$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 2/23. 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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Flight Deals

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$493
Santo Domingo
Santo Domingo1 stop$571
Montego Bay
Montego Bay1 stop$512
Oranjestad
Oranjestad2 stops$589
Nassau
Nassau1 stop$444
Kingston
Kingston1 stop$724
Simpson Bay
Simpson Bay2 stops$790
Providenciales
Providenciales1 stop$546
Port of Spain
Port of Spain2 stops$619
Bridgetown
Bridgetown2 stops$1,084
George Town
George Town2 stops$555
Willemstad
Willemstad2 stops$1,179
St. John's
St. John's2 stops$887
Puerto Plata
Puerto Plata2 stops$848
Aguadilla
Aguadilla2 stops$1,504
Punta Cana
Punta Cana2 stops$493
Santo Domingo
Santo Domingo1 stop$571
Montego Bay
Montego Bay1 stop$512
Oranjestad
Oranjestad2 stops$589
Nassau
Nassau1 stop$444
Kingston
Kingston1 stop$724
Simpson Bay
Simpson Bay2 stops$790
Providenciales
Providenciales1 stop$546
Port of Spain
Port of Spain2 stops$619
Bridgetown
Bridgetown2 stops$1,084
George Town
George Town2 stops$555
Willemstad
Willemstad2 stops$1,179
St. John's
St. John's2 stops$887
Puerto Plata
Puerto Plata2 stops$848
Aguadilla
Aguadilla2 stops$1,504

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, Mar 3 - Tue, Mar 10
Delta Logo
10:35 pm - 1:01 pm
SJC
-
SJU
10h 26m
1 stop
Delta Logo
7:30 am - 7:41 pm
SJU
-
SJC
15h 11m
2 stops
$296Delta
Tue, Apr 14 - Tue, Apr 21
Southwest Logo
9:40 pm - 1:10 pm
SJC
-
SJU
12h 30m
1 stop
Southwest Logo
11:25 am - 9:05 pm
SJU
-
SJC
12h 40m
2 stops
$351Southwest
Sat, Feb 21 - Wed, Feb 25
Delta Logo
10:35 pm - 1:01 pm
SJC
-
SJU
10h 26m
1 stop
Delta Logo
2:12 pm - 9:18 pm
SJU
-
SJC
11h 06m
1 stop
$360Delta
Tue, Mar 3 - Wed, Mar 11
Alaska Airlines Logo
6:00 am - 11:31 pm
SJC
-
SJU
13h 31m
1 stop
Alaska Airlines Logo
6:33 am - 9:21 pm
SJU
-
SJC
17h 48m
1 stop
$378Alaska Airlines
Mon, Feb 23 - Thu, Feb 26
American Airlines Logo
6:00 am - 11:31 pm
SJC
-
SJU
13h 31m
1 stop
American Airlines Logo
7:33 am - 3:50 pm
SJU
-
SJC
12h 17m
2 stops
$399American Airlines
Sun, Mar 15 - Wed, Mar 18
United Airlines Logo
10:55 pm - 3:22 pm
SJC
-
NAS
13h 27m
1 stop
United Airlines Logo
1:05 pm - 10:59 pm
NAS
-
SJC
12h 54m
2 stops
$450United Airlines
Sun, Mar 15 - Wed, Mar 18
United Airlines Logo
3:49 pm - 3:22 pm
SJC
-
NAS
20h 33m
2 stops
United Airlines Logo
1:05 pm - 10:59 pm
NAS
-
SJC
12h 54m
2 stops
$475United Airlines
Mon, Feb 23 - Mon, Mar 2
American Airlines Logo
4:20 pm - 9:33 am
SJC
-
NAS
14h 13m
2 stops
American Airlines Logo
3:47 pm - 10:11 am
NAS
-
SJC
21h 24m
1 stop
$487American Airlines
Mon, Feb 23 - Thu, Feb 26
Multiple Airlines Logo
11:30 am - 5:59 am
SJC
-
SDQ
14h 29m
2 stops
Multiple Airlines Logo
12:20 pm - 2:48 pm
SDQ
-
SJC
30h 28m
3 stops
$756Multiple Airlines
Wed, Mar 18 - Wed, Mar 25
Multiple Airlines Logo
11:30 am - 4:50 pm
SJC
-
SDQ
26h 20m
3 stops
Multiple Airlines Logo
7:49 pm - 3:48 pm
SDQ
-
SJC
22h 59m
2 stops
$770Multiple Airlines
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 $436, 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 $319 (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.

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 3 weeks before departure, which saves you about 23% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 18 weeks before departure.

Good to know

Low seasonOctober
Cheapest flight$133
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly and prices are also 3% 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 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.
7.9
DeltaOverall score based on 8138 reviews
8.5Crew
8.1Boarding
7.9Comfort
7.2Food
7.8Entertainment
Airline reviews

Delta One is extraordinary. I fly business when somebody hires me. I just wonder why there is such a chasm between business class and the insanely inhumane and nonsensical coach. The seats are not large enough to fit even my tiny wife. We fly 10% of what we did because we don’t want to pay 5-10 k but for $400 it’s unbearable. It seems like the accountants took over and made stupid decisions. Screw in 20 extra seats and make it so unbearable that people fly 90% less. Just put the damn price up and put some proper chairs in. But business, yay.

10.0 ExcellentDr. Simon, Jan 2026
LAX - JFK
Read more Delta reviews

Delta One is extraordinary. I fly business when somebody hires me. I just wonder why there is such a chasm between business class and the insanely inhumane and nonsensical coach. The seats are not large enough to fit even my tiny wife. We fly 10% of what we did because we don’t want to pay 5-10 k but for $400 it’s unbearable. It seems like the accountants took over and made stupid decisions. Screw in 20 extra seats and make it so unbearable that people fly 90% less. Just put the damn price up and put some proper chairs in. But business, yay.

Delta’s staff is unmatched. From the gate agents, to the pilots, to the flight attendants… all top of the industry.

The flight was delayed for about 2 hrs. Other than it, it was good.

I am extremely disappointed that delta internal pilot manuals now refer to the Gulf of Mexico as the “gulf of America”. You can bow down to the Orange turd on your own. I will never fly delta again

No lunch on a x-country flight scheduled for 10:50 am departure, arrived 5+ hrs later. That requires a black box label before you pay for the tickets. Worst, when I checked in online, it's specifically said that lunch was served on his flight for economy Plus passengers.

Our flight from SFO to MSP was right on time on 11/15/2025. No delays. As we approached MSP at about 8 pm, we circled in the air until 8:40 pm so I don't call that efficient for MSP. I think the captain should announce the delay and why. (as if we all don't know that we are just circling around the area, slowing down, speeding up, slowing down.) Thank you. Marilyn Fischer

Staff were friendly and happy. Delta could make sure passengers that don't have the app know of changes. Without Kayak I would not have known about the change of gate or the delay. Kayak was faster to notify me.

The flight used a B767 with a very old interior from before 2014. The entertainment system did not work at all during the flight despite attempts to reset the system. It was like they flew this route just to be competitive.

Delayed flight (1hour) plus a long layover after an overnight flight with no backup plane available.

Flight delayed for two and half hours and then canceled altogether due to mechanical issues. No mechanic onsite to fix so had to send one from LAX.

It would be nice to have some low carb options in the snacks.

The entertainment options were at best, fair. It was exactly the same as my outbound flight. It would have been more entertaining if there were some series from Apple TV, HBO, Showtime or other carriers for me to catch up with.

The flight was on time and arrived early. The crew were friendly and helpful.

While I didn’t watch much tv I would have liked a few more options of TV series from Apple TV or hbo max ..

Overall experience was great. Flights were almost on time in departing and we arrived at our destination as scheduled. No issues with amenities or flight crew. Everything went well as as expected. Will fly again with American Airlines in the future!

The flight was very smooth and the meal in business class was great.

I requested a low sodium meal. Reason being, I take medicine for high blood pressure and I wear compression socks on long flights to help with leg swelling. Having less sodium in meals really helps me feel better on long flights. I received my initial low sodium meal after takeoff. Just before landing, the crew came through with the meal cart and offered me what was being served. I said no thank you and then noticed my low sodium meal in the meal cart, with my name and seat assignment on it. I motioned to the crew member, but he grabbed the meal cart and proceeded to move to the rear of the aircraft. He didn’t see me or other passengers who had attempted to get this attention. He was more concerned about completing meal service since we were due to land in under 45 minutes. I pressed the call light five times from my seat to receive help, but no crew member responded to me. So, I didn’t receive a second meal, one that I requested (the low sodium option). This led me to have a migraine from only eating one meal on an 11-hour flight. This is why I’m not a fan of flying US-based airlines overseas. The crew members continue to show the absolute worst customer service experience. I would not recommend flying American for overseas flights.

Not great. Booked Extra seats and got nothing extra at all. It’s basically a big budget airline.

Horrible. Both legs of my flight were delayed more than 6 hours. No compensation, no screens on the plane, and the plane was not clean.

The flight was smooth, the pilot kept us informed about delays and we arrived more of less on time

For the price of the fare, there really isn’t much to complain about.

A Spirit agent caused me to miss my flight. The company has not responded for request of refund. Stay away from Spirit.

I arrived two hours early, and at 9:20 I was still queuing for security.

Got to LAX at 3:20 am, the counter personnel did not start to check in bags till 3:40 am. I patiently waited at the priority check in line as they started to take people from the general line. After about 15 minutes of waiting, I approached the lady exactly in front of the priority line and asked her if they would be taking people from the priority line or if I would need to switch to waiting in the general line. She responded “yes”, I then asked her yes to what? And she yelled back at me loudly “I SAID YES!” Needless to say, I waited at the end of the line of the general line. I could have been told the priority line would not be called upon and could have queued in the general line ahead of many people that arrived to cue after I did

Terrible they canceled the flight very sheepishly and ended up costing me 1200 dollars and kayak and xcover are doing nothing

No free snacks or drinks. Freezing. Uncomfortable. No plugs or entertainment. If you fly to LA the make you change terminals with a slow bus. Awful trip that took forever. Terrible airline- maybe the worst I’ve ever flown.

Crew are always very angry and dismissive like they seem they are being forced to work. In addition, there was a long line for the bathrooms, and only one was allowed to be used. No reason was given for only one bathroom being available; apparently, the stewardess was more interested in using the jumpseat instead of allowing the customers to use the bathroom.

No leg room. My knee was sore for a day.

Vegas is such a quick flight that amenities aren’t the important part, in my opinion. Just get me there efficiently and safely, and that’s exactly what they did!

The flight was severely delayed due to the missing flight attendants.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports