$78+ Cheap flights from the United States 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 5/27. Fares are subject to change and may not be available on all flights or dates of travel.
LAX — SJU
Jun 24 — Jul 11
Round-trip
1 adult, Economy
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Find cheap flights from USA 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
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.Cheap flight deals from USA to Caribbean
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Cheapest flights from USA to CaribbeanExplore the most affordable flight options available from USA to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 25, 2026.
Explore the most affordable flight options available from USA to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 25, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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.
Sat 8/14:35 pm
MCO
- SJU
Nonstop3h 07m
Frontier
Thu 8/68:37 pm
SJU
- MCO
Nonstop3h 09m
Frontier
Deal found 5/20![Frontier logo]()
$184
This Frontier deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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.
Tue 8/410:17 am
MCO
- SJU
Nonstop3h 03m
Frontier
Sun 8/164:05 pm
SJU
- MCO
Nonstop3h 14m
Frontier
Deal found 5/20![Frontier logo]()
$186
This Frontier deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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.
Wed 8/122:26 pm
MCO
- SJU
Nonstop3h 10m
Frontier
Mon 8/174:05 pm
SJU
- MCO
Nonstop3h 14m
Frontier
Deal found 5/20![Frontier logo]()
$187
This Cheapflightsfares deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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 7/276:35 pm
MCO
- SJU
Nonstop3h 08m
Frontier
Thu 7/308:37 pm
SJU
- MCO
Nonstop3h 09m
Frontier
Deal found 5/20![Frontier logo]()
$202
This Frontier deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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.
Mon 7/610:17 am
MCO
- SJU
Nonstop3h 03m
Frontier
Thu 7/94:05 pm
SJU
- MCO
Nonstop3h 14m
Frontier
Deal found 5/20![Frontier logo]()
$210
This Cheapflightsfares deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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.
Tue 8/43:38 pm
MCO
- SJU
1 stop8h 29m
Frontier
Mon 8/108:37 pm
SJU
- MCO
Nonstop3h 09m
Frontier
Deal found 5/20![Frontier logo]()
$219
This Kiwi.com deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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 7/1711:17 pm
MCO
- SJU
Nonstop2h 58m
Frontier
Tue 7/2112:13 pm
SJU
- MCO
Nonstop3h 14m
Frontier
Deal found 5/20![Frontier logo]()
$225
This Cheapflightsfares deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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.
Fri 7/178:15 am
MCO
- SJU
Nonstop3h 01m
Frontier
Mon 7/2010:48 pm
SJU
- MCO
Nonstop3h 09m
Frontier
Deal found 5/20![Frontier logo]()
$226
This Cheapflightsfares deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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.
Sat 7/45:01 am
MCO
- SJU
Nonstop2h 54m
Frontier
Thu 7/98:37 pm
SJU
- MCO
Nonstop3h 09m
Frontier
Deal found 5/20![Frontier logo]()
$227
This Frontier deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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.
Sat 7/45:01 am
MCO
- SJU
Nonstop2h 54m
Frontier
Tue 7/76:00 am
SJU
- MCO
Nonstop3h 09m
Frontier
Deal found 5/20![Frontier logo]()
$229
This CheapOair deal was found by Cheapflights users on 5/24. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/148:03 pm
PHL
- SJU
Nonstop3h 55m
Frontier
Fri 8/282:36 pm
SJU
- PHL
Nonstop4h 06m
Frontier
Deal found 5/24![Frontier logo]()
$230
This Frontier deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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.
Fri 9/117:20 am
PHL
- SJU
Nonstop3h 44m
Frontier
Thu 9/171:59 am
SJU
- PHL
Nonstop4h 05m
Frontier
Deal found 5/20![Frontier logo]()
$232
Best flights from USA to CaribbeanDiscover carefully curated flight deals from USA to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 25, 2026.
Discover carefully curated flight deals from USA to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 25, 2026.
This Delta deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” 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 8/127:28 pm
JFK
- SJU
Nonstop4h 24m
Delta
Thu 8/207:30 am
SJU
- JFK
Nonstop3h 55m
Delta
Deal found 5/21![Delta logo]()
$302
This United Airlines deal was found by Cheapflights users on 5/23. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/132:51 pm
LGA
- SJU
1 stop6h 33m
United Airlines
Tue 6/162:05 am
SJU
- LGA
1 stop10h 35m
United Airlines
Deal found 5/23![United Airlines logo]()
$336
This JetBlue deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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.
