$138 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 1/26. 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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 23% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
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$578
Santo Domingo
Santo Domingo2 stops$592
Montego Bay
Montego Bay1 stop$587
Oranjestad
Oranjestad2 stops$572
Nassau
Nassau1 stop$425
Kingston
Kingston2 stops$768
Simpson Bay
Simpson Bay2 stops$808
Providenciales
Providenciales1 stop$693
Port of Spain
Port of Spain2 stops$729
Bridgetown
Bridgetown1 stop$638
George Town
George Town1 stop$552
Willemstad
Willemstad2 stops$794
Puerto Plata
Puerto Plata2 stops$600
Aguadilla
Aguadilla2 stops$610
Punta Cana
Punta Cana2 stops$578
Santo Domingo
Santo Domingo2 stops$592
Montego Bay
Montego Bay1 stop$587
Oranjestad
Oranjestad2 stops$572
Nassau
Nassau1 stop$425
Kingston
Kingston2 stops$768
Simpson Bay
Simpson Bay2 stops$808
Providenciales
Providenciales1 stop$693
Port of Spain
Port of Spain2 stops$729
Bridgetown
Bridgetown1 stop$638
George Town
George Town1 stop$552
Willemstad
Willemstad2 stops$794
Puerto Plata
Puerto Plata2 stops$600
Aguadilla
Aguadilla2 stops$610

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

Wed, Dec 31 - Mon, Jan 12
American Airlines Logo
9:56 am - 9:35 amSJC-SJU
19h 39m2 stops
American Airlines Logo
4:28 pm - 12:10 pmSJU-SJC
23h 42m2 stops
$351American Airlines
Find Deal
Tue, Dec 2 - Tue, Dec 9
Southwest Logo
10:05 am - 12:35 amSJC-SJU
10h 30m2 stops
Southwest Logo
8:55 am - 5:20 pmSJU-SJC
12h 25m2 stops
$380Southwest
Find Deal
Wed, Dec 31 - Tue, Jan 13
Delta Logo
6:35 am - 11:20 pmSJC-SJU
12h 45m1 stop
Delta Logo
7:00 am - 4:20 pmSJU-SJC
13h 20m2 stops
$425Delta
Find Deal
Tue, Mar 3 - Thu, Mar 5
Delta Logo
10:30 pm - 1:30 pmSJC-NAS
12h 00m1 stop
Delta Logo
2:55 pm - 9:32 pmNAS-SJC
9h 37m1 stop
$425Delta
Find Deal
Sat, Nov 15 - Tue, Nov 18
United Airlines Logo
6:30 am - 12:36 amSJC-SJU
14h 06m2 stops
United Airlines Logo
2:05 am - 1:42 pmSJU-SJC
15h 37m2 stops
$490United Airlines
Find Deal
Mon, Nov 17 - Wed, Nov 19
United Airlines Logo
6:30 am - 12:36 amSJC-SJU
14h 06m2 stops
United Airlines Logo
7:45 am - 5:38 pmSJU-SJC
13h 53m2 stops
$557United Airlines
Find Deal
Sun, Jan 4 - Sun, Jan 11
Frontier Logo
3:27 pm - 5:54 pmSJC-SJU
22h 27m2 stops
Frontier Logo
3:55 am - 5:55 pmSJU-SJC
18h 00m2 stops
$569Frontier
Find Deal
Mon, Nov 10 - Wed, Nov 12
Alaska Airlines Logo
6:00 am - 9:35 pmSJC-SJU
11h 35m1 stop
Alaska Airlines Logo
7:15 am - 4:43 pmSJU-SJC
13h 28m1 stop
$613Alaska Airlines
Find Deal
Tue, Jan 13 - Tue, Jan 20
Alaska Airlines Logo
6:00 am - 10:26 pmSJC-SJU
12h 26m1 stop
Alaska Airlines Logo
7:07 am - 1:42 pmSJU-SJC
10h 35m1 stop
$633Alaska Airlines
Find Deal
Mon, Nov 24 - Mon, Dec 1
Frontier Logo
4:40 pm - 11:38 amSJC-SJU
14h 58m2 stops
Frontier Logo
6:01 am - 3:55 pmSJU-SJC
13h 54m2 stops
$737Frontier
Find Deal
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 $458, 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 $602 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 3 weeks before departure, which saves you about 11% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 18 weeks before departure.

Good to know

Low seasonMay
Cheapest flight$138
Best time to beat the crowds with an average 27% drop in price.
Most popular time to fly with an average 9% 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.

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 7993 reviews
7.9Comfort
7.9Entertainment
7.3Food
8.2Boarding
8.5Crew
Airline reviews

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.

8.0 ExcellentJulie, Oct 2025LAX - SFO
Read more Delta reviews

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.

My husband upgraded our seats and I don't know if it was due to the type of planet was or if they didn't upgrade our seats. We were supposed to be in I believe comfort seats and they were just as tight as any other seat- no leg room and we are very tall people but at least it wasn't extremely cold. My husband did put in a complaint about our seating because he paid extra and if we would have known that the space and the tightness would have been the same, we just would have gotten the emergency row emergency row seats that we normally get. We love Delta but both our flights coming home we're not good. Oh I forgot to mention that on our flight to Hawaii our luggage wheels got broke and we had to purse new luggage on vacation then we never had this problem so we didn't know protocol and reported it after we got home only for them to tell is we only had 24hrs to report the damage. Not sure what was going on with Delta this vacation trip.

Crew was excellent. Comfort seats not as nice as other kinds of planes.

It was a great flight and the stewards and stewardess were all kind and accommodating!! The seats were comfortable and entertainment screen excellent!

There are 4 flights in consecutive gates with about the same departure time. Two flights were boarding at the same time. One was delayed or boarding would be happening at the same time. I am not sure what Delta and LAX need to do to have a better layout at the end of Terminal 2

There was a security issue at the airport and we were unable to land. We circled endlessly and then landed at another airfield for fuel. We then circled the airport again, almost landed but didn’t fully touch down before circling again. I am thankful to the crew for keeping us safe- the issue was the airline and staff at the airport getting us seats on our connecting flights. That part was hours of searching for someone and getting in double my steps.

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.

The flight was flawless and we even arrived between 20 and 25 minutes early!

Always seated jammed in rear of aircraft Admirals Club food at DFW terminal D was absolute worst food experience and I pay $600/year to eat this dried out junk

Mostly good. Flight was crowded but Airline personnel were very friendly & accommodating. It would be good to have savory snacks rather than just sweet Biscoff cookies.

It was a red eye flight, so no meals were provided, but it was fine with snacks. The seats felt cramped and almost too narrow.

Very crowded flight but what can you expect these days?? Crew was accommodating.

The seats in economy were appeared to be quite thin and lack sufficient cushioning to be comfortable. Perhaps it was my seating position but the plane seemed notably load.

The entertainment package was vast and the selections were very current. Keep updating it was great.

The seat was so hard my tailbone was aching The crew was kind of a b**** because I made a joke that I didn't care if they close the door I total c*** when she was trying to f****** act like she was mad at me because I said that The flight was bumpy. Sure you didnt have control over that.

4 hours late, including over +1 hour waiting in plane to take off. Baggage left behind too.

While waiting to claim my checked luggage, I discovered the airline had lost it. After a long wait and inquiries, I discovered it was on another flight. Fortunately, the airline finally sent my luggage home.

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.

Flight was cancelled without warning close to flight date. Stuck witha credit has to buy a new ticket from another airline in either to get to location. Email cancelling was lost in mail.

Spirit Airlines was ok but TRAVELHELPDESK, the 3rd party travel agent IS A JOKE! VERY RUDE CUSTOMER AGENTS ont he phone. NO HELP AT ALL. But the airlines was ok.

No frills - because you get what you pay for. The crew was amazing!! I had plenty of room to spread out because the flight was half full. Which made it easy to sleep.

The staff was very very rude in Las Vegas when boarding the flight. When presenting the boarding ticket. Las Vegas flight, it was hot and stuffy, it smelled really bad.

Dear All, I have harassment and accident with the flight attendant . This is my phone to talk 8168073567, please, leave phone message . Regards Emily,

Flight was on time but the amount of noise from several children and the kicking of my seat the entire flight was overwhelming.

Unbelievable check in horrible. Asked to print tickets at the gate after a delay

check in at security was a hassle being scanned. Spirit employees were helpful and professional.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.