$158 Find Cheap Flights from San José 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 José to Caribbean Islands departing on 7/21. 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 José 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 José to Caribbean Islands, as well as popular online travel agencies
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Flight Deals

Cheap Flights from San José to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$469
Santo Domingo
Santo Domingononstop$281
Montego Bay
Montego Bay1 stop$699
Oranjestad
Oranjestad1 stop$456
Nassau
Nassau1 stop$427
Kingston
Kingston1 stop$749
Willemstad
Willemstad2 stops$380
Punta Cana
Punta Cana1 stop$469
Santo Domingo
Santo Domingononstop$281
Montego Bay
Montego Bay1 stop$699
Oranjestad
Oranjestad1 stop$456
Nassau
Nassau1 stop$427
Kingston
Kingston1 stop$749
Willemstad
Willemstad2 stops$380

Book Cheap San José 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 José 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 José to Caribbean Islands

Sat, Sep 5 - Sat, Sep 12
Arajet Logo
5:48 pm - 10:52 pm
SJO
-
SDQ
3h 04mnonstop
Arajet Logo
4:00 pm - 5:03 pm
SDQ
-
SJO
3h 03mnonstop
$281Arajet
Wed, Jul 15 - Sat, Jul 25
Arajet Logo
11:23 am - 4:27 pm
SJO
-
SDQ
3h 04mnonstop
Arajet Logo
6:00 pm - 7:03 pm
SDQ
-
SJO
3h 03mnonstop
$285Arajet
Tue, Jun 16 - Tue, Jun 23
Arajet Logo
7:48 pm - 12:52 am
SJO
-
SDQ
3h 04mnonstop
Arajet Logo
6:00 pm - 7:03 pm
SDQ
-
SJO
3h 03mnonstop
$286Arajet
Wed, Jul 15 - Tue, Jul 21
Copa Airlines Logo
10:03 am - 2:25 am
SJO
-
SDQ
14h 22m
1 stop
Copa Airlines Logo
6:42 pm - 8:21 am
SDQ
-
SJO
15h 39m
1 stop
$293Copa Airlines
Tue, May 26 - Sun, Jun 7
Copa Airlines Logo
8:14 am - 4:09 pm
SJO
-
SJU
5h 55m
1 stop
Copa Airlines Logo
6:17 pm - 8:21 am
SJU
-
SJO
16h 04m
1 stop
$306Copa Airlines
Sat, Aug 1 - Sat, Aug 8
Frontier Logo
9:35 am - 11:29 pm
SJO
-
SJU
11h 54m
1 stop
Frontier Logo
3:06 am - 8:20 am
SJU
-
SJO
7h 14m
1 stop
$308Frontier
Tue, Jun 9 - Tue, Jun 16
Avianca Logo
1:50 am - 10:45 am
SJO
-
AUA
6h 55m
1 stop
Avianca Logo
5:20 pm - 11:55 pm
AUA
-
SJO
8h 35m
1 stop
$456Avianca
Mon, May 25 - Tue, Jun 2
Avianca Logo
1:50 am - 5:00 pm
SJO
-
CUR
13h 10m
1 stop
Avianca Logo
11:35 am - 11:55 pm
CUR
-
SJO
14h 20m
1 stop
$456Avianca
Wed, May 6 - Fri, May 8
American Airlines Logo
6:30 am - 11:51 am
SJO
-
MBJ
52h 21m
1 stop
American Airlines Logo
4:37 pm - 11:07 am
MBJ
-
SJO
19h 30m
1 stop
$699American Airlines
Mon, Jun 15 - Mon, Jun 22
American Airlines Logo
6:01 am - 1:50 pm
SJO
-
SXM
29h 49m
2 stops
American Airlines Logo
2:53 pm - 11:49 am
SXM
-
SJO
22h 56m
2 stops
$721American Airlines
Booking Insights

KAYAK's insights & trends for San José to Caribbean Islands flights

Get data-powered insights and trends into flights from San José to Caribbean Islands to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest San José to Caribbean Islands flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Caribbean Islands from San José found in the last 72 hours was to Santo Domingo, at $201 round-trip. The most popular route is from San José (SJO) to Santo Domingo (SDQ), and the cheapest round-trip airline ticket found on this route in the last 72 hours was $201.

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

The average price for all round-trip flights from San José to Caribbean Islands depending on the time of departure, clicked by users on KAYAK in the last 2 weeks.

The cheapest time of day to fly to Caribbean Islands is generally in the morning, when round-trip flights cost $231 on average. The most expensive time of day to fly to Caribbean Islands is generally in the morning, which is peak travel time and where the average cost of a ticket is $231.

Can I save money by flying with a layover from San José 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 $421, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from San José 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 José 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 José to Caribbean Islands is May, when tickets cost $297 (return) on average. On the other hand, the most expensive months are July and March, when the average cost of round-trip tickets is $418 and $409 respectively.

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

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

If your flying dates are flexible, you should consider flying to Caribbean Islands on a Monday, as we generally find the cheapest rates on that day for this route. On the other hand, Monday is the most expensive day to fly from San José to Caribbean Islands. For your return ticket, we recommend flying on a Thursday and avoiding Mondays for the best deals.

How far in advance should I book a flight from San José 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 José 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 José to Caribbean Islands, you should book around 4 weeks before departure, which saves you about 17% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 11 weeks before departure.

Good to know

Low seasonNovember
Cheapest flight$158
Best time to beat the crowds with an average 3% drop in price.
Most popular time to fly and prices are also 2% lower on average.
Flight from San José to Santo Domingo

FAQs - booking Caribbean Islands flights

  • How does KAYAK find such low prices on flights from San José 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 José to Caribbean Islands.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from San José to Caribbean Islands?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from San José 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 José 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 José 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 José 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 José 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 4 airlines serving from San José to Caribbean Islands

 
See real verified KAYAK customer reviews for airlines flying from San José 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 José 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.
7.5
Copa AirlinesOverall score based on 1578 reviews
7.8Boarding
7.4Comfort
6.8Entertainment
6.8Food
8.1Crew
Airline reviews

Friendly crew, good food options, food not the best and seats not as comfy but that’s typical.

10.0 ExcellentSasha, Mar 2026
ASU - PTY
Read more Copa Airlines reviews

Friendly crew, good food options, food not the best and seats not as comfy but that’s typical.

Do not book it’s a scam! They stole $1200 from me

Flight got delayed; had to go through security three times.

Seats were awful. Media should have been included for such a long flight.

There should be a warning regarding the quality of the aircraft on the website as we reserve the tickets. There was no TV or any type of screen onboard. The wifi they offer is good for nothing. Traveling 9 hours straight with kids and no type of entetainment was horrible. I wish I had been informed prior so I could buy a ticket with another airline. The food was a joke too. A very tiny portion per passenger. They also charged $100 per checked bag. With United I used to pay $60. So, fair to say that I wont be flying Copa anymore. Their aircraft was super old, outdated, no entertainment, with nearly no onboard food.

The flight was good overall. Everything went smoothly, although the landing was a bit rough. Still, it was a pleasant experience

I always enjoy flying Copa. There are very few airlines where I can enjoy a comfortable sleep in-flight. The snacks weren't the best, but they sufficed. The in-flight entertainment was fantastic, and I crossed another movie off my watch list.

Simply as follows:- First, there was no vegetarian option for the meal Second, only 2 washrooms for the entire economy class.

They were super friendly bumped me up to exit row free of charge, All flight legs were on time

As always, Copa Airlines is great to fly on. The flights are always on time, the staff are pleasant and helpful and it's always a wonderful flying experience.

My original flight got delayed day of so I had to rebook it from one layover to two layovers. The flight also left earlier which was a slight inconvenience but manageable. Then my first connection flight got delayed 3 separate times for a total of 2 hours delayed, causing me to miss my second connection flight back to Santa Barbara. Now, because of this missed flight, I am missing my college classes that I pay for.

Departed late but made up the time en route. Uncrowded and clean aircraft.

