$122 Find Cheap Flights from San José to Caribbean Islands - Compare and Save

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Cheap Flights from San José to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Punta Cana
Punta Cana1 stop$492
Santo Domingo
Santo Domingononstop$240
Montego Bay
Montego Bay1 stop$619
Oranjestad
Oranjestad1 stop$458
Nassau
Nassau1 stop$395
Willemstad
Willemstad1 stop$442
Punta Cana
Punta Cana1 stop$492
Santo Domingo
Santo Domingononstop$240
Montego Bay
Montego Bay1 stop$619
Oranjestad
Oranjestad1 stop$458
Nassau
Nassau1 stop$395
Willemstad
Willemstad1 stop$442
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?

The cheapest ticket to Caribbean Islands from San José found in the last 5 days was to Santo Domingo, at $219 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 5 days was $219.

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 morning, when round-trip flights cost $266 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 $266.

Can I save money by flying with a layover from San José to Caribbean Islands?

No, with an average price for the route of $438, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from San José to Caribbean Islands?

The cheapest month for flights from San José to Caribbean Islands is November, when tickets cost $373 (return) on average. On the other hand, the most expensive months are August and July, when the average cost of round-trip tickets is $467 and $446 respectively.

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

To get a below average price on the flight from San José to Caribbean Islands, you should book around 3 weeks before departure, which saves you about 6% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 8 weeks before departure.

Good to know

Low season

June

Cheapest flight

$122
Best time to beat the crowds but there is an average 6% increase in price.
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

 
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.
7.6
Copa AirlinesOverall score based on 1539 reviews
7.4Comfort
6.9Entertainment
7.8Boarding
6.9Food
8.1Crew
Airline reviews

Flight delayed, luggage delayed. I am still waiting for my luggage after 2 days arrival of Lima.

2.0 MediocreAnonymous, Aug 2026
Read more Copa Airlines reviews

Flight delayed, luggage delayed. I am still waiting for my luggage after 2 days arrival of Lima.

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

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

There was no individual at the front check in when I arrived. I waited for at least 15 minutes and walked around asking security/janitors if they could help and they did not have a solution. So I had to take my checked bag through security and they threw away some of my items. I ended up making it to the gate only a few minutes before it closed due to my waiting for an agent at check in.

It was reasonably comfortable trip considering its duration (7 hours). Crew was very good and friendly, seats very more comfortable than other planes. Only negative comment would be that the bathroom light did not get its full brightness 🙃

Copa stranded us ans then tried to charge us thousands to leave Panama.

Friendly flight team and seamless travel from one stop to next.

Just a minor inconvinient with weather delay! but not Copa's fault

No boarding announcements leading to the usual confusion and people trying to board before their group number.

As usual, the flight with normal legroom was not very comfortable, but the second flight was much better because we had paid for extra legroom. It was very nice to check our bags without an extra fee.

Terrible experience flying with American Airlines. Too many delays and cancellations.

Flight was delayed and after being in the airport for like seven hours, it was canceled.

When I'm on a 5hr 22 minute flight I expect food to be purchased. Especially when American makes a very tight connection time where u have to run to make the long flight. Chips and nuts are unacceptable and being told you should be in first class to get a meal is also unacceptable. I didn't change the flight times American Airlines did.

Flight attendants on American Airlines are rude very harsh with their time of voice. Nearly identical experience as spirit airlines. However, from Spirit Airlines, you expect this level of mediocre service. You do not expect this from the big three..

The plane had maintenance issues and didn't leave after 72 hours

The staff were very nice! However when our first flight got delayed an hour, the second connection flight was not delayed and the layover was only 40 minutes. When we rushed and made it to our gate for the connection flight, the gate said it had moved to another section of the airport. We barley made it to the connection flight, and overall we were very stressed. We asked about taking a later time for the second connection flight, but the other option was much later and we would have to wait at the airport for 9+ hours. I just wish American Airlines could have moved the second connection flight to a later time too for its customers, and thank you for taking the time to read my review.

The only poor experience was the flight the day before was canceled. I have flown enough to change as soon as notified. That was a huge plus for AA. Obviously I paid out of pocket for a hotel. Not AA choice , it was mine. I had resources. Other friends on the same flight were more affected. I know everyone is doing their best and the ability to change my flight was a good move AA.😀

Flight was canceled and then rescheduled on another flight. Paid for first class but moved to the back of the plane. Then put up in the worst/dirtiest hotel I’ve ever stayed in. American Airlines should be ashamed of putting their passengers/customers in a place that filthy.

We appreciated that the AA agent at the check in desk was aware that we might not make our connecting flight from Liberia to Miami due to delays. He immediately got us on an earlier flight, which meant less time in the airport and the ability to catch our flight home. Without him, we might had to spend a night in Miami, which we could not do due to work schedules once we got home. This action is what made this flight sequence excellent.

The flight was on time, boarding process good. Good value flight.

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 worst experience I've ever had because the "people" @ Avianca wouldn't let me fly because they said I needed a round trip ticket

Did not fly with Pakistan International Airlines. Have never flown with Pakistan International Airlines.

Not what it used to be. The sale of food makes them look greedy!

The incoming plane was late and no information was shared. They even announced we would board in 10 muntes 40 minutes prior to the plane arriving, and the website said until takeoff that we had taken off an hour earlier

Flight delayed by an hour and 5 mnts, missed my connection from Ccs to porlamar, had to stay over night hotel cost and new tickets.

I expected the plane to be as the one I took from manaos to Bogota and unfortunately it wasn’t as nice, the sits didn’t recline and there was not onboard entertainment.

Awful. I checked in online and there was no option to pay for baggage, at the airport when I checked in my baggage was received and Iwas not charged. When I got to LA during the boarding process I was told I didn't pay for baggage, the crew resolved I was let in the plane. When I got to my final destination my baggage was not there. It took me two days to receive my baggage. Bad service ever!

My international flight from LAX to Argentina had one free check in bag included in the price I paid, however your crew in LAX made me pay $95 USD to carry it on! Please note I had only on small size luggage (carry on size) and one backpack. I demand my $95 USD back that you guys charged me illegally in LAX.

I paid extra for seats up front, I expected unless the beverages wold be included,

I got to the airport and the airline told me i did not have a flight. I never got a confirmation email yet I did get charged. Please refund my money asap

Was charged for ticket, unable to check in online, made the line to speak to someone at the counter but was told I did not show up in the system as having a ticket to fly - even though I have the email with confirmation and credit card was charged. I could not purchase another ticket at the counter, only online which was not working. Ended up buying a flight on another airline at the airport. Called customer service to claim the cost of the original ticket, was told I showed up in their system as having a ticket but did not check-in or show up to board the flight. Currently pending review for refund via their customer service team, they were very nice and helpful over the phone despite the many glitches.

Do not book with this airline. Flights delayed over 3 hours and no explanation. They keep changing your itinerary every hour.

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.

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

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

More options for your flight to Caribbean Islands

Complete your trip to Caribbean Islands with a hotel stay or car rental