$105+ Cheap flights to Caribbean Islands
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 5/14. Fares are subject to change and may not be available on all flights or dates of travel.
— SJU
mag 27 — giu 31
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights to Caribbean Islands 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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Flights to Caribbean Islands in 2026
Cheapest
Best
Last-minute
One-way
Cheapest flights to Caribbean IslandsExplore the most affordable flight options available to Caribbean Islands. Find the lowest fares based on data from user searches, with prices last updated on aprile 27, 2026.
Explore the most affordable flight options available to Caribbean Islands. Find the lowest fares based on data from user searches, with prices last updated on aprile 27, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/25. 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.
mer 5/2711:30 am
EWR
- SJU
1 stop14h 38m
Frontier
ven 6/55:15 pm
SJU
- EWR
1 stop8h 03m
Frontier
Deal found 4/25![Frontier logo]()
$214
This Kiwi.com deal was found by Cheapflights users on 4/25. 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.
mer 6/37:45 am
EWR
- SJU
Nonstop3h 55m
Multiple Airlines
mer 6/105:15 pm
SJU
- EWR
1 stop7h 50m
Multiple Airlines
Deal found 4/25![Multiple Airlines logo]()
$215
This Kiwi.com deal was found by Cheapflights users on 4/23. 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.
dom 5/176:00 am
EWR
- SJU
1 stop12h 59m
Spirit Airlines
mer 5/2712:59 am
SJU
- EWR
Nonstop4h 07m
Spirit Airlines
Deal found 4/23![Spirit Airlines logo]()
$216
This Mytrip deal was found by Cheapflights users on 4/25. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar 6/27:45 am
EWR
- SJU
Nonstop3h 55m
Multiple Airlines
mar 6/165:15 pm
SJU
- EWR
1 stop7h 50m
Multiple Airlines
Deal found 4/25![Multiple Airlines logo]()
$217
This CheapOair deal was found by Cheapflights users on 4/22. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer 5/278:30 pm
EWR
- SJU
Nonstop4h 05m
Multiple Airlines
ven 6/512:59 am
SJU
- EWR
Nonstop4h 07m
Multiple Airlines
Deal found 4/22![Multiple Airlines logo]()
$218
This Kiwi.com deal was found by Cheapflights users on 4/23. 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.
lun 5/256:42 pm
EWR
- SJU
Nonstop4h 00m
Spirit Airlines
sab 6/67:30 am
SJU
- EWR
Nonstop4h 13m
Spirit Airlines
Deal found 4/23![Spirit Airlines logo]()
$219
This Kiwi.com deal was found by Cheapflights users on 4/25. 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.
lun 5/256:42 pm
EWR
- SJU
Nonstop4h 00m
Multiple Airlines
gio 6/46:09 pm
SJU
- EWR
1 stop16h 23m
Multiple Airlines
Deal found 4/25![Multiple Airlines logo]()
$220
This Cheapflightsfares deal was found by Cheapflights users on 4/26. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
gio 5/286:42 pm
EWR
- SJU
Nonstop4h 00m
Spirit Airlines
ven 6/52:59 am
SJU
- EWR
1 stop10h 46m
Spirit Airlines
Deal found 4/26![Spirit Airlines logo]()
$221
This Kiwi.com deal was found by Cheapflights users on 4/26. 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.
dom 5/316:42 pm
EWR
- SJU
Nonstop4h 00m
Spirit Airlines
mer 6/104:28 pm
SJU
- EWR
Nonstop4h 17m
Spirit Airlines
Deal found 4/26![Spirit Airlines logo]()
$222
This Cheapflightsfares deal was found by Cheapflights users on 4/22. 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.
dom 5/3111:30 am
EWR
- SJU
1 stop14h 38m
Frontier
mer 6/105:15 pm
SJU
- EWR
1 stop7h 50m
Frontier
Deal found 4/22![Frontier logo]()
$223
This Cheapflightsfares deal was found by Cheapflights users on 4/22. 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.
sab 5/21:45 pm
EWR
- SJU
1 stop20h 54m
Frontier
mer 5/65:15 pm
SJU
- EWR
1 stop8h 03m
Frontier
Deal found 4/22![Frontier logo]()
$224
This Frontier deal was found by Cheapflights users on 4/26. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer 5/65:55 am
EWR
- SJU
1 stop8h 12m
Frontier
gio 5/145:15 pm
SJU
- EWR
1 stop8h 03m
Frontier
Deal found 4/26![Frontier logo]()
$225
Best flights to Caribbean IslandsDiscover carefully curated flight deals to Caribbean Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated aprile 27, 2026.