When I booked my flight a month ago - I selected a seat. That seat was NOT the one I ended up with when I checked into my flight the day before. This is the second time this has occurred. So, I checked my next flight on Wednesday and Thursday and no seat was assigned. Poor, very poor customer service.

Wifi was spotty. Tray table was very dirty when I sat down.

Delays with no explanation. It could have been handled better.

They put me on an earlier and I got home sooner

Meals were not so good. Snack between the meals was very bad. Like Japan Airlines, they could eliminate the snack and make the second meal much better.

Flight delay for mechanical. Inbound arrived on time. No one said why mechanical delay.

Long delays, lack of information about the status of the flight. The flight was delayed 4 times.

The professionals have excellent customer service, the seats don´t have enough space.

The employees at the gate were not communicating, they preferred to give the upgrade to pilots and not to the elite passengers Every flight I more disappointing, clients shooed be priority instead of other employees even if they are pilots, there was plenty room for pilots in economy

The crew was great! They waited for me as Air Canada flight was delayed by 1:15 hours from Ottawa to Toronto. I am a bit disappointed that we could only use wifi for entertainment but I survived! The only thing I would of liked is a more comfortable seat. The seat cushions are not thick enough for flights longer than 3 hours. Aside from that, everything was great.

They should provide water to passengers who ask for it

Horrible experience with Avianca, they delayed their flight and when we arrived to NYC, AVIANCA took 1 hr y 30 mins to park the airplane and all passenger get off the plane, it made me lost all my trains to get back home and I came back to my place at 3 am instead of 12 am. On the top of that their plane seat are so uncomfortable and is not enough space and killed my legs and knees, Avianca used to be good when it was a Colombian company, now after Brasilian company bought them, their service quality is bad and their flights are delayed and oversold.

I upgraded to businesses class. Because of that the flight was comfortable.

only a bag of chips and a bottle of water in business class was served

Deplaning was a mess, I sat in business (seats are horrible) and the front door had a problem so we had to deplane from the rear exit. The stairs were not tall enough to reach so there was a large step down from the plane to the top of the stairs.

The flight attendant smashed her beverage cart into my knee, causing significant amount of pain. The seats were extremely uncomfortable. No food or drink is offered unless you want to pay the ridiculous prices for it. The schedule of flying in the overnight hours is also very uncomfortable.

Here we have another airline flying to Guatemala but doesn't have a plus or a less, just in the middle. Why? Well, first we don't have even free water Movie selection is poor Seats don't recline in some places Food selection is carb based Forgot to mention, customer service on the web is the worst. Good things; Very reliable on schedule Kind crew

We waited for one hour to deboard the plane after landing. That could be better

Awful. Not water, or chargers or space under the seats, the plane was very old and poor maintenance, seats really dirty, sticky, seats pockets with wires pinching your knees. Connection with no announcements, plane departed 1.30 hour earlier for an extra stop to refueling in Trinidad & Tobago. Even that we had a 3 hrs delay, seated in the plane in the runway.

Really bad. Uncommunicated stop in Trinidad & Tobago for refueling. Extra stop added 3 hours of discomfort without allowing off the seat. Not even water, or chargers or boarding groups.

Staff were unfriendly and rude. Was stuck on runway for 2 hours after arrival in Boston.

Horrible service. No communication from the crew as to why a 6 hour delay then cancellation

We waited in an overcrowded bus for over a half hour. It was uncomfortable. It would have been better to have waited in the terminal in a line

The food for sale on board has opportunity for improvement.

I paid extra for a comfortable seat in the second flight, but the plane didn't have those seats, the first one did

The Arajet person who greeted us initially was unhelpful & rude about the mandatory migration form which has to be completed digitally but the systems don’t work properly. The boarding gate was changed twice and initial boarding was delayed. Once on board we we had to wait an hour and a half before take off. It was hot and there was very little room for tall-ish people to fit their knees in. The crew were pleasant but working in a poor situation. The plane was delayed because we were waiting for people from a delayed interconnecting flight. Arajet must have known that before we were asked to board. Better information, decisions & communication were needed.

My seat was broken and the crew had to find me somewhere else to sit. The crew was extremely courteous about this

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports