$148+ Cheap flights from San Jose, CA (SJC) 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 3/23. Fares are subject to change and may not be available on all flights or dates of travel.
SJC — SJU
Mar 4 — Mar 111
1 adult, Economy
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Find cheap flights from San Jose to Caribbean with Cheapflights
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Cheapest flights from San Jose to CaribbeanExplore the most affordable flight options available from San Jose to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 2, 2026.
Explore the most affordable flight options available from San Jose to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 2, 2026.
This Delta deal was found by Cheapflights users on 2/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/310:35 pm
SJC
- SJU
1 stop10h 26m
Delta
Tue 3/107:30 am
SJU
- SJC
2 stops15h 11m
Delta
Deal found 2/1![Delta logo]()
$296
This Southwest deal was found by Cheapflights users on 2/1. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/149:40 pm
SJC
- SJU
1 stop12h 30m
Southwest
Tue 4/2111:25 am
SJU
- SJC
2 stops12h 40m
Southwest
Deal found 2/1![Southwest logo]()
$351
This Delta deal was found by Cheapflights users on 2/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/2110:35 pm
SJC
- SJU
1 stop10h 26m
Delta
Wed 2/252:12 pm
SJU
- SJC
1 stop11h 06m
Delta
Deal found 2/1![Delta logo]()
$360
This Alaska Airlines deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/36:00 am
SJC
- SJU
1 stop13h 31m
Alaska Airlines
Wed 3/116:33 am
SJU
- SJC
1 stop17h 48m
Alaska Airlines
Deal found 2/2![Alaska Airlines logo]()
$378
This American Airlines deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/236:00 am
SJC
- SJU
1 stop13h 31m
American Airlines
Thu 2/267:33 am
SJU
- SJC
2 stops12h 17m
American Airlines
Deal found 2/2![American Airlines logo]()
$399
This Southwest deal was found by Cheapflights users on 1/31. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/279:45 pm
SJC
- SJU
1 stop12h 25m
Southwest
Sat 5/211:15 am
SJU
- SJC
2 stops12h 10m
Southwest
Deal found 1/31![Southwest logo]()
$406
This Delta deal was found by Cheapflights users on 2/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/36:45 am
SJC
- SJU
2 stops13h 13m
Delta
Wed 3/117:30 am
SJU
- SJC
2 stops17h 32m
Delta
Deal found 2/1![Delta logo]()
$421
This Delta deal was found by Cheapflights users on 2/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/2210:35 pm
SJC
- SJU
1 stop10h 26m
Delta
Wed 2/252:12 pm
SJU
- SJC
1 stop11h 06m
Delta
Deal found 2/1![Delta logo]()
$424
This Southwest deal was found by Cheapflights users on 1/31. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/410:30 pm
SJC
- SJU
1 stop11h 20m
Southwest
Thu 8/135:30 am
SJU
- SJC
1 stop10h 30m
Southwest
Deal found 1/31![Southwest logo]()
$428
This Southwest deal was found by Cheapflights users on 1/31. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/258:10 pm
SJC
- SJU
2 stops12h 50m
Southwest
Sat 5/211:15 am
SJU
- SJC
2 stops12h 10m
Southwest
Deal found 1/31![Southwest logo]()
$440
This Delta deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” 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 2/2110:35 pm
SJC
- SJU
1 stop10h 26m
Delta
Tue 2/246:15 am
SJU
- SJC
2 stops12h 41m
Delta
Deal found 2/2![Delta logo]()
$443
This Delta deal was found by Cheapflights users on 2/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/1910:55 pm
SJC
- NAS
1 stop9h 53m
Delta
Fri 4/241:13 pm
NAS
- SJC
1 stop11h 32m
Delta
Deal found 2/1![Delta logo]()
$444
Best flights from San Jose to CaribbeanDiscover carefully curated flight deals from San Jose to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 2, 2026.
Discover carefully curated flight deals from San Jose to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 2, 2026.
This Delta deal was found by Cheapflights users on 2/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/36:30 pm
SJC
- SJU
2 stops14h 31m
Delta
Tue 3/107:30 am
SJU
- SJC
2 stops17h 32m
Delta
Deal found 2/1![Delta logo]()
$296
This Southwest deal was found by Cheapflights users on 1/31. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/279:35 pm
SJC
- SJU
2 stops10h 00m
Southwest
Sat 5/211:15 am
SJU
- SJC
2 stops12h 10m
Southwest
Deal found 1/31![Southwest logo]()
$406
This United Airlines deal was found by Cheapflights users on 1/31. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/1810:55 pm
SJC
- NAS
1 stop13h 27m
United Airlines
Wed 3/253:35 pm
NAS
- SJC
1 stop10h 24m
United Airlines
Deal found 1/31![United Airlines logo]()
$446
This American Airlines deal was found by Cheapflights users on 1/31. 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.
Mon 2/237:15 pm
SJC
- NAS
2 stops14h 42m
American Airlines
Mon 3/23:47 pm
NAS
- SJC
1 stop21h 24m
American Airlines
Deal found 1/31![American Airlines logo]()
$487
This Delta deal was found by Cheapflights users on 2/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/2210:35 pm
SJC
- SJU
1 stop10h 26m
Delta
Wed 2/256:15 am
SJU
- SJC
2 stops15h 18m
Delta
Deal found 2/1![Delta logo]()
$360
This Delta deal was found by Cheapflights users on 2/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/2110:35 pm
SJC
- SJU
1 stop10h 26m
Delta
Wed 2/252:12 pm
SJU
- SJC
1 stop11h 06m
Delta
Deal found 2/1![Delta logo]()
$360
This Southwest deal was found by Cheapflights users on 1/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/258:10 pm
SJC
- SJU
2 stops12h 50m
Southwest
Sat 5/211:15 am
SJU
- SJC
2 stops12h 10m
Southwest
Deal found 1/30![Southwest logo]()
$440
This United Airlines deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” 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.
Sun 3/1510:55 pm
SJC
- NAS
1 stop13h 27m
United Airlines
Wed 3/181:05 pm
NAS
- SJC
2 stops12h 54m
United Airlines
Deal found 2/2![United Airlines logo]()
$450
This Delta deal was found by Cheapflights users on 1/30. 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.
Sat 2/216:20 am
SJC
- SJU
2 stops13h 38m
Delta
Tue 2/246:15 am
SJU
- SJC
2 stops12h 41m
Delta
Deal found 1/30![Delta logo]()
$373
This Delta deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/36:30 pm
SJC
- SJU
2 stops14h 31m
Delta
Wed 3/117:30 am
SJU
- SJC
2 stops15h 54m
Delta
Deal found 2/2![Delta logo]()
$373
This Southwest deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” 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.
Mon 2/237:00 pm
SJC
- PUJ
2 stops14h 40m
Southwest
Thu 2/262:25 pm
PUJ
- SJC
2 stops22h 55m
Southwest
Deal found 2/2![Southwest logo]()
$493
This United Airlines deal was found by Cheapflights users on 1/31. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/233:55 pm
SJC
- NAS
2 stops20h 27m
United Airlines
Mon 3/23:35 pm
NAS
- SJC
2 stops25h 06m
United Airlines
Deal found 1/31![United Airlines logo]()
$493
This Delta deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/210:35 pm
SJC
- SJU
1 stop10h 26m
Delta
Wed 3/117:30 am
SJU
- SJC
2 stops19h 28m
Delta
Deal found 2/2![Delta logo]()
$373
This American Airlines deal was found by Cheapflights users on 2/1. 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.
Wed 3/47:15 pm
SJC
- GCM
2 stops15h 59m
American Airlines
Sun 3/82:15 pm
GCM
- SJC
2 stops22h 01m
American Airlines
Deal found 2/1![American Airlines logo]()
$555
This American Airlines deal was found by Cheapflights users on 2/1. 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.
Thu 2/56:00 am
SJC
- SDQ
2 stops12h 39m
American Airlines
Sun 2/84:47 pm
SDQ
- SJC
2 stops18h 17m
American Airlines
Deal found 2/1![American Airlines logo]()
$576
This United Airlines deal was found by Cheapflights users on 1/31. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/173:49 pm
SJC
- GCM
2 stops18h 26m
United Airlines
Tue 3/244:45 pm
GCM
- SJC
2 stops22h 56m
United Airlines
Deal found 1/31![United Airlines logo]()
$578
This Delta deal was found by Cheapflights users on 2/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/2010:55 pm
SJC
- NAS
1 stop14h 38m
Delta
Fri 4/241:13 pm
NAS
- SJC
1 stop11h 32m
Delta
Deal found 2/1![Delta logo]()
$444
This Southwest deal was found by Cheapflights users on 1/31. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/179:15 pm
SJC
- AUA
2 stops13h 10m
Southwest
Tue 3/242:25 pm
AUA
- SJC
2 stops20h 20m
Southwest
Deal found 1/31![Southwest logo]()
$594
This American Airlines deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” 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 5/82:02 pm
SJC
- AUA
2 stops20h 09m
American Airlines
Sat 5/162:30 pm
AUA
- SJC
2 stops22h 40m
American Airlines
Deal found 2/2![American Airlines logo]()
$594
This United Airlines deal was found by Cheapflights users on 1/31. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/178:45 am
SJC
- AUA
2 stops25h 05m
United Airlines
Tue 3/242:00 pm
AUA
- SJC
1 stop11h 59m
United Airlines
Deal found 1/31![United Airlines logo]()
$589
This Delta deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/1810:50 pm
SJC
- NAS
1 stop14h 55m
Delta
Wed 3/251:18 pm
NAS
- SJC
1 stop11h 15m
Delta
Deal found 2/2![Delta logo]()
$446
This American Airlines deal was found by Cheapflights users on 1/31. 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 3/172:26 pm
SJC
- GCM
1 stop21h 59m
American Airlines
Tue 3/243:30 pm
GCM
- SJC
1 stop20h 46m
American Airlines
Deal found 1/31![American Airlines logo]()
$599
This United Airlines deal was found by Cheapflights users on 1/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/710:55 pm
SJC
- PUJ
1 stop10h 27m
United Airlines
Sat 3/141:05 pm
PUJ
- SJC
1 stop11h 11m
United Airlines
Deal found 1/30![United Airlines logo]()
$594
This Delta deal was found by Cheapflights users on 2/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/216:00 pm
SJC
- NAS
2 stops14h 48m
Delta
Fri 4/241:13 pm
NAS
- SJC
1 stop11h 32m
Delta
Deal found 2/1![Delta logo]()
$448
This Southwest deal was found by Cheapflights users on 1/31. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/249:50 pm
SJC
- MBJ
1 stop14h 40m
Southwest
Tue 3/311:00 pm
MBJ
- SJC
1 stop10h 45m
Southwest
Deal found 1/31![Southwest logo]()
$662
This American Airlines deal was found by Cheapflights users on 1/31. 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 3/247:15 pm
SJC
- MBJ
2 stops11h 52m
American Airlines
Tue 3/311:27 pm
MBJ
- SJC
2 stops22h 49m
American Airlines
Deal found 1/31![American Airlines logo]()
$613
This Delta deal was found by Cheapflights users on 2/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/198:05 pm
SJC
- NAS
2 stops12h 43m
Delta
Fri 4/241:13 pm
NAS
- SJC
2 stops12h 24m
Delta
Deal found 2/1![Delta logo]()
$449
This United Airlines deal was found by Cheapflights users on 1/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/1710:55 pm
SJC
- PUJ
1 stop11h 27m
United Airlines
Tue 3/241:55 pm
PUJ
- SJC
1 stop12h 04m
United Airlines
Deal found 1/30![United Airlines logo]()
$599
This American Airlines deal was found by Cheapflights users on 1/31. 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 4/16:00 am
SJC
- SDQ
2 stops13h 53m
American Airlines
Wed 4/85:55 pm
SDQ
- SJC
2 stops22h 17m
American Airlines
Deal found 1/31![American Airlines logo]()
$668
This United Airlines deal was found by Cheapflights users on 1/31. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/2410:55 pm
SJC
- MBJ
1 stop11h 51m
United Airlines
Tue 3/314:12 pm
MBJ
- SJC
2 stops32h 24m
United Airlines
Deal found 1/31![United Airlines logo]()
$613
Last-minute flights from San Jose to CaribbeanDiscover last-minute flight deals from San Jose to Caribbean. Data last updated February 2, 2026 and is based on user searches.