Discover carefully curated flight deals to Caribbean Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated aprile 27, 2026.
This Delta deal was found by Cheapflights users on 4/23. 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.
sab 6/207:25 pm
JFK
- SJU
Nonstop4h 18m
Delta
mar 6/307:05 am
SJU
- JFK
Nonstop3h 56m
Delta
Deal found 4/23![Delta logo]()
$277
This Arajet deal was found by Cheapflights users on 4/22. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven 10/212:00 pm
EWR
- SDQ
Nonstop4h 30m
Multiple Airlines
sab 10/171:40 pm
SDQ
- EWR
1 stop9h 50m
Multiple Airlines
Deal found 4/22![Multiple Airlines logo]()
$300
This Arajet deal was found by Cheapflights users on 4/26. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom 9/2712:59 am
EWR
- SDQ
Nonstop4h 30m
Arajet
lun 10/57:10 pm
SDQ
- EWR
Nonstop4h 20m
Arajet
Deal found 4/26![Arajet logo]()
$305
This JetBlue deal was found by Cheapflights users on 4/25. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar 7/149:00 pm
JFK
- SJU
1 stop10h 56m
JetBlue
mar 7/217:50 pm
SJU
- JFK
Nonstop3h 59m
JetBlue
Deal found 4/25![JetBlue logo]()
$326
This United Airlines deal was found by Cheapflights users on 4/25. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sab 5/97:45 pm
EWR
- SJU
Nonstop4h 05m
United Airlines
mer 5/131:00 am
SJU
- EWR
Nonstop4h 10m
United Airlines
Deal found 4/25![United Airlines logo]()
$327
This Southwest deal was found by Cheapflights users on 4/22. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom 5/36:00 am
LGA
- SJU
2 stops10h 30m
Southwest
gio 5/75:05 am
SJU
- LGA
2 stops10h 55m
Southwest
Deal found 4/22![Southwest logo]()
$440
This Copa Airlines deal was found by Cheapflights users on 4/23. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
gio 10/16:00 am
JFK
- PUJ
1 stop11h 40m
Copa Airlines
dom 10/45:41 am
PUJ
- JFK
1 stop19h 19m
Copa Airlines
Deal found 4/23![Copa Airlines logo]()
$456
This Avianca deal was found by Cheapflights users on 4/27. 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sab 5/233:35 am
JFK
- PUJ
2 stops13h 10m
Avianca
mer 6/312:50 pm
PUJ
- JFK
1 stop10h 55m
Avianca
Deal found 4/27![Avianca logo]()
$466
This Delta deal was found by Cheapflights users on 4/25. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar 7/147:29 pm
JFK
- SJU
Nonstop4h 24m
Delta
mar 7/217:35 am
SJU
- JFK
Nonstop3h 55m
Delta
Deal found 4/25![Delta logo]()
$302
This Arajet deal was found by Cheapflights users on 4/25. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sab 10/1712:00 pm
EWR
- SDQ
1 stop9h 40m
Multiple Airlines
ven 10/306:18 am
SDQ
- EWR
Nonstop4h 12m
Multiple Airlines
Deal found 4/25![Multiple Airlines logo]()
$310
This JetBlue deal was found by Cheapflights users on 4/26. 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.
lun 6/159:02 pm
JFK
- SJU
1 stop10h 54m
JetBlue
mer 6/245:01 am
SJU
- JFK
Nonstop3h 53m
JetBlue
Deal found 4/26![JetBlue logo]()
$326
This United Airlines deal was found by Cheapflights users on 4/26. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom 5/38:00 am
EWR
- SJU
Nonstop4h 04m
United Airlines
gio 5/143:56 pm
SJU
- EWR
1 stop9h 34m
United Airlines
Deal found 4/26![United Airlines logo]()
$332
This Delta deal was found by Cheapflights users on 4/22. 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.
mer 6/1712:30 pm
JFK
- SJU
Nonstop3h 59m
Delta
sab 6/205:45 pm
SJU
- JFK
Nonstop4h 16m
Delta
Deal found 4/22![Delta logo]()
$322
This Arajet deal was found by Cheapflights users on 4/22. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom 9/612:59 am
EWR
- SDQ
Nonstop4h 30m
Multiple Airlines
mar 9/151:45 pm
SDQ
- EWR
1 stop9h 45m
Multiple Airlines
Deal found 4/22![Multiple Airlines logo]()
$325
This Arajet deal was found by Cheapflights users on 4/23. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven 9/1112:59 am
EWR
- SDQ
Nonstop4h 30m
Arajet
sab 9/196:10 am
SDQ
- EWR
Nonstop4h 20m
Arajet
Deal found 4/23![Arajet logo]()
$359
This JetBlue deal was found by Cheapflights users on 4/26. 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.
sab 5/239:30 pm
JFK
- SJU
Nonstop4h 08m
JetBlue
ven 5/293:25 am
SJU
- JFK
Nonstop3h 59m
JetBlue
Deal found 4/26![JetBlue logo]()
$327
This Delta deal was found by Cheapflights users on 4/26. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven 7/107:29 pm
JFK
- SJU
Nonstop4h 24m
Delta
mar 7/215:50 pm
SJU
- JFK
Nonstop4h 14m
Delta
Deal found 4/26![Delta logo]()
$327
This United Airlines deal was found by Cheapflights users on 4/22. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom 5/106:10 am
EWR
- AUA
1 stop6h 30m
United Airlines
mer 5/134:30 pm
AUA
- EWR
1 stop7h 29m
United Airlines
Deal found 4/22![United Airlines logo]()
$361
This Arajet deal was found by Cheapflights users on 4/26. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer 6/312:59 am
EWR
- SDQ
Nonstop4h 30m
Arajet
sab 6/136:10 am
SDQ
- EWR
Nonstop4h 20m
Arajet
Deal found 4/26![Arajet logo]()
$379
This JetBlue deal was found by Cheapflights users on 4/22. 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.
lun 6/154:59 pm
JFK
- SJU
1 stop7h 00m
JetBlue
lun 6/227:50 am
SJU
- JFK
Nonstop4h 04m
JetBlue
Deal found 4/22![JetBlue logo]()
$351
This Delta deal was found by Cheapflights users on 4/22. 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.
dom 7/1912:45 pm
JFK
- SJU
Nonstop3h 53m
Delta
mer 8/57:35 am
SJU
- JFK
Nonstop3h 55m
Delta
Deal found 4/22![Delta logo]()
$327
This Southwest deal was found by Cheapflights users on 4/25. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun 5/411:05 am
LGA
- SJU
2 stops12h 20m
Southwest
gio 5/75:05 am
SJU
- LGA
2 stops10h 55m
Southwest
Deal found 4/25![Southwest logo]()
$443
This Arajet deal was found by Cheapflights users on 4/26. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
gio 9/1712:00 pm
EWR
- PUJ
Nonstop4h 19m
Multiple Airlines
sab 9/192:05 am
PUJ
- EWR
1 stop8h 25m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$367
This United Airlines deal was found by Cheapflights users on 4/26. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer 5/137:45 pm
EWR
- SJU
Nonstop4h 05m
United Airlines
ven 5/151:00 am
SJU
- EWR
Nonstop4h 10m
United Airlines
Deal found 4/26![United Airlines logo]()
$369
This Copa Airlines deal was found by Cheapflights users on 4/23. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun 7/204:10 am
JFK
- PUJ
1 stop11h 54m
Copa Airlines
dom 7/265:37 am
PUJ
- JFK
1 stop10h 40m
Copa Airlines
Deal found 4/23![Copa Airlines logo]()
$456
This United Airlines deal was found by Cheapflights users on 4/25. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer 5/610:40 am
EWR
- SJU
1 stop9h 58m
United Airlines
sab 5/91:00 am
SJU
- EWR
Nonstop4h 10m
United Airlines
Deal found 4/25![United Airlines logo]()
$370
This Delta deal was found by Cheapflights users on 4/24. 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.
