$113 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 5/9. 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.
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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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Flights Deals

Best Caribbean Islands Flight Deals from San José

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Punta Cana
Punta Cana1 stop$310
Santo Domingo
Santo Domingononstop$204
Montego Bay
Montego Bay2 stops$423
Oranjestad
Oranjestad1 stop$284
Nassau
Nassau1 stop$376
Kingston
Kingston1 stop$405
Willemstad
Willemstad1 stop$334
Punta Cana
Punta Cana1 stop$310
Santo Domingo
Santo Domingononstop$204
Montego Bay
Montego Bay2 stops$423
Oranjestad
Oranjestad1 stop$284
Nassau
Nassau1 stop$376
Kingston
Kingston1 stop$405
Willemstad
Willemstad1 stop$334

Cheap Flights from San José to Caribbean Islands

 
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.

Recent round-trip flight deals from San José to Caribbean Islands

Recommended round-trip deals departing in the coming months from the most popular airlines that fly from San José to Caribbean Islands.
Discover the best prices for you by selecting your travel dates on KAYAK.
 Logo
7:30 am - 12:40 pmSJO-SJU
3h 10mnonstop
 Logo
8:12 pm - 11:33 amSJU-SJO
17h 21m1 stop
Mon, May 19 - Sat, May 24
Avianca Logo
1:55 am - 4:50 pmSJO-SJU
12h 55m1 stop
Avianca Logo
2:10 pm - 3:25 pmSJU-SJO
3h 15mnonstop
$186Avianca
Find Deal
Tue, May 13 - Mon, May 19
Copa Airlines Logo
5:52 am - 3:52 pmSJO-SJU
8h 00m1 stop
Copa Airlines Logo
5:42 pm - 7:35 amSJU-SJO
15h 53m1 stop
$193Copa Airlines
Find Deal
Thu, May 22 - Fri, May 30
Copa Airlines Logo
4:10 am - 10:20 pmSJO-SJU
16h 10m1 stop
Copa Airlines Logo
5:32 am - 4:22 pmSJU-SJO
12h 50m1 stop
$195Copa Airlines
Find Deal
Thu, Aug 21 - Sun, Aug 24
Arajet Logo
8:20 pm - 1:24 amSJO-SDQ
3h 04mnonstop
Arajet Logo
6:54 am - 7:57 amSDQ-SJO
3h 03mnonstop
$204Arajet
Find Deal
Mon, Jun 9 - Thu, Jun 12
Arajet Logo
8:20 pm - 1:24 amSJO-SDQ
3h 04mnonstop
Arajet Logo
6:32 pm - 7:35 pmSDQ-SJO
3h 03mnonstop
$210Arajet
Find Deal
Mon, Jul 14 - Mon, Aug 4
Spirit Airlines Logo
11:32 am - 12:54 amSJO-SJU
11h 22m1 stop
Spirit Airlines Logo
1:59 am - 10:27 amSJU-SJO
10h 28m1 stop
$254Spirit Airlines
Find Deal
Sat, May 24 - Fri, May 30
Spirit Airlines Logo
11:32 am - 12:54 amSJO-SJU
11h 22m1 stop
Spirit Airlines Logo
8:24 pm - 11:17 amSJU-SJO
16h 53m1 stop
$261Spirit Airlines
Find Deal
Sun, Jun 8 - Thu, Jun 12
American Airlines Logo
6:03 am - 7:15 pmSJO-NAS
11h 12m1 stop
American Airlines Logo
1:10 pm - 8:09 pmNAS-SJO
8h 59m1 stop
$510American Airlines
Find Deal
Tue, Jun 3 - Wed, Jun 11
American Airlines Logo
6:18 am - 5:40 pmSJO-NAS
9h 22m1 stop
American Airlines Logo
2:35 pm - 8:14 pmNAS-SJO
7h 39m1 stop
$516American Airlines
Find Deal
Mon, Aug 4 - Mon, Aug 11
Useful Info

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 price for flight routes found by users searching on KAYAK in the last 2 weeks for round-trip flights from San José to Caribbean Islands.

The cheapest ticket to Caribbean Islands from San José found in the last 72 hours was to San Juan, at $180 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 $244.

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 $187 (return) on average. On the other hand, the most expensive months are January and December, when the average cost of round-trip tickets is $450 and $419 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, Saturday 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 Sundays 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 5 weeks before departure. For the absolute cheapest price, our data suggests you should book 11 weeks before departure.


Good to know

Low seasonNovember
High seasonJanuary
Cheapest flight$113
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly with an average 8% increase in price.
Flight from San José to San Juan

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.

  • 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 $189 on average. Morning departures are around 46% cheaper than evening flights, on average. The most expensive time of day to fly to Caribbean Islands is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $357.

Top 5 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 1414 reviews
7.8Boarding
7.4Comfort
6.8Food
6.8Entertainment
8.1Crew
Airline reviews

We were in transit from Lima (flight at 1.10am) and we were in stand by in our flight from Panama to Washington. We wait from 4.30 am to 18.30pm in the Airport. The company give us 2 x 15 dollars for eat during the day and a personnal travel voucher of 400 dollars each. Do they buy food one time something in the Airport ??? And one of us live in France so the voucher is not usable. More than 24 hours travel !! And our place were near the toilets, with 8 children around us. The boy behind my seat stamped his feet on my back all the flight. Really Wonder full ! So we are totally unhappy with our travel. Thanks Copa Airlines....

2.0 MediocreCec, Apr 2025PTY - IAD
Read more Copa Airlines reviews

We were in transit from Lima (flight at 1.10am) and we were in stand by in our flight from Panama to Washington. We wait from 4.30 am to 18.30pm in the Airport. The company give us 2 x 15 dollars for eat during the day and a personnal travel voucher of 400 dollars each. Do they buy food one time something in the Airport ??? And one of us live in France so the voucher is not usable. More than 24 hours travel !! And our place were near the toilets, with 8 children around us. The boy behind my seat stamped his feet on my back all the flight. Really Wonder full ! So we are totally unhappy with our travel. Thanks Copa Airlines....

My flight delayed and i misss the connection they send me to orlando no to tampa i have to pay a uber to my house

It would have been better if they don't separate families in seating. We were seated in the aile row in the middle of a family of four. It would have been better if they they seat the family of four together than separated.

I upgraded myself to Business Class at the last minute so I had a DREAMS window seat. Seeing as I've never flown Business before everything was novel and fun for me and it made the 7 hour flight much more enjoyable for sure.

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 🙃

The flight was delayed about 4 hours without any explanation. No wifi or entertainment at all on planes. Had to pay for checked bags I was allowed according to reservations.

Great from check in all the way to the end. Very happy with Copa

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

Well the airline was fine. The only thing is I was charged for a checked in luggage. But when I reserved the ticket it showed a check in bag allowed. Who can I get in contact with for reimbursement.? The airline said I had to speak to whoever I booked ticket with.

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

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

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.

Same as before being upgraded to business class made it perfect

Boarded over an hour late, no communication, the sign just changed, no attendant to answer questions - she disappeared forever (hiding). Small plane and couldn’t hear the overhead nor understand.

Flight was delayed due to a steering issue with plane. The delay caused me to miss the connecting flight. The delay caused me to spend an extra 21 hours in airports and flights to get to my destination. The plane issue obviously should have been found and fixed before we even boarded. Ridiculous.

Delayed due to no crew. On a major holiday travel day.

Its usually good but this flight was just mediocre. It WAS, however, on time, and got us home early. We had asked for a special meal. The one we got was not what we had requested and the staff said there were no extras so we my family essentially went without food on this 10 hr flight. Not the end of the work. Breakfast was a dry cold bun with some salad leaves and a slice of tomato. That’s it. Skipped it too and ate at home. I expect better from American.

The flight was good. The only reason I did not say “excellent” was the delay

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..

RE Food: Wish there was a choice for No Rating. Flew from Honolulu to Los Angeles on a Red-Eye flight (11:00 pm to 7:30 am). Other than a package of cookies with a beverage choice offered soon after take-off, and a beverage choice shortly before landing, no other food choices were offered. Everyone slept or rested for most of the trip. Nothing to rate. RE Entertainment: Everyone was sleeping most of the flight. Only saw one passenger watch about 30 minutes of entertainment on his iPad. I never attempted to access any entertainment options.

The luggage was completely damaged. It was ripped at the corner and the lock was stuck. We had to rip it open.

i think the flight was late because they were so strict about measuring everyone's personal items to try and charge them $119. It was really petty and made us late.

Terrible, We had to stay in Bogota for two days due to weather but the airline did not provide for the same day flight. Only two days later

Purchased a business class ticket and got a economy seat with center seat blocked they call it business. 3100usd ticket on a flight where economy costs 500usd The biggest scam insult have had on a regular airline. Avianca should be in the low cost category and kicked out of Star Alliance. I want the difference to be credited. Ets see what Avianca does. No reply so far. Avianca = low cost airline. Beware

Business class seats did not lie flat. There was only powdered milk for your coffee....in Business Class!! Food was good.

There isn't much space in-between seats and even water needs to be paid for during the flight.

We did not know about the bag fees until check in. They are way too high. It’s insane. We also had a huge delay and everything costed extra which was very annoying.

Boarding was somewhat confusing in that the wrong messages were being displayed at the gate. It was somewhat annoying that I got off one flight and straight onto another (from the same gate), but in between they re-checked my hand luggage and made me get rid of my water (which they charge for on the plane). I was sitting in their 'Plus' seating, but the leg room was still too small to be able to sit square. The food options on the flights are pretty cheap quality (but not price). They got me from 'A' to 'B' on-time and for a relatively good price, but the experience itself was below average.

So so, you feel like you have to pay for everything each time

please see previous response; it covers the whole travel trajectory.

My whole return flight itinerary, 3 flights, got canceled without any warning to me because I missed one of the earlier flights 3 weeks ago

I love Spirit. New aircraft, great cabin service, the airfares are low cost which helps me visit my hospitalized daughter anytime I can without paying a fortune.

terrible service, no room for a dog underfoot, a broken chair that is impossible to sit on and all this costs a lot of money

Everything on the flight was OK. However, the price is very deceiving the way that it is marketed. It seems like it’s going to be very low cost, but when you add in the charges for luggage, choosing a seat, food & drink, etc., that are already included in other competitors fares, it really is no cheaper, and possibly even more expensive than the other carriers. It actually makes your carrier seem dishonest.

Don't charge so much for the luggage. Bis so much

Our experience was not a good one. Our flight got cancelled and was not given any accommodations due to the inconvenience. We lost time on our vacation due to this inconvenience

Needs legroom for tall people. Needs to offer a glass of water.

It was smooth. It’ll always be annoying that nothing is included in the booking (seats and bags particularly).

Everything was excellent and as expected. The boarding process was great but deboarding was a bit slow. No fault of the crew; it just seemed like the passengers didn’t want to leave! 😂

No carry on available to purchase at any point, charged for water, no power to charge phone. Other discount airlines have this.

Smooth enough, delay-free and safe. All went as expected,

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports

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