$114 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 1/28. 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$383
Santo Domingo
Santo Domingononstop$241
Montego Bay
Montego Bay1 stop$429
Oranjestad
Oranjestad1 stop$377
Nassau
Nassau1 stop$309
Kingston
Kingston1 stop$437
Willemstad
Willemstad1 stop$371
Punta Cana
Punta Cana1 stop$383
Santo Domingo
Santo Domingononstop$241
Montego Bay
Montego Bay1 stop$429
Oranjestad
Oranjestad1 stop$377
Nassau
Nassau1 stop$309
Kingston
Kingston1 stop$437
Willemstad
Willemstad1 stop$371

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

Wed, Jan 14 - Tue, Jan 20
Avianca Logo
4:15 pm - 11:35 am
SJO
-
SJU
17h 20m1 stop
Avianca Logo
6:30 pm - 12:15 am
SJU
-
SJO
7h 45m1 stop
$209Avianca
Sun, Jan 25 - Wed, Feb 4
Avianca Logo
1:45 am - 5:05 pm
SJO
-
SJU
13h 20m1 stop
Avianca Logo
6:30 pm - 8:50 am
SJU
-
SJO
16h 20m1 stop
$227Avianca
Sat, Feb 21 - Wed, Feb 25
Arajet Logo
8:55 am - 1:52 pm
SJO
-
SDQ
2h 57mnonstop
Arajet Logo
9:28 am - 10:38 am
SDQ
-
SJO
3h 10mnonstop
$241Arajet
Thu, Jan 22 - Sat, Jan 31
Copa Airlines Logo
10:08 am - 10:28 pm
SJO
-
SJU
10h 20m1 stop
Copa Airlines Logo
6:14 pm - 8:21 am
SJU
-
SJO
16h 07m1 stop
$242Copa Airlines
Thu, Jan 29 - Thu, Feb 5
Copa Airlines Logo
8:11 am - 10:28 pm
SJO
-
SJU
12h 17m1 stop
Copa Airlines Logo
6:14 pm - 4:46 pm
SJU
-
SJO
24h 32m3 stops
$247Copa Airlines
Wed, Apr 15 - Tue, Apr 21
Arajet Logo
11:23 am - 4:27 pm
SJO
-
SDQ
3h 04mnonstop
Arajet Logo
6:00 pm - 7:03 pm
SDQ
-
SJO
3h 03mnonstop
$255Arajet
Sat, Jan 31 - Sat, Feb 7
Spirit Airlines Logo
1:30 pm - 4:36 pm
SJO
-
PUJ
25h 06m1 stop
Spirit Airlines Logo
5:47 pm - 12:22 pm
PUJ
-
SJO
20h 35m1 stop
$387Spirit Airlines
Sat, Jan 31 - Sat, Feb 7
Spirit Airlines Logo
1:30 pm - 4:36 pm
SJO
-
PUJ
25h 06m1 stop
Spirit Airlines Logo
5:47 pm - 11:37 am
PUJ
-
SJO
19h 50m2 stops
$397Spirit Airlines
Mon, Jan 19 - Mon, Feb 2
American Airlines Logo
6:00 am - 8:20 pm
SJO
-
GCM
13h 20m1 stop
American Airlines Logo
12:50 pm - 9:02 pm
GCM
-
SJO
9h 12m1 stop
$476American Airlines
Sun, Mar 1 - Fri, Mar 6
American Airlines Logo
7:45 am - 8:15 pm
SJO
-
GCM
11h 30m1 stop
American Airlines Logo
1:00 pm - 8:58 pm
GCM
-
SJO
8h 58m1 stop
$482American 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 $134 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 $134.

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 $384, 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 March, when the average cost of round-trip tickets is $329 and $305 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 32% 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$114
Best time to beat the crowds with an average 7% drop in price.
Most popular time to fly with an average 3% 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 39% 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 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.
7.6
Copa AirlinesOverall score based on 1556 reviews
6.8Food
6.8Entertainment
7.8Boarding
7.4Comfort
8.1Crew
Airline reviews

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

8.0 ExcellentAnonymous, Dec 2025
PTY - CUR
Read more Copa Airlines reviews

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.

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)

The inflight staff is never the issue always the extra and charges american charges! Literally 30 bucks for WiFi! Is insane and then it’s choppy and slow. If you pay for it once you don’t need to pay again for switching aircraft especially when there is flight delays

The flight attendant, a black woman with curly hair who sat near Row 21, was wonderful and kind.

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

in chicago, you have to go out to drop off your luggage for a connecting flight and come back into a security check. which was horrible with a government shut down. some airports you down off luggage and go to your gate. things were not cleanly marked.

Air Marco’s fleet of airplanes are old and pathetic. The seats are torn and stained. The monitors don’t work properly. If this wasn’t a business trip and I had control of booking the flight, I would not travel on this carrier.

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.

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

No free snacks nor drinks on very short 30min flight. Entertainment system is over wifi to your own phone or tablet, which is good but often a show or movie just stops and refuses to continue

I like the crew they're very friendly. I don't like. on five hour flight they not offered snacks. Any drink. Not even coffee

Not even water is offered on the flight. You cannot lean back on the seats and the seats are so narrow you can’t avoid rubbing elbows with the person next to you.

I had to go to the boarding counter for them to enter my return flight as it’s not with Avianca. There was a long queue as there were lots of people being called to the counter.

This low cost airline looks and fells more like a local bus. In a 6 hour flight not being able to recline a seat is torture. The only thing available with no charge is a glass of water provided by, mostly, rude staff. Our luggage didn’t arrive

6 hour flight and have to pay for everything 100 dollars to add a carry-on bag is insane

Horrible experience. Flight cancelled. Arrived at destination 12 hs later. No one gave us an answer or any information. Very very poor service. We won’t ever travel again with Avianca

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

Usb plugs for charging your phone does not work in every flight. uncomfortable chairs even in higher categories.

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 .

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports