$248+ Cheap flights from Caribbean Islands to Oakland, CA (OAK)
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 6/1. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — OAK
Mar 18 — Mar 251
1 adult, Economy
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Find cheap flights from Caribbean Islands to Oakland 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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Caribbean Islands to Oakland
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Best
Last-minute
One-way
Cheapest flights from Caribbean Islands to OaklandExplore the most affordable flight options available from Caribbean Islands to Oakland. 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 Caribbean Islands to Oakland. 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 2/14. 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 5/152:00 pm
SJU
- OAK
2 stops11h 30m
Southwest
Mon 5/258:55 pm
OAK
- SJU
2 stops10h 40m
Southwest
Deal found 2/14![Southwest logo]()
$456
This Alaska Airlines 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/286:45 am
SJU
- OAK
2 stops14h 54m
Alaska Airlines
Wed 4/296:46 am
OAK
- SJU
2 stops13h 16m
Alaska Airlines
Deal found 2/12![Alaska Airlines logo]()
$688
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 3/26:10 am
SJU
- OAK
2 stops19h 15m
Southwest
Fri 3/611:55 pm
OAK
- SJU
1 stop11h 30m
Southwest
Deal found 2/15![Southwest logo]()
$754
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 3/142:35 pm
SJU
- OAK
1 stop12h 45m
Southwest
Sat 3/215:30 am
OAK
- SJU
1 stop8h 20m
Southwest
Deal found 2/14![Southwest logo]()
$771
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/102:35 pm
SJU
- OAK
2 stops12h 14m
Delta
Mon 7/205:05 pm
OAK
- SJU
2 stops17h 20m
Delta
Deal found 2/12![Delta logo]()
$878
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/102:35 pm
SJU
- OAK
2 stops12h 14m
Delta
Fri 7/245:05 pm
OAK
- SJU
2 stops17h 20m
Delta
Deal found 2/12![Delta logo]()
$903
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.
Sun 3/17:00 am
SJU
- OAK
2 stops15h 15m
Southwest
Thu 3/57:35 pm
OAK
- SJU
2 stops10h 50m
Southwest
Deal found 2/12![Southwest logo]()
$912
This Alaska Airlines 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/85:37 am
SJU
- OAK
2 stops20h 08m
Alaska Airlines
Wed 7/226:30 am
OAK
- SJU
2 stops19h 02m
Alaska Airlines
Deal found 2/12![Alaska Airlines logo]()
$945
This Alaska Airlines 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/85:37 am
SJU
- OAK
2 stops20h 08m
Alaska Airlines
Sat 7/256:30 am
OAK
- SJU
2 stops19h 02m
Alaska Airlines
Deal found 2/12![Alaska Airlines logo]()
$956
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.
Sun 3/17:00 am
SJU
- OAK
2 stops15h 15m
Southwest
Fri 3/68:30 pm
OAK
- SJU
2 stops10h 20m
Southwest
Deal found 2/12![Southwest logo]()
$964
Best flights from Caribbean Islands to OaklandDiscover carefully curated flight deals from Caribbean Islands to Oakland 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 Caribbean Islands to Oakland 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 2/14. 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 5/152:00 pm
SJU
- OAK
2 stops11h 30m
Southwest
Mon 5/258:55 pm
OAK
- SJU
2 stops10h 40m
Southwest
Deal found 2/14![Southwest logo]()
$456
This Alaska Airlines 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/286:45 am
SJU
- OAK
2 stops14h 54m
Alaska Airlines
Wed 4/296:46 am
OAK
- SJU
2 stops13h 16m
Alaska Airlines
Deal found 2/12![Alaska Airlines logo]()
$688
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/102:35 pm
SJU
- OAK
2 stops12h 14m
Delta
Tue 7/215:05 pm
OAK
- SJU
2 stops17h 20m
Delta
Deal found 2/12![Delta logo]()
$878
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 3/26:10 am
SJU
- OAK
2 stops19h 15m
Southwest
Fri 3/611:55 pm
OAK
- SJU
1 stop11h 30m
Southwest
Deal found 2/15![Southwest logo]()
$754
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/102:35 pm
SJU
- OAK
2 stops12h 14m
Delta
Mon 7/205:05 pm
OAK
- SJU
2 stops17h 20m
Delta
Deal found 2/12![Delta logo]()
$878
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 3/142:35 pm
SJU
- OAK
2 stops12h 35m
Southwest
Sat 3/215:30 am
OAK
- SJU
1 stop8h 20m
Southwest
Deal found 2/14![Southwest logo]()
$814
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.
