$248+ Cheap flights from Oakland, CA (OAK) 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 4/24. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — SJU
Mar 18 — Mar 251
1 adult, Economy
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Find cheap flights from Oakland 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 Oakland to Caribbean IslandsExplore the most affordable flight options available from Oakland to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 16, 2026.
Explore the most affordable flight options available from Oakland to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 16, 2026.
This Southwest deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” 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 5/27:35 pm
OAK
- SJU
2 stops10h 30m
Southwest
Wed 5/68:10 am
SJU
- OAK
2 stops13h 55m
Southwest
Deal found 2/13![Southwest logo]()
$391
This Southwest deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” 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 6/1710:25 am
OAK
- SJU
2 stops10h 50m
Southwest
Wed 6/2411:15 am
SJU
- OAK
2 stops12h 00m
Southwest
Deal found 2/12![Southwest logo]()
$416
This Southwest deal was found by Cheapflights users on 2/14. Clicking the “Pick Dates” 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 4/127:35 pm
OAK
- SJU
2 stops10h 35m
Southwest
Tue 4/218:10 am
SJU
- OAK
2 stops13h 40m
Southwest
Deal found 2/14![Southwest logo]()
$419
This Southwest deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” 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 6/57:40 pm
OAK
- SJU
2 stops11h 50m
Southwest
Thu 6/115:00 am
SJU
- OAK
2 stops11h 30m
Southwest
Deal found 2/15![Southwest logo]()
$438
This Southwest deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” 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 7/289:45 am
OAK
- SJU
2 stops11h 30m
Southwest
Wed 8/55:15 am
SJU
- OAK
2 stops11h 40m
Southwest
Deal found 2/13![Southwest logo]()
$456
This Southwest deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” 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 5/137:35 pm
OAK
- SJU
2 stops10h 35m
Southwest
Wed 5/208:10 am
SJU
- OAK
2 stops13h 55m
Southwest
Deal found 2/12![Southwest logo]()
$463
This Southwest deal was found by Cheapflights users on 2/14. Clicking the “Pick Dates” 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 4/117:35 pm
OAK
- SJU
2 stops10h 30m
Southwest
Tue 4/218:10 am
SJU
- OAK
2 stops13h 55m
Southwest
Deal found 2/14![Southwest logo]()
$484
This Southwest deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” 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 7/27:50 am
OAK
- SJU
2 stops13h 35m
Southwest
Wed 7/81:30 pm
SJU
- OAK
2 stops12h 00m
Southwest
Deal found 2/12![Southwest logo]()
$491
This Southwest deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” 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 2/286:25 pm
OAK
- SJU
2 stops11h 30m
Southwest
Wed 3/410:20 am
SJU
- OAK
2 stops13h 30m
Southwest
Deal found 2/13![Southwest logo]()
$500
This Southwest deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” 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 3/237:35 pm
OAK
- SJU
2 stops10h 45m
Southwest
Thu 3/261:05 pm
SJU
- OAK
2 stops12h 15m
Southwest
Deal found 2/12![Southwest logo]()
$503
This Southwest deal was found by Cheapflights users on 2/14. Clicking the “Pick Dates” 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 5/1511:55 pm
OAK
- SJU
1 stop10h 25m
Southwest
Tue 5/2611:25 am
SJU
- OAK
2 stops13h 30m
Southwest
Deal found 2/14![Southwest logo]()
$531
This Delta deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” 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 10/245:05 pm
OAK
- NAS
2 stops15h 46m
Delta
Sat 10/313:15 pm
NAS
- OAK
2 stops11h 41m
Delta
Deal found 2/13![Delta logo]()
$536
Best flights from Oakland to Caribbean IslandsDiscover carefully curated flight deals from Oakland to Caribbean Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 16, 2026.
Discover carefully curated flight deals from Oakland to Caribbean Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 16, 2026.
This Southwest deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” 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 6/1710:25 am
OAK
- SJU
2 stops10h 50m
Southwest
Wed 6/246:30 am
SJU
- OAK
1 stop10h 20m
Southwest
Deal found 2/12![Southwest logo]()
$416
This Mytrip deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/17:16 pm
OAK
- PUJ
2 stops24h 08m
Multiple Airlines
Sat 3/79:34 am
PUJ
- OAK
2 stops15h 56m
Multiple Airlines
Deal found 2/13![Multiple Airlines logo]()
$693
This Delta deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” 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 3/25:55 am
OAK
- MBJ
2 stops26h 15m
Delta
Sat 3/74:44 pm
MBJ
- OAK
2 stops21h 07m
Delta
Deal found 2/13![Delta logo]()
$723
This Southwest deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” 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 5/137:35 pm
OAK
- SJU
2 stops10h 35m
Southwest
Wed 5/208:10 am
SJU
- OAK
2 stops13h 55m
Southwest
Deal found 2/12![Southwest logo]()
$463
This Southwest deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” 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 8/37:50 am
OAK
- SJU
2 stops13h 35m
Southwest
Sat 8/155:05 am
SJU
- OAK
2 stops11h 35m
Southwest
Deal found 2/12![Southwest logo]()
$463
This Southwest deal was found by Cheapflights users on 2/14. Clicking the “Pick Dates” 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 4/117:35 pm
OAK
- SJU
2 stops10h 30m
Southwest
Tue 4/218:10 am
SJU
- OAK
2 stops13h 55m
Southwest
Deal found 2/14![Southwest logo]()
$484
This Southwest deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” 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 7/27:50 am
OAK
- SJU
2 stops13h 35m
Southwest
Wed 7/81:30 pm
SJU
- OAK
2 stops12h 00m
Southwest
Deal found 2/12![Southwest logo]()
$491
This Mytrip deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/27:16 pm
OAK
- PUJ
2 stops18h 50m
Multiple Airlines
Sat 3/79:34 am
PUJ
- OAK
2 stops15h 56m
Multiple Airlines
Deal found 2/13![Multiple Airlines logo]()
$700
This Delta deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” 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 2/285:55 am
OAK
- MBJ
2 stops26h 15m
Delta
Sat 3/74:44 pm
MBJ
- OAK
2 stops21h 07m
Delta
Deal found 2/13![Delta logo]()
$723
This Southwest deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” 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 3/110:35 am
OAK
- SJU
2 stops11h 00m
Southwest
Wed 3/410:20 am
SJU
- OAK
2 stops13h 30m
Southwest
Deal found 2/15![Southwest logo]()
$500
This Southwest deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” 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 3/237:35 pm
OAK
- SJU
2 stops10h 45m
Southwest
Thu 3/261:05 pm
SJU
- OAK
2 stops12h 15m
Southwest
Deal found 2/12![Southwest logo]()
$503
This Mytrip deal was found by Cheapflights users on 2/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/289:17 pm
OAK
- PUJ
2 stops35h 18m
Multiple Airlines
Sat 3/79:34 am
PUJ
- OAK
2 stops15h 56m
Multiple Airlines
Deal found 2/14![Multiple Airlines logo]()
$742
This Delta deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” 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 3/295:55 am
OAK
- AUA
2 stops27h 00m
Delta
Mon 4/63:35 pm
AUA
- OAK
2 stops27h 25m
Delta
Deal found 2/13![Delta logo]()
$794
This Southwest deal was found by Cheapflights users on 2/14. Clicking the “Pick Dates” 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 5/1511:55 pm
OAK
- SJU
1 stop10h 25m
Southwest
Tue 5/2611:25 am
SJU
- OAK
2 stops13h 30m
Southwest
Deal found 2/14![Southwest logo]()
$531
This Mytrip deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/111:30 pm
OAK
- PUJ
2 stops14h 11m
Multiple Airlines
Mon 5/42:40 pm
PUJ
- OAK
3 stops24h 12m
Multiple Airlines
Deal found 2/13![Multiple Airlines logo]()
$804
This Delta deal was found by Cheapflights users on 2/16. Clicking the “Pick Dates” 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 5/186:00 am
OAK
- MBJ
2 stops27h 37m
Delta
Tue 5/261:05 pm
MBJ
- OAK
2 stops29h 21m
Delta
Deal found 2/16![Delta logo]()
$847
This Southwest deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” 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 5/1511:55 pm
OAK
- SJU
1 stop10h 25m
Southwest
Fri 5/222:00 pm
SJU
- OAK
2 stops11h 30m
Southwest
Deal found 2/15![Southwest logo]()
$531
This Delta deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” 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 3/174:49 pm
OAK
- AUA
2 stops16h 06m
Delta
Tue 3/241:10 pm
AUA
- OAK
2 stops13h 36m
Delta
Deal found 2/15![Delta logo]()
$860
This Southwest deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” 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 3/26:30 am
OAK
- SJU
