Find Cheap Flights 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: Wed Oct 4 2017 Return: Mon Oct 9 2017 Trip spans 6 days
Alaska Airlines
Alaska Airlines
SJC
HAV
7h 35m
1 stop
HAV
SJC
19h 04m
1 stop
Depart: Sat Sep 16 2017 Return: Sat Sep 23 2017 Trip spans 8 days
American Airlines
American Airlines
SJC
HAV
17h 00m
2 stops
HAV
SJC
11h 47m
2 stops
Depart: Fri Oct 20 2017 Return: Sat Oct 21 2017 Trip spans 2 days
United
United
SJC
BQN
15h 40m
1 stop
BQN
SJC
22h 54m
1 stop
Depart: Sat Oct 28 2017 Return: Thu Nov 2 2017 Trip spans 6 days
Delta
Delta
SJC
SJU
14h 58m
2 stops
SJU
SJC
10h 00m
1 stop
Depart: Fri Feb 9 2018 Return: Sun Feb 25 2018 Trip spans 17 days
Aeromexico
Aeromexico
SJC
HAV
23h 45m
2 stops
HAV
SJC
21h 45m
2 stops
Depart: Sun Oct 1 2017 Return: Thu Oct 12 2017 Trip spans 12 days
JetBlue
JetBlue
SJC
STI
11h 08m
1 stop
STI
SJC
15h 26m
1 stop
Depart: Tue Sep 19 2017 Return: Tue Sep 26 2017 Trip spans 8 days
Air Canada
Air Canada
SJC
MBJ
19h 45m
2 stops
MBJ
SJC
21h 00m
2 stops
Depart: Fri Dec 1 2017 Return: Wed Dec 6 2017 Trip spans 6 days
Alaska Airlines
Alaska Airlines
SJC
HAV
18h 15m
1 stop
HAV
SJC
18h 59m
1 stop
Depart: Sun Nov 19 2017 Return: Mon Nov 27 2017 Trip spans 9 days
United
United
SJC
BQN
14h 59m
1 stop
BQN
SJC
23h 24m
1 stop
Depart: Wed Dec 6 2017 Return: Thu Dec 14 2017 Trip spans 9 days
Delta
Delta
SJC
SJU
13h 24m
2 stops
SJU
SJC
11h 23m
1 stop
Depart: Tue Oct 31 2017 Return: Sat Nov 4 2017 Trip spans 5 days
American Airlines
American Airlines
SJC
NAS
14h 21m
2 stops
NAS
SJC
10h 47m
2 stops
Depart: Fri Sep 29 2017 Return: Sat Oct 7 2017 Trip spans 9 days
United
United
SJC
SJU
21h 10m
2 stops
SJU
SJC
22h 18m
2 stops
Depart: Fri Sep 15 2017 Return: Wed Sep 20 2017 Trip spans 6 days
Delta
Delta
SJC
HAV
11h 10m
1 stop
HAV
SJC
10h 36m
1 stop
Depart: Tue Jan 23 2018 Return: Tue Jan 30 2018 Trip spans 8 days
American Airlines
American Airlines
SJC
NAS
9h 19m
2 stops
NAS
SJC
10h 27m
2 stops
Depart: Thu Oct 19 2017 Return: Mon Oct 23 2017 Trip spans 5 days
Alaska Airlines
Alaska Airlines
SJC
HAV
7h 35m
1 stop
HAV
SJC
19h 04m
1 stop
Depart: Sat Nov 4 2017 Return: Wed Nov 8 2017 Trip spans 5 days
United
United
SJC
SJU
15h 10m
1 stop
SJU
SJC
25h 15m
2 stops
Depart: Sat Sep 23 2017 Return: Wed Sep 27 2017 Trip spans 5 days
Delta
Delta
SJC
NAS
15h 20m
2 stops
NAS
SJC
12h 15m
2 stops
Depart: Tue Nov 14 2017 Return: Thu Nov 23 2017 Trip spans 10 days
United
United
SJC
SJU
20h 20m
2 stops
SJU
SJC
25h 53m
2 stops
Depart: Thu Jan 11 2018 Return: Thu Jan 18 2018 Trip spans 8 days
American Airlines
American Airlines
SJC
GCM
11h 35m
2 stops
GCM
SJC
13h 48m
2 stops
Depart: Sat Jan 13 2018 Return: Sat Jan 20 2018 Trip spans 8 days
United
United
SJC
SJU
16h 44m
2 stops
SJU
SJC
10h 41m
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.

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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
$406
Destination

Aguadilla
$433
Nassau
$460
San Juan
$434
Montego Bay
$708
George Town
$490
Havana
$406
Santiago de los Caballeros
$590