Wed 6/242:59 pm
JFK
- SJU
1 stop8h 18m
JetBlue
Sat 7/48:20 pm
SJU
- JFK
Nonstop4h 02m
JetBlue
Deal found 5/20![JetBlue logo]()
$346
This Southwest deal was found by Cheapflights users on 5/22. 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.
Thu 8/2012:15 pm
MCO
- SJU
2 stops10h 50m
Southwest
Fri 8/286:00 am
SJU
- MCO
2 stops11h 50m
Southwest
Deal found 5/22![Southwest logo]()
$354
This Copa Airlines deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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.
Sat 6/133:32 pm
JFK
- PUJ
1 stop10h 39m
Copa Airlines
Wed 6/171:59 pm
PUJ
- JFK
1 stop9h 01m
Copa Airlines
Deal found 5/20![Copa Airlines logo]()
$476
This Arajet deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” 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.
Sun 6/712:00 pm
EWR
- PUJ
Nonstop4h 19m
Arajet
Sun 6/77:10 pm
PUJ
- EWR
Nonstop4h 20m
Arajet
Deal found 5/21![Arajet logo]()
$490
This Arajet deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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.
Thu 6/1112:59 am
EWR
- PUJ
1 stop9h 51m
Multiple Airlines
Sun 6/142:05 am
PUJ
- EWR
1 stop8h 25m
Multiple Airlines
Deal found 5/20![Multiple Airlines logo]()
$526
This Delta deal was found by Cheapflights users on 5/22. 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.
Wed 8/125:15 am
PHL
- SJU
1 stop6h 31m
Delta
Tue 8/186:48 am
SJU
- PHL
1 stop7h 52m
Delta
Deal found 5/22![Delta logo]()
$320
This United Airlines deal was found by Cheapflights users on 5/24. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/228:20 am
PHL
- SJU
2 stops12h 18m
United Airlines
Sat 8/293:56 pm
SJU
- PHL
1 stop9h 03m
United Airlines
Deal found 5/24![United Airlines logo]()
$347
This Southwest deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” 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.
Tue 8/189:00 am
MCO
- SJU
2 stops13h 00m
Southwest
Fri 8/213:20 pm
SJU
- MCO
1 stop7h 15m
Southwest
Deal found 5/21![Southwest logo]()
$354
This Delta deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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 8/48:00 am
JFK
- SJU
Nonstop4h 08m
Delta
Mon 8/177:30 am
SJU
- JFK
Nonstop3h 55m
Delta
Deal found 5/20![Delta logo]()
$322
This JetBlue deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” 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 6/99:29 am
JFK
- PUJ
Nonstop4h 13m
JetBlue
Fri 6/1211:40 am
PUJ
- JFK
Nonstop4h 11m
JetBlue
Deal found 5/21![JetBlue logo]()
$365
This Southwest deal was found by Cheapflights users on 5/22. 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.
Tue 8/1110:20 am
MCO
- SJU
2 stops11h 40m
Southwest
Sat 8/155:55 am
SJU
- MCO
2 stops11h 00m
Southwest
Deal found 5/22![Southwest logo]()
$354
This Delta deal was found by Cheapflights users on 5/24. 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.
Sat 7/257:29 pm
JFK
- SJU
Nonstop4h 24m
Delta
Thu 7/307:35 am
SJU
- JFK
Nonstop3h 55m
Delta
Deal found 5/24![Delta logo]()
$322
This Delta deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” 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 8/217:28 pm
JFK
- SJU
Nonstop4h 24m
Delta
Mon 8/247:30 am
SJU
- JFK
Nonstop3h 55m
Delta
Deal found 5/21![Delta logo]()
$322
This JetBlue deal was found by Cheapflights users on 5/24. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/99:55 pm
EWR
- SJU
Nonstop4h 04m
JetBlue
Tue 7/146:00 am
SJU
- EWR
Nonstop3h 59m
JetBlue
Deal found 5/24![JetBlue logo]()
$391
This United Airlines deal was found by Cheapflights users on 5/24. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/1511:50 am
EWR
- AUA
Nonstop4h 50m
United Airlines
Fri 6/195:50 pm
AUA
- EWR
Nonstop4h 57m
United Airlines
Deal found 5/24![United Airlines logo]()
$392
This Southwest deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” 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.
Sat 8/17:10 am
MCO
- SJU
1 stop7h 35m
Southwest
Thu 8/135:30 am
SJU
- MCO
2 stops13h 00m
Southwest
Deal found 5/21![Southwest logo]()
$372
This Copa Airlines deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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.
Mon 6/152:30 am
JFK
- PUJ
1 stop15h 06m
Copa Airlines
Sat 6/275:37 am
PUJ
- JFK
1 stop19h 23m
Copa Airlines
Deal found 5/20![Copa Airlines logo]()
$483
This United Airlines deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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.
Sat 6/66:00 am
LGA
- SJU
1 stop6h 34m
United Airlines
Sat 6/132:05 am
SJU
- LGA
1 stop9h 24m
United Airlines
Deal found 5/20![United Airlines logo]()
$406
This Arajet deal was found by Cheapflights users on 5/24. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/1312:00 pm
EWR
- PUJ
Nonstop4h 19m
Arajet
Thu 6/187:10 pm
PUJ
- EWR
Nonstop4h 20m
Arajet
Deal found 5/24![Arajet logo]()
$497
This Southwest deal was found by Cheapflights users on 5/22. 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.
Sat 6/137:10 am
MCO
- SJU
1 stop7h 35m
Southwest
Sun 6/219:05 pm
SJU
- MCO
Nonstop3h 00m
Southwest
Deal found 5/22![Southwest logo]()
$392
This Delta deal was found by Cheapflights users on 5/24. 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.
Sat 6/2012:25 pm
JFK
- SJU
Nonstop4h 02m
Delta
Sat 6/275:45 pm
SJU
- JFK
Nonstop4h 16m
Delta
Deal found 5/24![Delta logo]()
$362
This Arajet deal was found by Cheapflights users on 5/24. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/1212:00 pm
EWR
- PUJ
Nonstop4h 19m
Arajet
Tue 7/147:10 pm
PUJ
- EWR
Nonstop4h 20m
Arajet
Deal found 5/24![Arajet logo]()
$497
This JetBlue deal was found by Cheapflights users on 5/23. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/123:40 pm
LGA
- SJU
1 stop7h 40m
JetBlue
Wed 7/155:32 am
SJU
- LGA
1 stop9h 27m
JetBlue
Deal found 5/23![JetBlue logo]()
$453
This United Airlines deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” 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.
Fri 9/118:06 pm
EWR
- PUJ
1 stop16h 09m
United Airlines
Fri 9/181:50 pm
PUJ
- EWR
Nonstop4h 06m
United Airlines
Deal found 5/21![United Airlines logo]()
$422
This Arajet deal was found by Cheapflights users on 5/24. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/612:00 pm
EWR
- PUJ
Nonstop4h 19m
Arajet
Sun 9/137:10 pm
PUJ
- EWR
Nonstop4h 20m
Arajet
Deal found 5/24![Arajet logo]()
$497
This JetBlue deal was found by Cheapflights users on 5/24. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/219:00 pm
JFK
- STI
Nonstop3h 59m
JetBlue
Thu 10/223:15 pm
STI
- JFK
Nonstop3h 44m
JetBlue
Deal found 5/24![JetBlue logo]()
$468
This Delta deal was found by Cheapflights users on 5/23. 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.
Thu 7/307:29 pm
JFK
- SJU
Nonstop4h 24m
Delta
Tue 8/45:50 pm
SJU
- JFK
Nonstop4h 14m
Delta
Deal found 5/23![Delta logo]()
$387
This United Airlines deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” 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.
Tue 8/48:05 am
LGA
- SJU
2 stops13h 19m
United Airlines
Wed 8/124:55 pm
SJU
- LGA
1 stop6h 35m
United Airlines
Deal found 5/21![United Airlines logo]()
$426
Last-minute flights from USA to CaribbeanDiscover last-minute flight deals from USA to Caribbean. Data last updated May 25, 2026 and is based on user searches.
Discover last-minute flight deals from USA to Caribbean. Data last updated May 25, 2026 and is based on user searches.
This eDestinos deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/2710:21 am
MCO
- SJU
Nonstop2h 54m
Frontier
Wed 6/36:00 am
SJU
- MCO
Nonstop3h 16m
Frontier
Deal found 5/20![Frontier logo]()
$260
This eDestinos deal was found by Cheapflights users on 5/24. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/3011:59 pm
PHL
- SJU
Nonstop4h 02m
Frontier
Sun 6/76:46 pm
SJU
- PHL
Nonstop4h 08m
Frontier
Deal found 5/24![Frontier logo]()
$243
This Kiwi.com deal was found by Cheapflights users on 5/24. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/3011:59 pm
PHL
- SJU
Nonstop4h 02m
Frontier
Wed 6/36:46 pm
SJU
- PHL
Nonstop4h 08m
Frontier
Deal found 5/24![Frontier logo]()
$265
This eDestinos deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/310:11 am
MCO
- SJU
1 stop7h 03m
Frontier
Fri 6/56:00 am
SJU
- MCO
Nonstop3h 16m
Frontier
Deal found 5/20![Frontier logo]()
$234
This CheapOair deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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.
Sat 6/611:20 pm
MCO
- SJU
Nonstop2h 48m
Frontier
Tue 6/96:00 am
SJU
- MCO
Nonstop3h 12m
Frontier
Deal found 5/20![Frontier logo]()
$242
This Cheapflightsfares deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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.
Sat 6/138:25 pm
MCO
- SJU
Nonstop3h 04m
Frontier
Wed 6/178:50 am
SJU
- MCO
1 stop13h 05m
Frontier
Deal found 5/20![Frontier logo]()
$237
This Kiwi.com deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/138:25 pm
MCO
- SJU
Nonstop3h 04m
Frontier
Tue 6/166:44 am
SJU
- MCO
1 stop9h 25m
Frontier
Deal found 5/20![Frontier logo]()
$258
This Frontier deal was found by Cheapflights users on 5/24. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/1411:59 pm
PHL
- SJU
Nonstop3h 58m
Frontier
Fri 6/196:44 am
SJU
- PHL
Nonstop4h 06m
Frontier
Deal found 5/24![Frontier logo]()
$268
This Expedia deal was found by Cheapflights users on 5/23. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/2111:03 am
EWR
- SJU
Nonstop3h 55m
JetBlue
Wed 6/247:40 pm
SJU
- EWR
Nonstop4h 03m
JetBlue
Deal found 5/23![JetBlue logo]()
$257
This Cheapflightsfares deal was found by Cheapflights users on 5/23. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/236:15 am
MCO
- SJU
1 stop9h 40m
Frontier
Tue 7/75:15 pm
SJU
- MCO
1 stop13h 25m
Frontier
Deal found 5/23![Frontier logo]()
$253
This Cheapflightsfares deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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 6/2811:15 pm
MCO
- SJU
Nonstop2h 54m
Frontier
Sun 7/53:36 pm
SJU
- MCO
1 stop24h 56m
Frontier
Deal found 5/20![Frontier logo]()
$256
This Kiwi.com deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/2911:15 pm
MCO
- SJU
Nonstop2h 54m
Frontier
Mon 7/68:37 pm
SJU
- MCO
Nonstop3h 09m
Frontier
Deal found 5/20![Frontier logo]()
$231
One-way flights from USA to CaribbeanSearch for one-way flight options from USA to Caribbean. Find affordable one-way fares based on user searches. Data last updated May 25, 2026.
Search for one-way flight options from USA to Caribbean. Find affordable one-way fares based on user searches. Data last updated May 25, 2026.
This eDestinos deal was found by Cheapflights users on 5/22. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/278:07 pm
PHL
- SJU
Nonstop3h 52m
Frontier
Deal found 5/22![Frontier logo]()
$78
This Frontier deal was found by Cheapflights users on 5/24. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/308:07 pm
PHL
- SJU
Nonstop3h 52m
Frontier
Deal found 5/24![Frontier logo]()
$84
This Super.com deal was found by Cheapflights users on 5/24. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/158:03 pm
PHL
- SJU
Nonstop3h 55m
Frontier
Deal found 5/24![Frontier logo]()
$94
This Cheapflightsfares deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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 6/2811:15 pm
MCO
- SJU
Nonstop2h 54m
Frontier
Deal found 5/20![Frontier logo]()
$109
This Frontier deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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.
Wed 7/298:24 pm
MCO
- SJU
Nonstop3h 05m
Frontier
Deal found 5/20![Frontier logo]()
$111
This SmartFares deal was found by Cheapflights users on 5/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/118:00 pm
JFK
- SJU
Nonstop4h 10m
JetBlue
Deal found 5/21![JetBlue logo]()
$113
This Cheapflightsfares deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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 7/64:25 pm
MCO
- SJU
Nonstop3h 07m
Frontier
Deal found 5/20![Frontier logo]()
$115
This SmartFares deal was found by Cheapflights users on 5/23. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/128:00 pm
JFK
- SJU
Nonstop4h 10m
JetBlue
Deal found 5/23![JetBlue logo]()
$117
This Mytrip deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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.
Sun 7/55:01 am
MCO
- SJU
Nonstop2h 56m
Frontier
Deal found 5/20![Frontier logo]()
$118
This Frontier deal was found by Cheapflights users on 5/24. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/1711:59 pm
PHL
- SJU
Nonstop3h 59m
Frontier
Deal found 5/24![Frontier logo]()
$118
This Frontier deal was found by Cheapflights users on 5/24. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/217:47 pm
PHL
- SJU
Nonstop4h 10m
Frontier
Deal found 5/24![Frontier logo]()
$119
This Cheapflightsfares deal was found by Cheapflights users on 5/20. Clicking the “Pick Dates” 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.
Tue 8/1111:59 pm
PHL
- SJU
Nonstop3h 59m
Frontier
Deal found 5/20![Frontier logo]()
$121
Find flight deals from USA to Caribbean
Keep the following information in mind while searching for USA to Caribbean flight deals. Data was last updated May 25, 2026.
Round-trip from | $184 (Cheapflightsfares) |
|---|---|
One-way from | $78 (eDestinos) |
Popular in | April |
Cheapest in | October |
Average price | $350 |
Good round-trip deal | $198 or less |
Good one-way deal | $79 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from USA 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 May 25, 2026.
Use the filters below to find and compare flights from the United States to Caribbean that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
New YorkSan Juan
JFK - SJU
JFKSJU
New York John F Kennedy Intl
Wed 8/12
7:28 pm-11:52 pm
Nonstop4h 24m
San Juan Luis Munoz Marin Intl
Thu 8/20
7:30 am-11:25 am
Nonstop3h 55m
$302
PhiladelphiaSan Juan
PHL - SJU
PHLSJU
Philadelphia
Wed 8/12
5:15 am-11:46 am
1 stop6h 31m
San Juan Luis Munoz Marin Intl
Tue 8/18
6:48 am-2:40 pm
1 stop7h 52m
$320
New YorkSan Juan
JFK - SJU
JFKSJU
New York John F Kennedy Intl
Tue 8/4
8:00 am-12:08 pm
Nonstop4h 08m
San Juan Luis Munoz Marin Intl
Mon 8/17
7:30 am-11:25 am
Nonstop3h 55m
$322
New YorkSan Juan
JFK - SJU
JFKSJU
New York John F Kennedy Intl
Sat 7/25
7:29 pm-11:53 pm
Nonstop4h 24m
San Juan Luis Munoz Marin Intl
Thu 7/30
7:35 am-11:30 am
Nonstop3h 55m
$322
New YorkSan Juan
JFK - SJU
JFKSJU
New York John F Kennedy Intl
Fri 8/21
7:28 pm-11:52 pm
Nonstop4h 24m
San Juan Luis Munoz Marin Intl
Mon 8/24
7:30 am-11:25 am
Nonstop3h 55m
$322
New YorkSan Juan
LGA - SJU
LGASJU
New York LaGuardia
Sat 6/13
2:51 pm-9:24 pm
1 stop6h 33m
San Juan Luis Munoz Marin Intl
Tue 6/16
2:05 am-12:40 pm
1 stop10h 35m
$336
New YorkSan Juan
JFK - SJU
JFKSJU
New York John F Kennedy Intl
Wed 6/24
2:59 pm-11:17 pm
1 stop8h 18m
San Juan Luis Munoz Marin Intl
Sat 7/4
8:20 pm-12:22 am
Nonstop4h 02m
$346
PhiladelphiaSan Juan
PHL - SJU
PHLSJU
Philadelphia
Sat 8/22
8:20 am-8:38 pm
2 stops12h 18m
San Juan Luis Munoz Marin Intl
Sat 8/29
3:56 pm-12:59 am
1 stop9h 03m
$347
OrlandoSan Juan
MCO - SJU
MCOSJU
Orlando
Thu 8/20
12:15 pm-11:05 pm
2 stops10h 50m
San Juan Luis Munoz Marin Intl
Fri 8/28
6:00 am-5:50 pm
2 stops11h 50m
$354
OrlandoSan Juan
MCO - SJU
MCOSJU
Orlando
Tue 8/18
9:00 am-10:00 pm
2 stops13h 00m
San Juan Luis Munoz Marin Intl
Fri 8/21
3:20 pm-10:35 pm
1 stop7h 15m
$354
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from USA to Caribbean
Have a flexible travel schedule? Discover the best time to fly to Caribbean from USA with our price prediction graph.
