$137 Find Cheap Flights from San Jose to Caribbean Islands

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from San Jose to Caribbean Islands departing on 8/18. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Caribbean Islands

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from San Jose to Caribbean Islands, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from San Jose to Caribbean Islands, as well as popular online travel agencies
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Cheap Flights from San Jose to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana2 stops$634
Santo Domingo
Santo Domingo2 stops$715
Montego Bay
Montego Bay2 stops$437
Oranjestad
Oranjestad2 stops$676
Nassau
Nassau1 stop$550
Kingston
Kingston2 stops$747
Simpson Bay
Simpson Bay2 stops$714
Providenciales
Providenciales2 stops$586
Port of Spain
Port of Spain2 stops$669
Bridgetown
Bridgetown2 stops$853
George Town
George Town2 stops$686
Willemstad
Willemstad2 stops$785
Aguadilla
Aguadilla2 stops$706
Puerto Plata
Puerto Plata2 stops$740
St. John's
St. John's2 stops$758
Punta Cana
Punta Cana2 stops$634
Santo Domingo
Santo Domingo2 stops$715
Montego Bay
Montego Bay2 stops$437
Oranjestad
Oranjestad2 stops$676
Nassau
Nassau1 stop$550
Kingston
Kingston2 stops$747
Simpson Bay
Simpson Bay2 stops$714
Providenciales
Providenciales2 stops$586
Port of Spain
Port of Spain2 stops$669
Bridgetown
Bridgetown2 stops$853
George Town
George Town2 stops$686
Willemstad
Willemstad2 stops$785
Aguadilla
Aguadilla2 stops$706
Puerto Plata
Puerto Plata2 stops$740
St. John's
St. John's2 stops$758

Book Cheap San Jose to Caribbean Islands Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from San Jose to Caribbean Islands that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from San Jose to Caribbean Islands

Tue, Aug 18 - Mon, Aug 24
American Airlines Logo
6:00 am - 11:59 pm
SJC
-
SJU
14h 59m
2 stops
American Airlines Logo
6:00 am - 6:33 pm
SJU
-
SJC
15h 33m
2 stops
$384American Airlines
Tue, Sep 29 - Thu, Oct 8
Delta Logo
2:56 pm - 12:03 pm
SJC
-
SJU
18h 07m
2 stops
Delta Logo
7:00 am - 9:47 pm
SJU
-
SJC
17h 47m
2 stops
$386Delta
Thu, Oct 1 - Tue, Oct 6
Southwest Logo
7:30 pm - 9:20 am
SJC
-
SJU
10h 50m
2 stops
Southwest Logo
9:55 am - 6:10 pm
SJU
-
SJC
11h 15m
2 stops
$391Southwest
Wed, Sep 16 - Wed, Sep 30
United Airlines Logo
6:37 pm - 12:54 pm
SJC
-
SJU
15h 17m
2 stops
United Airlines Logo
2:00 pm - 8:48 pm
SJU
-
SJC
9h 48m
1 stop
$396United Airlines
Fri, Oct 2 - Sun, Oct 11
Southwest Logo
9:45 pm - 12:40 pm
SJC
-
SJU
11h 55m
1 stop
Southwest Logo
5:00 am - 12:50 pm
SJU
-
SJC
10h 50m
1 stop
$416Southwest
Tue, Aug 18 - Mon, Aug 24
American Airlines Logo
6:00 am - 11:59 pm
SJC
-
SJU
14h 59m
2 stops
American Airlines Logo
3:44 pm - 10:32 pm
SJU
-
SJC
9h 48m
1 stop
$417American Airlines
Fri, Oct 2 - Thu, Oct 8
Delta Logo
10:40 pm - 1:47 pm
SJC
-
SJU
12h 07m
1 stop
Delta Logo
7:00 am - 9:47 pm
SJU
-
SJC
17h 47m
2 stops
$427Delta
Fri, Oct 2 - Sun, Oct 11
Southwest Logo
9:45 pm - 12:40 pm
SJC
-
SJU
11h 55m
1 stop
Southwest Logo
5:30 am - 2:00 pm
SJU
-
SJC
11h 30m
2 stops
$432Southwest
Thu, Oct 1 - Tue, Oct 6
United Airlines Logo
6:35 pm - 11:57 am
SJC
-
SJU
14h 22m
2 stops
United Airlines Logo
2:00 pm - 8:48 pm
SJU
-
SJC
9h 48m
1 stop
$434United Airlines
Sat, Oct 10 - Mon, Oct 19
Delta Logo
11:30 am - 12:07 pm
SJC
-
MBJ
22h 37m
2 stops
Delta Logo
4:59 pm - 5:15 pm
MBJ
-
SJC
26h 16m
2 stops
$437Delta
Booking Insights

KAYAK's insights & trends for San Jose to Caribbean Islands flights

Get data-powered insights and trends into flights from San Jose to Caribbean Islands to help you find the cheapest flights, the best time to fly and much more.

