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.
Compare vs. KAYAK all | none
Browse Origins:
Browse Destinations:

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 5 2017 Return: Tue Sep 12 2017 Trip spans 8 days
Major Airline
Major Airline
OAK
HAV
20h 45m
2 stops
HAV
OAK
34h 25m
2 stops
Depart: Tue Oct 31 2017 Return: Wed Nov 8 2017 Trip spans 9 days
American Airlines
American Airlines
OAK
SJU
14h 37m
2 stops
SJU
OAK
16h 03m
2 stops
Depart: Fri Sep 8 2017 Return: Sat Sep 16 2017 Trip spans 9 days
JetBlue
JetBlue
OAK
NAS
11h 01m
1 stop
NAS
OAK
13h 55m
1 stop
Depart: Wed Jul 12 2017 Return: Mon Jul 17 2017 Trip spans 6 days
Delta
Delta
OAK
NAS
18h 32m
1 stop
NAS
OAK
16h 48m
1 stop
Depart: Wed Nov 15 2017 Return: Sun Nov 26 2017 Trip spans 12 days
Aeromexico
Aeromexico
OAK
HAV
37h 20m
2 stops
HAV
OAK
54h 30m
2 stops
Depart: Thu Sep 21 2017 Return: Sun Sep 24 2017 Trip spans 4 days
Alaska Airlines
Alaska Airlines
OAK
HAV
25h 27m
3 stops
HAV
OAK
16h 55m
2 stops
Depart: Thu Jun 1 2017 Return: Mon Jun 5 2017 Trip spans 5 days
Spirit Airlines
Spirit Airlines
OAK
SDQ
22h 00m
2 stops
SDQ
OAK
18h 27m
2 stops
Depart: Tue Aug 22 2017 Return: Wed Aug 30 2017 Trip spans 9 days
Major Airline
Major Airline
OAK
HAV
15h 30m
3 stops
HAV
OAK
21h 30m
2 stops
Depart: Wed Aug 30 2017 Return: Wed Sep 6 2017 Trip spans 8 days
American Airlines
American Airlines
OAK
NAS
12h 15m
2 stops
NAS
OAK
19h 57m
2 stops
Depart: Sun Nov 5 2017 Return: Wed Nov 15 2017 Trip spans 11 days
JetBlue
JetBlue
OAK
SJU
12h 09m
1 stop
SJU
OAK
12h 55m
1 stop
Depart: Tue Sep 12 2017 Return: Thu Nov 9 2017 Trip spans 59 days
Major Airline
Major Airline
OAK
SJU
11h 02m
3 stops
SJU
OAK
17h 33m
3 stops
Depart: Sun Nov 12 2017 Return: Wed Nov 15 2017 Trip spans 4 days
JetBlue
JetBlue
OAK
SJU
12h 09m
1 stop
SJU
OAK
12h 55m
1 stop
Depart: Sat Sep 30 2017 Return: Fri Oct 6 2017 Trip spans 7 days
American Airlines
American Airlines
OAK
SJU
14h 59m
3 stops
SJU
OAK
21h 50m
2 stops
Depart: Thu Sep 28 2017 Return: Tue Oct 3 2017 Trip spans 6 days
Delta
Delta
OAK
NAS
10h 52m
2 stops
NAS
OAK
12h 45m
2 stops
Depart: Mon Jul 3 2017 Return: Tue Jul 11 2017 Trip spans 9 days
Major Airline
Major Airline
OAK
NAS
12h 04m
1 stop
NAS
OAK
17h 31m
1 stop
Depart: Wed Aug 30 2017 Return: Wed Sep 6 2017 Trip spans 8 days
American Airlines
American Airlines
OAK
SJU
14h 59m
3 stops
SJU
OAK
15h 40m
3 stops
Depart: Fri Aug 18 2017 Return: Wed Aug 23 2017 Trip spans 6 days
Major Airline
Major Airline
OAK
HAV
26h 28m
3 stops
HAV
OAK
41h 08m
3 stops
Depart: Sun Aug 13 2017 Return: Wed Aug 23 2017 Trip spans 11 days
Delta
Delta
OAK
PAP
13h 55m
1 stop
PAP
OAK
20h 35m
2 stops
Depart: Sat Jul 8 2017 Return: Sat Jul 15 2017 Trip spans 8 days
Aeromexico
Aeromexico
OAK
HAV
40h 56m
2 stops
HAV
OAK
19h 40m
2 stops
Depart: Sun Jun 25 2017 Return: Mon Jul 10 2017 Trip spans 16 days
American Airlines
American Airlines
OAK
KIN
27h 50m
2 stops
KIN
OAK
30h 53m
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.

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
$413
Destination

Port Au Prince
$581
Santo Domingo
$713
Nassau
$453
San Juan
$418
Kingston
$518
Havana
$413