mar 5/127:20 pm
JFK
- SJU
Nonstop4h 15m
Delta
sab 5/167:05 am
SJU
- JFK
Nonstop3h 58m
Delta
Deal found 4/24![Delta logo]()
$337
This Arajet deal was found by Cheapflights users on 4/23. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven 5/1512:00 pm
EWR
- SDQ
Nonstop4h 30m
Arajet
mer 6/37:10 pm
SDQ
- EWR
Nonstop4h 20m
Arajet
Deal found 4/23![Arajet logo]()
$416
This JetBlue deal was found by Cheapflights users on 4/25. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun 7/1310:15 pm
EWR
- SJU
Nonstop4h 05m
JetBlue
mer 7/225:30 am
SJU
- EWR
Nonstop3h 58m
JetBlue
Deal found 4/25![JetBlue logo]()
$406
This Copa Airlines deal was found by Cheapflights users on 4/25. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom 6/141:30 am
JFK
- PUJ
1 stop16h 06m
Copa Airlines
ven 6/1911:46 am
PUJ
- JFK
1 stop13h 14m
Copa Airlines
Deal found 4/25![Copa Airlines logo]()
$493
Last-minute flights to Caribbean IslandsDiscover last-minute flight deals to Caribbean Islands. Data last updated aprile 27, 2026 and is based on user searches.
Discover last-minute flight deals to Caribbean Islands. Data last updated aprile 27, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 4/22. 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.
sab 5/21:45 pm
EWR
- SJU
1 stop20h 54m
Frontier
mer 5/65:15 pm
SJU
- EWR
1 stop8h 03m
Frontier
Deal found 4/22![Frontier logo]()
$224
This Kiwi.com deal was found by Cheapflights users on 4/23. 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.
mar 5/55:55 am
EWR
- SJU
1 stop8h 12m
Frontier
mar 5/193:03 am
SJU
- EWR
1 stop7h 29m
Frontier
Deal found 4/23![Frontier logo]()
$217
This Frontier deal was found by Cheapflights users on 4/26. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer 5/65:55 am
EWR
- SJU
1 stop8h 12m
Frontier
gio 5/145:15 pm
SJU
- EWR
1 stop8h 03m
Frontier
Deal found 4/26![Frontier logo]()
$225
This Kiwi.com deal was found by Cheapflights users on 4/23. 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.
dom 5/176:00 am
EWR
- SJU
1 stop12h 59m
Spirit Airlines
mer 5/2712:59 am
SJU
- EWR
Nonstop4h 07m
Spirit Airlines
Deal found 4/23![Spirit Airlines logo]()
$216
This Kiwi.com deal was found by Cheapflights users on 4/25. 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.
lun 5/256:42 pm
EWR
- SJU
Nonstop4h 00m
Spirit Airlines
mer 6/34:28 pm
SJU
- EWR
Nonstop4h 17m
Spirit Airlines
Deal found 4/25![Spirit Airlines logo]()
$219
This Kiwi.com deal was found by Cheapflights users on 4/25. 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.
lun 5/256:42 pm
EWR
- SJU
Nonstop4h 00m
Multiple Airlines
gio 6/46:09 pm
SJU
- EWR
1 stop16h 23m
Multiple Airlines
Deal found 4/25![Multiple Airlines logo]()
$220
This Kiwi.com deal was found by Cheapflights users on 4/25. 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.
mer 5/2711:30 am
EWR
- SJU
1 stop14h 38m
Frontier
ven 6/55:15 pm
SJU
- EWR
1 stop8h 03m
Frontier
Deal found 4/25![Frontier logo]()
$214
This Kiwi.com deal was found by Cheapflights users on 4/25. 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.
mer 5/276:42 pm
EWR
- SJU
Nonstop4h 00m
Spirit Airlines
gio 6/47:30 am
SJU
- EWR
Nonstop4h 13m
Spirit Airlines
Deal found 4/25![Spirit Airlines logo]()
$215
This CheapOair deal was found by Cheapflights users on 4/22. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer 5/278:30 pm
EWR
- SJU
Nonstop4h 05m
Multiple Airlines
ven 6/512:59 am
SJU
- EWR
Nonstop4h 07m
Multiple Airlines
Deal found 4/22![Multiple Airlines logo]()
$218
This Cheapflightsfares deal was found by Cheapflights users on 4/26. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
gio 5/286:42 pm
EWR
- SJU
Nonstop4h 00m
Spirit Airlines
ven 6/52:59 am
SJU
- EWR
1 stop10h 46m
Spirit Airlines
Deal found 4/26![Spirit Airlines logo]()
$221
This Kiwi.com deal was found by Cheapflights users on 4/26. 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.
dom 5/316:42 pm
EWR
- SJU
Nonstop4h 00m
Spirit Airlines
mer 6/104:28 pm
SJU
- EWR
Nonstop4h 17m
Spirit Airlines
Deal found 4/26![Spirit Airlines logo]()
$222
This Cheapflightsfares deal was found by Cheapflights users on 4/22. 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.
dom 5/3111:30 am
EWR
- SJU
1 stop14h 38m
Frontier
mer 6/105:15 pm
SJU
- EWR
1 stop7h 50m
Frontier
Deal found 4/22![Frontier logo]()
$223
One-way flights to Caribbean IslandsSearch for one-way flight options to Caribbean Islands. Find affordable one-way fares based on user searches. Data last updated aprile 27, 2026.
Search for one-way flight options to Caribbean Islands. Find affordable one-way fares based on user searches. Data last updated aprile 27, 2026.
This Super.com deal was found by Cheapflights users on 4/22. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
gio 5/1410:45 pm
LGA
- SJU
1 stop14h 30m
Frontier
Deal found 4/22![Frontier logo]()
$105
This Cheapflightsfares deal was found by Cheapflights users on 4/26. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sab 5/3011:30 am
EWR
- SJU
1 stop11h 52m
Frontier
Deal found 4/26![Frontier logo]()
$105
This Frontier deal was found by Cheapflights users on 4/22. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
ven 5/158:15 pm
LGA
- SJU
1 stop11h 49m
Frontier
Deal found 4/22![Frontier logo]()
$106
This Frontier deal was found by Cheapflights users on 4/22. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer 5/65:55 am
EWR
- SJU
1 stop8h 12m
Frontier
Deal found 4/22![Frontier logo]()
$106
This Booking.com deal was found by Cheapflights users on 4/26. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun 5/188:15 pm
LGA
- SJU
1 stop17h 00m
Frontier
Deal found 4/26![Frontier logo]()
$107
This Frontier deal was found by Cheapflights users on 4/26. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun 5/1811:30 am
EWR
- SJU
1 stop11h 13m
Frontier
Deal found 4/26![Frontier logo]()
$107
This Trip.com deal was found by Cheapflights users on 4/24. 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.
lun 5/116:29 am
LGA
- SJU
1 stop7h 38m
Frontier
Deal found 4/24![Frontier logo]()
$108
This Jetabroad deal was found by Cheapflights users on 4/24. 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 Jetabroad is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer 5/138:15 pm
LGA
- SJU
1 stop11h 49m
Frontier
Deal found 4/24![Frontier logo]()
$109
This Super.com deal was found by Cheapflights users on 4/22. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom 6/78:15 pm
LGA
- SJU
1 stop27h 07m
Frontier
Deal found 4/22![Frontier logo]()
$110
This Super.com deal was found by Cheapflights users on 4/22. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer 6/311:30 am
EWR
- SJU
1 stop25h 45m
Frontier
Deal found 4/22![Frontier logo]()
$110
This Super.com deal was found by Cheapflights users on 4/26. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mer 5/208:15 pm
LGA
- SJU
1 stop27h 07m
Frontier
Deal found 4/26![Frontier logo]()
$111
This Super.com deal was found by Cheapflights users on 4/23. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
gio 5/711:30 am
EWR
- SJU
1 stop29h 44m
Frontier
Deal found 4/23![Frontier logo]()
$111
Find flights to Caribbean Islands
Browse one-way and round-trip flights deals to Caribbean Islands on Cheapflights. Flight deals are based on user searches and were last updated on aprile 27, 2026
Explore Caribbean Islands
Find flight deals to Caribbean Islands
Find the latest flights to Caribbean Islands in 2026, with up-to-date prices and availability. In the last 7 days, Cheapflights users made a total of 2,558,603 searches and data was last updated on aprile 27, 2026.
