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

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Cheap Flights from San Jose to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Punta Cana
Punta Cana2 stops$621
Santo Domingo
Santo Domingo2 stops$855
Montego Bay
Montego Bay2 stops$492
Nassau
Nassau1 stop$566
Kingston
Kingston2 stops$915
Providenciales
Providenciales2 stops$635
Port of Spain
Port of Spain2 stops$730
Bridgetown
Bridgetown1 stop$871
George Town
George Town1 stop$670
Aguadilla
Aguadilla2 stops$870
Puerto Plata
Puerto Plata2 stops$928
Punta Cana
Punta Cana2 stops$621
Santo Domingo
Santo Domingo2 stops$855
Montego Bay
Montego Bay2 stops$492
Nassau
Nassau1 stop$566
Kingston
Kingston2 stops$915
Providenciales
Providenciales2 stops$635
Port of Spain
Port of Spain2 stops$730
Bridgetown
Bridgetown1 stop$871
George Town
George Town1 stop$670
Aguadilla
Aguadilla2 stops$870
Puerto Plata
Puerto Plata2 stops$928
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?

The cheapest month for flights from San Jose to Caribbean is January, when tickets cost $298 (return) on average. On the other hand, the most expensive months are November and December, when the average cost of round-trip tickets is $852 and $844 respectively.

Good to know

Low season

January

Cheapest flight

$187
Best time to beat the crowds with an average 58% drop in price.
Most popular time to fly with an average 12% increase in price.
Flight from San Jose to San Juan

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 13129 reviews
7.0Entertainment
8.1Boarding
8.5Crew
7.8Comfort
7.0Food
Airline reviews

The flight attendant for first class was excellent. Very attentive to the needs of the passengers The time scheduled for the connection flight on to Kona was too short and we missed that flight. But another flight was only an hour later. But it should have been scheduled that was in the first place.

10.0 ExcellentAnonymous, Sep 2026
Read more Alaska Airlines reviews

The flight attendant for first class was excellent. Very attentive to the needs of the passengers The time scheduled for the connection flight on to Kona was too short and we missed that flight. But another flight was only an hour later. But it should have been scheduled that was in the first place.

The problem was going through San Diego, a trip that's become a new development.

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.

Friendly crew. Snacks were carb-heavy. Flight was quite delaye

the flight was significantly delayed. Not much was done by the airline to compensate passengers

Despite paying for an ‘upgraded’ seat in row 1, I had to put my luggage in the middle of the plane. Snacks were bleh and seat was small and uncomfortable and I am not large. Attendants were fine but not super helpful. Plane just seemed outdated.

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

Rude staff from baggage check to gate crew. Poor instructions. Inconsistent application of baggage rules.

Requested an aisle seat at the gate and got it. The staff so friendly

Had to deplane 2 x due to problems with plane. Delayed over 6 hours ans was given a $12 food credit which barely oaud for anything and limited to wear incoukd redeem.

more room in seats, larger snacks, more comms with delays

Gate agent and flight attendants were efficient, but more stern than warm.

The only issue is that the plane was HOT. This was not the case on my first flight so not sure why, but thankfully I had a portable fan with me. Everything else was great!

Seemingly unnecessary delays were compounded by a lack of communication from the flight crew which turned a four hour delay into an overly stressful experience.

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

New Max 10, first class seats have been shrunk. End of a 20 hour journey, it was United not Lufthansa, just glad to get home

Seats are uncomfortable and left me in pain in my tailbone area. I got about one hour of sleep.

Delay of two hours due to some mechanical issue. Staff was wonderful and the pilot did let us know what was going on.

One of my checked luggage was damaged. Cracked on the top by the handle.

Not so good. Crew was not as attentive as they should have been especially if flying business class. Only offered dinner 2 hours after takeoff. My flight attendant seemed overwhelmed. Pushed my help button but no one came. I explained everything on my previous review.

I have been flying united for a long time but now I’m done

Delayed - leaving, delayed getting to the gate at destination. What should have been a very easy flight and experience was not.

Better management of the boarding process. Is there any way you could forward all the window seats first? That's the Way Reno Air used to do it, and they had the fastest boarding in the industry!

I understand stuff happens, but plane failures are likely due to lack of maintenance. Additionally, air conditioning wasn't working, no snack/drink service, no WiFi. Fortunately, the crew was communicative and light-hearted. United grabbed another plane and we were able to get to our destination.

A good, solid, no frills experience. Departed and arrived on time, staff were pleasant and attentive. Loved the Bluetooth connectivity on the SJC to IAH leg. Being able to watch movies and listen to them with my noise cancelling headphones was lovely. Missed that on the IAH to LHR leg (so I put the wired buds on and my over ear Quiet Comforts over those).

American Airlines was horrible! The layover flight to DFW was delayed with no clear communication and for us having to stay the whole day which led to staying a night in Dallas was comped with 2 $12 dollar vouchers and a crappy hotel. We missed a whole day in Tokyo for our honeymoon and stressed the whole 24 hours. We were supposed to leave at the same time the following day, but that was delayed hours again. And instead of letting the delayed flight go first, they let the flight that was scheduled ahead of us. American should refund us the day wasted in Dallas that should have been in Tokyo! We had lost out on paid events that we can’t get refunded. When we finally did leave, it was a good flight. You would think that was the only issue with American but we from the LAX layover, we were delayed 6 hours and were given a $12 dollar voucher that covered a drink only. The only communication we were given then was that because they were delayed in a prior flight we were delayed again. I don’t understand why it was only with American that we had such a bad time with! They have definitely left a sour taste in our mouths for our honeymoon! And then they did send an email saying we could have 2K miles…. For what? To be delayed into another day and miss our flight again?

The delay was not handled well and the offers to move flights and get travel credit was also not ideal.

The worst seat in any business class. Food are worst then economy class.

No food on 4.5 hour flight, wi-fi did not work. Terrible experience for a long haul flight.

first leg from san diego to chicago, only had cookies for snack. 1 flavor of sparkling water chicago to washington dc had option of cookies, pretzels, or gold fish. had 2 flavors of sparkling water. 2nd flight better however the best part was there was no delays!!! Got to chicago and washington dc early. That was wonderful!!!!

Multiple delays and made us miss the connecting flight and lost our bags

Business class flight attendant was very good. But our flight was delayed two hours for a “mechanical” bathroom issue that literally took 5 minutes to fix. Our plane landed early from its previous flight but still waited for a mechanic to show up to fix an obvious minor issue for almost three hours. This caused us to miss our connecting flight. They put us up in a Days Inn that was 17 miles away from the airport that took a half hour of driving just to get to and this was at 11pm at night. Then when we finally got back on a plane after a full day delay they left our luggage back in the airport. This was an international flight, so no luggage or belongings after flying 8 hours to a different country. We will NEVER fly American Airlines again.

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.

More options for your flight to Caribbean

Complete your trip to Caribbean with a hotel stay or car rental