JFK-SJU
LGA-SJU
MCO-SJU
JFK-PUJ
EWR-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 from the United States to Caribbean
US0-0CB
JFK-SJU
LGA-SJU
MCO-SJU
JFK-PUJ
What is the cheapest month to book a flight from USA to Caribbean?
Currently, September is the cheapest month in which you can book a flight from USA to Caribbean (average of $408). Flying from USA to Caribbean in December is currently the most expensive (average of $567). 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 US to CB?
Find hourly flight availability from USA 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 May 25, 2026.
One of the essential ways to save on airfare from USA to Caribbean is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the evening could potentially save you up to 18% on airfare.
How far ahead should I book a flight from USA to Caribbean?
To ensure you get the cheapest price possible for a flight from USA to Caribbean, you should look to book at least 29 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
What is the cheapest day to fly from USA to Caribbean?
Use this chart to determine the cheapest time to fly round-trip from USA to Caribbean. Price data was last updated on May 16, 2026.
Travelers seeking maximum savings on their USA to Caribbean flight should consider departing on Monday mornings when fares are most often at their lowest. Wednesday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
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 May 25, 2026.
Get a feel of what it's like to fly with Delta,United Airlines, andJetBlue from the United States to Caribbean by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
8.1
Crew
8.5
Overall
7.9
Comfort
7.8
Food
7.2
Entertainment
7.8
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Boarding
8.1
Crew
8.5
Overall
7.9
Comfort
7.8
Food
7.2
Entertainment
7.8
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Boarding
8.1
Crew
8.5
Overall
7.9
Comfort
7.8
Food
7.2
Entertainment
7.8
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Boarding
8.1
Crew
8.5
Overall
7.9
Comfort
7.8
Food
7.2
Entertainment
7.8
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Boarding
8.1
Crew
8.5
Overall
7.9
Comfort
7.8
Food
7.2
Entertainment
7.8
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Boarding
8.1
Crew
8.5
Overall
7.9
Comfort
7.8
Food
7.2
Entertainment
7.8
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Related info for your journey
Find useful and relevant information for your journey from USA 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
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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Alternative routes for USA 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 USA to Caribbean by cabin class
Find flights from USA to Caribbean, based on your preferred cabin class, be it economy, premium economy, business, or first class.
USA and Caribbean flights
Browse other USA and Caribbean flight options. Last updated on May 25, 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 USA after your stay in Caribbean
Fly to Caribbean countries
Consider these flights traveling to countries located in Caribbean.
USA to Caribbean flights
Consider these flights traveling from USA to Caribbean.
Top 10 airlines flying from USA to Caribbean
Discover the top 10 airlines that operate flights from USA 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 May 25, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$83 | Average$368 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$86 | Average$396 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$99 | Average$336 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$108 | Average$568 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$112 | Average$425 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$125 | Average$497 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$129 | Average$724 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$144 | Average$492 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$150 | Average$509 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$161 | Average$617 | FlexibilityNo cancel fee | On-time71% |