$178+ Cheap flights from Oakland, CA (OAK) to Caribbean
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/7. Fares are subject to change and may not be available on all flights or dates of travel.
OAK — SJU
Mar 6 — Mar 131
1 adult, Economy
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Find cheap flights from Oakland to Caribbean with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Cheapest flights from Oakland to CaribbeanExplore the most affordable flight options available from Oakland to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 4, 2026.
Explore the most affordable flight options available from Oakland to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 4, 2026.
This Southwest deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/266:15 am
OAK
- SJU
2 stops11h 50m
Southwest
Tue 9/16:00 am
SJU
- OAK
2 stops17h 00m
Southwest
Deal found 2/2![Southwest logo]()
$381
This Southwest deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/246:05 am
OAK
- SJU
2 stops15h 40m
Southwest
Mon 6/2910:20 pm
SJU
- OAK
2 stops15h 05m
Southwest
Deal found 2/2![Southwest logo]()
$461
This Southwest deal was found by Cheapflights users on 2/3. 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.
Fri 5/811:55 pm
OAK
- SJU
1 stop10h 25m
Southwest
Mon 5/112:00 pm
SJU
- OAK
2 stops13h 25m
Southwest
Deal found 2/3![Southwest logo]()
$481
This Southwest deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/87:35 pm
OAK
- SJU
2 stops10h 50m
Southwest
Wed 3/1110:10 am
SJU
- OAK
2 stops14h 35m
Southwest
Deal found 2/2![Southwest logo]()
$511
This Southwest deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/111:55 pm
OAK
- SJU
1 stop10h 25m
Southwest
Sat 5/99:40 am
SJU
- OAK
2 stops12h 20m
Southwest
Deal found 2/2![Southwest logo]()
$528
This Southwest deal was found by Cheapflights users on 2/3. 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.
Tue 4/79:20 pm
OAK
- SJU
2 stops10h 15m
Southwest
Mon 4/132:00 pm
SJU
- OAK
2 stops11h 30m
Southwest
Deal found 2/3![Southwest logo]()
$556
This Southwest deal was found by Cheapflights users on 2/3. 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.
Wed 5/1311:55 pm
OAK
- PUJ
2 stops12h 05m
Southwest
Mon 5/181:40 pm
PUJ
- OAK
2 stops20h 55m
Southwest
Deal found 2/3![Southwest logo]()
$566
This Delta deal was found by Cheapflights users on 2/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/175:55 am
OAK
- PUJ
2 stops29h 30m
Delta
Tue 3/245:05 pm
PUJ
- OAK
2 stops21h 46m
Delta
Deal found 2/3![Delta logo]()
$581
This Southwest deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/276:25 pm
OAK
- MBJ
2 stops14h 20m
Southwest
Fri 7/3111:45 am
MBJ
- OAK
2 stops14h 00m
Southwest
Deal found 2/2![Southwest logo]()
$596
This Southwest deal was found by Cheapflights users on 2/3. 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.
Tue 2/176:20 pm
OAK
- PUJ
2 stops15h 20m
Southwest
Fri 2/202:25 pm
PUJ
- OAK
2 stops20h 10m
Southwest
Deal found 2/3![Southwest logo]()
$597
This Southwest deal was found by Cheapflights users on 2/3. 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.
Fri 8/146:15 am
OAK
- SJU
2 stops10h 50m
Southwest
Sun 8/161:50 pm
SJU
- OAK
2 stops12h 15m
Southwest
Deal found 2/3![Southwest logo]()
$611
This Delta deal was found by Cheapflights users on 2/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/175:55 am
OAK
- PUJ
2 stops29h 30m
Delta
Mon 3/233:18 pm
PUJ
- OAK
2 stops27h 42m
Delta
Deal found 2/3![Delta logo]()
$641
Best flights from Oakland to CaribbeanDiscover carefully curated flight deals from Oakland to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 4, 2026.
Discover carefully curated flight deals from Oakland to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 4, 2026.
This Southwest deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/246:05 am
OAK
- SJU
2 stops15h 40m
Southwest
Mon 6/2910:20 pm
SJU
- OAK
2 stops15h 05m
Southwest
Deal found 2/2![Southwest logo]()
$461
This Delta deal was found by Cheapflights users on 2/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/175:55 am
OAK
- PUJ
2 stops29h 30m
Delta
Tue 3/245:05 pm
PUJ
- OAK
2 stops21h 46m
Delta
Deal found 2/3![Delta logo]()
$581
This Trip.com deal was found by Cheapflights users on 2/3. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/171:25 pm
OAK
- PUJ
3 stops23h 20m
Multiple Airlines
Fri 2/2012:40 pm
PUJ
- OAK
3 stops27h 05m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$783
This Southwest deal was found by Cheapflights users on 2/3. 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.
Fri 5/811:55 pm
OAK
- SJU
1 stop10h 25m
Southwest
Mon 5/112:00 pm
SJU
- OAK
2 stops13h 25m
Southwest
Deal found 2/3![Southwest logo]()
$481
This Southwest deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/87:35 pm
OAK
- SJU
2 stops10h 50m
Southwest
Wed 3/1110:10 am
SJU
- OAK
2 stops14h 35m
Southwest
Deal found 2/2![Southwest logo]()
$511
This Southwest deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/111:55 pm
OAK
- SJU
1 stop10h 25m
Southwest
Sat 5/99:40 am
SJU
- OAK
2 stops12h 20m
Southwest
Deal found 2/2![Southwest logo]()
$528
This Delta deal was found by Cheapflights users on 2/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/175:55 am
OAK
- PUJ
2 stops29h 30m
Delta
Mon 3/233:18 pm
PUJ
- OAK
2 stops27h 42m
Delta
Deal found 2/3![Delta logo]()
$641
This Southwest deal was found by Cheapflights users on 2/3. 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.
Wed 5/1311:55 pm
OAK
- PUJ
2 stops12h 05m
Southwest
Mon 5/181:40 pm
PUJ
- OAK
2 stops20h 55m
Southwest
Deal found 2/3![Southwest logo]()
$566
This Mytrip deal was found by Cheapflights users on 2/3. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/239:17 pm
OAK
- SDQ
2 stops23h 28m
Multiple Airlines
Tue 3/312:20 pm
SDQ
- OAK
2 stops34h 36m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$841
This Southwest deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/276:25 pm
OAK
- MBJ
2 stops14h 20m
Southwest
Fri 7/3111:45 am
MBJ
- OAK
2 stops14h 00m
Southwest
Deal found 2/2![Southwest logo]()
$596
This Southwest deal was found by Cheapflights users on 2/3. 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.
Thu 6/47:40 pm
OAK
- PUJ
2 stops13h 45m
Southwest
Wed 6/101:45 pm
PUJ
- OAK
2 stops19h 45m
Southwest
Deal found 2/3![Southwest logo]()
$597
This Delta deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/412:35 pm
OAK
- MBJ
2 stops22h 07m
Delta
Fri 4/102:42 pm
MBJ
- OAK
2 stops33h 01m
Delta
Deal found 2/2![Delta logo]()
$943
This Southwest deal was found by Cheapflights users on 2/3. 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.
Tue 2/176:20 pm
OAK
- PUJ
2 stops15h 20m
Southwest
Fri 2/202:25 pm
PUJ
- OAK
2 stops20h 10m
Southwest
Deal found 2/3![Southwest logo]()
$597
This Mytrip deal was found by Cheapflights users on 2/4. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/1512:30 pm
OAK
- SDQ
3 stops20h 20m
Multiple Airlines
Sat 7/186:50 pm
SDQ
- OAK
3 stops29h 21m
Multiple Airlines
Deal found 2/4![Multiple Airlines logo]()
$974
This Delta deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/412:35 pm
OAK
- MBJ
2 stops22h 07m
Delta
Sun 4/122:25 pm
MBJ
- OAK
2 stops23h 28m
Delta
Deal found 2/2![Delta logo]()
$966
This Southwest deal was found by Cheapflights users on 2/3. 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.
Wed 6/247:40 pm
OAK
- PUJ
2 stops13h 45m
Southwest
Sun 6/283:25 pm
PUJ
- OAK
2 stops18h 05m
Southwest
Deal found 2/3![Southwest logo]()
$641
This Delta deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/91:15 pm
OAK
- NAS
2 stops21h 28m
Delta
Tue 7/143:10 pm
NAS
- OAK
2 stops11h 39m
Delta
Deal found 2/2![Delta logo]()
$987
This Mytrip deal was found by Cheapflights users on 2/3. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/88:22 pm
OAK
- MBJ
3 stops35h 53m
Multiple Airlines
Sun 4/125:40 pm
MBJ
- OAK
2 stops30h 04m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$1,131
This Southwest deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/117:40 pm
OAK
- PUJ
2 stops13h 45m
Southwest
Mon 6/153:30 pm
PUJ
- OAK
2 stops18h 25m
Southwest
Deal found 2/2![Southwest logo]()
$665
This Delta deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/264:59 pm
OAK
- STT
2 stops16h 23m
Delta
Mon 3/21:50 pm
STT
- OAK
2 stops14h 01m
Delta
Deal found 2/2![Delta logo]()
$1,013
This Mytrip deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/2011:07 pm
OAK
- NAS
3 stops15h 33m
Multiple Airlines
Fri 3/275:30 pm
NAS
- OAK
2 stops29h 26m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$1,149
This Southwest deal was found by Cheapflights users on 2/4. 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 4/165:55 am
OAK
- SJU
2 stops11h 05m
Southwest
Mon 4/202:00 pm
SJU
- OAK
2 stops11h 30m
Southwest
Deal found 2/4![Southwest logo]()
$676
This Mytrip deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/1011:07 pm
OAK
- KIN
3 stops31h 46m
Multiple Airlines
Fri 3/131:55 pm
KIN
- OAK
3 stops30h 43m
Multiple Airlines
Deal found 2/2![Multiple Airlines logo]()
$1,203
This Southwest deal was found by Cheapflights users on 2/3. 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 4/1111:55 pm
OAK
- NAS
2 stops10h 25m
Southwest
Wed 4/152:10 pm
NAS
- OAK
2 stops10h 55m
Southwest
Deal found 2/3![Southwest logo]()
$697
This Delta deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/105:55 am
OAK
- KIN
2 stops12h 05m
Delta
Fri 3/139:00 am
KIN
- OAK
2 stops16h 46m
Delta
Deal found 2/2![Delta logo]()
$1,143
This Southwest deal was found by Cheapflights users on 2/3. 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.
Mon 3/25:55 pm
OAK
- PUJ
2 stops16h 35m
Southwest
Thu 3/121:25 pm
PUJ
- OAK
2 stops20h 55m
Southwest
Deal found 2/3![Southwest logo]()
$711
This Delta deal was found by Cheapflights users on 2/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/36:00 am
OAK
- KIN
2 stops12h 05m
Delta
Sun 6/79:00 am
KIN
- OAK
2 stops16h 49m
Delta
Deal found 2/3![Delta logo]()
$1,149
This Delta deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/275:55 am
OAK
- KIN
2 stops11h 05m
Delta
Wed 3/49:00 am
KIN
- OAK
2 stops17h 51m
Delta
Deal found 2/2![Delta logo]()
$1,168
This Southwest deal was found by Cheapflights users on 2/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/226:05 am
OAK
- SJU
2 stops10h 55m
Southwest
Mon 5/256:50 am
SJU
- OAK
2 stops14h 30m
Southwest
Deal found 2/1![Southwest logo]()
$749
This Southwest deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/138:30 pm
OAK
- SJU
2 stops10h 20m
Southwest
Fri 3/205:30 am
SJU
- OAK
2 stops11h 50m
Southwest
Deal found 2/2![Southwest logo]()
$749
Last-minute flights from Oakland to CaribbeanDiscover last-minute flight deals from Oakland to Caribbean. Data last updated February 4, 2026 and is based on user searches.
Discover last-minute flight deals from Oakland to Caribbean. Data last updated February 4, 2026 and is based on user searches.
This Southwest deal was found by Cheapflights users on 2/3. 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.
Tue 2/176:20 pm
OAK
- PUJ
2 stops15h 20m
Southwest
Fri 2/202:25 pm
PUJ
- OAK
2 stops20h 10m
Southwest
Deal found 2/3![Southwest logo]()
$597
This Trip.com deal was found by Cheapflights users on 2/3. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/171:25 pm
OAK
- PUJ
3 stops23h 20m
Multiple Airlines
Fri 2/2012:40 pm
PUJ
- OAK
3 stops27h 05m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$783
This Southwest deal was found by Cheapflights users on 2/4. 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.
Fri 2/208:25 pm
OAK
- SJU
2 stops16h 50m
Southwest
Mon 2/236:10 am
SJU
- OAK
2 stops19h 15m
Southwest
Deal found 2/4![Southwest logo]()
$691
This Southwest deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/208:25 pm
OAK
- SJU
2 stops16h 50m
Southwest
Sun 3/17:00 am
SJU
- OAK
2 stops15h 15m
Southwest
Deal found 2/2![Southwest logo]()
$821
This Southwest deal was found by Cheapflights users on 2/3. 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.
Mon 3/25:55 pm
OAK
- PUJ
2 stops16h 35m
Southwest
Thu 3/122:40 pm
PUJ
- OAK
1 stop12h 30m
Southwest
Deal found 2/3![Southwest logo]()
$711
This Mytrip deal was found by Cheapflights users on 2/3. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/211:17 pm
OAK
- PUJ
3 stops32h 13m
Multiple Airlines
Thu 3/129:09 am
PUJ
- OAK
2 stops16h 10m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$815
This Southwest deal was found by Cheapflights users on 2/3. 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.
Fri 3/68:30 pm
OAK
- SJU
2 stops10h 20m
Southwest
Sun 3/85:30 am
SJU
- OAK
2 stops11h 55m
Southwest
Deal found 2/3![Southwest logo]()
$786
This Southwest deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/87:35 pm
OAK
- SJU
2 stops10h 50m
Southwest
Wed 3/1110:10 am
SJU
- OAK
2 stops14h 35m
Southwest
Deal found 2/2![Southwest logo]()
$511
This Southwest deal was found by Cheapflights users on 2/3. 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.
Fri 3/138:30 pm
OAK
- SJU
2 stops10h 20m
Southwest
Tue 3/1710:10 am
SJU
- OAK
2 stops14h 35m
Southwest
Deal found 2/3![Southwest logo]()
$661
This Southwest deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/138:30 pm
OAK
- SJU
2 stops10h 20m
Southwest
Fri 3/205:30 am
SJU
- OAK
2 stops11h 50m
Southwest
Deal found 2/2![Southwest logo]()
$749
This Delta deal was found by Cheapflights users on 2/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/175:55 am
OAK
- PUJ
2 stops29h 30m
Delta
Tue 3/245:05 pm
PUJ
- OAK
2 stops21h 46m
Delta
Deal found 2/3![Delta logo]()
$581
This Delta deal was found by Cheapflights users on 2/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/175:55 am
OAK
- PUJ
2 stops29h 30m
Delta
Mon 3/233:18 pm
PUJ
- OAK
2 stops27h 42m
Delta
Deal found 2/3![Delta logo]()
$641
One-way flights from Oakland to CaribbeanSearch for one-way flight options from Oakland to Caribbean. Find affordable one-way fares based on user searches. Data last updated February 4, 2026.
Search for one-way flight options from Oakland to Caribbean. Find affordable one-way fares based on user searches. Data last updated February 4, 2026.
This Southwest deal was found by Cheapflights users on 2/3. 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.
Tue 4/79:05 pm
OAK
- SJU
2 stops10h 30m
Southwest
Deal found 2/3![Southwest logo]()
$178
This Southwest deal was found by Cheapflights users on 2/3. 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.
Wed 4/157:35 pm
OAK
- SJU
2 stops10h 35m
Southwest
Deal found 2/3![Southwest logo]()
$258
This Delta deal was found by Cheapflights users on 2/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/1812:40 pm
OAK
- PUJ
2 stops20h 27m
Delta
Deal found 2/3![Delta logo]()
$263
This Southwest deal was found by Cheapflights users on 2/3. 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 4/49:05 pm
OAK
- PLS
2 stops14h 00m
Southwest
Deal found 2/3![Southwest logo]()
$286
This Mytrip deal was found by Cheapflights users on 2/3. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/1711:17 pm
OAK
- PUJ
2 stops21h 37m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$295
This Kiwi.com deal was found by Cheapflights users on 2/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/156:40 pm
OAK
- SJU
3 stops48h 05m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$328
This Delta deal was found by Cheapflights users on 2/3. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/65:55 am
OAK
- PLS
2 stops27h 55m
Delta
Deal found 2/3![Delta logo]()
$333
This Southwest deal was found by Cheapflights users on 2/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/1210:55 am
OAK
- SJU
2 stops10h 40m
Southwest
Deal found 2/2![Southwest logo]()
$350
This Kiwi.com deal was found by Cheapflights users on 2/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/185:31 pm
OAK
- PUJ
3 stops19h 05m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$400
This Kiwi.com deal was found by Cheapflights users on 2/3. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/209:27 am
OAK
- NAS
3 stops28h 26m
Multiple Airlines
Deal found 2/3![Multiple Airlines logo]()
$400
This Alaska Airlines deal was found by Cheapflights users on 2/3. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/13:18 pm
OAK
- SJU
2 stops28h 44m
Alaska Airlines
Deal found 2/3![Alaska Airlines logo]()
$414
This Alaska Airlines deal was found by Cheapflights users on 2/3. 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/92:09 pm
OAK
- SJU
2 stops21h 33m
Alaska Airlines
Deal found 2/3![Alaska Airlines logo]()
$419
Find flight deals from Oakland to Caribbean
Keep the following information in mind while searching for Oakland to Caribbean flight deals. Data was last updated February 4, 2026.
Round-trip from | $461 (Southwest) |
|---|---|
One-way from | $178 (Southwest) |
Popular in | December |
Cheapest in | May |
Average price | $474 |
Cheapflights Fare Finder
Customize your flight search to find flights from Oakland to Caribbean that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 4, 2026.
Use the filters below to find and compare flights from Oakland to Caribbean that are best for you.
Fly from
Oakland
Fly to
Caribbean
Route
Depart
Return
Price
OaklandSan Juan
OAK - SJU
OAKSJU
Oakland
Wed 6/24
6:05 am-12:45 am
2 stops15h 40m
San Juan Luis Munoz Marin Intl
Mon 6/29
10:20 pm-10:25 am
2 stops15h 05m
$461
OaklandSan Juan
OAK - SJU
OAKSJU
Oakland
Fri 5/8
11:55 pm-1:20 pm
1 stop10h 25m
San Juan Luis Munoz Marin Intl
Mon 5/11
2:00 pm-12:25 am
2 stops13h 25m
$481
OaklandSan Juan
OAK - SJU
OAKSJU
Oakland
Sun 3/8
7:35 pm-9:25 am
2 stops10h 50m
San Juan Luis Munoz Marin Intl
Wed 3/11
10:10 am-9:45 pm
2 stops14h 35m
$511
OaklandSan Juan
OAK - SJU
OAKSJU
Oakland
Fri 5/1
11:55 pm-1:20 pm
1 stop10h 25m
San Juan Luis Munoz Marin Intl
Sat 5/9
9:40 am-7:00 pm
2 stops12h 20m
$528
OaklandPunta Cana
OAK - PUJ
OAKPUJ
Oakland
Wed 5/13
11:55 pm-3:00 pm
2 stops12h 05m
Punta Cana
Mon 5/18
1:40 pm-7:35 am
2 stops20h 55m
$566
OaklandPunta Cana
OAK - PUJ
OAKPUJ
Oakland
Tue 3/17
5:55 am-2:25 pm
2 stops29h 30m
Punta Cana
Tue 3/24
5:05 pm-11:51 am
2 stops21h 46m
$581
OaklandMontego Bay
OAK - MBJ
OAKMBJ
Oakland
Mon 7/27
6:25 pm-10:45 am
2 stops14h 20m
Montego Bay Sangster Intl
Fri 7/31
11:45 am-11:45 pm
2 stops14h 00m
$596
OaklandPunta Cana
OAK - PUJ
OAKPUJ
Oakland
Thu 6/4
7:40 pm-12:25 pm
2 stops13h 45m
Punta Cana
Wed 6/10
1:45 pm-6:30 am
2 stops19h 45m
$597
OaklandPunta Cana
OAK - PUJ
OAKPUJ
Oakland
Tue 2/17
6:20 pm-1:40 pm
2 stops15h 20m
Punta Cana
Fri 2/20
2:25 pm-6:35 am
2 stops20h 10m
$597
OaklandPunta Cana
OAK - PUJ
OAKPUJ
Oakland
Tue 3/17
5:55 am-2:25 pm
2 stops29h 30m
Punta Cana
Mon 3/23
3:18 pm-4:00 pm
2 stops27h 42m
$641
Showing 1-10 of 54 results
Best time to book a flight from Oakland to Caribbean
Have a flexible travel schedule? Discover the best time to fly to Caribbean from Oakland with our price prediction graph.
OAK-SJU
OAK-PUJ
OAK-MBJ
OAK-PLS
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
OAK-0CB
OAK-SJU
OAK-PUJ
OAK-MBJ
OAK-PLS
What is the cheapest month to book a flight from Oakland, California to Caribbean?
Currently, January is the cheapest month in which you can book a flight from Oakland, California to Caribbean (average of $169). Flying from Oakland, California to Caribbean in June is currently the most expensive (average of $296). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
Reviews of airlines servicing Caribbean
Get insights into the airlines that provide service to Caribbean. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean. Reviews last updated February 4, 2026.
Get a feel of what it's like to fly with Southwest from Oakland to Caribbean by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
7.0
Comfort
8.0
Crew
8.6
Overall
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Food
7.0
Comfort
8.0
Crew
8.6
Overall
8.0
Boarding
8.1
Entertainment
7.5
Reviews
1 / 20
10.0
ExcellentWilliam Drew,Nov 2025
SJC - HNL
Related info for your journey
Find useful and relevant information for your journey from Oakland to Caribbean. 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 Oakland to Caribbean
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Caribbean by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Oakland to Caribbean by cabin class
Find flights from Oakland to Caribbean, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Oakland and Caribbean flights
Browse other Oakland and Caribbean flight options. Last updated on February 4, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Fly to Caribbean countries
Consider these flights traveling to countries located in Caribbean.
Oakland to Caribbean flights
Consider these flights traveling from Oakland to Caribbean.
Top airline flying from Oakland to Caribbean
Discover the top airline that operate flights from Oakland to Caribbean. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$410 | Average$579 | FlexibilityNo cancel fee | On-time63% |