Find Cheap Flights from Oakland to Caribbean

Depart
Return
1 adult
Adults
18-64
Seniors
65+
Youths
12-17
Children
2-11
Seat Infants
under 2
Lap Infants
under 2
The price shown for each flight will be the average for all passengers including any infants.
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Dates flexible? Here are the best fares found in the past 48 hours...

Book cheap flights from Oakland to Caribbean

(Round-trip)
Depart: Tue Sep 19 2017 Return: Tue Sep 26 2017 Trip spans 8 days
Delta
Delta
OAK
SJU
14h 30m
2 stops
SJU
OAK
18h 52m
2 stops
Depart: Mon Sep 18 2017 Return: Fri Sep 22 2017 Trip spans 5 days
American Airlines
American Airlines
OAK
NAS
20h 11m
2 stops
NAS
OAK
19h 43m
2 stops
Depart: Sun Sep 3 2017 Return: Thu Sep 7 2017 Trip spans 5 days
JetBlue
JetBlue
OAK
SJU
10h 46m
1 stop
SJU
OAK
14h 01m
1 stop
Depart: Fri Jan 12 2018 Return: Sat Jan 27 2018 Trip spans 16 days
Aeromexico
Aeromexico
OAK
HAV
24h 59m
2 stops
HAV
OAK
19h 21m
2 stops
Depart: Wed Sep 6 2017 Return: Wed Sep 13 2017 Trip spans 8 days
Alaska Airlines
Alaska Airlines
OAK
HAV
19h 33m
2 stops
HAV
OAK
17h 23m
2 stops
Depart: Wed Aug 30 2017 Return: Mon Sep 4 2017 Trip spans 6 days
Spirit Airlines
Spirit Airlines
OAK
SDQ
22h 23m
2 stops
SDQ
OAK
18h 15m
2 stops
Depart: Tue Sep 19 2017 Return: Tue Sep 26 2017 Trip spans 8 days
Delta
Delta
OAK
SJU
14h 30m
2 stops
SJU
OAK
14h 02m
2 stops
Depart: Wed Oct 25 2017 Return: Mon Oct 30 2017 Trip spans 6 days
American Airlines
American Airlines
OAK
HAV
19h 10m
2 stops
HAV
OAK
17h 30m
2 stops
Depart: Thu Sep 7 2017 Return: Tue Sep 12 2017 Trip spans 6 days
Delta
Delta
OAK
HAV
23h 05m
2 stops
HAV
OAK
21h 47m
2 stops
Depart: Fri Sep 8 2017 Return: Mon Sep 18 2017 Trip spans 11 days
American Airlines
American Airlines
OAK
GND
16h 14m
2 stops
GND
OAK
23h 30m
2 stops
Depart: Wed Nov 1 2017 Return: Wed Nov 8 2017 Trip spans 8 days
JetBlue
JetBlue
OAK
SJU
12h 09m
1 stop
SJU
OAK
12h 55m
1 stop
Depart: Thu Nov 9 2017 Return: Thu Nov 16 2017 Trip spans 8 days
Aeromexico
Aeromexico
OAK
HAV
20h 45m
2 stops
HAV
OAK
19h 25m
2 stops
Depart: Mon Dec 4 2017 Return: Tue Dec 12 2017 Trip spans 9 days
Delta
Delta
OAK
SJU
18h 43m
2 stops
SJU
OAK
18h 35m
2 stops
Depart: Sat Oct 21 2017 Return: Wed Nov 1 2017 Trip spans 12 days
American Airlines
American Airlines
OAK
POP
22h 35m
2 stops
POP
OAK
23h 49m
2 stops
Depart: Sat Oct 7 2017 Return: Sat Oct 14 2017 Trip spans 8 days
JetBlue
JetBlue
OAK
NAS
11h 01m
1 stop
NAS
OAK
13h 55m
1 stop
Depart: Thu Aug 10 2017 Return: Mon Aug 14 2017 Trip spans 5 days
American Airlines
American Airlines
OAK
NAS
17h 12m
2 stops
NAS
OAK
19h 41m
2 stops
Depart: Sat Aug 12 2017 Return: Sat Aug 19 2017 Trip spans 8 days
Aeromexico
Aeromexico
OAK
HAV
33h 22m
2 stops
HAV
OAK
39h 09m
2 stops
Depart: Tue Jan 9 2018 Return: Fri Jan 26 2018 Trip spans 18 days
Delta
Delta
OAK
SJU
12h 19m
2 stops
SJU
OAK
13h 57m
2 stops
Depart: Fri Dec 1 2017 Return: Thu Dec 7 2017 Trip spans 7 days
JetBlue
JetBlue
OAK
NAS
11h 14m
1 stop
NAS
OAK
13h 54m
1 stop
Depart: Fri Oct 27 2017 Return: Tue Oct 31 2017 Trip spans 5 days
American Airlines
American Airlines
OAK
NAS
15h 10m
2 stops
NAS
OAK
19h 43m
2 stops
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

We attempt to get accurate prices, however, prices are not guaranteed.

Here's why:

We’re not the seller.
At KAYAK we don’t set the prices, so it’s not possible for us to guarantee what other companies are selling.

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Our service lets you quickly and easily compare results from hundreds of travel sites at once. In this sense, KAYAK is a search engine and we can't guarantee prices we find.

Why aren’t prices accurate 100% of the time?
Prices on airline seats, hotel rooms and car rentals can change frequently. Several people may also be trying to buy the same travel option simultaneously. As a result, you may find, on occasion, that certain prices are no longer available.

If you have more questions or if you have a bad price to report to us,
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Airports
Origin

Oakland
$387
Destination

Santo Domingo
$685
Nassau
$414
San Juan
$387
San Felipe de Puerto Plata
$461
Havana
$424
Grenada
$443