Can I save money by flying with a layover from San Jose to Caribbean Islands?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $494, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from San Jose to Caribbean Islands?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from San Jose to Caribbean Islands, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from San Jose to Caribbean Islands is January, when tickets cost $184 (return) on average. On the other hand, the most expensive months are March and May, when the average cost of round-trip tickets is $758 and $599 respectively.

Good to know

Low seasonFebruary
Cheapest flight$137
Best time to beat the crowds with an average 30% drop in price.
Most popular time to fly and prices are also 11% lower on average.
Flight from San Jose to San Juan

FAQs - booking Caribbean Islands flights

  • How does KAYAK find such low prices on flights from San Jose to Caribbean Islands?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from San Jose to Caribbean Islands.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from San Jose to Caribbean Islands?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from San Jose to Caribbean Islands is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from San Jose to Caribbean Islands?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from San Jose to Caribbean Islands with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from San Jose to Caribbean Islands?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from San Jose to Caribbean Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airlines flying from San Jose to Caribbean Islands

 
See real verified KAYAK customer reviews for airlines flying from San Jose to Caribbean Islands. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from San Jose to Caribbean Islands? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.8
DeltaOverall score based on 8423 reviews
7.2Food
8.1Boarding
8.5Crew
7.8Comfort
7.8Entertainment
Airline reviews

Be on time? When not on time a circling for over an hour offer more than 1 bag of chips to the passengers? It was a 7 hour flight by the time we got done.

4.0 OkayAndrew, Jun 2026
LAX - JFK
Read more Delta reviews

Be on time? When not on time a circling for over an hour offer more than 1 bag of chips to the passengers? It was a 7 hour flight by the time we got done.

Flight delayed four separate times. I’m now one hour hours late to landing.

Checkin was good, fllight ws good. Onlly complaint is lack of foot on 6 hour flight from Seattle to Boston. Snacks were flimsy - chips and cookies. could have offered something more substantial for such a long flight. I know you can buy food in airport but for the price you pay for a ticket, they should step up for the passengers.

Long story short, it was one of the better flight experiences I've had in some time when compared with other airlines.

While they turned off most cabin lights to allow people to sleep, I was bothered by how bright the side lights still were. It was still quite bright for me in a window seat, when I wish I could have slept!

Generally on time departures and arrivals, clean planes, sky miles membership provides great benefits (complimentary upgrades, etc).

N Everything was perfect from boarding to assistance to baggage in Tampa

Loved the crew! Sucks that we went from 1 hour and 8 minute layover to a 3 hour layover. But weather sucks like that.

Fast, lovely scenery, great info on the Delta flight screen about landmarks we were flying over. Great landing!

Long flight but comfortable and not freezing as I have experienced on Hawaiian flights to the islands. They gave us blankets just in case. Nice touch.

Agency very bad had to cancelled my booking too many changes in the flight changed my flight to 1 week

Luggage did not make it onto my plane. Business seats were economy with empty row seat. Just horrible experience. Why would the company allow for transfers that don’t give employees enough time to transfer luggages??

The gate experience at LAX was abysmal (same for the arrival experience two days prior). Despite the LAX -> SAT schedule of two flights daily, our departure gate was at a smaller hub that we had to be bussed to from Terminal 4. Fortunately, I arrived at LAX extra early and had time to spare, but if I had not known, I might have missed my flight. I looked at the LAX airport map in the AA app and there was no indication of the additional boarding process. Lastly the gate area we were bussed to was crowded with limited food and beverage options. On flight, the fight attendant was hospitable and attentive, the flight was smooth, and AA's free (and working) wifi for AA members were all on the positive side.

Our flight from JFK to Madrid was delayed. We had to go from one side of the Madrid airport (Terminal 4s to the far end of terminal 4 - Gate K98) to our gate in less than 30 minutes. Put passport control and security/baggage check and that’s very hard unless you’re Usain Bolt. I called Iberia Airlines and the telephone customer service told me that I was going to have to pay to re-book. Luckily the help desk in the airport (who was dealing with dozens of people from the same JFK-Madrid flight) did not charge us extra to reschedule to a flight 8 hours later. They also gave us a voucher for breakfast and lunch. Glad the actual person at the airport had some actual sense.

For an long range economy flight I feel more space and more meal options need to be offered for flights over 5 hours

Take-off delayed an hour because of a missing flight officer, so,arrived in Charlotte lates causing many passengers to miss connections. Otherwise a very good flight, safe and comfortable, with an excellent professional crew.

The flight from LA to Chicago was smooth and service was very good overall.

B-class on an old plane with antiquated amenities and poor service. Landed in Rome w/o bag that didn’t make the connection (plenty of time in London). Bag will come to hotel NOT the day it lands but the following night!! Still waiting for bag…BA had nothing to offer in support and couldn’t even tell me their comp, told to submit receipts and then I’ll learn what is or isn’t covered.

Ontario airport boarding was very easy to park and access, is clean and TSA took 10 minutes total. Check-in was a breeze and cruise was very nice.

It's a long flight and that is always difficult. I was comfortable and well. The movies available were great and the crew was good.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports