Find Deals on Flights from San Jose 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
Students
under 26
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 San Jose to Caribbean

(Round-trip)
Depart: Mon Jan 23 2017 Return: Thu Jan 26 2017 Trip spans 4 days
JetBlue
JetBlue
SJC
SJU
24h 05m
1 stop
SJU
SJC
21h 52m
1 stop
Depart: Tue Jan 17 2017 Return: Thu Feb 2 2017 Trip spans 17 days
Delta
Delta
SJC
STT
11h 19m
1 stop
STT
SJC
10h 38m
1 stop
Depart: Mon Jan 30 2017 Return: Wed Feb 8 2017 Trip spans 10 days
Major Airline
Major Airline
SJC
SJU
17h 55m
2 stops
SJU
SJC
20h 30m
2 stops
Depart: Tue Mar 14 2017 Return: Thu Mar 16 2017 Trip spans 3 days
American Airlines
American Airlines
SJC
GND
22h 16m
2 stops
GND
SJC
16h 36m
2 stops
Depart: Sun Jan 15 2017 Return: Sun Jan 22 2017 Trip spans 8 days
United
United
SJC
PLS
21h 41m
2 stops
PLS
SJC
24h 24m
2 stops
Depart: Wed Jan 18 2017 Return: Mon Jan 30 2017 Trip spans 13 days
Delta
Delta
SJC
STT
15h 00m
2 stops
STT
SJC
10h 38m
1 stop
Depart: Sat May 6 2017 Return: Tue May 16 2017 Trip spans 11 days
American Airlines
American Airlines
SJC
SJU
13h 03m
2 stops
SJU
SJC
12h 06m
2 stops
Depart: Tue Mar 7 2017 Return: Thu Mar 16 2017 Trip spans 9 days
JetBlue
JetBlue
SJC
SJU
18h 05m
2 stops
SJU
SJC
16h 10m
2 stops
Depart: Tue Feb 14 2017 Return: Wed Feb 22 2017 Trip spans 9 days
Delta
Delta
SJC
STT
11h 19m
1 stop
STT
SJC
11h 15m
1 stop
Depart: Fri Mar 3 2017 Return: Mon Mar 6 2017 Trip spans 4 days
United
United
SJC
PLS
16h 51m
2 stops
PLS
SJC
24h 28m
2 stops
Depart: Wed Jan 4 2017 Return: Sun Jan 15 2017 Trip spans 12 days
Major Airline
Major Airline
SJC
SJU
13h 15m
1 stop
SJU
SJC
15h 26m
1 stop
Depart: Wed Feb 22 2017 Return: Tue Feb 28 2017 Trip spans 7 days
American Airlines
American Airlines
SJC
ANU
22h 55m
2 stops
ANU
SJC
23h 30m
2 stops
Depart: Wed Feb 1 2017 Return: Sat Feb 11 2017 Trip spans 11 days
Delta
Delta
SJC
SJU
14h 58m
2 stops
SJU
SJC
14h 11m
2 stops
Depart: Fri Jan 6 2017 Return: Thu Jan 12 2017 Trip spans 7 days
United
United
SJC
NAS
13h 30m
2 stops
NAS
SJC
24h 03m
2 stops
Depart: Fri Jan 13 2017 Return: Tue Jan 17 2017 Trip spans 5 days
Major Airline
Major Airline
SJC
AUA
23h 20m
2 stops
AUA
SJC
33h 06m
2 stops
Depart: Fri Jan 20 2017 Return: Mon Feb 6 2017 Trip spans 18 days
JetBlue
JetBlue
SJC
GCM
13h 19m
1 stop
GCM
SJC
12h 17m
1 stop
Depart: Tue Feb 7 2017 Return: Wed Feb 15 2017 Trip spans 9 days
Delta
Delta
SJC
SJU
14h 15m
2 stops
SJU
SJC
10h 17m
1 stop
Depart: Wed Feb 22 2017 Return: Mon Feb 27 2017 Trip spans 6 days
American Airlines
American Airlines
SJC
NAS
13h 34m
2 stops
NAS
SJC
12h 43m
2 stops
Depart: Sat Feb 18 2017 Return: Sat Feb 25 2017 Trip spans 8 days
$1184
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Aeromexico
Aeromexico
SJC
SDQ
13h 16m
2 stops
SDQ
SJC
14h 29m
2 stops
Depart: Sat Jun 17 2017 Return: Wed Jun 21 2017 Trip spans 5 days
JetBlue
JetBlue
SJC
SJU
12h 11m
1 stop
SJU
SJC
11h 24m
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

San Jose
$377
Destination

Santo Domingo
$1184
Nassau
$484
Providenciales
$487
San Juan
$377
Saint Thomas Island
$413
Oranjestad
$504
St. John's
$451
George Town
$508
Grenada
$431