Find Deals on 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: Fri Apr 21 2017 Return: Tue May 2 2017 Trip spans 12 days
Major Airline
Major Airline
OAK
HAV
13h 15m
2 stops
HAV
OAK
14h 40m
2 stops
Depart: Thu May 4 2017 Return: Mon May 15 2017 Trip spans 12 days
Delta
Delta
OAK
SXM
23h 40m
2 stops
SXM
OAK
30h 05m
2 stops
Depart: Wed Apr 26 2017 Return: Wed May 3 2017 Trip spans 8 days
American Airlines
American Airlines
OAK
HAV
13h 00m
2 stops
HAV
OAK
12h 41m
2 stops
Depart: Sat May 20 2017 Return: Tue May 23 2017 Trip spans 4 days
JetBlue
JetBlue
OAK
SJU
10h 49m
1 stop
SJU
OAK
14h 10m
1 stop
Depart: Fri May 19 2017 Return: Sat May 27 2017 Trip spans 9 days
Aeromexico
Aeromexico
OAK
HAV
13h 15m
2 stops
HAV
OAK
14h 40m
2 stops
Depart: Tue Apr 18 2017 Return: Thu Apr 27 2017 Trip spans 10 days
Major Airline
Major Airline
OAK
NAS
31h 00m
2 stops
NAS
OAK
18h 00m
2 stops
Depart: Wed Aug 23 2017 Return: Wed Aug 30 2017 Trip spans 8 days
Delta
Delta
OAK
SJU
16h 07m
2 stops
SJU
OAK
24h 08m
2 stops
Depart: Wed Jun 14 2017 Return: Tue Jun 27 2017 Trip spans 14 days
American Airlines
American Airlines
OAK
PLS
39h 53m
2 stops
PLS
OAK
47h 35m
2 stops
Depart: Tue May 9 2017 Return: Tue May 16 2017 Trip spans 8 days
Major Airline
Major Airline
OAK
SJU
4h 13m
2 stops
SJU
OAK
10h 13m
2 stops
Depart: Sat May 6 2017 Return: Sun May 14 2017 Trip spans 9 days
Delta
Delta
OAK
HAV
20h 00m
2 stops
HAV
OAK
33h 30m
2 stops
Depart: Tue Mar 21 2017 Return: Thu Mar 30 2017 Trip spans 10 days
JetBlue
JetBlue
OAK
SJU
13h 59m
1 stop
SJU
OAK
12h 36m
1 stop
Depart: Sat Apr 29 2017 Return: Thu May 4 2017 Trip spans 6 days
American Airlines
American Airlines
OAK
AUA
22h 13m
2 stops
AUA
OAK
22h 11m
2 stops
Depart: Wed May 10 2017 Return: Thu May 18 2017 Trip spans 9 days
Delta
Delta
OAK
NAS
22h 35m
2 stops
NAS
OAK
33h 10m
2 stops
Depart: Sun Mar 19 2017 Return: Thu Mar 23 2017 Trip spans 5 days
Major Airline
Major Airline
OAK
SJU
32h 04m
1 stop
SJU
OAK
12h 36m
1 stop
Depart: Mon Apr 24 2017 Return: Thu Apr 27 2017 Trip spans 4 days
JetBlue
JetBlue
OAK
SDQ
12h 45m
1 stop
SDQ
OAK
17h 04m
1 stop
Depart: Mon Jun 12 2017 Return: Thu Jun 22 2017 Trip spans 11 days
Delta
Delta
OAK
SJU
10h 09m
1 stop
SJU
OAK
12h 00m
1 stop
Depart: Mon May 15 2017 Return: Fri May 19 2017 Trip spans 5 days
American Airlines
American Airlines
OAK
MBJ
14h 39m
2 stops
MBJ
OAK
23h 21m
2 stops
Depart: Mon May 15 2017 Return: Wed May 31 2017 Trip spans 17 days
JetBlue
JetBlue
OAK
SDQ
12h 49m
1 stop
SDQ
OAK
16h 56m
1 stop
Depart: Wed Jul 12 2017 Return: Wed Jul 19 2017 Trip spans 8 days
Major Airline
Major Airline
OAK
HAV
37h 15m
2 stops
HAV
OAK
22h 20m
3 stops
Depart: Sun Jul 23 2017 Return: Fri Aug 11 2017 Trip spans 20 days
Delta
Delta
OAK
SJU
11h 37m
1 stop
SJU
OAK
12h 00m
1 stop
* 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.

We compile tonnes of data for you
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,
please send us an email and someone from our team will get back to you promptly.

Airports
Origin

Oakland
$417
Destination

Santo Domingo
$558
Nassau
$451
Providenciales
$467
San Juan
$451
Simpson Bay
$437
Oranjestad
$504
Montego Bay
$544
Havana
$417