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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Book cheap flights from Oakland to Caribbean

(Round-trip)
Depart: Mon Sep 25 2017 Return: Mon Oct 2 2017 Trip spans 8 days
American Airlines
American Airlines
OAK
SJU
14h 59m
3 stops
SJU
OAK
14h 21m
3 stops
Depart: Sun Oct 29 2017 Return: Thu Nov 9 2017 Trip spans 12 days
JetBlue
JetBlue
OAK
SJU
12h 03m
1 stop
SJU
OAK
12h 56m
1 stop
Depart: Thu Nov 2 2017 Return: Mon Nov 6 2017 Trip spans 5 days
Multiple Airlines
Multiple Airlines
OAK
SJU
31h 07m
2 stops
SJU
OAK
45h 00m
2 stops
Depart: Wed Oct 25 2017 Return: Sat Oct 28 2017 Trip spans 4 days
Delta
Delta
OAK
HAV
17h 49m
2 stops
HAV
OAK
21h 48m
2 stops
Depart: Sat Jan 6 2018 Return: Sat Jan 13 2018 Trip spans 8 days
Alaska Airlines
Alaska Airlines
OAK
HAV
19h 28m
2 stops
HAV
OAK
17h 13m
2 stops
Depart: Wed Sep 27 2017 Return: Mon Oct 2 2017 Trip spans 6 days
American Airlines
American Airlines
OAK
SJU
11h 55m
2 stops
SJU
OAK
14h 21m
3 stops
Depart: Sat Feb 17 2018 Return: Sat Feb 24 2018 Trip spans 8 days
Spirit Airlines
Spirit Airlines
OAK
SDQ
15h 30m
2 stops
SDQ
OAK
21h 15m
2 stops
Depart: Tue Feb 13 2018 Return: Sun Feb 18 2018 Trip spans 6 days
Aeromexico
Aeromexico
OAK
SDQ
21h 34m
2 stops
SDQ
OAK
31h 34m
2 stops
Depart: Tue Sep 26 2017 Return: Tue Oct 3 2017 Trip spans 8 days
American Airlines
American Airlines
OAK
SJU
11h 55m
2 stops
SJU
OAK
13h 19m
2 stops
Depart: Sat Sep 23 2017 Return: Wed Oct 18 2017 Trip spans 26 days
Multiple Airlines
Multiple Airlines
OAK
SJU
32h 09m
2 stops
SJU
OAK
18h 50m
2 stops
Depart: Wed Nov 1 2017 Return: Wed Nov 8 2017 Trip spans 8 days
Delta
Delta
OAK
HAV
23h 02m
2 stops
HAV
OAK
23h 35m
2 stops
Depart: Sun Oct 29 2017 Return: Fri Nov 10 2017 Trip spans 13 days
JetBlue
JetBlue
OAK
SJU
12h 03m
1 stop
SJU
OAK
12h 56m
1 stop
Depart: Tue Nov 7 2017 Return: Mon Nov 13 2017 Trip spans 7 days
Delta
Delta
OAK
HAV
22h 37m
2 stops
HAV
OAK
13h 05m
2 stops
Depart: Mon Oct 16 2017 Return: Wed Oct 25 2017 Trip spans 10 days
Multiple Airlines
Multiple Airlines
OAK
SJU
13h 32m
1 stop
SJU
OAK
19h 02m
2 stops
Depart: Thu Oct 26 2017 Return: Thu Nov 9 2017 Trip spans 15 days
JetBlue
JetBlue
OAK
SJU
13h 32m
1 stop
SJU
OAK
12h 56m
1 stop
Depart: Thu Feb 15 2018 Return: Mon Feb 19 2018 Trip spans 5 days
Delta
Delta
OAK
PLS
24h 11m
2 stops
PLS
OAK
22h 16m
2 stops
Depart: Fri Feb 2 2018 Return: Fri Feb 23 2018 Trip spans 22 days
American Airlines
American Airlines
OAK
KIN
15h 54m
2 stops
KIN
OAK
25h 14m
2 stops
Depart: Tue Oct 24 2017 Return: Thu Oct 26 2017 Trip spans 3 days
Delta
Delta
OAK
STI
14h 20m
2 stops
STI
OAK
15h 11m
2 stops
Depart: Thu Oct 26 2017 Return: Fri Nov 10 2017 Trip spans 16 days
JetBlue
JetBlue
OAK
SJU
13h 32m
1 stop
SJU
OAK
12h 56m
1 stop
Depart: Sat Nov 4 2017 Return: Wed Nov 8 2017 Trip spans 5 days
Multiple Airlines
Multiple Airlines
OAK
MBJ
26h 46m
2 stops
MBJ
OAK
30h 41m
2 stops
* Prices are per person and are for e–tickets and include all taxes & fees in USD.

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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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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.

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Airports
Origin

Oakland
$346
Destination

Santo Domingo
$731
Providenciales
$456
San Juan
$346
Montego Bay
$566
Kingston
$501
Havana
$424
Santiago de los Caballeros
$461