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
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: Tue May 2 2017 Return: Tue May 9 2017 Trip spans 8 days
Delta
Delta
SJC
SJU
14h 46m
2 stops
SJU
SJC
13h 43m
2 stops
Depart: Mon Apr 3 2017 Return: Wed Apr 5 2017 Trip spans 3 days
Major Airline
Major Airline
SJC
SJU
11h 31m
2 stops
SJU
SJC
21h 22m
2 stops
Depart: Sun Aug 6 2017 Return: Wed Aug 30 2017 Trip spans 25 days
American Airlines
American Airlines
SJC
SJU
9h 16m
1 stop
SJU
SJC
12h 06m
1 stop
Depart: Tue May 23 2017 Return: Wed May 31 2017 Trip spans 9 days
United
United
SJC
PLS
22h 25m
2 stops
PLS
SJC
23h 30m
2 stops
Depart: Wed Mar 15 2017 Return: Tue Mar 21 2017 Trip spans 7 days
JetBlue
JetBlue
SJC
SDQ
11h 50m
1 stop
SDQ
SJC
15h 11m
1 stop
Depart: Sun Apr 9 2017 Return: Sun Apr 16 2017 Trip spans 8 days
Air Canada
Air Canada
SJC
BGI
16h 00m
2 stops
BGI
SJC
22h 45m
2 stops
Depart: Wed May 3 2017 Return: Wed May 10 2017 Trip spans 8 days
Delta
Delta
SJC
SJU
13h 09m
2 stops
SJU
SJC
15h 49m
2 stops
Depart: Wed Mar 29 2017 Return: Mon Apr 3 2017 Trip spans 6 days
Major Airline
Major Airline
SJC
SJU
25h 57m
1 stop
SJU
SJC
23h 14m
1 stop
Depart: Fri Feb 24 2017 Return: Tue Feb 28 2017 Trip spans 5 days
Aeromexico
Aeromexico
SJC
HAV
13h 05m
2 stops
HAV
SJC
14h 55m
2 stops
Depart: Fri Aug 4 2017 Return: Thu Aug 10 2017 Trip spans 7 days
American Airlines
American Airlines
SJC
SJU
20h 30m
1 stop
SJU
SJC
14h 04m
2 stops
Depart: Wed Apr 19 2017 Return: Tue Apr 25 2017 Trip spans 7 days
Delta
Delta
SJC
HAV
18h 32m
2 stops
HAV
SJC
22h 26m
2 stops
Depart: Wed Mar 22 2017 Return: Tue Mar 28 2017 Trip spans 7 days
Major Airline
Major Airline
SJC
HAV
17h 08m
3 stops
HAV
SJC
18h 27m
2 stops
Depart: Fri May 5 2017 Return: Tue May 9 2017 Trip spans 5 days
American Airlines
American Airlines
SJC
NAS
8h 57m
1 stop
NAS
SJC
11h 19m
1 stop
Depart: Thu May 4 2017 Return: Sun May 7 2017 Trip spans 4 days
Delta
Delta
SJC
HAV
18h 05m
2 stops
HAV
SJC
21h 54m
2 stops
Depart: Fri Jun 30 2017 Return: Mon Jul 3 2017 Trip spans 4 days
Major Airline
Major Airline
SJC
HAV
14h 55m
2 stops
HAV
SJC
14h 23m
2 stops
Depart: Wed Apr 19 2017 Return: Wed Apr 26 2017 Trip spans 8 days
JetBlue
JetBlue
SJC
SDQ
16h 53m
1 stop
SDQ
SJC
15h 11m
1 stop
Depart: Wed Mar 29 2017 Return: Mon Apr 3 2017 Trip spans 6 days
United
United
SJC
PUJ
18h 28m
2 stops
PUJ
SJC
24h 06m
2 stops
Depart: Mon May 1 2017 Return: Wed May 10 2017 Trip spans 10 days
JetBlue
JetBlue
SJC
SDQ
11h 55m
1 stop
SDQ
SJC
15h 04m
1 stop
Depart: Tue Jun 6 2017 Return: Wed Jun 14 2017 Trip spans 9 days
Delta
Delta
SJC
SJU
14h 54m
2 stops
SJU
SJC
16h 50m
2 stops
Depart: Wed Apr 5 2017 Return: Tue Apr 11 2017 Trip spans 7 days
American Airlines
American Airlines
SJC
GCM
11h 41m
2 stops
GCM
SJC
15h 38m
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.

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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
$431
Destination

Bridgetown
$794
Santo Domingo
$552
Nassau
$492
Providenciales
$531
San Juan
$431
George Town
$522
Punta Cana
$560
Havana
$443