Sun 3/17:00 am
SJU
- OAK
2 stops15h 15m
Southwest
Thu 3/57:35 pm
OAK
- SJU
2 stops10h 50m
Southwest
Deal found 2/12![Southwest logo]()
$912
Last-minute flights from Caribbean Islands to OaklandDiscover last-minute flight deals from Caribbean Islands to Oakland. Data last updated February 16, 2026 and is based on user searches.
Discover last-minute flight deals from Caribbean Islands to Oakland. 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.
Sun 3/17:00 am
SJU
- OAK
2 stops15h 15m
Southwest
Thu 3/57:35 pm
OAK
- SJU
2 stops10h 50m
Southwest
Deal found 2/12![Southwest logo]()
$912
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.
Sun 3/17:00 am
SJU
- OAK
2 stops15h 15m
Southwest
Fri 3/68:30 pm
OAK
- SJU
2 stops10h 20m
Southwest
Deal found 2/12![Southwest logo]()
$964
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 3/26:10 am
SJU
- OAK
2 stops19h 15m
Southwest
Fri 3/611:55 pm
OAK
- SJU
1 stop11h 30m
Southwest
Deal found 2/15![Southwest logo]()
$754
This Alaska Airlines 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/37:33 am
SJU
- OAK
2 stops29h 51m
Alaska Airlines
Tue 3/175:31 pm
OAK
- SJU
2 stops17h 38m
Alaska Airlines
Deal found 2/15![Alaska Airlines logo]()
$979
This Alaska Airlines 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/54:10 pm
SJU
- OAK
2 stops35h 44m
Alaska Airlines
Tue 3/175:31 pm
OAK
- SJU
2 stops17h 38m
Alaska Airlines
Deal found 2/15![Alaska Airlines logo]()
$1,016
This Alaska Airlines 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/76:33 am
SJU
- OAK
2 stops29h 41m
Alaska Airlines
Tue 3/175:31 pm
OAK
- SJU
2 stops17h 38m
Alaska Airlines
Deal found 2/15![Alaska Airlines logo]()
$1,002
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.
Tue 3/106:15 am
SJU
- OAK
2 stops12h 45m
Delta
Mon 3/165:55 am
OAK
- SJU
2 stops14h 20m
Delta
Deal found 2/14![Delta logo]()
$1,120
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 3/142:35 pm
SJU
- OAK
1 stop12h 45m
Southwest
Sat 3/215:30 am
OAK
- SJU
1 stop8h 20m
Southwest
Deal found 2/14![Southwest logo]()
$771
This Alaska Airlines 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/175:28 am
SJU
- OAK
2 stops20h 21m
Alaska Airlines
Tue 3/247:00 am
OAK
- SJU
2 stops28h 11m
Alaska Airlines
Deal found 2/14![Alaska Airlines logo]()
$1,059
One-way flights from Caribbean Islands to OaklandSearch for one-way flight options from Caribbean Islands to Oakland. Find affordable one-way fares based on user searches. Data last updated February 16, 2026.
Search for one-way flight options from Caribbean Islands to Oakland. Find affordable one-way fares based on user searches. Data last updated February 16, 2026.
This Southwest deal was found by Cheapflights users on 2/12. 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 6/12:00 pm
SJU
- OAK
2 stops11h 30m
Southwest
Deal found 2/12![Southwest logo]()
$248
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/245:05 pm
PUJ
- OAK
2 stops21h 46m
Delta
Deal found 2/12![Delta logo]()
$330
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.
Tue 3/2410:10 am
SJU
- OAK
2 stops13h 20m
Southwest
Deal found 2/15![Southwest logo]()
$333
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/255:05 pm
PUJ
- OAK
2 stops25h 55m
Delta
Deal found 2/12![Delta logo]()
$335
This Alaska Airlines 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/196:45 am
SJU
- OAK
2 stops19h 52m
Alaska Airlines
Deal found 2/14![Alaska Airlines logo]()
$344
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 3/301:05 pm
SJU
- OAK
2 stops12h 15m
Southwest
Deal found 2/15![Southwest logo]()
$388
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.
Mon 3/235:30 am
SJU
- OAK
2 stops14h 00m
Southwest
Deal found 2/13![Southwest logo]()
$418
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/102:35 pm
SJU
- OAK
2 stops12h 14m
Delta
Deal found 2/12![Delta logo]()
$439
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.
Mon 5/255:05 am
SJU
- OAK
2 stops13h 00m
Southwest
Deal found 2/14![Southwest logo]()
$448
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/233:18 pm
PUJ
- OAK
2 stops27h 42m
Delta
Deal found 2/12![Delta logo]()
$451
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/32:35 pm
SJU
- OAK
2 stops12h 14m
Delta
Deal found 2/12![Delta logo]()
$464
This Alaska Airlines 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 Alaska Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/85:37 am
SJU
- OAK
2 stops20h 08m
Alaska Airlines
Deal found 2/12![Alaska Airlines logo]()
$484
Find flight deals from Caribbean Islands to Oakland
Keep the following information in mind while searching for Caribbean Islands to Oakland flight deals. Data was last updated February 16, 2026.
Round-trip from | $456 (Southwest) |
|---|---|
One-way from | $248 (Southwest) |
Cheapflights Fare Finder
Customize your flight search to find flights from Caribbean Islands to Oakland 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 Caribbean Islands to Oakland that are best for you.
Fly from
Caribbean Islands
Fly to
Oakland
Route
Depart
Return
Price
San JuanOakland
SJU - OAK
SJUOAK
San Juan Luis Munoz Marin Intl
Fri 5/15
2:00 pm-10:30 pm
2 stops11h 30m
Oakland
Mon 5/25
8:55 pm-10:35 am
2 stops10h 40m
$456
San JuanOakland
SJU - OAK
SJUOAK
San Juan Luis Munoz Marin Intl
Tue 4/28
6:45 am-6:39 pm
2 stops14h 54m
Oakland
Wed 4/29
6:46 am-11:02 pm
2 stops13h 16m
$688
San JuanOakland
SJU - OAK
SJUOAK
San Juan Luis Munoz Marin Intl
Mon 3/2
6:10 am-9:25 pm
2 stops19h 15m
Oakland
Fri 3/6
11:55 pm-3:25 pm
1 stop11h 30m
$754
San JuanOakland
SJU - OAK
SJUOAK
San Juan Luis Munoz Marin Intl
Sat 3/14
2:35 pm-12:10 am
2 stops12h 35m
Oakland
Sat 3/21
5:30 am-4:50 pm
1 stop8h 20m
$814
San JuanOakland
SJU - OAK
SJUOAK
San Juan Luis Munoz Marin Intl
Fri 7/10
2:35 pm-11:49 pm
2 stops12h 14m
Oakland
Tue 7/21
5:05 pm-1:25 pm
2 stops17h 20m
$878
San JuanOakland
SJU - OAK
SJUOAK
San Juan Luis Munoz Marin Intl
Fri 7/10
2:35 pm-11:49 pm
2 stops12h 14m
Oakland
Mon 7/20
5:05 pm-1:25 pm
2 stops17h 20m
$878
San JuanOakland
SJU - OAK
SJUOAK
San Juan Luis Munoz Marin Intl
Sun 3/1
7:00 am-6:15 pm
2 stops15h 15m
Oakland
Thu 3/5
7:35 pm-10:25 am
2 stops10h 50m
$912
San JuanOakland
SJU - OAK
SJUOAK
San Juan Luis Munoz Marin Intl
Mon 6/1
2:00 pm-10:30 pm
2 stops11h 30m
$248
Punta CanaOakland
PUJ - OAK
PUJOAK
Punta Cana
Tue 3/24
5:05 pm-11:51 am
2 stops21h 46m
$331
San JuanOakland
SJU - OAK
SJUOAK
San Juan Luis Munoz Marin Intl
Tue 3/24
10:10 am-8:30 pm
2 stops13h 20m
$333
Showing 1-10 of 28 results
Best time to book a flight from Caribbean Islands to Oakland
Have a flexible travel schedule? Discover the best time to fly to Oakland from Caribbean Islands with our price prediction graph.
SJU-OAK
PUJ-OAK
NAS-OAK
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 Caribbean Islands to Oakland
zzEPX-OAK
SJU-OAK
PUJ-OAK
NAS-OAK
What is the cheapest month to book a flight from Caribbean Islands to Oakland, California?
Currently, June is the cheapest month in which you can book a flight from Caribbean Islands to Oakland, California (average of $118). Flying from Caribbean Islands to Oakland, California in January is currently the most expensive (average of $298). 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 Caribbean Islands to Oakland. 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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