$137+ Cheap flights from San Diego (SAN) to Caribbean Islands
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/4. Fares are subject to change and may not be available on all flights or dates of travel.
SAN — SJU
Oct 8 — Oct 151
Round-trip
1 adult, Economy
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Find cheap flights from San Diego to Caribbean Islands with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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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 September 8, 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 September 8, 2026.
This American Airlines deal was found by Cheapflights users on 9/4. 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.
Tue 10/209:25 pm -
1 stop14h 36m
Tue 10/276:30 am -
2 stops10h 47m
Deal found 9/4![American Airlines logo]()
$274
This American Airlines deal was found by Cheapflights users on 9/4. 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.
Sat 10/1712:56 pm -
1 stop17h 50m
Sat 10/247:30 am -
1 stop14h 27m
Deal found 9/4![American Airlines logo]()
$275
This American Airlines deal was found by Cheapflights users on 9/5. 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 10/2810:40 pm -
2 stops11h 48m
Wed 11/188:30 am -
1 stop14h 59m
Deal found 9/5![American Airlines logo]()
$279
This American Airlines deal was found by Cheapflights users on 9/5. 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.
Fri 10/166:45 pm -
1 stop17h 38m
Wed 10/2112:41 pm -
1 stop11h 56m
Deal found 9/5![American Airlines logo]()
$280
This American Airlines deal was found by Cheapflights users on 9/7. 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.
Sun 10/49:25 pm -
1 stop10h 55m
Tue 10/136:30 am -
2 stops20h 08m
Deal found 9/7![American Airlines logo]()
$348
This American Airlines deal was found by Cheapflights users on 9/4. 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.
Sat 10/2410:40 pm -
2 stops13h 15m
Sat 10/313:58 pm -
2 stops21h 22m
Deal found 9/4![American Airlines logo]()
$356
This American Airlines deal was found by Cheapflights users on 9/6. 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.
Fri 10/167:15 pm -
2 stops11h 31m
Fri 10/232:53 pm -
1 stop11h 26m
Deal found 9/6![American Airlines logo]()
$360
This American Airlines deal was found by Cheapflights users on 9/4. 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.
Sat 10/310:46 pm -
2 stops12h 11m
Wed 10/72:53 pm -
1 stop11h 26m
Deal found 9/4![American Airlines logo]()
$389
This American Airlines deal was found by Cheapflights users on 9/8. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/289:25 pm -
2 stops13h 03m
Mon 11/27:30 am -
2 stops12h 09m
Deal found 9/8![American Airlines logo]()
$394
This Copa Airlines deal was found by Cheapflights users on 9/6. 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.
Sun 10/1110:30 pm -
1 stop16h 50m
Sun 10/187:21 pm -
1 stop26h 09m
Deal found 9/6![Copa Airlines logo]()
$440
This United Airlines deal was found by Cheapflights users on 9/8. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/106:28 pm -
2 stops13h 37m
Sun 12/133:35 pm -
1 stop9h 57m
Deal found 9/8![United Airlines logo]()
$446
This American Airlines deal was found by Cheapflights users on 9/5. 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.
Thu 11/129:25 pm -
1 stop10h 53m
Wed 11/1812:08 pm -
1 stop14h 30m
Deal found 9/5![American Airlines logo]()
$496
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 September 8, 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 September 8, 2026.
This American Airlines deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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 2/201:02 pm -
1 stop16h 33m
Fri 2/266:00 am -
1 stop16h 55m
Deal found 9/3![American Airlines logo]()
$274
This United Airlines deal was found by Cheapflights users on 9/4. 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.
Sun 12/66:50 am -
1 stop10h 10m
Fri 12/112:05 am -
1 stop12h 15m
Deal found 9/4![United Airlines logo]()
$426
This Southwest deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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 2/201:50 pm -
2 stops16h 00m
Fri 2/267:25 am -
2 stops12h 10m
Deal found 9/3![Southwest logo]()
$426
This Copa Airlines deal was found by Cheapflights users on 9/4. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/1110:30 pm -
1 stop16h 50m
Sun 10/187:21 pm -
1 stop26h 09m
Deal found 9/4![Copa Airlines logo]()
$440
This Air Canada deal was found by Cheapflights users on 9/8. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/25:15 pm -
2 stops24h 25m
Mon 12/710:40 pm -
2 stops21h 45m
Deal found 9/8![Air Canada logo]()
$528
This JetBlue deal was found by Cheapflights users on 9/6. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/268:26 pm -
1 stop16h 33m
Fri 10/3010:57 am -
1 stop12h 28m
Deal found 9/6![JetBlue logo]()
$582
This Delta deal was found by Cheapflights users on 9/7. 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.
Fri 12/410:30 pm -
1 stop10h 45m
Thu 12/104:35 pm -
1 stop11h 04m
Deal found 9/7![Delta logo]()
$589
This United Airlines deal was found by Cheapflights users on 9/4. 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.
Thu 12/106:28 pm -
2 stops13h 37m
Sun 12/133:35 pm -
1 stop9h 57m
Deal found 9/4![United Airlines logo]()
$446
This Southwest deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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 10/38:50 am -
2 stops12h 00m
Sat 10/107:50 am -
2 stops11h 25m
Deal found 9/3![Southwest logo]()
$502
This Copa Airlines deal was found by Cheapflights users on 9/4. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/2510:30 pm -
1 stop24h 55m
Sun 10/116:06 am -
1 stop15h 24m
Deal found 9/4![Copa Airlines logo]()
$512
This American Airlines deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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 10/176:45 pm -
2 stops14h 33m
Tue 11/106:09 pm -
2 stops19h 09m
Deal found 9/3![American Airlines logo]()
$517
This Southwest deal was found by Cheapflights users on 9/5. 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 10/98:45 am -
1 stop11h 25m
Mon 10/194:10 pm -
2 stops11h 25m
Deal found 9/5![Southwest logo]()
$504
This United Airlines deal was found by Cheapflights users on 9/7. 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.
Sat 10/1710:30 pm -
2 stops13h 00m
Sat 10/312:01 pm -
1 stop10h 39m
Deal found 9/7![United Airlines logo]()
$512
This American Airlines deal was found by Cheapflights users on 9/6. 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.
Fri 10/23:05 pm -
2 stops19h 48m
Sat 10/102:23 pm -
1 stop11h 20m
Deal found 9/6![American Airlines logo]()
$522
This Air Canada deal was found by Cheapflights users on 9/7. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/712:55 pm -
2 stops21h 20m
Thu 12/102:05 pm -
2 stops24h 55m
Deal found 9/7![Air Canada logo]()
$581
This Southwest deal was found by Cheapflights users on 9/4. 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.
Thu 2/2510:35 pm -
1 stop15h 25m
Sun 3/78:45 pm -
2 stops18h 35m
Deal found 9/4![Southwest logo]()
$506
This United Airlines deal was found by Cheapflights users on 9/7. 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.
Wed 2/36:50 am -
2 stops13h 46m
Sat 2/62:05 am -
1 stop12h 15m
Deal found 9/7![United Airlines logo]()
$516
This Air Canada deal was found by Cheapflights users on 9/7. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/195:15 pm -
2 stops24h 10m
Fri 11/272:05 pm -
2 stops24h 55m
Deal found 9/7![Air Canada logo]()
$581
This American Airlines deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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 1/242:02 pm -
2 stops15h 56m
Sat 1/3010:58 am -
1 stop16h 47m
Deal found 9/3![American Airlines logo]()
$539
This Southwest deal was found by Cheapflights users on 9/7. 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.
Thu 3/410:35 pm -
2 stops10h 55m
Sun 3/78:45 pm -
2 stops18h 35m
Deal found 9/7![Southwest logo]()
$519
This Delta deal was found by Cheapflights users on 9/5. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/193:00 pm -
2 stops18h 40m
Wed 10/282:10 pm -
2 stops25h 15m
Deal found 9/5![Delta logo]()
$701
This United Airlines deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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 12/297:10 pm -
2 stops14h 40m
Thu 1/75:00 pm -
2 stops19h 37m
Deal found 9/3![United Airlines logo]()
$529
This Copa Airlines deal was found by Cheapflights users on 9/4. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/2110:30 pm -
1 stop10h 12m
Mon 10/58:47 am -
1 stop12h 43m
Deal found 9/4![Copa Airlines logo]()
$657
This American Airlines deal was found by Cheapflights users on 9/4. 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.
Fri 1/810:10 pm -
1 stop13h 31m
Fri 1/154:41 pm -
1 stop24h 30m
Deal found 9/4![American Airlines logo]()
$563
This Southwest deal was found by Cheapflights users on 9/6. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/87:05 am -
2 stops10h 10m
Sat 1/166:55 am -
2 stops18h 30m
Deal found 9/6![Southwest logo]()
$519
This United Airlines deal was found by Cheapflights users on 9/6. 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 10/176:28 pm -
2 stops16h 19m
Thu 10/222:53 pm -
1 stop9h 31m
Deal found 9/6![United Airlines logo]()
$532
This American Airlines deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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 10/186:20 am -
1 stop7h 52m
Sun 10/2512:18 pm -
1 stop22h 06m
Deal found 9/3![American Airlines logo]()
$569
This Copa Airlines deal was found by Cheapflights users on 9/5. 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.
Sun 10/1810:30 pm -
1 stop13h 06m
Thu 10/221:22 pm -
2 stops33h 46m
Deal found 9/5![Copa Airlines logo]()
$695
This Southwest deal was found by Cheapflights users on 9/8. 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.
Sun 12/610:35 pm -
1 stop10h 40m
Mon 12/141:10 pm -
1 stop8h 45m
Deal found 9/8![Southwest logo]()
$526
This United Airlines deal was found by Cheapflights users on 9/5. 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.
Thu 11/1210:30 pm -
2 stops12h 03m
Tue 11/1712:55 pm -
1 stop11h 27m
Deal found 9/5![United Airlines logo]()
$532
Last-minute flights from San Diego to Caribbean IslandsDiscover last-minute flight deals from San Diego to Caribbean Islands. Data last updated September 8, 2026 and is based on user searches.
Discover last-minute flight deals from San Diego to Caribbean Islands. Data last updated September 8, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 9/4. 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.
Sat 10/310:46 pm -
2 stops12h 11m
Wed 10/72:53 pm -
1 stop11h 26m
Deal found 9/4![American Airlines logo]()
$389
This American Airlines deal was found by Cheapflights users on 9/7. 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.
Sun 10/46:45 pm -
1 stop17h 38m
Wed 10/72:53 pm -
1 stop11h 26m
Deal found 9/7![American Airlines logo]()
$348
This American Airlines deal was found by Cheapflights users on 9/7. 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.
Sun 10/49:25 pm -
1 stop10h 55m
Sat 10/1012:18 pm -
1 stop9h 42m
Deal found 9/7![American Airlines logo]()
$496
This Kiwi.com deal was found by Cheapflights users on 9/7. 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.
Sun 10/410:30 pm -
1 stop10h 11m
Sun 10/118:47 am -
1 stop12h 43m
Deal found 9/7![Copa Airlines logo]()
$498
This Copa Airlines deal was found by Cheapflights users on 9/6. 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.
Sun 10/1110:30 pm -
1 stop16h 50m
Sun 10/187:21 pm -
1 stop26h 09m
Deal found 9/6![Copa Airlines logo]()
$440
This American Airlines deal was found by Cheapflights users on 9/5. 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.
Fri 10/166:45 pm -
1 stop17h 38m
Wed 10/2112:41 pm -
1 stop11h 56m
Deal found 9/5![American Airlines logo]()
$280
This American Airlines deal was found by Cheapflights users on 9/6. 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.
Fri 10/167:15 pm -
2 stops11h 31m
Fri 10/232:53 pm -
1 stop11h 26m
Deal found 9/6![American Airlines logo]()
$360
This American Airlines deal was found by Cheapflights users on 9/4. 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.
Sat 10/1712:56 pm -
1 stop17h 50m
Sat 10/247:30 am -
1 stop14h 27m
Deal found 9/4![American Airlines logo]()
$275
This American Airlines deal was found by Cheapflights users on 9/4. 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.
Tue 10/209:25 pm -
1 stop14h 36m
Tue 10/276:30 am -
2 stops10h 47m
Deal found 9/4![American Airlines logo]()
$274
This American Airlines deal was found by Cheapflights users on 9/4. 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.
Sat 10/2410:40 pm -
2 stops13h 15m
Sat 10/313:58 pm -
2 stops21h 22m
Deal found 9/4![American Airlines logo]()
$356
This American Airlines deal was found by Cheapflights users on 9/5. 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 10/2810:40 pm -
2 stops11h 48m
Wed 11/188:30 am -
1 stop14h 59m
Deal found 9/5![American Airlines logo]()
$279
This American Airlines deal was found by Cheapflights users on 9/8. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/289:25 pm -
2 stops13h 03m
Mon 11/27:30 am -
2 stops12h 09m
Deal found 9/8![American Airlines logo]()
$394
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 September 8, 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 September 8, 2026.
This American Airlines deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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 10/49:25 pm -
2 stops11h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![American Airlines logo]()
$137
This American Airlines deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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 10/56:20 am -
1 stop14h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![American Airlines logo]()
$140
This American Airlines deal was found by Cheapflights users on 9/6. 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 10/289:25 pm -
1 stop10h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![American Airlines logo]()
$142
This Kiwi.com deal was found by Cheapflights users on 9/4. 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.
Tue 9/295:54 pm -
2 stops18h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Frontier logo]()
$171
This Kiwi.com deal was found by Cheapflights users on 9/4. 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.
Thu 10/19:03 pm -
2 stops33h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Frontier logo]()
$190
This American Airlines deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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 1/612:08 pm -
1 stop17h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![American Airlines logo]()
$192
This Kiwi.com deal was found by Cheapflights users on 9/4. 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.
Mon 12/74:41 pm -
2 stops27h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Frontier logo]()
$201
This American Airlines deal was found by Cheapflights users on 9/5. 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.
Tue 10/279:25 pm -
1 stop13h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![American Airlines logo]()
$203
This Kiwi.com deal was found by Cheapflights users on 9/5. 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.
Wed 9/234:54 pm -
2 stops54h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![Frontier logo]()
$205
This Kiwi.com deal was found by Cheapflights users on 9/4. 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 9/269:03 am -
2 stops22h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Frontier logo]()
$209
This Kiwi.com deal was found by Cheapflights users on 9/6. 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.
Wed 10/76:25 am -
2 stops40h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Frontier logo]()
$211
This Kiwi.com deal was found by Cheapflights users on 9/8. 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.
Mon 11/96:25 am -
2 stops37h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Frontier logo]()
$212
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 September 8, 2026.
Round-trip from | $274 (American Airlines) |
|---|---|
One-way from | $137 (American Airlines) |
Popular in | December |
Cheapest in | October |
Average price | $426 |
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 7,457,451 searches. Data last updated September 8, 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 DiegoSan Juan
SAN San Diego - SJU San Juan Luis Munoz Marin Intl
SANSJU
San Diego
Sun 10/4
9:25 pm-11:31 am
2 stops11h 06m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$137
San DiegoOranjestad
SAN San Diego - AUA Oranjestad Reina Beatrix
SANAUA
San Diego
Tue 10/27
9:25 pm-1:31 pm
1 stop13h 06m
Oranjestad Reina Beatrix
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$203
San DiegoSan Juan
SAN San Diego - SJU San Juan Luis Munoz Marin Intl
SANSJU
San Diego
Sat 9/26
4:23 pm-12:03 pm
2 stops16h 40m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$213
Quickest round-trip
San DiegoSan Juan
SAN San Diego - SJU San Juan Luis Munoz Marin Intl
SANSJU
San Diego
Thu 2/4
9:55 am-10:00 pm
1 stop8h 05m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$213
San DiegoSan Juan
SAN San Diego - SJU San Juan Luis Munoz Marin Intl
SANSJU
San Diego
Wed 2/17
7:00 am-11:55 pm
1 stop12h 55m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$213
San DiegoSan Juan
SAN San Diego - SJU San Juan Luis Munoz Marin Intl
SANSJU
San Diego
Sun 9/27
9:45 pm-11:45 am
1 stop11h 00m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$213
San DiegoSimpson Bay
SAN San Diego - SXM Simpson Bay Princess Juliana
SANSXM
San Diego
Thu 12/31
1:04 pm-12:57 pm
1 stop19h 53m
Simpson Bay Princess Juliana
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$214
San DiegoNassau
SAN San Diego - NAS Nassau Intl
SANNAS
San Diego
Wed 11/11
2:33 pm-11:53 am
1 stop18h 20m
Nassau Intl
Wed 12/31
12:00 am-9:00 pm
Nonstop0h 00m
$220
San DiegoSaint Thomas Island
SAN San Diego - STT Saint Thomas Island Cyril E King
SANSTT
San Diego
Sat 12/5
6:28 pm-12:05 pm
2 stops13h 37m
Saint Thomas Island Cyril E King
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$221
San DiegoSaint Thomas Island
SAN San Diego - STT Saint Thomas Island Cyril E King
SANSTT
San Diego
Sat 10/24
10:30 pm-1:31 pm
1 stop12h 01m
Saint Thomas Island Cyril E King
Wed 12/31
12:00 am-8:00 pm
Nonstop0h 00m
$221
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-SJU
SAN-STT
SAN-CUR
SAN-NAS
SAN-SDQ
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-SJU
SAN-STT
SAN-CUR
SAN-NAS
What is the cheapest month to book a flight from San Diego to Caribbean Islands?
Currently, May is the cheapest month in which you can book a flight from San Diego to Caribbean Islands (average of $563). Flying from San Diego to Caribbean Islands in December is currently the most expensive (average of $833). 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.
How far ahead should I book a flight from San Diego to Caribbean Islands?
To ensure you get the cheapest price possible for a flight from San Diego to Caribbean Islands, you should look to book at least 12 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.
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 September 8, 2026.
Peruse reviews from past customers who have flown with Southwest,Delta, andCopa 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.
Crew
8.6
Entertainment
7.5
Food
7.0
Comfort
8.0
Boarding
8.1
Overall
8.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Crew
8.6
Entertainment
7.5
Food
7.0
Comfort
8.0
Boarding
8.1
Overall
8.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Crew
8.6
Entertainment
7.5
Food
7.0
Comfort
8.0
Boarding
8.1
Overall
8.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Crew
8.6
Entertainment
7.5
Food
7.0
Comfort
8.0
Boarding
8.1
Overall
8.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Crew
8.6
Entertainment
7.5
Food
7.0
Comfort
8.0
Boarding
8.1
Overall
8.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Crew
8.6
Entertainment
7.5
Food
7.0
Comfort
8.0
Boarding
8.1
Overall
8.0
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
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 September 8, 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 8 airlines flying from San Diego to Caribbean Islands
Discover the top 8 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 7,457,451 searches. Data last updated September 8, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$138 | Average$476 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$158 | Average$580 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$189 | Average$506 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$254 | Average$640 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$295 | Average$571 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$316 | Average$677 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$407 | Average$749 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$523 | Average$595 | FlexibilityNo cancel fee | On-time75% |