$133 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 8/17. 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

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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Flights Deals

Best Caribbean Islands Flight Deals from San Jose

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana2 stops$452
Santo Domingo
Santo Domingo2 stops$558
Montego Bay
Montego Bay2 stops$482
Oranjestad
Oranjestad2 stops$512
Nassau
Nassau1 stop$425
Kingston
Kingston2 stops$521
Simpson Bay
Simpson Bay2 stops$542
Providenciales
Providenciales1 stop$576
Port of Spain
Port of Spain2 stops$717
Bridgetown
Bridgetown2 stops$836
George Town
George Town1 stop$632
Willemstad
Willemstad2 stops$1,523
St. John's
St. John's2 stops$2,215
Aguadilla
Aguadilla2 stops$1,112
Punta Cana
Punta Cana2 stops$452
Santo Domingo
Santo Domingo2 stops$558
Montego Bay
Montego Bay2 stops$482
Oranjestad
Oranjestad2 stops$512
Nassau
Nassau1 stop$425
Kingston
Kingston2 stops$521
Simpson Bay
Simpson Bay2 stops$542
Providenciales
Providenciales1 stop$576
Port of Spain
Port of Spain2 stops$717
Bridgetown
Bridgetown2 stops$836
George Town
George Town1 stop$632
Willemstad
Willemstad2 stops$1,523
St. John's
St. John's2 stops$2,215
Aguadilla
Aguadilla2 stops$1,112

Cheap Flights from San Jose to Caribbean Islands

 
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

Sun, Aug 31 - Sat, Sep 6
Delta Logo
3:17 pm - 1:10 pmSJC-SJU
18h 53m2 stops
Delta Logo
7:30 am - 5:04 pmSJU-SJC
12h 34m2 stops
$265Delta
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Wed, Sep 24 - Tue, Sep 30
American Airlines Logo
2:08 pm - 2:53 pmSJC-SJU
21h 45m2 stops
American Airlines Logo
6:10 am - 10:43 pmSJU-SJC
19h 33m2 stops
$267American Airlines
Find Deal
Mon, Sep 1 - Sat, Sep 6
Delta Logo
6:30 am - 10:07 pmSJC-SJU
12h 37m1 stop
Delta Logo
7:30 am - 7:13 pmSJU-SJC
14h 43m2 stops
$315Delta
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Tue, Jul 1 - Sat, Jul 12
Spirit Airlines Logo
11:01 am - 7:19 pmSJC-SJU
29h 18m2 stops
Spirit Airlines Logo
6:12 pm - 12:05 pmSJU-SJC
20h 53m1 stop
$337Spirit Airlines
Find Deal
Fri, Jul 11 - Wed, Jul 16
Spirit Airlines Logo
6:30 am - 11:32 amSJC-SJU
26h 02m2 stops
Spirit Airlines Logo
1:21 am - 12:05 pmSJU-SJC
13h 44m2 stops
$344Spirit Airlines
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Tue, Jul 29 - Tue, Aug 5
American Airlines Logo
6:00 am - 5:25 pmSJC-NAS
8h 25m1 stop
American Airlines Logo
6:30 pm - 12:19 pmNAS-SJC
20h 49m1 stop
$435American Airlines
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Mon, Jul 7 - Sat, Jul 19
United Airlines Logo
2:31 pm - 3:10 pmSJC-MBJ
22h 39m2 stops
United Airlines Logo
12:52 pm - 8:53 pmMBJ-SJC
10h 01m1 stop
$515United Airlines
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Fri, Sep 26 - Mon, Sep 29
United Airlines Logo
3:55 pm - 1:50 pmSJC-NAS
18h 55m2 stops
United Airlines Logo
2:33 pm - 9:52 amNAS-SJC
22h 19m2 stops
$538United Airlines
Find Deal
Thu, Aug 21 - Mon, Aug 25
Southwest Logo
8:55 pm - 12:40 pmSJC-SJU
12h 45m1 stop
Southwest Logo
5:00 am - 7:20 pmSJU-SJC
17h 20m2 stops
$565Southwest
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Thu, Jul 24 - Tue, Jul 29
Southwest Logo
7:40 am - 11:05 pmSJC-SJU
12h 25m2 stops
Southwest Logo
6:30 am - 5:00 pmSJU-SJC
13h 30m1 stop
$605Southwest
Find Deal
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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 $848, 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 September, when tickets cost $394 (return) on average. On the other hand, the most expensive months are June and December, when the average cost of round-trip tickets is $633 and $615 respectively.

What’s the cheapest day of the week to fly from San Jose to Caribbean Islands?

The average price of all round-trip flights from San Jose to Caribbean Islands clicked on KAYAK for each day over the last 12 months.

Your flight ticket price will generally be cheaper if you fly to Caribbean Islands on a Sunday and more expensive on a Friday. On your return trip to San Jose, you should consider flying back on a Wednesday, and avoid Sundays for better deals.

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

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 Islands, 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 Islands, you should book around 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 7 weeks before departure.


Good to know

Low seasonMay
High seasonJuly
Cheapest flight$133
Best time to beat the crowds with an average 25% drop in price.
Most popular time to fly with an average 1% increase in price.
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.

  • What is the cheapest time of day to fly to Caribbean Islands?

    The cheapest time of day to fly to Caribbean Islands is generally in the afternoon, when round-trip flights cost $487 on average. Morning departures are around 4% cheaper than evening flights, on average. The most expensive time of day to fly to Caribbean Islands is generally in the evening, which is peak travel time and where the average cost of a ticket is $597.

Top 3 airlines serving 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.
8.0
DeltaOverall score based on 7963 reviews
7.9Entertainment
8.2Boarding
7.9Comfort
8.5Crew
7.3Food
Airline reviews

Most aspects were good however if they assign boarding zones they ought to enforce them or why bother? My luggage from SAN-JFK-MAD was lost in NY so I without my main bag for two days upon arrival in Spain. They were helpful in tracking it and eventually delivered it to my hotel. The flub was because of a delay upon arrival in NYC. I had booked 2 1/2 hours between flights but we had to hold on the taxiway for an hour after landing while waiting for a clear gate which likely caused the baggage error.

8.0 ExcellentMathew, Jun 2025SAN - JFK
Read more Delta reviews

Most aspects were good however if they assign boarding zones they ought to enforce them or why bother? My luggage from SAN-JFK-MAD was lost in NY so I without my main bag for two days upon arrival in Spain. They were helpful in tracking it and eventually delivered it to my hotel. The flub was because of a delay upon arrival in NYC. I had booked 2 1/2 hours between flights but we had to hold on the taxiway for an hour after landing while waiting for a clear gate which likely caused the baggage error.

Excellent flight, the planes were newer, they did a nice job with boarding, great service overall.

It would be nice if was given wires ear buds. Overall was a good experience was able to sleep on the plane

737-800 in first class was pretty dumpy. Seat had an uncomfortable angle, storage under the seat was blocked so even my very modest backpack didn't fit, power outlet was flaky. Weird tiny seat pockets that couldn't hold a gallon ziploc bag, emesis bag missing, etc. etc. No in-flight service due to turbulence. Crew was excellent, boarding was smooth despite a full flight.

Delta flight was on time, seats were comfortable, and crew was nice.

Bathrooms dirty sinks clogged. No one seemed to clean them. Plane very old

Thank you for not flipping the plane on the run way. You guys get a 5 star rating for the flight!!!

Boarding is, as it always is… horrible. Gate lice. Slow moving zones. Too many people with carry ons

It was terrible, if they ran flights on time it would make a big difference.

Delta seems to be improving in many areas, except they are super bad with the food available. Bring back normal food service on long flights.

The chair cushions may need an upgrade. I have been noticing they are so worn out, thin so you’d sit in a dip 😄. Other than that, all was an enjoyable trip. Thanks AA!

Cramped seats. FAA should make airlines have more legroom, for even short people complain

Flight was full, and would have preferred an aisle seat, but due to getting a late ticket ,the seat I had was adequate. The flight crew were very help full and hard working. Food and drink were excellent for the 11hr flight. Overall I was pleased with flight, and would recommend British Airways again.

Eventless. It was a good flight and good crew. Can’t complaint.

Very helpful ground crew after an earlier flight delay and being rebooked on a different flight.

British Airways staff are very polite and willing to help.

The plane was late and then sat on the runway for almost 45 minutes before taking off.

We kept being told that the flight was full and that all overhead compartments were full and therefore had to check in our hand luggage. We were some of the last people to board and noticed that there was still sufficient space in the overhead compartments. We were obliged to check in hand luggage when there was space and so had to wait at luggage retrieval which took a while to then noticed damage to our luggage - not a great experience!

Worst seats I’ve ever had !!! The seats were very narrow and uncomfortable and misaligned with the seats in front of mine leading to bottom of the seat in front of mine pressing on my legs for 15.5 hours !

This was an overnight flight. There was no meal service in first class, just a simple snack basket was offered along with beverages. There should have been some type of continental breakfast prior to arrival in PHL. As an Executive Platinum American Airlines Advantage member, I received no name recognition from the first class flight attendant. When disembarking at PHL, the flight attendants were more interested in their cell phones than saying "thank you" to the passengers as they disembarked.

Good experience except for the drunk woman who was with a child. Sad

Too many time late and postponed No electrical power for my electric devices

Spirit is by far the worst airline to travel with, period. Seats are cardboard, flight attendants need anger management and if you ask for water, you’re basically a criminal. I don’t care how much it costs but I will travel with an airline who actually cares about their customers. Oh and one more thing, the next time your gate agent puts his foot on someone’s baggage's scale, I hope they get what’s coming next, a viral video of your scams. You suck Spirit, do better.

I mean, it’s Spirit. But it was frustrating to have our flight canceled, get bumped to a later flight, and then Spirit was unwilling to check our bag until 4 hours before our flight… tell us we could not sit in the waiting area’s chairs… and really negative experience getting checked in and dropping the bag.

terrible service, no room for a dog underfoot, a broken chair that is impossible to sit on and all this costs a lot of money

It was fast but uncomfortable seats. Had to pay a bit extra not sure why? Maybe in selection of all my 4 tix together ? Just knew I had a balance before getting boarding pass online when departing from satx ? And flight was delayed..

Last minute 2-3 hr delay in flight schedule; no explanation Unexpected extra $52 charge What's the benefit of choosing a cheap airline if you trick people last minute and force them to pay extra last minute? Did not appreciate being cornered.

Seats are uncomfortable and too close together. Also, you missed my connection in Vegas on the way back and I ended up sleeping in the airport, flying back to Burbank instead of LAX and I got home 12 hours late.

Surprising everything went well. Nice attendants and fast getting on and off the plane. Overall, was happy with the experience.

Non-professional acting crew, Very uncomfortable seats…!! Very bad pricing with all the add-ons for seat choice, luggage fees, etc….soon you’ll charge extra for oxygen. The ticket price means Nothing because in the end, the actual amount i paid, i could have and will in the future continue to fly on a real airline…

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports

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