2 stops14h 10m
Southwest
Fri 3/66:30 am
SJU
- OAK
2 stops11h 50m
Southwest
Deal found 2/15![Southwest logo]()
$540
This Mytrip deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/281:22 pm
OAK
- SDQ
3 stops19h 28m
Multiple Airlines
Tue 8/116:00 pm
SDQ
- OAK
2 stops30h 44m
Multiple Airlines
Deal found 2/15![Multiple Airlines logo]()
$945
This Delta deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” 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 3/2512:35 pm
OAK
- AUA
2 stops19h 45m
Delta
Mon 4/63:35 pm
AUA
- OAK
2 stops27h 25m
Delta
Deal found 2/13![Delta logo]()
$881
This Southwest deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” 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 5/111:55 pm
OAK
- PUJ
1 stop12h 05m
Southwest
Mon 5/41:40 pm
PUJ
- OAK
2 stops21h 00m
Southwest
Deal found 2/13![Southwest logo]()
$571
This Southwest deal was found by Cheapflights users on 2/16. Clicking the “Pick Dates” 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 3/107:35 pm
OAK
- MBJ
2 stops14h 20m
Southwest
Tue 3/311:00 pm
MBJ
- OAK
2 stops20h 20m
Southwest
Deal found 2/16![Southwest logo]()
$590
This Delta deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/91:15 pm
OAK
- NAS
2 stops21h 28m
Delta
Tue 7/143:10 pm
NAS
- OAK
2 stops11h 39m
Delta
Deal found 2/13![Delta logo]()
$969
This Mytrip deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/311:16 pm
OAK
- NAS
2 stops15h 24m
Multiple Airlines
Fri 4/107:15 am
NAS
- OAK
3 stops16h 45m
Multiple Airlines
Deal found 2/13![Multiple Airlines logo]()
$1,144
This Southwest deal was found by Cheapflights users on 2/14. Clicking the “Pick Dates” 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 4/117:35 pm
OAK
- STT
2 stops14h 35m
Southwest
Mon 4/202:30 pm
STT
- OAK
2 stops12h 25m
Southwest
Deal found 2/14![Southwest logo]()
$613
This Delta deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” 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 3/2812:35 pm
OAK
- AUA
2 stops19h 35m
Delta
Mon 4/63:35 pm
AUA
- OAK
2 stops23h 16m
Delta
Deal found 2/13![Delta logo]()
$1,008
This Southwest deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” 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 5/2311:55 pm
OAK
- MBJ
2 stops12h 25m
Southwest
Tue 5/2612:15 pm
MBJ
- OAK
2 stops12h 20m
Southwest
Deal found 2/13![Southwest logo]()
$614
This Delta deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” 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 3/295:55 am
OAK
- AUA
2 stops27h 00m
Delta
Thu 4/212:25 pm
AUA
- OAK
2 stops26h 26m
Delta
Deal found 2/13![Delta logo]()
$1,028
This Southwest deal was found by Cheapflights users on 2/16. Clicking the “Pick Dates” 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 7/147:40 pm
OAK
- NAS
2 stops14h 35m
Southwest
Sat 7/182:20 pm
NAS
- OAK
2 stops12h 00m
Southwest
Deal found 2/16![Southwest logo]()
$621
Last-minute flights from Oakland to Caribbean IslandsDiscover last-minute flight deals from Oakland to Caribbean Islands. Data last updated February 16, 2026 and is based on user searches.
Discover last-minute flight deals from Oakland to Caribbean Islands. Data last updated February 16, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” 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 2/167:50 pm
OAK
- SJU
2 stops10h 40m
Southwest
Wed 2/185:40 am
SJU
- OAK
2 stops13h 15m
Southwest
Deal found 2/12![Southwest logo]()
$547
This Southwest deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” 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 2/286:25 pm
OAK
- SJU
2 stops11h 30m
Southwest
Wed 3/410:20 am
SJU
- OAK
2 stops13h 30m
Southwest
Deal found 2/13![Southwest logo]()
$500
This Mytrip deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/17:16 pm
OAK
- PUJ
2 stops24h 08m
Multiple Airlines
Sat 3/79:34 am
PUJ
- OAK
2 stops15h 56m
Multiple Airlines
Deal found 2/13![Multiple Airlines logo]()
$693
This Southwest deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” 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 3/16:55 pm
OAK
- MBJ
2 stops14h 35m
Southwest
Sat 3/71:00 pm
MBJ
- OAK
2 stops12h 35m
Southwest
Deal found 2/13![Southwest logo]()
$693
This Southwest deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” 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 3/26:30 am
OAK
- SJU
2 stops14h 10m
Southwest
Fri 3/66:30 am
SJU
- OAK
2 stops11h 50m
Southwest
Deal found 2/15![Southwest logo]()
$540
This Southwest deal was found by Cheapflights users on 2/16. Clicking the “Pick Dates” 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 3/47:25 pm
OAK
- SJU
2 stops11h 00m
Southwest
Mon 3/95:30 am
SJU
- OAK
2 stops11h 50m
Southwest
Deal found 2/16![Southwest logo]()
$628
This Southwest deal was found by Cheapflights users on 2/16. Clicking the “Pick Dates” 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 3/107:35 pm
OAK
- MBJ
2 stops14h 20m
Southwest
Tue 3/311:00 pm
MBJ
- OAK
2 stops20h 20m
Southwest
Deal found 2/16![Southwest logo]()
$590
This Southwest deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” 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 3/148:55 pm
OAK
- SJU
2 stops11h 30m
Southwest
Thu 3/195:30 am
SJU
- OAK
2 stops11h 50m
Southwest
Deal found 2/15![Southwest logo]()
$656
This Southwest deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” 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 3/237:35 pm
OAK
- SJU
2 stops10h 45m
Southwest
Thu 3/261:05 pm
SJU
- OAK
2 stops12h 15m
Southwest
Deal found 2/12![Southwest logo]()
$503
This Southwest deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” 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 3/237:35 pm
OAK
- SJU
2 stops10h 45m
Southwest
Tue 3/3110:10 am
SJU
- OAK
2 stops14h 35m
Southwest
Deal found 2/15![Southwest logo]()
$621
This Southwest deal was found by Cheapflights users on 2/14. Clicking the “Pick Dates” 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 3/288:10 pm
OAK
- SJU
2 stops12h 15m
Southwest
Wed 4/811:25 am
SJU
- OAK
2 stops13h 40m
Southwest
Deal found 2/14![Southwest logo]()
$581
This Southwest deal was found by Cheapflights users on 2/14. Clicking the “Pick Dates” 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 3/297:35 pm
OAK
- SJU
2 stops10h 40m
Southwest
Sat 4/46:00 am
SJU
- OAK
2 stops13h 40m
Southwest
Deal found 2/14![Southwest logo]()
$531
One-way flights from Oakland to Caribbean IslandsSearch for one-way flight options from Oakland to Caribbean Islands. Find affordable one-way fares based on user searches. Data last updated February 16, 2026.
Search for one-way flight options from Oakland to Caribbean Islands. Find affordable one-way fares based on user searches. Data last updated February 16, 2026.
This Southwest deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” 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 4/2411:55 pm
OAK
- SJU
1 stop10h 25m
Southwest
Deal found 2/13![Southwest logo]()
$248
This Southwest deal was found by Cheapflights users on 2/16. Clicking the “Pick Dates” 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 5/1511:55 pm
OAK
- MBJ
1 stop11h 50m
Southwest
Deal found 2/16![Southwest logo]()
$305
This Southwest deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” 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 5/307:35 pm
OAK
- PUJ
2 stops14h 10m
Southwest
Deal found 2/15![Southwest logo]()
$312
This Kiwi.com deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” 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 3/156:15 am
OAK
- SDQ
2 stops30h 53m
Multiple Airlines
Deal found 2/13![Multiple Airlines logo]()
$331
This Southwest deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” 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 3/149:05 pm
OAK
- SJU
2 stops11h 20m
Southwest
Deal found 2/13![Southwest logo]()
$333
This Trip.com deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” 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.
Sat 5/3011:30 pm
OAK
- PUJ
1 stop14h 30m
Multiple Airlines
Deal found 2/15![Multiple Airlines logo]()
$348
This Southwest deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” 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 5/237:35 pm
OAK
- NAS
2 stops14h 45m
Southwest
Deal found 2/13![Southwest logo]()
$377
This Kiwi.com deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” 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 4/246:20 am
OAK
- SJU
3 stops28h 48m
Multiple Airlines
Deal found 2/13![Multiple Airlines logo]()
$396
This Delta deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” 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 7/65:05 pm
OAK
- SJU
2 stops17h 20m
Delta
Deal found 2/13![Delta logo]()
$439
This Delta deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” 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 7/35:05 pm
OAK
- SJU
2 stops17h 20m
Delta
Deal found 2/13![Delta logo]()
$464
This Delta deal was found by Cheapflights users on 2/14. Clicking the “Pick Dates” 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 5/305:55 pm
OAK
- PUJ
2 stops15h 23m
Delta
Deal found 2/14![Delta logo]()
$471
This Alaska Airlines deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” 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.
Wed 7/16:30 am
OAK
- SJU
2 stops14h 05m
Alaska Airlines
Deal found 2/13![Alaska Airlines logo]()
$484
Find flight deals from Oakland to Caribbean Islands
Keep the following information in mind while searching for Oakland to Caribbean Islands flight deals. Data was last updated February 16, 2026.
Round-trip from | $391 (Southwest) |
|---|---|
One-way from | $248 (Southwest) |
Popular in | December |
Cheapest in | May |
Average price | $498 |
Cheapflights Fare Finder
Customize your flight search to find flights from Oakland 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 February 16, 2026.
Use the filters below to find and compare flights from Oakland to Caribbean Islands that are best for you.
Fly from
Oakland
Fly to
Caribbean Islands
Route
Depart
Return
Price
OaklandSan Juan
OAK - SJU
OAKSJU
Oakland
Wed 6/17
10:25 am-12:15 am
2 stops10h 50m
San Juan Luis Munoz Marin Intl
Wed 6/24
6:30 am-1:50 pm
1 stop10h 20m
$416
OaklandSan Juan
OAK - SJU
OAKSJU
Oakland
Wed 5/13
7:35 pm-9:10 am
2 stops10h 35m
San Juan Luis Munoz Marin Intl
Wed 5/20
8:10 am-7:05 pm
2 stops13h 55m
$463
OaklandSan Juan
OAK - SJU
OAKSJU
Oakland
Mon 8/3
7:50 am-12:25 am
2 stops13h 35m
San Juan Luis Munoz Marin Intl
Sat 8/15
5:05 am-1:40 pm
2 stops11h 35m
$463
OaklandSan Juan
OAK - SJU
OAKSJU
Oakland
Sat 4/11
7:35 pm-9:05 am
2 stops10h 30m
San Juan Luis Munoz Marin Intl
Tue 4/21
8:10 am-7:05 pm
2 stops13h 55m
$484
OaklandSan Juan
OAK - SJU
OAKSJU
Oakland
Thu 7/2
7:50 am-12:25 am
2 stops13h 35m
San Juan Luis Munoz Marin Intl
Wed 7/8
1:30 pm-10:30 pm
2 stops12h 00m
$491
OaklandSan Juan
OAK - SJU
OAKSJU
Oakland
Sun 3/1
10:35 am-1:35 am
2 stops11h 00m
San Juan Luis Munoz Marin Intl
Wed 3/4
10:20 am-7:50 pm
2 stops13h 30m
$500
OaklandSan Juan
OAK - SJU
OAKSJU
Oakland
Mon 3/23
7:35 pm-9:20 am
2 stops10h 45m
San Juan Luis Munoz Marin Intl
Thu 3/26
1:05 pm-10:20 pm
2 stops12h 15m
$503
OaklandSan Juan
OAK - SJU
OAKSJU
Oakland
Fri 5/15
11:55 pm-1:20 pm
1 stop10h 25m
San Juan Luis Munoz Marin Intl
Tue 5/26
11:25 am-9:55 pm
2 stops13h 30m
$531
OaklandSan Juan
OAK - SJU
OAKSJU
Oakland
Fri 5/15
11:55 pm-1:20 pm
1 stop10h 25m
San Juan Luis Munoz Marin Intl
Fri 5/22
2:00 pm-10:30 pm
2 stops11h 30m
$531
OaklandSan Juan
OAK - SJU
OAKSJU
Oakland
Mon 3/2
6:30 am-12:40 am
2 stops14h 10m
San Juan Luis Munoz Marin Intl
Fri 3/6
6:30 am-2:20 pm
2 stops11h 50m
$540
Showing 1-10 of 57 results
Best time to book a flight from Oakland to Caribbean Islands
Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands from Oakland with our price prediction graph.
OAK-SJU
OAK-SDQ
OAK-MBJ
OAK-PUJ
OAK-NAS
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 Oakland to Caribbean Islands
OAK-zzEPX
OAK-SJU
OAK-SDQ
OAK-MBJ
OAK-PUJ
What is the cheapest month to book a flight from Oakland, California to Caribbean Islands?
Currently, January is the cheapest month in which you can book a flight from Oakland, California to Caribbean Islands (average of $162). Flying from Oakland, California to Caribbean Islands 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.
Related info for your journey
Find useful and relevant information for your journey from Oakland to Caribbean Islands. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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Alternative routes for Oakland 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 Oakland to Caribbean Islands by cabin class
Find flights from Oakland to Caribbean Islands, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Oakland and Caribbean Islands flights
Browse other Oakland and Caribbean Islands flight options. Last updated on February 16, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Oakland to Caribbean Islands flights
Consider these flights traveling from Oakland to Caribbean Islands.
Top airline flying from Oakland to Caribbean Islands
Discover the top airline that operate flights from Oakland 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 February 16, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$385 | Average$558 | FlexibilityNo cancel fee | On-time63% |