$182 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 4/27. 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 Cana1 stop$533
Santo Domingo
Santo Domingo2 stops$619
Montego Bay
Montego Bay2 stops$397
Oranjestad
Oranjestad2 stops$687
Nassau
Nassau2 stops$540
Kingston
Kingston2 stops$799
Simpson Bay
Simpson Bay1 stop$760
Providenciales
Providenciales1 stop$471
Port of Spain
Port of Spain2 stops$799
Bridgetown
Bridgetown2 stops$837
George Town
George Town2 stops$527
Willemstad
Willemstad2 stops$852
Puerto Plata
Puerto Plata2 stops$733
St. John's
St. John's2 stops$935
Aguadilla
Aguadilla2 stops$1,386
Punta Cana
Punta Cana1 stop$533
Santo Domingo
Santo Domingo2 stops$619
Montego Bay
Montego Bay2 stops$397
Oranjestad
Oranjestad2 stops$687
Nassau
Nassau2 stops$540
Kingston
Kingston2 stops$799
Simpson Bay
Simpson Bay1 stop$760
Providenciales
Providenciales1 stop$471
Port of Spain
Port of Spain2 stops$799
Bridgetown
Bridgetown2 stops$837
George Town
George Town2 stops$527
Willemstad
Willemstad2 stops$852
Puerto Plata
Puerto Plata2 stops$733
St. John's
St. John's2 stops$935
Aguadilla
Aguadilla2 stops$1,386

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

Mon, May 4 - Thu, May 7
American Airlines Logo
6:00 am - 11:02 pm
SJC
-
SJU
14h 02m
1 stop
American Airlines Logo
11:59 pm - 10:10 am
SJU
-
SJC
13h 11m
1 stop
$366American Airlines
Thu, Jul 23 - Thu, Jul 30
Southwest Logo
9:20 am - 12:25 am
SJC
-
SJU
12h 05m
1 stop
Southwest Logo
5:30 am - 3:25 pm
SJU
-
SJC
12h 55m
1 stop
$396Southwest
Sat, May 2 - Sat, May 9
American Airlines Logo
12:46 pm - 9:13 am
SJC
-
MBJ
18h 27m
2 stops
American Airlines Logo
12:56 pm - 10:10 am
MBJ
-
SJC
23h 14m
2 stops
$397American Airlines
Sat, May 2 - Wed, May 6
Delta Logo
6:00 pm - 11:45 am
SJC
-
SJU
14h 45m
2 stops
Delta Logo
7:15 am - 7:07 pm
SJU
-
SJC
14h 52m
2 stops
$405Delta
Mon, May 4 - Thu, May 7
United Airlines Logo
6:19 pm - 12:34 pm
SJC
-
SJU
15h 15m
2 stops
United Airlines Logo
7:40 am - 5:23 pm
SJU
-
SJC
12h 43m
2 stops
$413United Airlines
Mon, Apr 13 - Thu, Apr 16
Delta Logo
11:00 pm - 1:25 pm
SJC
-
SJU
11h 25m
1 stop
Delta Logo
6:15 am - 11:42 pm
SJU
-
SJC
20h 27m
2 stops
$415Delta
Sun, Apr 12 - Sat, Apr 18
United Airlines Logo
8:45 am - 12:50 pm
SJC
-
MBJ
26h 05m
2 stops
United Airlines Logo
12:52 pm - 9:07 pm
MBJ
-
SJC
10h 15m
1 stop
$417United Airlines
Mon, Apr 20 - Wed, May 6
Alaska Airlines Logo
2:02 pm - 4:32 am
SJC
-
SJU
11h 30m
1 stop
Alaska Airlines Logo
11:59 pm - 10:10 am
SJU
-
SJC
13h 11m
1 stop
$439Alaska Airlines
Wed, May 13 - Sun, May 17
JetBlue Logo
10:00 pm - 2:10 pm
SJC
-
PLS
13h 10m
1 stop
JetBlue Logo
3:25 pm - 10:55 pm
PLS
-
SJC
10h 30m
1 stop
$617JetBlue
Mon, Jul 6 - Fri, Jul 10
JetBlue Logo
10:00 pm - 1:17 pm
SJC
-
SDQ
12h 17m
1 stop
JetBlue Logo
2:42 pm - 10:49 pm
SDQ
-
SJC
11h 07m
1 stop
$768JetBlue
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 $447, 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 January, when tickets cost $300 (return) on average. On the other hand, the most expensive months are December and October, when the average cost of round-trip tickets is $615 and $555 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 1 week before departure. For the absolute cheapest price, our data suggests you should book 18 weeks before departure.

