Find Cheap 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 Nov 7 2017 Return: Tue Nov 14 2017 Trip spans 8 days
Major Airline
Major Airline
SJC
HAV
13h 14m
2 stops
HAV
SJC
20h 27m
3 stops
Depart: Mon Sep 18 2017 Return: Tue Sep 26 2017 Trip spans 9 days
Delta
Delta
SJC
HAV
11h 10m
1 stop
HAV
SJC
9h 38m
1 stop
Depart: Mon Aug 14 2017 Return: Thu Aug 24 2017 Trip spans 11 days
Multiple Airlines
Multiple Airlines
SJC
STT
14h 51m
2 stops
STT
SJC
9h 41m
1 stop
Depart: Tue Oct 10 2017 Return: Wed Oct 18 2017 Trip spans 9 days
American Airlines
American Airlines
SJC
SJU
14h 39m
2 stops
SJU
SJC
12h 49m
2 stops
Depart: Mon Nov 20 2017 Return: Thu Nov 30 2017 Trip spans 11 days
United
United
SJC
SJU
23h 20m
2 stops
SJU
SJC
10h 41m
1 stop
Depart: Tue Oct 10 2017 Return: Wed Oct 18 2017 Trip spans 9 days
JetBlue
JetBlue
SJC
PLS
12h 10m
1 stop
PLS
SJC
33h 34m
1 stop
Depart: Sat Sep 30 2017 Return: Sat Oct 7 2017 Trip spans 8 days
Air Canada
Air Canada
SJC
PLS
27h 25m
2 stops
PLS
SJC
24h 45m
2 stops
Depart: Sat Jul 8 2017 Return: Fri Jul 14 2017 Trip spans 7 days
Aeromexico
Aeromexico
SJC
HAV
16h 00m
3 stops
HAV
SJC
29h 50m
2 stops
Depart: Tue Aug 22 2017 Return: Thu Aug 24 2017 Trip spans 3 days
Major Airline
Major Airline
SJC
HAV
13h 48m
3 stops
HAV
SJC
14h 30m
2 stops
Depart: Tue Dec 5 2017 Return: Wed Dec 6 2017 Trip spans 2 days
American Airlines
American Airlines
SJC
SJU
14h 39m
2 stops
SJU
SJC
10h 04m
1 stop
Depart: Wed Sep 20 2017 Return: Tue Sep 26 2017 Trip spans 7 days
Multiple Airlines
Multiple Airlines
SJC
SJU
19h 39m
2 stops
SJU
SJC
15h 53m
2 stops
Depart: Tue Jul 25 2017 Return: Tue Aug 1 2017 Trip spans 8 days
United
United
SJC
SJU
14h 58m
1 stop
SJU
SJC
22h 29m
1 stop
Depart: Tue Nov 7 2017 Return: Tue Nov 14 2017 Trip spans 8 days
Delta
Delta
SJC
NAS
10h 01m
1 stop
NAS
SJC
15h 58m
1 stop
Depart: Tue Oct 3 2017 Return: Mon Oct 9 2017 Trip spans 7 days
Major Airline
Major Airline
SJC
HAV
28h 15m
2 stops
HAV
SJC
24h 44m
2 stops
Depart: Mon Aug 21 2017 Return: Thu Aug 24 2017 Trip spans 4 days
Multiple Airlines
Multiple Airlines
SJC
SJU
14h 44m
2 stops
SJU
SJC
9h 49m
1 stop
Depart: Wed Dec 6 2017 Return: Sun Dec 10 2017 Trip spans 5 days
Major Airline
Major Airline
SJC
HAV
16h 59m
2 stops
HAV
SJC
24h 25m
2 stops
Depart: Mon Aug 28 2017 Return: Wed Sep 6 2017 Trip spans 10 days
American Airlines
American Airlines
SJC
AUA
19h 01m
2 stops
AUA
SJC
22h 54m
2 stops
Depart: Mon Oct 2 2017 Return: Wed Oct 11 2017 Trip spans 10 days
Multiple Airlines
Multiple Airlines
SJC
NAS
12h 18m
2 stops
NAS
SJC
8h 53m
1 stop
Depart: Sun Jul 2 2017 Return: Fri Jul 7 2017 Trip spans 6 days
United
United
SJC
BQN
15h 28m
1 stop
BQN
SJC
21h 59m
1 stop
Depart: Fri Nov 3 2017 Return: Sat Nov 11 2017 Trip spans 9 days
Delta
Delta
SJC
NAS
19h 33m
2 stops
NAS
SJC
16h 13m
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.

^ The fares displayed in KAYAK ads found on other sites include all taxes and fees for economy class travel and were found by KAYAK users in the last 72 hours. Seats are limited and may not be available on all flights and days. Fares are subject to change and may not be available on all flights or dates of travel. Some carriers charge additional fees for extra checked bags. Please check the carriers' sites.
Airports
Origin

San Jose
$409
Destination

Aguadilla
$509
Nassau
$457
Providenciales
$639
San Juan
$426
Saint Thomas Island
$422
Oranjestad
$488
Havana
$409