$187 Find Cheap Flights from San Jose to Caribbean - Compare and Save

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 departing on 8/29. 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

Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 21% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Free to useThere are no hidden charges or fees.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
Flight Deals

Cheap Flights from San Jose to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana2 stops$592
Santo Domingo
Santo Domingo1 stop$682
Montego Bay
Montego Bay2 stops$422
Oranjestad
Oranjestad2 stops$702
Nassau
Nassau1 stop$566
Kingston
Kingston1 stop$806
Simpson Bay
Simpson Bay2 stops$619
Providenciales
Providenciales2 stops$657
Port of Spain
Port of Spain2 stops$759
Bridgetown
Bridgetown2 stops$795
George Town
George Town2 stops$692
Willemstad
Willemstad2 stops$753
Aguadilla
Aguadilla2 stops$634
Puerto Plata
Puerto Plata2 stops$855
St. John's
St. John's2 stops$1,062
Punta Cana
Punta Cana2 stops$592
Santo Domingo
Santo Domingo1 stop$682
Montego Bay
Montego Bay2 stops$422
Oranjestad
Oranjestad2 stops$702
Nassau
Nassau1 stop$566
Kingston
Kingston1 stop$806
Simpson Bay
Simpson Bay2 stops$619
Providenciales
Providenciales2 stops$657
Port of Spain
Port of Spain2 stops$759
Bridgetown
Bridgetown2 stops$795
George Town
George Town2 stops$692
Willemstad
Willemstad2 stops$753
Aguadilla
Aguadilla2 stops$634
Puerto Plata
Puerto Plata2 stops$855
St. John's
St. John's2 stops$1,062

Book Cheap San Jose to Caribbean 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 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

Tue, Sep 15 - Sat, Sep 19
American Airlines Logo
2:36 pm - 3:40 pm
SJC
-
SJU
22h 04m
2 stops
American Airlines Logo
4:38 pm - 10:53 am
SJU
-
SJC
21h 15m
2 stops
$379American Airlines
Fri, Oct 23 - Sat, Oct 31
Delta Logo
6:12 pm - 11:36 am
SJC
-
SJU
14h 24m
2 stops
Delta Logo
2:31 pm - 10:58 pm
SJU
-
SJC
11h 27m
1 stop
$386Delta
Fri, Oct 23 - Sat, Oct 31
Southwest Logo
9:45 pm - 12:40 pm
SJC
-
SJU
11h 55m
1 stop
Southwest Logo
5:30 am - 2:45 pm
SJU
-
SJC
12h 15m
1 stop
$391Southwest
Sun, Nov 8 - Wed, Nov 11
Delta Logo
6:12 pm - 12:45 pm
SJC
-
SJU
14h 33m
2 stops
Delta Logo
3:35 pm - 10:58 pm
SJU
-
SJC
11h 23m
1 stop
$396Delta
Thu, Sep 24 - Mon, Sep 28
Southwest Logo
7:35 pm - 9:10 am
SJC
-
SJU
10h 35m
2 stops
Southwest Logo
11:35 am - 9:35 pm
SJU
-
SJC
13h 00m
2 stops
$406Southwest
Tue, Aug 18 - Mon, Aug 24
Southwest Logo
6:30 am - 9:05 pm
SJC
-
SJU
11h 35m
2 stops
Southwest Logo
11:35 am - 10:00 pm
SJU
-
SJC
13h 25m
2 stops
$411Southwest
Mon, Sep 21 - Sat, Sep 26
United Airlines Logo
6:37 pm - 11:43 am
SJC
-
MBJ
15h 06m
2 stops
United Airlines Logo
12:52 pm - 8:48 pm
MBJ
-
SJC
9h 56m
1 stop
$422United Airlines
Sat, Nov 7 - Thu, Nov 12
American Airlines Logo
6:00 am - 5:30 am
SJC
-
SJU
19h 30m
1 stop
American Airlines Logo
6:44 am - 1:17 pm
SJU
-
SJC
10h 33m
1 stop
$441American Airlines
Mon, Jun 22 - Fri, Jun 26
JetBlue Logo
10:00 pm - 3:34 pm
SJC
-
MBJ
15h 34m
1 stop
JetBlue Logo
2:37 pm - 10:57 pm
MBJ
-
SJC
10h 20m
1 stop
$504JetBlue
Mon, Nov 9 - Thu, Nov 12
United Airlines Logo
4:00 pm - 12:07 pm
SJC
-
MBJ
17h 07m
2 stops
United Airlines Logo
2:48 pm - 10:36 pm
MBJ
-
SJC
10h 48m
1 stop
$539United Airlines
Booking Insights

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

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

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

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, 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 is September, when tickets cost $128 (return) on average. On the other hand, the most expensive months are March and October, when the average cost of round-trip tickets is $465 and $388 respectively.

Good to know

Low seasonFebruary
Cheapest flight$187
Best time to beat the crowds with an average 29% drop in price.
Most popular time to fly and prices are also 9% lower on average.
Flight from San Jose to Montego Bay

FAQs - booking Caribbean flights

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

    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.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from San Jose to Caribbean 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?

    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 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?

    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 up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 5 airlines serving from San Jose to Caribbean

 
Need help choosing which airline to fly with from San Jose to Caribbean? 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.
7.9
Alaska AirlinesOverall score based on 12478 reviews
7.8Comfort
8.5Crew
7.0Entertainment
7.0Food
8.1Boarding
Airline reviews

Not able to get boarding pass for domestic connection flight when check in at international airport. I was told I need to get connection flight boarding pass after I entered US. It us very inconvenient.

6.0 GoodVI, Jun 2026
SFO - SAN
Read more Alaska Airlines reviews

Not able to get boarding pass for domestic connection flight when check in at international airport. I was told I need to get connection flight boarding pass after I entered US. It us very inconvenient.

Wish there were more complimentary drinks available - only had water and apple juice. Also - no snacks were provided during the flight, but we were offered some items as we exited the plane.

No negatives. Crew was great, flight was on time and there were no crazy passengers. 🤩

It might not have been their fault, but there was a two hour delay due to weather. Then we boarded and were about to leave when they said there were more problems at the destination, took us back to the gate where we had to fully deplane. But then five minutes later, they said everything was fine and to get back on the plane. This was the part that pissed everybody off.

The gate agents begged us to check our carryons. They BEGGED us, over and over, and said that the flight was completely, totally full, and said that if we don't check our bags, it will cause huge delays. They finally said that "group suchandsuch will be required to check bags!" So I checked mine. Well, the flight wasn't close to being full, and many of the overhead compartments were *empty*! Moreover, my bag was delayed at the carousel, and it wasn't on the carousel that was posted. COME ON, AIRLINE, you can look at the seating for the flight on your computer and decide whether it's really necessary to beg and beg and beg people to go through the hassle of checking their bags! This is annoying as hell and makes me not want to use your crummy airline ever again.

Flight got delayed like 5 times, then they put and ada passenger in the back of the plane.

They called me 2 hours before my original flight from SFO was to depart to let me know it was delayed and that I would miss my connection. They then rebooked on a different flight leaving a half hour earlier to a different connecting airport, so that I would not miss my connection. It all worked out and I arrived at my destination without a problem and 15 minutes earlier than the original flight would have. Nice!

Flight delayed no communication. The gate was changed so many times.

Comfortable seats, good drinks with lots of water refills, staff was kind and understanding of my disabled mother!

It is a hassle to not have entertainment screens on the backs of the seats.

Was fine, delayed and feels like southwest is always late

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

Delayed flight, lack of information, boarding process is a mess as is the carryon luggage causing issues when leaving the plane….just a poor experience.

Comfortable. Easy. No problems. Just wish they had gf options for snacks.

The crew was very kind and made going to Hawaii relaxing and fun to look forward to! Thank you Southwest for a pleasant flight!

Terrible. Even though there’s assigned seating now, they are still the slowest boarding airline of anyone.

It was good from LAX to Phoenix, But the connection in Phoenix to Tulsa was not that great. The staff on both flights were great. The choice of free entertainment was ok nothing to brag about. The 45 min delay because of some electrical issue wasn't great from Phoenix to Tulsa. We sat there with hardly any air, The seat I had was between windows so the side of the plane pushed in on you. My being a bigger man it then made the seating area uncomfortable. The seats on the plane had no power to connect to recharge your phone or anything. I would recommend that they should look into a slot or clamp to hold your phone to enjoy while watching the entertainment choices hands-free. Also make it possible to raise the inner seat by the window be able to raise the arm rest up to make more room for larger people to set more comfortably. I would also say other then that stop price gouging the airfare or nickel and diming everything. Not fair for people having to fly for emergencies and be paying for higher prices due to the season or holidays. Your making your money either way and the cost of flying is still going to be the same regardless if there's 100 people or 200 people.

Southwest was greaat! The most expensive but the least upsetting for those we were flying to see.

Boarding was easy. The seats are small and fairly uncomfortable

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

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.

I took seat 15A in anticipation of window seat, there is no window.

Flight late, the waited for a long time for “personal” to arrive at gate to dock the plane in Rochester. So annoying. This flight was expected, why aren’t personel available for the jet bridge?

My recent experience was excellent on Delta! I flew with Delta Comfort and I was really comfortable in my seat. I enjoyed the in-flight service. The flight attendants were so friendly and hospitable. I love the snack on the flight as well. This was my first time flying on Delta and I will definitely consider flying with them again.

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.

Premium Economy Good crew, good service, excellent food. Seat back screen just not bright enough.

The crew was very attentive through out the flight. Seats were comfortable, nice flight bag with pillow and blanket. Food was okay, since it was a overnight flight seemed to go by fast.

Left early arrived early..right amount of talking from pilots..of course had to love the biscuit and water!

The gate attendant in Boston had a high raspy voice and spoke much too fast to be understood. Not pleasant.

The flight was delayed for more than 3 hours the flight attendant was so angry, it was my first flight with JetBlue but i don’t think I flight with them again.

First the flt was delayed over 2 hrs bc of plane mechanics that should have been handled better! No text or email was sent so only found out at the airport so there we sat for 5 hours! THATS RIDICULOUS! The gate area was filthy! No agents showed up till hr before so no additional info was given-waited online for 15 mins while the gate agent chatted and got together then given last seat in back of plane!! No priority for senior or anything-took attendants over 2hrs to serve drinks and snack-WHY are they not served together? By time snack came needed another drink! Worst service in my life!

Since we started at syr the service, crews, and flights were just excellent

All the TV screens in my rows was non functional . The map shown for an international route was antiqued..

It was fine for what it was. It’s not luxury travel but it was efficient, for the most part. Having my carry-on transferred into luggage however, was unwelcome.

We had better-than-average leg room and I loved the access to shows and movies. During boarding, we could not hear the agent even though we were close to the boarding door, which was kind of scary when we realized that half of the passengers had already boarded. Also, the entertainment was awesome, but I could not hear the movie as well as I would have liked, because my headphones were crappy. It would have been better if I could connect my own ear buds via Bluetooth or if JetBlue provided headphones.

On time, friendly attendants, quick wheelchair assistance and help checking in bags. Also appreciated change in seats, more forward to make it easier for my 97 year old mother to board and exit the plane. Thank you, JetBlue!

Flight did not have onboard charging and TV screen flickering.

I was seated next to an autistic child who was out of control and had a child behind me kicking my seat for most of the trip. I will never fly JetBlue again. Ever. I don't care how cheap it is. It's terrible.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports