$139+ Cheap flights from San Diego (SAN) 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 5/5. Fares are subject to change and may not be available on all flights or dates of travel.
SAN — SJU
May 9 — May 161
Round-trip
1 adult, Economy
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Find cheap flights from San Diego to Caribbean Islands with Cheapflights
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Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Cheapest flights from San Diego to Caribbean IslandsExplore the most affordable flight options available from San Diego to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 9, 2026.
Explore the most affordable flight options available from San Diego to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 9, 2026.
This Delta deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 4/205:48 pm
SAN
- STT
2 stops18h 00m
Delta
Thu 4/231:59 pm
STT
- SAN
1 stop12h 26m
Delta
Deal found 4/6![Delta logo]()
$310
This American Airlines deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/39:45 pm
SAN
- STT
1 stop10h 02m
American Airlines
Thu 5/711:27 am
STT
- SAN
1 stop14h 22m
American Airlines
Deal found 4/6![American Airlines logo]()
$316
This American Airlines deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 4/297:20 pm
SAN
- STT
2 stops12h 27m
American Airlines
Thu 5/711:27 am
STT
- SAN
1 stop14h 22m
American Airlines
Deal found 4/6![American Airlines logo]()
$321
This Kiwi.com deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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.
Thu 5/76:25 am
SAN
- SJU
1 stop28h 07m
Multiple Airlines
Tue 5/128:30 am
SJU
- SAN
2 stops18h 20m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$322
This Trip.com deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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.
Thu 4/307:45 am
SAN
- SJU
2 stops39h 16m
Frontier
Sun 5/36:30 am
SJU
- SAN
2 stops20h 28m
Frontier
Deal found 4/6![Frontier logo]()
$325
This Kiwi.com deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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 5/27:15 am
SAN
- SJU
2 stops24h 24m
Multiple Airlines
Fri 5/82:37 pm
SJU
- SAN
1 stop27h 49m
Multiple Airlines
Deal found 4/7![Multiple Airlines logo]()
$326
This Kiwi.com deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” 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 5/211:42 am
SAN
- SJU
2 stops19h 57m
Multiple Airlines
Tue 5/57:00 am
SJU
- SAN
1 stop31h 44m
Multiple Airlines
Deal found 4/4![Multiple Airlines logo]()
$327
This Kiwi.com deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/17:00 am
SAN
- SJU
1 stop13h 10m
Multiple Airlines
Thu 5/77:00 am
SJU
- SAN
2 stops19h 50m
Multiple Airlines
Deal found 4/8![Multiple Airlines logo]()
$329
This American Airlines deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/207:20 pm
SAN
- STT
2 stops13h 47m
American Airlines
Thu 4/235:05 pm
STT
- SAN
2 stops18h 33m
American Airlines
Deal found 4/6![American Airlines logo]()
$330
This Kiwi.com deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/86:25 am
SAN
- SJU
1 stop28h 07m
Multiple Airlines
Thu 5/143:12 pm
SJU
- SAN
2 stops20h 30m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$333
This Kiwi.com deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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.
Thu 4/307:45 am
SAN
- SJU
1 stop12h 25m
Multiple Airlines
Mon 5/48:04 pm
SJU
- SAN
2 stops24h 55m
Multiple Airlines
Deal found 4/7![Multiple Airlines logo]()
$345
This Kiwi.com deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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.
Thu 5/76:25 am
SAN
- SJU
1 stop28h 07m
Multiple Airlines
Wed 5/136:41 pm
SJU
- SAN
2 stops26h 44m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$351
Best flights from San Diego to Caribbean IslandsDiscover carefully curated flight deals from San Diego to Caribbean Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 9, 2026.
Discover carefully curated flight deals from San Diego to Caribbean Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 9, 2026.
This Delta deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” 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 4/209:45 pm
SAN
- STT
1 stop13h 06m
Delta
Thu 4/231:59 pm
STT
- SAN
1 stop9h 51m
Delta
Deal found 4/4![Delta logo]()
$310
This American Airlines deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/310:05 pm
SAN
- STT
1 stop10h 30m
American Airlines
Thu 5/75:05 pm
STT
- SAN
2 stops18h 33m
American Airlines
Deal found 4/6![American Airlines logo]()
$316
This United Airlines deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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 5/126:26 pm
SAN
- STT
2 stops14h 54m
United Airlines
Thu 5/141:22 pm
STT
- SAN
1 stop11h 03m
United Airlines
Deal found 4/5![United Airlines logo]()
$400
This Southwest deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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 5/410:20 am
SAN
- SJU
2 stops10h 35m
Southwest
Thu 5/75:05 am
SJU
- SAN
2 stops12h 00m
Southwest
Deal found 4/7![Southwest logo]()
$446
This JetBlue deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/279:15 pm
SAN
- SDQ
1 stop12h 45m
JetBlue
Thu 4/305:40 am
SDQ
- SAN
1 stop17h 24m
JetBlue
Deal found 4/5![JetBlue logo]()
$502
This Copa Airlines deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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.
Wed 6/310:00 pm
SAN
- PUJ
1 stop10h 03m
Copa Airlines
Sun 6/75:37 am
PUJ
- SAN
1 stop16h 03m
Copa Airlines
Deal found 4/5![Copa Airlines logo]()
$558
This Delta deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” 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 4/1910:30 pm
SAN
- STT
1 stop12h 21m
Delta
Thu 4/233:05 pm
STT
- SAN
1 stop11h 20m
Delta
Deal found 4/4![Delta logo]()
$310
This American Airlines deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” 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 4/297:20 pm
SAN
- STT
2 stops14h 55m
American Airlines
Thu 5/711:27 am
STT
- SAN
2 stops13h 28m
American Airlines
Deal found 4/4![American Airlines logo]()
$321
This United Airlines deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” 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 4/207:14 pm
SAN
- STT
2 stops14h 06m
United Airlines
Wed 4/222:10 pm
STT
- SAN
1 stop11h 49m
United Airlines
Deal found 4/4![United Airlines logo]()
$400
This Priceline deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/228:30 pm
SAN
- UVF
1 stop16h 05m
Multiple Airlines
Fri 5/293:05 pm
UVF
- SAN
1 stop24h 13m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$803
This Justfly.com deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/211:15 pm
SAN
- UVF
1 stop21h 50m
Air Canada
Fri 5/293:05 pm
UVF
- SAN
1 stop24h 13m
Air Canada
Deal found 4/4![Air Canada logo]()
$824
This Delta deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 4/2710:10 pm
SAN
- SJU
1 stop11h 42m
Delta
Tue 5/57:30 am
SJU
- SAN
2 stops16h 12m
Delta
Deal found 4/6![Delta logo]()
$386
This United Airlines deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” 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 5/239:59 pm
SAN
- MBJ
1 stop15h 11m
United Airlines
Sat 5/302:40 pm
MBJ
- SAN
1 stop8h 44m
United Airlines
Deal found 4/4![United Airlines logo]()
$410
This American Airlines deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/77:20 pm
SAN
- STT
2 stops12h 27m
American Airlines
Thu 5/1411:27 am
STT
- SAN
2 stops13h 28m
American Airlines
Deal found 4/4![American Airlines logo]()
$429
This Southwest deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/59:35 am
SAN
- SJU
2 stops11h 05m
Southwest
Sun 5/105:35 am
SJU
- SAN
2 stops11h 10m
Southwest
Deal found 4/8![Southwest logo]()
$500
This United Airlines deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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 5/46:05 pm
SAN
- STT
2 stops16h 03m
United Airlines
Mon 5/111:22 pm
STT
- SAN
2 stops13h 37m
United Airlines
Deal found 4/7![United Airlines logo]()
$429
This Delta deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” 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 5/268:00 am
SAN
- SJU
1 stop9h 30m
Delta
Tue 6/26:15 am
SJU
- SAN
2 stops15h 30m
Delta
Deal found 4/4![Delta logo]()
$444
This American Airlines deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/71:31 pm
SAN
- CUR
1 stop22h 01m
American Airlines
Thu 5/142:42 pm
CUR
- SAN
2 stops20h 56m
American Airlines
Deal found 4/7![American Airlines logo]()
$465
This Southwest deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” 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.
Wed 7/19:00 am
SAN
- SJU
2 stops12h 15m
Southwest
Wed 8/2611:50 am
SJU
- SAN
2 stops11h 55m
Southwest
Deal found 4/4![Southwest logo]()
$521
This Delta deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 9/510:40 pm
SAN
- SXM
1 stop12h 16m
Delta
Sun 9/203:20 pm
SXM
- SAN
1 stop10h 24m
Delta
Deal found 4/6![Delta logo]()
$445
This American Airlines deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/67:20 pm
SAN
- SXM
2 stops13h 17m
American Airlines
Wed 5/132:21 pm
SXM
- SAN
2 stops20h 54m
American Airlines
Deal found 4/7![American Airlines logo]()
$465
This United Airlines deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 5/410:20 pm
SAN
- MBJ
1 stop11h 23m
United Airlines
Mon 5/114:12 pm
MBJ
- SAN
2 stops19h 03m
United Airlines
Deal found 4/6![United Airlines logo]()
$469
This Justfly.com deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/28:40 pm
SAN
- PLS
1 stop11h 32m
JetBlue
Sat 10/1012:20 pm
PLS
- SAN
1 stop24h 32m
JetBlue
Deal found 4/6![JetBlue logo]()
$656
This Southwest deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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.
Fri 5/86:30 am
SAN
- SJU
2 stops10h 30m
Southwest
Sun 5/101:15 pm
SJU
- SAN
2 stops13h 10m
Southwest
Deal found 4/5![Southwest logo]()
$544
This American Airlines deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/21:36 pm
SAN
- MBJ
1 stop17h 37m
American Airlines
Mon 7/275:17 pm
MBJ
- SAN
2 stops18h 48m
American Airlines
Deal found 4/6![American Airlines logo]()
$469
This United Airlines deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” 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 4/277:14 pm
SAN
- SJU
2 stops15h 31m
United Airlines
Tue 5/57:20 am
SJU
- SAN
2 stops18h 19m
United Airlines
Deal found 4/4![United Airlines logo]()
$476
This Delta deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” 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 5/69:45 pm
SAN
- NAS
1 stop13h 19m
Delta
Tue 5/126:00 pm
NAS
- SAN
1 stop8h 27m
Delta
Deal found 4/4![Delta logo]()
$478
This Copa Airlines deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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.
Thu 8/68:32 pm
SAN
- CUR
2 stops18h 59m
Copa Airlines
Mon 8/103:39 pm
CUR
- SAN
2 stops35h 50m
Copa Airlines
Deal found 4/6![Copa Airlines logo]()
$715
This Southwest deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” 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 5/410:20 am
SAN
- SJU
2 stops10h 35m
Southwest
Mon 5/116:50 am
SJU
- SAN
2 stops12h 00m
Southwest
Deal found 4/4![Southwest logo]()
$546
This United Airlines deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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 6/910:40 pm
SAN
- NAS
2 stops11h 53m
United Airlines
Tue 6/163:59 pm
NAS
- SAN
1 stop9h 35m
United Airlines
Deal found 4/5![United Airlines logo]()
$478
Last-minute flights from San Diego to Caribbean IslandsDiscover last-minute flight deals from San Diego to Caribbean Islands. Data last updated April 9, 2026 and is based on user searches.
Discover last-minute flight deals from San Diego to Caribbean Islands. Data last updated April 9, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 4/205:48 pm
SAN
- STT
2 stops18h 00m
Delta
Thu 4/231:59 pm
STT
- SAN
1 stop12h 26m
Delta
Deal found 4/6![Delta logo]()
$310
This American Airlines deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/207:20 pm
SAN
- STT
2 stops13h 47m
American Airlines
Thu 4/235:05 pm
STT
- SAN
2 stops18h 33m
American Airlines
Deal found 4/6![American Airlines logo]()
$330
This American Airlines deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 4/297:20 pm
SAN
- STT
2 stops12h 27m
American Airlines
Thu 5/711:27 am
STT
- SAN
1 stop14h 22m
American Airlines
Deal found 4/6![American Airlines logo]()
$321
This Trip.com deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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.
Thu 4/307:45 am
SAN
- SJU
2 stops39h 16m
Frontier
Sun 5/36:30 am
SJU
- SAN
2 stops20h 28m
Frontier
Deal found 4/6![Frontier logo]()
$325
This Kiwi.com deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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.
Thu 4/307:45 am
SAN
- SJU
1 stop12h 25m
Multiple Airlines
Mon 5/48:04 pm
SJU
- SAN
2 stops24h 55m
Multiple Airlines
Deal found 4/7![Multiple Airlines logo]()
$345
This Kiwi.com deal was found by Cheapflights users on 4/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/17:00 am
SAN
- SJU
1 stop13h 10m
Multiple Airlines
Thu 5/77:00 am
SJU
- SAN
2 stops19h 50m
Multiple Airlines
Deal found 4/8![Multiple Airlines logo]()
$329
This Kiwi.com deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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 5/27:15 am
SAN
- SJU
2 stops24h 24m
Multiple Airlines
Fri 5/82:37 pm
SJU
- SAN
1 stop27h 49m
Multiple Airlines
Deal found 4/7![Multiple Airlines logo]()
$326
This Kiwi.com deal was found by Cheapflights users on 4/4. Clicking the “Pick Dates” 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 5/211:42 am
SAN
- SJU
2 stops19h 57m
Multiple Airlines
Tue 5/57:00 am
SJU
- SAN
1 stop31h 44m
Multiple Airlines
Deal found 4/4![Multiple Airlines logo]()
$327
This American Airlines deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/39:45 pm
SAN
- STT
1 stop10h 02m
American Airlines
Thu 5/711:27 am
STT
- SAN
1 stop14h 22m
American Airlines
Deal found 4/6![American Airlines logo]()
$316
This Kiwi.com deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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.
Thu 5/76:25 am
SAN
- SJU
1 stop28h 07m
Multiple Airlines
Tue 5/128:30 am
SJU
- SAN
2 stops18h 20m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$322
This Kiwi.com deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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.
Thu 5/76:25 am
SAN
- SJU
1 stop28h 07m
Multiple Airlines
Wed 5/136:41 pm
SJU
- SAN
2 stops26h 44m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$351
This Kiwi.com deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/86:25 am
SAN
- SJU
1 stop28h 07m
Multiple Airlines
Thu 5/143:12 pm
SJU
- SAN
2 stops20h 30m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$333
One-way flights from San Diego to Caribbean IslandsSearch for one-way flight options from San Diego to Caribbean Islands. Find affordable one-way fares based on user searches. Data last updated April 9, 2026.
Search for one-way flight options from San Diego to Caribbean Islands. Find affordable one-way fares based on user searches. Data last updated April 9, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” 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.
Tue 5/56:25 am
SAN
- SJU
2 stops37h 18m
Frontier
Deal found 4/5![Frontier logo]()
$139
This United Airlines deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 5/1110:20 pm
SAN
- STT
1 stop11h 48m
United Airlines
Deal found 4/6![United Airlines logo]()
$153
This Delta deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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 8/310:30 pm
SAN
- STT
1 stop13h 50m
Delta
Deal found 4/7![Delta logo]()
$156
This American Airlines deal was found by Cheapflights users on 4/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/207:20 pm
SAN
- STT
2 stops12h 43m
American Airlines
Deal found 4/5![American Airlines logo]()
$161
This United Airlines deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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 8/46:27 pm
SAN
- STT
2 stops18h 16m
United Airlines
Deal found 4/7![United Airlines logo]()
$163
This Delta deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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 6/117:10 pm
SAN
- STT
2 stops16h 09m
Delta
Deal found 4/7![Delta logo]()
$166
This United Airlines deal was found by Cheapflights users on 4/6. Clicking the “Pick Dates” 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 5/210:40 pm
SAN
- MBJ
2 stops12h 50m
United Airlines
Deal found 4/6![United Airlines logo]()
$172
This Kiwi.com deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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 4/2012:25 pm
SAN
- SJU
3 stops50h 34m
Multiple Airlines
Deal found 4/7![Multiple Airlines logo]()
$178
This SmartFares deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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 4/289:15 pm
SAN
- CUR
1 stop13h 21m
JetBlue
Deal found 4/7![JetBlue logo]()
$180
This Kiwi.com deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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 4/2012:25 pm
SAN
- SJU
2 stops34h 36m
Frontier
Deal found 4/7![Frontier logo]()
$180
This United Airlines deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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.
Thu 7/25:15 pm
SAN
- MBJ
1 stop18h 15m
United Airlines
Deal found 4/7![United Airlines logo]()
$182
This Kiwi.com deal was found by Cheapflights users on 4/7. Clicking the “Pick Dates” 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.
Tue 4/2112:29 pm
SAN
- SJU
3 stops27h 53m
Multiple Airlines
Deal found 4/7![Multiple Airlines logo]()
$182
Find flight deals from San Diego to Caribbean Islands
Keep the following information in mind while searching for San Diego to Caribbean Islands flight deals. Data was last updated April 9, 2026.
Round-trip from | $310 (Delta) |
|---|---|
One-way from | $139 (Kiwi.com) |
Popular in | December |
Cheapest in | October |
Average price | $450 |
Cheapflights Fare Finder
Customize your flight search to find flights from San Diego to Caribbean Islands that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 9, 2026.
Use the filters below to find and compare flights from San Diego to Caribbean Islands that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
San DiegoSaint Thomas Island
SAN - STT
SANSTT
San Diego
Mon 4/20
9:45 pm-1:51 pm
1 stop13h 06m
Saint Thomas Island Cyril E King
Thu 4/23
1:59 pm-8:50 pm
1 stop9h 51m
$310
San DiegoSaint Thomas Island
SAN - STT
SANSTT
San Diego
Sun 4/19
10:30 pm-1:51 pm
1 stop12h 21m
Saint Thomas Island Cyril E King
Thu 4/23
3:05 pm-11:25 pm
1 stop11h 20m
$310
San DiegoSaint Thomas Island
SAN - STT
SANSTT
San Diego
Sun 5/3
10:05 pm-11:35 am
1 stop10h 30m
Saint Thomas Island Cyril E King
Thu 5/7
5:05 pm-8:38 am
2 stops18h 33m
$316
San DiegoSaint Thomas Island
SAN - STT
SANSTT
San Diego
Wed 4/29
7:20 pm-1:15 pm
2 stops14h 55m
Saint Thomas Island Cyril E King
Thu 5/7
11:27 am-9:55 pm
2 stops13h 28m
$321
San DiegoSan Juan
SAN - SJU
SANSJU
San Diego
Mon 4/27
10:10 pm-12:52 pm
1 stop11h 42m
San Juan Luis Munoz Marin Intl
Tue 5/5
7:30 am-8:42 pm
2 stops16h 12m
$386
San DiegoSaint Thomas Island
SAN - STT
SANSTT
San Diego
Tue 5/12
6:26 pm-12:20 pm
2 stops14h 54m
Saint Thomas Island Cyril E King
Thu 5/14
1:22 pm-9:25 pm
1 stop11h 03m
$400
San DiegoSaint Thomas Island
SAN - STT
SANSTT
San Diego
Mon 4/20
7:14 pm-12:20 pm
2 stops14h 06m
Saint Thomas Island Cyril E King
Wed 4/22
2:10 pm-10:59 pm
1 stop11h 49m
$400
San DiegoMontego Bay
SAN - MBJ
SANMBJ
San Diego
Sat 5/23
9:59 pm-3:10 pm
1 stop15h 11m
Montego Bay Sangster Intl
Sat 5/30
2:40 pm-9:24 pm
1 stop8h 44m
$410
San DiegoSaint Thomas Island
SAN - STT
SANSTT
San Diego
Thu 5/7
7:20 pm-10:47 am
2 stops12h 27m
Saint Thomas Island Cyril E King
Thu 5/14
11:27 am-9:55 pm
2 stops13h 28m
$429
San DiegoSaint Thomas Island
SAN - STT
SANSTT
San Diego
Mon 5/4
6:05 pm-1:08 pm
2 stops16h 03m
Saint Thomas Island Cyril E King
Mon 5/11
1:22 pm-11:59 pm
2 stops13h 37m
$429
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from San Diego to Caribbean Islands
Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands from San Diego with our price prediction graph.
SAN-STT
SAN-SJU
SAN-SDQ
SAN-PUJ
SAN-UVF
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 Diego to Caribbean Islands
SAN-zzEPX
SAN-STT
SAN-SJU
SAN-SDQ
SAN-PUJ
What is the cheapest month to book a flight from San Diego to Caribbean Islands?
Currently, October is the cheapest month in which you can book a flight from San Diego to Caribbean Islands (average of $165). Flying from San Diego to Caribbean Islands in December is currently the most expensive (average of $315). 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 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 April 9, 2026.
Peruse reviews from past customers who have flown with Delta,Copa Airlines, andUnited Airlines from San Diego to Caribbean Islands to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Food
7.2
Boarding
8.1
Overall
7.9
Comfort
7.9
Entertainment
7.8
Crew
8.5
Reviews
1 / 20
10.0
ExcellentAaron,Oct 2024
LAX - LHR
Food
7.2
Boarding
8.1
Overall
7.9
Comfort
7.9
Entertainment
7.8
Crew
8.5
Reviews
1 / 20
10.0
ExcellentAaron,Oct 2024
LAX - LHR
Food
7.2
Boarding
8.1
Overall
7.9
Comfort
7.9
Entertainment
7.8
Crew
8.5
Reviews
1 / 20
10.0
ExcellentAaron,Oct 2024
LAX - LHR
Food
7.2
Boarding
8.1
Overall
7.9
Comfort
7.9
Entertainment
7.8
Crew
8.5
Reviews
1 / 20
10.0
ExcellentAaron,Oct 2024
LAX - LHR
Food
7.2
Boarding
8.1
Overall
7.9
Comfort
7.9
Entertainment
7.8
Crew
8.5
Reviews
1 / 20
10.0
ExcellentAaron,Oct 2024
LAX - LHR
Food
7.2
Boarding
8.1
Overall
7.9
Comfort
7.9
Entertainment
7.8
Crew
8.5
Reviews
1 / 20
10.0
ExcellentAaron,Oct 2024
LAX - LHR
Related info for your journey
Find useful and relevant information for your journey from San Diego to Caribbean Islands. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for San Diego to Caribbean Islands
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Caribbean Islands by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from San Diego to Caribbean Islands by cabin class
Find flights from San Diego to Caribbean Islands, based on your preferred cabin class, be it economy, premium economy, business, or first class.
San Diego and Caribbean Islands flights
Browse other San Diego and Caribbean Islands flight options. Last updated on April 9, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
San Diego to Caribbean Islands flights
Consider these flights traveling from San Diego to Caribbean Islands.
Top 9 airlines flying from San Diego to Caribbean Islands
Discover the top 9 airlines that operate flights from San Diego to Caribbean Islands. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 9, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$176 | Average$555 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$189 | Average$514 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$215 | Average$463 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$260 | Average$444 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$277 | Average$552 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$306 | Average$636 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$309 | Average$652 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$382 | Average$750 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$442 | Average$599 | FlexibilityNo cancel fee | On-time75% |