Popular in | December |
|---|---|
Cheapest in | October |
Average price | $347 |
Round-trip from | $214 |
One-way from | $105 |
Cheapflights Fare Finder
Locate flights to Caribbean Islands that fit your budget, with regularly updated fares and availability. In the last 7 days, Cheapflights users made a total of 2,558,603 searches and data was last updated on aprile 27, 2026.
Use the filters below to find and compare flights to Caribbean Islands that are best for you.
Fly from
Route
Depart
Return
Cheapest round-trip
New YorkSan Juan
JFK - SJU
JFKSJU
New York John F Kennedy Intl
sab 6/20
7:25 pm-11:43 pm
Nonstop4h 18m
San Juan Luis Munoz Marin Intl
mar 6/30
7:05 am-11:01 am
Nonstop3h 56m
$277
NewarkSanto Domingo
EWR - SDQ
EWRSDQ
Newark
ven 10/2
12:00 pm-4:30 pm
Nonstop4h 30m
Santo Domingo Las Americas
sab 10/17
1:40 pm-11:30 pm
1 stop9h 50m
$300
New YorkSan Juan
JFK - SJU
JFKSJU
New York John F Kennedy Intl
mar 7/14
7:29 pm-11:53 pm
Nonstop4h 24m
San Juan Luis Munoz Marin Intl
mar 7/21
7:35 am-11:30 am
Nonstop3h 55m
$302
NewarkSanto Domingo
EWR - SDQ
EWRSDQ
Newark
dom 9/27
12:59 am-5:29 am
Nonstop4h 30m
Santo Domingo Las Americas
lun 10/5
7:10 pm-11:30 pm
Nonstop4h 20m
$305
NewarkSanto Domingo
EWR - SDQ
EWRSDQ
Newark
sab 10/17
12:00 pm-9:40 pm
1 stop9h 40m
Santo Domingo Las Americas
ven 10/30
6:18 am-10:30 am
Nonstop4h 12m
$310
New YorkSan Juan
JFK - SJU
JFKSJU
New York John F Kennedy Intl
mer 6/17
12:30 pm-4:29 pm
Nonstop3h 59m
San Juan Luis Munoz Marin Intl
sab 6/20
5:45 pm-10:01 pm
Nonstop4h 16m
$322
NewarkSanto Domingo
EWR - SDQ
EWRSDQ
Newark
dom 9/6
12:59 am-5:29 am
Nonstop4h 30m
Santo Domingo Las Americas
mar 9/15
1:45 pm-11:30 pm
1 stop9h 45m
$325
New YorkSan Juan
JFK - SJU
JFKSJU
New York John F Kennedy Intl
mar 7/14
9:00 pm-7:56 am
1 stop10h 56m
San Juan Luis Munoz Marin Intl
mar 7/21
7:50 pm-11:49 pm
Nonstop3h 59m
$326
New YorkSan Juan
JFK - SJU
JFKSJU
New York John F Kennedy Intl
lun 6/15
9:02 pm-7:56 am
1 stop10h 54m
San Juan Luis Munoz Marin Intl
mer 6/24
5:01 am-8:54 am
Nonstop3h 53m
$326
NewarkSan Juan
EWR - SJU
EWRSJU
Newark
sab 5/9
7:45 pm-11:50 pm
Nonstop4h 05m
San Juan Luis Munoz Marin Intl
mer 5/13
1:00 am-5:10 am
Nonstop4h 10m
$327
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight to Caribbean Islands
Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands with our price prediction graph.
EWR-SJU
JFK-SJU
EWR-SDQ
LGA-SJU
JFK-PUJ
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 to Caribbean Islands
NYC-zzEPX
EWR-SJU
JFK-SJU
EWR-SDQ
LGA-SJU
When is the best time to book a flight to Caribbean Islands?
Booking 29 days in advance of your planned departure date is, on average, the best time to get cheap flights to Caribbean Islands. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
How long is the flight to Caribbean Islands?
On average, a flight from New York to Caribbean Islands takes 11 hours 43 minutes. Flights to Caribbean Islands from other popular cities in USA will vary in length. Below are a few examples of popular routes and their flight times.
When is the cheapest time to fly to Caribbean Islands?
Use this chart to determine the cheapest time to fly round-trip from New York to Caribbean Islands. Price data was last updated on April 25, 2026.
Users looking for the lowest fares to Caribbean Islands should consider flying on Friday evenings, when prices are typically cheapest. Budget-minded travelers will want to avoid Thursday mornings, when prices are usually at their highest.
Weekly flight availability to Caribbean Islands
The most flights from New York to Caribbean Islands are scheduled on a Monday (55 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (29 on average).
What are the most popular airlines that fly to Caribbean Islands?
The most popular airlines flying from New York to Caribbean Islands are JetBlue, United Airlines and Delta.
What are the cheapest airlines that fly to Caribbean Islands?
The cheapest airlines flying from New York to Caribbean Islands are Frontier, Arajet and JetBlue.
Rainfall in Caribbean Islands by month
Plan your trip to Caribbean Islands by taking into account the average rainfall totals by month.
In terms of precipitation, rainfall in Caribbean Islands ranges from 2.2 - 6.1 inches per month. November is typically the wettest month, when rainfall can reach 6.1 in. February is typically the driest time to visit Caribbean Islands when rainfall is around 2.2 in.
Temperature in Caribbean Islands by month
Plan your trip to Caribbean Islands by taking into account the average temperature totals by month.
If weather is an important factor for your trip to Caribbean Islands, use this chart to help with planning. For those seeking warmer temperatures, June is the ideal time of year to visit, when temperatures reach an average of 82.4 F. Travelers looking to avoid the cold should look outside of January, when temperatures are typically at their lowest (around 77.0 F).
Reviews of airlines servicing Caribbean Islands
Get insights into the airlines that provide service to Caribbean Islands. 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 Islands. Reviews last updated aprile 27, 2026.
Get a feel of what it's like to fly with Delta,United Airlines, andJetBlue to Caribbean Islands by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
7.9
Crew
8.5
Entertainment
7.8
Overall
7.9
Boarding
8.1
Food
7.2
Reviews
1 / 20
10.0
ExcellentKymberlee,Oct 2024
JFK - ATL
Comfort
7.9
Crew
8.5
Entertainment
7.8
Overall
7.9
Boarding
8.1
Food
7.2
Reviews
1 / 20
10.0
ExcellentKymberlee,Oct 2024
JFK - ATL
Comfort
7.9
Crew
8.5
Entertainment
7.8
Overall
7.9
Boarding
8.1
Food
7.2
Reviews
1 / 20
10.0
ExcellentKymberlee,Oct 2024
JFK - ATL
Comfort
7.9
Crew
8.5
Entertainment
7.8
Overall
7.9
Boarding
8.1
Food
7.2
Reviews
1 / 20
10.0
ExcellentKymberlee,Oct 2024
JFK - ATL
Comfort
7.9
Crew
8.5
Entertainment
7.8
Overall
7.9
Boarding
8.1
Food
7.2
Reviews
1 / 20
10.0
ExcellentKymberlee,Oct 2024
JFK - ATL
FAQs about flying to Caribbean Islands
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Flights by cabin class
Popular flights
Popular destinations
Popular routes
Popular destinations
Complete your trip