Good to know

Low seasonFebruary
Cheapest flight$182
Best time to beat the crowds with an average 27% drop in price.
Most popular time to fly and prices are also 12% lower on average.
Flight from San Jose to Montego Bay

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 8314 reviews
7.8Entertainment
8.5Crew
7.9Comfort
7.2Food
8.1Boarding
Airline reviews

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.

10.0 ExcellentShirley, Mar 2026
LAX - ATL
Read more Delta reviews

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.

My flight was canceled on Sunday. Rebooking took three hours. Had to pay for accommodations another night. New flight was delayed for 5 hours, all that was sent was a 12 dollar food voucher, which doesn’t tell you how to use it. Then when we landed we had to sit on the plane for an hour before we could get off.

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.

Flight was delayed by 3-hours and their fix was… complimentary pretzels.

The crew, and fellow passengers, were super gracious and kind. There seemed to be plenty of bin space even though the plane was full. It’s nice to get a glass of wine with dinner in Premiere seating, and there was a lot of food.

Everything I mentioned earlier - the airbus was more comfortable indeed and the experience was further enhanced.

The plane was an older model, so it wasn’t as comfortable as others. The flight attendants were not helpful during onboarding. It was a full flight so there was chaos finding space for baggage.

Awesome! On time flight, early arrival, and a complimentary upgrade!

It was nt delta. It was aeromexo. Service was awful. They served a very small drink and NO snack for a 3hr and 35min flight. Then for the first 30 min of the flight is was talk and talk over head interruption the movie/ show i picked to watch.

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.

Terrible planning. And even worse gate agents. Absolutely rude behavior.

Flight was scheduled at 11:26am but they keep Delaying until midnight. They waited at airport restless.

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

Not good. One of my luggage is missing. And until now they can’t find it

My 9:50AM flight was delayed to 3:40PM "due to incoming aircraft delay". No aircraft is "delayed" that long. Found out once we did board (after several changes in times) that the aircraft had a maintenance issue and we had to wait for another aircraft. Just tell us that. The aircraft we did get was old and the seats need to be updated. I have been traveling for several weeks with AA and you should refresh your entertainment content as frequent flyers have gone through most of your new content. I have Celiac and a shellfish allergy and continue to have struggles with meals on business and first class flights. Please keep this in mind. Sorry - was a long travel day yesterday and a bit cranky this morning with my experience comments. Still an AA fan.

Delay after delay with little communication then AA lost my luggage and at airport would not assist just said scan this QR code to track your luggage and submit a claim. However QR code provided did not work so have to go back to airport

Dloght delayed by 2.5 hrs . Common theme in my last four american floghts

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

My seat was assigned last row behind restrooms No legroom’s I’m very Pettit Still was not comfortable Food choice was excellent

The worst Airline ever. They centered my second flight and leave me in NY. They don’t have any representatives at the airport and they don’t respond to calls. Basically I got stuck. I will never purchase through there again.

My flight was delayed by over an hour and the turbulance was horrible.

I was double booked for my ticket- they have record of it and admitted to their error but wouldn’t let me board until I paid once again for the fare- have documentation of their mistake -

I cannot effectively rate the food and drink as I had not. Otherwise, the trip was fine. The seats were nice, the crew was fine. They could smile once in a while. They all look like they were mad.

They cancelled the flight due to crew unavailability. The next day they cancelled the flight again.

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.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports