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: Sun Jan 21 2018 Return: Thu Jan 25 2018 Trip spans 5 days
Multiple Airlines
Multiple Airlines
OAK
GCM
11h 14m
1 stop
GCM
OAK
21h 56m
2 stops
Depart: Sun Jan 21 2018 Return: Fri Jan 26 2018 Trip spans 6 days
JetBlue
JetBlue
OAK
GCM
11h 14m
1 stop
GCM
OAK
13h 48m
1 stop
Depart: Mon Mar 12 2018 Return: Tue Mar 20 2018 Trip spans 9 days
Delta
Delta
OAK
SJU
14h 39m
2 stops
SJU
OAK
13h 57m
2 stops
Depart: Mon Feb 12 2018 Return: Wed Feb 21 2018 Trip spans 10 days
American Airlines
American Airlines
OAK
UVF
16h 17m
2 stops
UVF
OAK
21h 02m
2 stops
Depart: Fri Jan 19 2018 Return: Sun Jan 28 2018 Trip spans 10 days
Spirit Airlines
Spirit Airlines
OAK
SJU
15h 52m
2 stops
SJU
OAK
20h 45m
2 stops
Depart: Wed Jan 24 2018 Return: Thu Feb 8 2018 Trip spans 16 days
Aeromexico
Aeromexico
OAK
HAV
37h 30m
2 stops
HAV
OAK
29h 47m
2 stops
Depart: Sat Feb 3 2018 Return: Sat Feb 10 2018 Trip spans 8 days
Multiple Airlines
Multiple Airlines
OAK
MBJ
27h 00m
2 stops
MBJ
OAK
27h 26m
2 stops
Depart: Mon Jan 15 2018 Return: Thu Jan 25 2018 Trip spans 11 days
Multiple Airlines
Multiple Airlines
OAK
GCM
15h 47m
2 stops
GCM
OAK
21h 56m
2 stops
Depart: Wed Jan 17 2018 Return: Thu Jan 25 2018 Trip spans 9 days
Multiple Airlines
Multiple Airlines
OAK
GCM
13h 54m
2 stops
GCM
OAK
21h 56m
2 stops
Depart: Sun Mar 11 2018 Return: Thu Mar 22 2018 Trip spans 11 days
JetBlue
JetBlue
OAK
SJU
12h 37m
1 stop
SJU
OAK
12h 43m
1 stop
Depart: Fri Jan 12 2018 Return: Sun Jan 14 2018 Trip spans 3 days
Delta
Delta
OAK
HAV
16h 06m
2 stops
HAV
OAK
11h 46m
2 stops
Depart: Thu Jan 18 2018 Return: Thu Jan 25 2018 Trip spans 8 days
Multiple Airlines
Multiple Airlines
OAK
GCM
13h 54m
2 stops
GCM
OAK
21h 56m
2 stops
Depart: Mon Mar 12 2018 Return: Thu Mar 22 2018 Trip spans 11 days
JetBlue
JetBlue
OAK
SJU
12h 37m
1 stop
SJU
OAK
12h 43m
1 stop
Depart: Thu Jan 11 2018 Return: Tue Jan 16 2018 Trip spans 6 days
Delta
Delta
OAK
UVF
29h 26m
2 stops
UVF
OAK
25h 19m
2 stops
Depart: Fri Jan 19 2018 Return: Thu Jan 25 2018 Trip spans 7 days
Multiple Airlines
Multiple Airlines
OAK
GCM
15h 47m
2 stops
GCM
OAK
21h 56m
2 stops
Depart: Fri Dec 1 2017 Return: Fri Dec 8 2017 Trip spans 8 days
Spirit Airlines
Spirit Airlines
OAK
PAP
47h 56m
2 stops
PAP
OAK
27h 25m
2 stops
Depart: Wed Apr 11 2018 Return: Tue Apr 17 2018 Trip spans 7 days
Aeromexico
Aeromexico
OAK
HAV
13h 15m
2 stops
HAV
OAK
19h 50m
2 stops
Depart: Thu Mar 15 2018 Return: Thu Mar 22 2018 Trip spans 8 days
JetBlue
JetBlue
OAK
SJU
12h 37m
1 stop
SJU
OAK
12h 43m
1 stop
Depart: Fri Jan 12 2018 Return: Tue Jan 16 2018 Trip spans 5 days
Delta
Delta
OAK
UVF
23h 32m
2 stops
UVF
OAK
25h 19m
2 stops
Depart: Sat Jan 20 2018 Return: Thu Jan 25 2018 Trip spans 6 days
Multiple Airlines
Multiple Airlines
OAK
GCM
12h 39m
2 stops
GCM
OAK
21h 56m
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 and someone from our team will get back to you promptly.

Airports
Origin

Oakland
$470
Destination

Port Au Prince
$637
Vieux Fort
$544
San Juan
$522
Montego Bay
$591
George Town
$470
Havana
$547