$122 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 9/22. 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

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$364
Santo Domingo
Santo Domingononstop$242
Montego Bay
Montego Bay1 stop$473
Oranjestad
Oranjestad1 stop$377
Nassau
Nassau1 stop$342
Kingston
Kingston1 stop$426
Willemstad
Willemstad1 stop$325
Punta Cana
Punta Cana1 stop$364
Santo Domingo
Santo Domingononstop$242
Montego Bay
Montego Bay1 stop$473
Oranjestad
Oranjestad1 stop$377
Nassau
Nassau1 stop$342
Kingston
Kingston1 stop$426
Willemstad
Willemstad1 stop$325

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

Fri, Sep 26 - Mon, Sep 29
Copa Airlines Logo
5:57 am - 3:58 pmSJO-SJU
8h 01m1 stop
Copa Airlines Logo
5:50 pm - 7:27 amSJU-SJO
15h 37m1 stop
$216Copa Airlines
Find Deal
Fri, Oct 10 - Fri, Oct 24
Copa Airlines Logo
5:57 am - 10:21 pmSJO-SJU
14h 24m1 stop
Copa Airlines Logo
5:31 am - 4:52 pmSJU-SJO
13h 21m2 stops
$221Copa Airlines
Find Deal
Mon, Sep 29 - Mon, Oct 6
Avianca Logo
7:30 am - 12:40 pmSJO-SJU
3h 10mnonstop
Avianca Logo
2:10 pm - 3:25 pmSJU-SJO
3h 15mnonstop
$233Avianca
Find Deal
Wed, Jan 14 - Tue, Jan 20
Avianca Logo
1:45 am - 11:35 amSJO-SJU
7h 50m1 stop
Avianca Logo
4:45 pm - 7:00 amSJU-SJO
16h 15m1 stop
$234Avianca
Find Deal
Wed, Oct 29 - Sun, Nov 2
Arajet Logo
11:23 am - 4:20 pmSJO-SDQ
2h 57mnonstop
Arajet Logo
5:53 pm - 7:03 pmSDQ-SJO
3h 10mnonstop
$242Arajet
Find Deal
Wed, Nov 5 - Sun, Nov 9
Arajet Logo
11:23 am - 4:20 pmSJO-SDQ
2h 57mnonstop
Arajet Logo
5:53 pm - 7:03 pmSDQ-SJO
3h 10mnonstop
$243Arajet
Find Deal
Sun, Oct 12 - Fri, Oct 17
Spirit Airlines Logo
12:35 pm - 4:07 pmSJO-SDQ
25h 32m1 stop
Spirit Airlines Logo
5:12 pm - 10:41 amSDQ-SJO
19h 29m2 stops
$345Spirit Airlines
Find Deal
Mon, Sep 22 - Sat, Sep 27
Spirit Airlines Logo
12:19 pm - 11:45 amSJO-PUJ
21h 26m2 stops
Spirit Airlines Logo
3:19 pm - 11:14 amPUJ-SJO
21h 55m1 stop
$381Spirit Airlines
Find Deal
Wed, Dec 3 - Sat, Dec 6
American Airlines Logo
7:00 am - 2:20 pmSJO-SKB
29h 20m1 stop
American Airlines Logo
4:22 pm - 1:39 pmSKB-SJO
23h 17m2 stops
$955American Airlines
Find Deal
Thu, Dec 4 - Sat, Dec 6
American Airlines Logo
3:38 pm - 2:07 pmSJO-SKB
44h 29m2 stops
American Airlines Logo
4:22 pm - 2:02 pmSKB-SJO
23h 40m2 stops
$965American Airlines
Find Deal
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 $176 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 $176.

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 $380, 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 $186 (return) on average. On the other hand, the most expensive months are December and January, when the average cost of round-trip tickets is $381 and $372 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 Friday, 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, which saves you about 39% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 11 weeks before departure.

Good to know

Low seasonJune
Cheapest flight$122
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly with an average 7% 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 $210 on average. Morning departures are around 40% 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.

Reviews of the 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.
7.6
Copa AirlinesOverall score based on 1531 reviews
7.4Comfort
6.8Entertainment
6.8Food
8.1Crew
7.8Boarding
Airline reviews

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.

10.0 ExcellentNeil, Aug 2025PTY - BGI
Read more Copa Airlines reviews

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.

We had a great flight just wished they had a tv so we can see a movie that would of made my trip excellent.

the food served was an embarrassment. No connection for charging the cellphone... What a crappy airline.

Great experience with a crew always thinking in the passenger

The flighr attandants were very rude they ignored me didnt offer me anything to drink throughoit the 4 hour flight i feel i was targeted and ignored because i was a darkskin latino man.

Did upgrade, travel in business it was great (more room I could sleep)

We paid extra with copa for seats near one another The plane was changed and we lost our seats We were all Separated. We have not received a refund for our seats despite emailing and calling.

It was ok. However, the food was quite poor since I don't eat pasta.

Enforce the boarding process by group numbers. Tell people to stay seated during the meal/drink distribution. It took forever to get food and drinks because people would not stay out the isle and let the crew do their jobs. Everyone wanted to go to the bathroom forcing the crew to enter and leave the isle constantly so people can pass. Tell people to keep their electronics off speaker mode. No one wants to hear phone conversations and music playing.

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.

Flight from Miami to Lima was very good, like the free WiFi to get movies and TV.

Dreadful experience. Our flight was delayed more than 8 hours due to a maintenance issue and the assistance from rebooking was poor. I was travelling with a bad knee and needed assistance waited in one place more than 3 hours before someone came with a wheelchair. The woman next to me was a 91 year old great grandmother who had waited more than 4 hours. There were moments of support from the staff but it appeared as they were going against the direction of management. It was apathy, lack of ownership and dismissive responses with small moments of kindness and understanding typically from grey haired, female, veteran staff..

Very clean and comfortable cabin. Amazing Mediterranean salad for lunch before landing. Great range of films to watch. Really quiet and easy to sleep on the flight also. The initial food was a bit weird: odd fried chicken pieces in some weird white gloop, but that would be my lack of cultural knowledge on the grub. Salad more than made up for it at the other end. Staff were super attentive and helpful. Great and easy flight

Delayed flight, so I switched fights to SFO to Phoenix , Phoenix to DSM. Excellent service through American Airlines

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

No entertainment yatem in flight at seat 51H. Would not shut down either leaving a self moving and openin and changing menus with changes in colors,images brightness levels sort of the type when you get sleep deprivation and image overload when being tortured during an interrogation. 8 hours worth of it. Unable to place backpack underneath seat on that chair. One female stewardess was excellent as she gave up her carryon's space for my backpack but the rest of the iberia crew were very sharp an chtting during the whole flight. The plane did not have hot water so nobody had coffee nor tea. The plane was not up to par to be flying.

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.

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.

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

Boarding, crew were excellent, food was ok and entertainment need to improve

Luggage lost and nowhere to be found, no response from either airline regarding my bag

The usb plugs for charging your phone didn’t work, the seats were coarse and hard. Not very comfortable. No inflight WiFi

Very uncomfortable planes , poor service on the plane , take your own water so you don’t dehydrate , in a 6 hs flight they sold one time food and beverage . 1 plane was delayed 6 hs , I lost a connecting flight . Then in the way back they announce a delay of 2 hs so I had to take a different flight to arrive on time for my connecting flight . Avoid this airline .

The check in is the only positive thing in Avianca. The seat is the most uncomfortable I have traveled, the distance is minimal.

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

It was horrible. My experience with Avianca. I didn’t know it was Pakistan international Airlines but anyway, whatever it is it is bad horrible you guys need to upgrade everything in those planes. And you guys charge $130 for a carry-on did they wanna let me in with my carry-on that I travel everywhere with the luggage you guys are such a dog thank you

why did we have to go through security mid flight

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

The chicken that was served in business class was cold!

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 flight was on time, boarding was efficient, staff was nice. Seats seem to have been upgraded on this model and were clean and tidy. I did not purchase in flight snacks.

The staff was excellent and I appreciated the zero tolerance for noise making electronics and the only bad part was It took forever for the luggage to get to the baggage claim. It took over 40 minutes. And Norfolk is a small airport so it was probably airport. Staff’s fault.

Booked through kayak, everything seemed normal but when it came time to go, my flight ticket didn’t exist, so I had to purchase another set of tickets at the airport the day of the flight, for about double. When I reached kayaks customer service, they claimed no responsibility, and pushed me onto another 3rd party booking service, airfare assist, where I have had no luck getting any kind of help or refund. I’ve used kayak many times, but I’ll never again after I’ve been burned by this.

it was a quick trip. seats aren't that comfortable but because it was a quick trip it was ok. You need to have an N/A in your rating as I didn't have any food or entertainment so the only thing I could do was score low.

I wanted to upgrade my seat because I’m 6’2 and never have enough leg room for my comfort. They upgraded my seat for free putting me in an emergency exit seat. I was very comfortable

Good on that leg. When I arrived in Detroit I had to wait over an hour for luggage.

We had an almost 7 hour flight delay. We left the gate twice and taxi-ed and then returned the gate twice. Finally we got a new flight crew (our third one) and then left the gate to the final time before departing at 6:45pm (original flight time was 12pm). Out of Newark.

Plane delayed which seems to be the norm with spirt. Everything is an up charge. I had to pay an additional fee because I was late getting back to my car. Will never fly spirit again

It amaze me how other airlines leave on time and Spirit always have some type of delay. I’ve flown with Spirit many times, but it reached a point I’d rather pay twice the amount and not deal with this corporation they never do nothing to reimburse people for their time or headaches.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports

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