Discover last-minute flight deals from San Jose to Caribbean. Data last updated February 2, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” 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 2/156:00 am
SJC
- SJU
1 stop13h 31m
American Airlines
Wed 2/182:23 pm
SJU
- SJC
2 stops12h 08m
American Airlines
Deal found 2/2![American Airlines logo]()
$482
This Delta deal was found by Cheapflights users on 2/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/2110:35 pm
SJC
- SJU
1 stop10h 26m
Delta
Wed 2/252:12 pm
SJU
- SJC
1 stop11h 06m
Delta
Deal found 2/1![Delta logo]()
$360
This Delta deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” 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 2/2110:35 pm
SJC
- SJU
1 stop10h 26m
Delta
Tue 2/246:15 am
SJU
- SJC
2 stops12h 41m
Delta
Deal found 2/2![Delta logo]()
$443
This Delta deal was found by Cheapflights users on 2/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/2210:35 pm
SJC
- SJU
1 stop10h 26m
Delta
Wed 2/252:12 pm
SJU
- SJC
1 stop11h 06m
Delta
Deal found 2/1![Delta logo]()
$424
This American Airlines deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/236:00 am
SJC
- SJU
1 stop13h 31m
American Airlines
Thu 2/267:33 am
SJU
- SJC
2 stops12h 17m
American Airlines
Deal found 2/2![American Airlines logo]()
$399
This Alaska Airlines deal was found by Cheapflights users on 1/31. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/16:00 am
SJC
- SJU
1 stop13h 31m
Alaska Airlines
Wed 3/47:33 am
SJU
- SJC
2 stops32h 35m
Alaska Airlines
Deal found 1/31![Alaska Airlines logo]()
$479
This Delta deal was found by Cheapflights users on 2/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/210:35 pm
SJC
- NAS
1 stop11h 58m
Delta
Sat 3/71:15 pm
NAS
- SJC
1 stop11h 03m
Delta
Deal found 2/1![Delta logo]()
$470
This Delta deal was found by Cheapflights users on 2/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/310:35 pm
SJC
- SJU
1 stop10h 26m
Delta
Tue 3/106:15 am
SJU
- SJC
2 stops16h 26m
Delta
Deal found 2/1![Delta logo]()
$296
This Delta deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/310:35 pm
SJC
- SJU
1 stop10h 26m
Delta
Wed 3/117:30 am
SJU
- SJC
2 stops19h 28m
Delta
Deal found 2/2![Delta logo]()
$373
This Alaska Airlines deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/36:00 am
SJC
- SJU
1 stop13h 31m
Alaska Airlines
Wed 3/116:33 am
SJU
- SJC
1 stop17h 48m
Alaska Airlines
Deal found 2/2![Alaska Airlines logo]()
$378
This United Airlines deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” 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.
Sun 3/1510:55 pm
SJC
- NAS
1 stop13h 27m
United Airlines
Wed 3/181:05 pm
NAS
- SJC
2 stops12h 54m
United Airlines
Deal found 2/2![United Airlines logo]()
$450
This Delta deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/1810:50 pm
SJC
- NAS
1 stop14h 55m
Delta
Wed 3/251:18 pm
NAS
- SJC
1 stop11h 15m
Delta
Deal found 2/2![Delta logo]()
$446
One-way flights from San Jose to CaribbeanSearch for one-way flight options from San Jose to Caribbean. Find affordable one-way fares based on user searches. Data last updated February 2, 2026.
Search for one-way flight options from San Jose to Caribbean. Find affordable one-way fares based on user searches. Data last updated February 2, 2026.
This Delta deal was found by Cheapflights users on 2/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/236:15 pm
SJC
- SJU
2 stops17h 00m
Delta
Deal found 2/1![Delta logo]()
$148
This Delta deal was found by Cheapflights users on 2/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/2310:50 pm
SJC
- NAS
2 stops13h 09m
Delta
Deal found 2/1![Delta logo]()
$169
This CheapOair deal was found by Cheapflights users on 1/31. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/202:02 pm
SJC
- SJU
1 stop11h 30m
Alaska Airlines
Deal found 1/31![Alaska Airlines logo]()
$189
This United Airlines deal was found by Cheapflights users on 1/31. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/236:37 pm
SJC
- SJU
2 stops14h 27m
United Airlines
Deal found 1/31![United Airlines logo]()
$193
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/237:42 pm
SJC
- SJU
3 stops26h 37m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$195
This United Airlines deal was found by Cheapflights users on 1/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/56:37 pm
SJC
- NAS
2 stops18h 19m
United Airlines
Deal found 1/30![United Airlines logo]()
$200
This American Airlines deal was found by Cheapflights users on 2/1. 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 2/86:00 am
SJC
- NAS
2 stops11h 19m
American Airlines
Deal found 2/1![American Airlines logo]()
$213
This American Airlines deal was found by Cheapflights users on 2/1. 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.
Mon 2/96:00 am
SJC
- SJU
2 stops13h 59m
American Airlines
Deal found 2/1![American Airlines logo]()
$251
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/237:42 pm
SJC
- NAS
3 stops22h 03m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$267
This Delta deal was found by Cheapflights users on 2/1. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/108:35 pm
SJC
- AUA
2 stops11h 55m
Delta
Deal found 2/1![Delta logo]()
$269
This Alaska Airlines deal was found by Cheapflights users on 1/31. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/76:10 pm
SJC
- SJU
2 stops24h 21m
Alaska Airlines
Deal found 1/31![Alaska Airlines logo]()
$270
This Kiwi.com deal was found by Cheapflights users on 2/1. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/228:12 pm
SJC
- SJU
3 stops26h 09m
Multiple Airlines
Deal found 2/1![Multiple Airlines logo]()
$277
Find flight deals from San Jose to Caribbean
Keep the following information in mind while searching for San Jose to Caribbean flight deals. Data was last updated February 2, 2026.
Round-trip from | $296 (Delta) |
|---|---|
One-way from | $148 (Delta) |
Popular in | June |
Cheapest in | September |
Average price | $498 |
Cheapflights Fare Finder
Customize your flight search to find flights from San Jose to Caribbean that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 2, 2026.
Use the filters below to find and compare flights from San Jose to Caribbean that are best for you.
Fly from
San Jose
Fly to
Caribbean
Route
Depart
Return
Price
San JoseSan Juan
SJC - SJU
SJCSJU
San Jose
Tue 3/3
6:30 pm-1:01 pm
2 stops14h 31m
San Juan Luis Munoz Marin Intl
Tue 3/10
7:30 am-10:02 pm
2 stops17h 32m
$296
San JoseSan Juan
SJC - SJU
SJCSJU
San Jose
Sun 2/22
10:35 pm-1:01 pm
1 stop10h 26m
San Juan Luis Munoz Marin Intl
Wed 2/25
6:15 am-5:33 pm
2 stops15h 18m
$360
San JoseSan Juan
SJC - SJU
SJCSJU
San Jose
Sat 2/21
10:35 pm-1:01 pm
1 stop10h 26m
San Juan Luis Munoz Marin Intl
Wed 2/25
2:12 pm-9:18 pm
1 stop11h 06m
$360
San JoseSan Juan
SJC - SJU
SJCSJU
San Jose
Sat 2/21
6:20 am-11:58 pm
2 stops13h 38m
San Juan Luis Munoz Marin Intl
Tue 2/24
6:15 am-2:56 pm
2 stops12h 41m
$373
San JoseSan Juan
SJC - SJU
SJCSJU
San Jose
Tue 3/3
6:30 pm-1:01 pm
2 stops14h 31m
San Juan Luis Munoz Marin Intl
Wed 3/11
7:30 am-8:24 pm
2 stops15h 54m
$373
San JoseSan Juan
SJC - SJU
SJCSJU
San Jose
Mon 3/2
10:35 pm-1:01 pm
1 stop10h 26m
San Juan Luis Munoz Marin Intl
Wed 3/11
7:30 am-11:58 pm
2 stops19h 28m
$373
San JoseSan Juan
SJC - SJU
SJCSJU
San Jose
Mon 4/27
9:35 pm-10:35 am
2 stops10h 00m
San Juan Luis Munoz Marin Intl
Sat 5/2
11:15 am-8:25 pm
2 stops12h 10m
$406
San JoseSan Juan
SJC - SJU
SJCSJU
San Jose
Sat 4/25
8:10 pm-12:00 pm
2 stops12h 50m
San Juan Luis Munoz Marin Intl
Sat 5/2
11:15 am-8:25 pm
2 stops12h 10m
$440
San JoseNassau
SJC - NAS
SJCNAS
San Jose
Mon 4/20
10:55 pm-4:33 pm
1 stop14h 38m
Nassau Intl
Fri 4/24
1:13 pm-9:45 pm
1 stop11h 32m
$444
San JoseNassau
SJC - NAS
SJCNAS
San Jose
Wed 3/18
10:55 pm-3:22 pm
1 stop13h 27m
Nassau Intl
Wed 3/25
3:35 pm-10:59 pm
1 stop10h 24m
$446
Showing 1-10 of 60 results
Best time to book a flight from San Jose to Caribbean
Have a flexible travel schedule? Discover the best time to fly to Caribbean from San Jose with our price prediction graph.
SJC-SJU
SJC-NAS
SJC-AUA
SJC-PLS
SJC-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 San Jose to Caribbean
SJC-0CB
SJC-SJU
SJC-NAS
SJC-AUA
SJC-PLS
What is the cheapest month to book a flight from San Jose, California to Caribbean?
Currently, January is the cheapest month in which you can book a flight from San Jose, California to Caribbean (average of $169). Flying from San Jose, California to Caribbean in June is currently the most expensive (average of $296). 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.
Reviews of airlines servicing Caribbean
Get insights into the airlines that provide service to Caribbean. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean. Reviews last updated February 2, 2026.
Peruse reviews from past customers who have flown with Southwest, Delta, and United Airlines from San Jose to Caribbean to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Crew
8.6
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Crew
8.6
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Crew
8.6
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Crew
8.6
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Crew
8.6
Comfort
8.0
Entertainment
7.5
Food
7.0
Overall
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Related info for your journey
Find useful and relevant information for your journey from San Jose 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.
Alternative routes for San Jose to Caribbean
See prices for flight routes from nearby airports that may be better suited for you.
Top 6 airlines flying from San Jose to Caribbean
Discover the top 6 airlines that operate flights from San Jose to Caribbean. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 2, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$232 | Average$361 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$238 | Average$681 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$298 | Average$541 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$369 | Average$549 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$409 | Average$574 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$414 | Average$640 | FlexibilityNo cancel fee | On-time71% |