1 stop20h 00m
American Airlines
Deal found 3/30![American Airlines logo]()
$155
This Kiwi.com deal was found by Cheapflights users on 3/31. 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.
Fri 5/156:09 pm
HPN
- SJU
2 stops29h 50m
Multiple Airlines
Deal found 3/31![Multiple Airlines logo]()
$156
This Delta deal was found by Cheapflights users on 3/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/166:40 pm
HPN
- AUA
1 stop17h 20m
Delta
Deal found 3/29![Delta logo]()
$157
This Delta deal was found by Cheapflights users on 3/31. 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 5/165:15 pm
HPN
- MBJ
2 stops23h 19m
Delta
Deal found 3/31![Delta logo]()
$158
This American Airlines deal was found by Cheapflights users on 3/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/127:49 am
HPN
- SJU
1 stop13h 02m
American Airlines
Deal found 3/29![American Airlines logo]()
$158
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 April 1, 2026.
Round-trip from | $280 (American Airlines) |
|---|---|
One-way from | $138 (Delta) |
Popular in | December |
Cheapest in | October |
Average price | $325 |
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 April 1, 2026.
Use the filters below to find and compare flights from Westchester County to Caribbean that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
White PlainsSaint Thomas Island
HPN - STT
HPNSTT
White Plains Westchester County
Thu 5/14
6:00 am-4:15 pm
1 stop10h 15m
Saint Thomas Island Cyril E King
Mon 5/18
12:25 pm-10:30 am
2 stops22h 05m
$281
White PlainsSaint Thomas Island
HPN - STT
HPNSTT
White Plains Westchester County
Thu 5/7
6:00 am-4:15 pm
1 stop10h 15m
Saint Thomas Island Cyril E King
Mon 5/11
12:25 pm-10:52 pm
1 stop10h 27m
$332
Quickest round-trip
White PlainsSan Juan
HPN - SJU
HPNSJU
White Plains Westchester County
Sun 5/3
8:30 am-12:20 pm
Nonstop3h 50m
San Juan Luis Munoz Marin Intl
Thu 5/7
4:55 pm-9:00 pm
Nonstop4h 05m
$335
White PlainsMontego Bay
HPN - MBJ
HPNMBJ
White Plains Westchester County
Sat 4/25
6:00 am-3:37 pm
1 stop10h 37m
Montego Bay Sangster Intl
Sat 5/2
12:56 pm-9:29 am
2 stops19h 33m
$337
White PlainsMontego Bay
HPN - MBJ
HPNMBJ
White Plains Westchester County
Sun 4/19
6:00 am-3:37 pm
1 stop10h 37m
Montego Bay Sangster Intl
Sun 5/3
12:56 pm-9:29 am
2 stops19h 33m
$342
White PlainsSan Juan
HPN - SJU
HPNSJU
White Plains Westchester County
Wed 4/22
12:48 pm-8:24 pm
1 stop7h 36m
San Juan Luis Munoz Marin Intl
Wed 4/29
6:15 am-6:16 pm
1 stop12h 01m
$344
White PlainsSan Juan
HPN - SJU
HPNSJU
White Plains Westchester County
Tue 5/5
8:30 am-12:20 pm
Nonstop3h 50m
San Juan Luis Munoz Marin Intl
Wed 5/6
4:55 pm-9:00 pm
Nonstop4h 05m
$355
White PlainsSaint Thomas Island
HPN - STT
HPNSTT
White Plains Westchester County
Sun 4/26
6:00 am-2:48 pm
1 stop8h 48m
Saint Thomas Island Cyril E King
Fri 5/1
1:22 pm-10:03 pm
1 stop8h 41m
$359
White PlainsSaint Thomas Island
HPN - STT
HPNSTT
White Plains Westchester County
Mon 4/27
6:00 am-2:48 pm
1 stop8h 48m
Saint Thomas Island Cyril E King
Fri 5/1
1:22 pm-10:03 pm
1 stop8h 41m
$359
White PlainsSantiago de los Caballeros
HPN - STI
HPNSTI
White Plains Westchester County
Sun 4/26
8:59 pm-8:02 am
1 stop11h 03m
Santiago de los Caballeros
Wed 4/29
7:30 am-2:34 pm
1 stop7h 04m
$363
Showing 1-10 of 60 resultsSorted by cheapest first
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-STT
HPN-SJU
HPN-MBJ
HPN-PUJ
HPN-NAS
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-STT
HPN-SJU
HPN-MBJ
HPN-PUJ
What is the cheapest month to book a flight from Westchester County to Caribbean?
Currently, January is the cheapest month in which you can book a flight from Westchester County to Caribbean (average of $157). Flying from Westchester County to Caribbean in August is currently the most expensive (average of $305). 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 April 1, 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 April 1, 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 April 1, 2026.
Read reviews from past customers who have flown Delta,JetBlue, andAmerican Airlines 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
Overall
7.9
Entertainment
7.8
Food
7.2
Crew
8.5
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentKymberlee,Oct 2024
JFK - ATL
Comfort
7.9
Overall
7.9
Entertainment
7.8
Food
7.2
Crew
8.5
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentKymberlee,Oct 2024
JFK - ATL
Comfort
7.9
Overall
7.9
Entertainment
7.8
Food
7.2
Crew
8.5
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentKymberlee,Oct 2024
JFK - ATL
Comfort
7.9
Overall
7.9
Entertainment
7.8
Food
7.2
Crew
8.5
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentKymberlee,Oct 2024
JFK - ATL
Comfort
7.9
Overall
7.9
Entertainment
7.8
Food
7.2
Crew
8.5
Boarding
8.1
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.
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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 April 1, 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 April 1, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$28 | Average$289 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$118 | Average$377 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$205 | Average$480 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$329 | Average$498 | FlexibilityNo cancel fee | On-time71% |