$193 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 8/22. 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.
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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 Cana1 stop$560
Santo Domingo
Santo Domingo2 stops$705
Montego Bay
Montego Bay1 stop$452
Oranjestad
Oranjestad2 stops$716
Nassau
Nassau1 stop$494
Kingston
Kingston2 stops$816
Simpson Bay
Simpson Bay2 stops$603
Providenciales
Providenciales2 stops$491
Port of Spain
Port of Spain2 stops$753
Bridgetown
Bridgetown2 stops$803
George Town
George Town2 stops$716
Willemstad
Willemstad2 stops$739
Aguadilla
Aguadilla2 stops$581
St. John's
St. John's2 stops$839
Puerto Plata
Puerto Plata2 stops$1,084
Punta Cana
Punta Cana1 stop$560
Santo Domingo
Santo Domingo2 stops$705
Montego Bay
Montego Bay1 stop$452
Oranjestad
Oranjestad2 stops$716
Nassau
Nassau1 stop$494
Kingston
Kingston2 stops$816
Simpson Bay
Simpson Bay2 stops$603
Providenciales
Providenciales2 stops$491
Port of Spain
Port of Spain2 stops$753
Bridgetown
Bridgetown2 stops$803
George Town
George Town2 stops$716
Willemstad
Willemstad2 stops$739
Aguadilla
Aguadilla2 stops$581
St. John's
St. John's2 stops$839
Puerto Plata
Puerto Plata2 stops$1,084

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

Fri, Jan 22 - Sat, Jan 30
Delta Logo
5:05 pm - 4:50 pm
SJC
-
SJU
19h 45m
2 stops
Delta Logo
6:15 am - 8:58 pm
SJU
-
SJC
18h 43m
2 stops
$406Delta
Sun, Jan 24 - Sat, Jan 30
Delta Logo
5:05 pm - 2:15 pm
SJC
-
SJU
17h 10m
2 stops
Delta Logo
6:15 am - 8:58 pm
SJU
-
SJC
18h 43m
2 stops
$406Delta
Mon, Nov 9 - Mon, Nov 16
Southwest Logo
7:30 pm - 11:45 am
SJC
-
SJU
12h 15m
2 stops
Southwest Logo
7:40 am - 4:40 pm
SJU
-
SJC
13h 00m
2 stops
$406Southwest
Mon, Sep 21 - Fri, Sep 25
Southwest Logo
10:30 pm - 12:50 pm
SJC
-
SJU
11h 20m
1 stop
Southwest Logo
5:30 am - 1:00 pm
SJU
-
SJC
10h 30m
1 stop
$406Southwest
Fri, Sep 25 - Wed, Sep 30
American Airlines Logo
4:00 pm - 1:32 pm
SJC
-
SJU
18h 32m
2 stops
American Airlines Logo
4:38 pm - 10:53 am
SJU
-
SJC
21h 15m
2 stops
$406American Airlines
Tue, Nov 3 - Tue, Nov 10
American Airlines Logo
6:00 am - 12:16 am
SJC
-
SJU
14h 16m
1 stop
American Airlines Logo
11:34 am - 10:48 pm
SJU
-
SJC
15h 14m
2 stops
$406American Airlines
Mon, Sep 21 - Wed, Sep 30
United Airlines Logo
6:37 pm - 11:57 am
SJC
-
SJU
14h 20m
2 stops
United Airlines Logo
2:00 pm - 8:48 pm
SJU
-
SJC
9h 48m
1 stop
$406United Airlines
Mon, Nov 9 - Thu, Nov 12
United Airlines Logo
6:30 am - 9:00 pm
SJC
-
SJU
10h 30m
1 stop
United Airlines Logo
2:21 pm - 9:08 pm
SJU
-
SJC
10h 47m
1 stop
$496United Airlines
Thu, Jan 21 - Tue, Feb 2
Alaska Airlines Logo
6:00 am - 10:22 pm
SJC
-
SJU
12h 22m
1 stop
Alaska Airlines Logo
7:00 am - 9:29 pm
SJU
-
SJC
18h 29m
1 stop
$526Alaska Airlines
Sat, Jan 23 - Tue, Feb 2
Alaska Airlines Logo
6:00 am - 10:22 pm
SJC
-
SJU
12h 22m
1 stop
Alaska Airlines Logo
7:00 am - 9:29 pm
SJU
-
SJC
18h 29m
1 stop
$526Alaska 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 August, when tickets cost $478 (return) on average. On the other hand, the most expensive months are November and July, when the average cost of round-trip tickets is $773 and $742 respectively.

How far in advance should I book a flight from San Jose to Caribbean?

To calculate weekly average prices, KAYAK takes all prices for each week before departure 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 average of all the values for each week.

To get a below average price on the flight from San Jose to Caribbean, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 15 weeks before departure.

Good to know

Low season

February

Cheapest flight

$193
Best time to beat the crowds with an average 32% drop in price.
Most popular time to fly and prices are also 10% lower on average.
Flight from San Jose to Nassau

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.
8.0
SouthwestOverall score based on 4228 reviews
8.0Comfort
7.0Food
8.6Crew
8.1Boarding
7.5Entertainment
Airline reviews

Red eye from San Diego. Temperature of the cabin was way too warm and the air duct flowed very little air.

6.0 GoodGordon, Jul 2026
SAN - MCO
Read more Southwest reviews

Red eye from San Diego. Temperature of the cabin was way too warm and the air duct flowed very little air.

I think Southwest is the number one airline that anyone can fly I have flown for the first time Frontier and what a joke and their customer service United was a very strange experience I'm only sticking to Southwest from here on out for sure

Great job Southwest! My family doesn't fly often but we felt safe the whole time.

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.

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.

Good but I prefer choose your own seat. With the new assigned seats they should board from the back I see no advantage to this new boarding. Just like every other airline

I recently flew Southwest from San Jose to Honolulu. I was very impressed with the flight crew, especially the flight attendant in charge of the front of the plane. She came through the aisle at least five times for drinks and water, and two times for snacks. I have not seen such service since I flew first class. Also, for the first time, they gave us the correct baggage claim number, and the luggage came out quickly. I can't wait for Southwest to have assigned seating! I absolutely hate the Cattle Call boarding procedure and the mad dash to get seats and overhead bins. However, the boarding was efficient.

Forget beverage, they didn't even have water for half the passangers?

Flight was not full! Had a whole row to myself.

Wifi didn’t work, no service, seats are hard as rocks

No complimentary snacks or food. Had to buy drinks and food.

in-flight wifi was not working well. also the cabin temperature was a bit hot.

I wasn’t able to check in prior to arriving at the airport, I was told by the agent I may not get a seat on the plane as others were waiting for seats, I sat there for 2 hours before being assigned a seat, very stressful. The plane was delayed. Overall not a great travel experience for a 44 minute flight.

Larger seats and more room would elevate the experience. Otherwise, it was good!

Check in went pretty well and you didn't lose my bag. After I got a drink from the drink cart they charged me for it, and at the crazy overpriced airport rates. Never had that happen before, is that an american thing? what madness.

I was delayed several times. Missed a very important event. The airline only provided a $12 voucher after being delayed 3 times.

One the nicest and great air crews I’ve experienced and I’ve flown a lot

Staff at Gate desk were helpful. My connecting flight from the first part of my trip Kona to Seattle was late. I had to run through SeaTac Seattle to catch my flight to San Jose. They made an exception to let me board. On my return trip San Jose to San Diego and San Diego to Honolulu the same thing happened. One flight arrived late and I had to run through the terminal to catch my connection. There are no Gluten-free & Vegan options meals and snacks to purchase.

Short flight was fine, but no entertainment and bathrooms broken.

My email notifications were silenced, so I didn't get word that the departing flight had changed gates. It wasn't until I noticed that few people had gathered for the flight that I checked the airport schedule board, 20 minutes before boarding. I then told several people at the old gate of the change. If I was to receive a text I would have been notified of the change earlier, Or to hear an announcement over the airport intercom.

Delta is always late. Ruined our first day of a short vacation. Timing is important. We pay to stay on an itinerary

My son’s suitcase was left behind at SFO and did not make the flight.

Seats were not bad enough and uncomfortable good legroom in the emergency exit row we were in, but we were forbidden to hold my grandson on my lap for a little while, and the stewardess passed us saying it was against regulations which makes little or no sense when you’re 36,000 feet. The food snacks were really bad. Tasteless tasted like wallpaper, but we’re supposed to be protein bars, and the announcements were all completely incoherent because of the noise of the airplane and the lowness and crackly nature of the PA system.. this was disgraceful. No one in our party could understand a word of what the captain or the flight attendant were saying —not a word! The landing was a little hairy in a pretty stiff crosswind -we bounced before the plane stabilized on the runway

Flight team was great and we even arrived ahead of plan!

First The flight got delayed because one of the crew members was late and we couldn’t board until she arrived. Then we all boarded and got held in the tarmac for another 30 min.

Crew was absolutely fantastic and we’re so welcoming and friendly ❤️

It was as good as it could be. Flying is not a pleasant experience these days.

I was in first class and literally the men behind me were so aggressively loud I moved myself to economy. This has become so common on Delta - people using audio without headphones, and men on 12am / late night flights drinking and yelling to talk to each other which prevents anyone around them from resting. Pretty crazy to have to move from first to economy (poorer service, less comfort...). Wild wild. Looking into other airlines.

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

Plane was turned around due to fog half way into the flight, Delta did not properly direct passengers to stay on same flight and instead failed to properly rebook on Alaska

My seat had a worn out cushion, which made it a bit uncomfortable. Other than that, the flight was excellent.

American was the airline that Starlux contracted for this trip. I arrived in time to make the connecting flight on American, and then the baggage-handler debacle happened. For some reason, the first class and premium economy passengers' luggage was unloaded first. Never seen this happen before. They had handlers removing the bags from the carousel for those passengers. Meanwhile, all of the economy passengers were waiting for their bags, including me. And there were a lot of bags because it was an international flight packed full. While waiting for 45 minutes, my bag didn't show. Meanwhile, an American representative showed up asking if anyone has a connecting flight to Phoenix. Of course I spoke up, and they proceeded to try to find my bag because I had to take a bus to the actual terminal to catch my flight. Which I was not informed of before I arrived. After another 15 minutes of searching, my bag was finally found with the first-class passengers' bags because they had pulled it by mistake. So I rushed to the terminal with the American representative to catch my flight, and they informed me that I missed it and could not get another flight until the next day. Of course, after being on an international flight for 18 hours, I was in no mood to hear this. Now, to be fair, there were a few American employees who tried to help me. After hearing about the missed flight, they got a supervisor to talk to. I expressed my situation to the supervisor, and she was not helpful until I asked for compensation. She agreed to get me a hotel room for the night. So I agreed, and she disappeared into her office, and I waited. And waited. And waited. And waited. While waiting, I was asked by three different employees who knew of my situation if I had been helped. I told them I was waiting for the supervisor to get the hotel room, and they said they would check. Finally, after waiting for 75 minutes, one of the employees who had asked me if I had been helped arrived with my hotel room and arranged a ride to the hotel for me. Never saw the supervisor again. It was now 8 o'clock; I arrived at 5:45! My rebooked fight was scheduled for 6:11 this morning and I have now been informed it has been delayed until 10:00. So am I happy with American? NO I'M NOT!! ;

Not good. Flight crew, was not friendly and just shoved stuff at us. Not the way I like to travel.

The WiFi didn’t work entire flight, couldn’t watch a movie. The recline button didn’t work

Well, true to American Airlines, both of my flights were delayed. But it’s a good thing that American is so consistently incompetent because if the first flight was delayed in the second flight was on time then I might’ve had a problem..

Aside from the little delay, overall was flight good. Made it safely. Thanks!

Over the course of 7 months of travel, I can count on my hand the number of times the flight has departed on time. Majority of the instances have been related to non-weather reasons. Would not recommend flying this Airline

Rough flight No beverage service due to turbulence Bottom Seat cushion was non existent

They are rarely on time! Very hard to plan your travels when flights or connections keep getting delayed.

Apart from the delay due to unforeseen circumstances. The leg from sjc to dfw was fine. It was the leg from dfw to orf that we encountered issues mainly due to the flight attendant crew not being friendly. We had two small children and we needed some assistance to warm up milk so the baby would sleep. The crew just didn’t get it and made things very difficult. One made a remark that the baby’s dirty diaper smell was a “gift” to the plane in a rude way. Normally I’d brush that off as a funny comment if the rest of the trip the attendants were helpful or understanding of the difficulty we faced. But that wasn’t the case. We were met with rudeness on the second leg. Whereas on the first leg the crew were so nice and helpful.

The seats were roomier than other airplanes I’ve been on.

Seats were great, the staff was great, and the food was about the best I've had on a plane, and is especially the best of any US-based carrier I've flown. Free Wi-Fi was also great.

It was inexplicably canceled and we are stuck in LA, haven't gotten home and it has been an inconvenience having lost work (on unpaid leave for my husband).

It was good. I’m very disappointed that they don’t give commentary ear pods for the movie. I forgot mine at home

Boarding was quick and efficient. The flight crew were friendly. There were limited food options available on the flight. The pocket guide said there would be salad and sandwich sections available on flights over 3.5 hours. The only food available were snack boxes. And those were limited as well. My flight was over 5 hours. The entertainment system worked well. I had both extra legroom seats and regular coach seats. The seats were not very comfortable. The entertainment controls in the armrest made it difficult to rest my arm without changing the channel on my neighbors TV. Overall, my experience was mediocre.

Entertainment and wifi were very sub-par - audio issues and no wifi

I was denied a plastic fork to eat my food and was told plastic forks are for paying customers who buy Jet Blue’s food. So I had to make a utensil out of a cup so nourish my body. Like a refugee. Because decency is dead.

Flights with JetBlue from San Diego to Boston are a miserable experience. The flight was delayed about 1.5 hours due to “weather” supposedly but the flights for other airlines left on time so it just have been some kind of weather that only affects JetBlue. I had a small carry on - purse. The crew stored it in a bin 2 rows down from me because they were using the bin next to my seat for other people’s stuff. The TV screen in the emergency row seats does not work. It just was awful from start to finish. When we landed, we had to sit inside the plane for a very long time because the plane had to be moved to a different gate.

Rude crew member. She seemed annoyed at me without me saying a single word. Also loudly admonished me for having my bag next to my seat instead of tucked away before landing. Just telling me to put it away and guiding me without giving me a lecture would have been enough.

I don’t usually fly budget airlines or airlines in the United States. It was as good as any other airline. The seats are comfortable and the airline attendants are not rude & surly. Very nice flight (s).

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports