$124 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 7/16. 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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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$229
Santo Domingo
Santo Domingononstop$171
Montego Bay
Montego Bay1 stop$469
Oranjestad
Oranjestad1 stop$402
Nassau
Nassau1 stop$438
Kingston
Kingston1 stop$426
Willemstad
Willemstad1 stop$368
Punta Cana
Punta Cana1 stop$229
Santo Domingo
Santo Domingononstop$171
Montego Bay
Montego Bay1 stop$469
Oranjestad
Oranjestad1 stop$402
Nassau
Nassau1 stop$438
Kingston
Kingston1 stop$426
Willemstad
Willemstad1 stop$368

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.
Discover the best prices for you by selecting your travel dates on KAYAK.

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

Tue, Nov 4 - Tue, Nov 11
Arajet Logo
7:48 pm - 12:45 amSJO-SDQ
2h 57mnonstop
Arajet Logo
5:53 pm - 7:03 pmSDQ-SJO
3h 10mnonstop
$171Arajet
Find Deal
Sat, Aug 23 - Sat, Aug 30
Arajet Logo
5:35 pm - 10:39 pmSJO-SDQ
3h 04mnonstop
Arajet Logo
3:47 pm - 4:50 pmSDQ-SJO
3h 03mnonstop
$210Arajet
Find Deal
Thu, Aug 21 - Sun, Aug 24
Avianca Logo
1:40 am - 4:50 pmSJO-SJU
13h 10m1 stop
Avianca Logo
4:25 pm - 5:58 amSJU-SJO
15h 33m1 stop
$211Avianca
Find Deal
Wed, Aug 6 - Mon, Aug 11
Avianca Logo
1:55 am - 4:50 pmSJO-SJU
12h 55m1 stop
Avianca Logo
2:10 pm - 3:25 pmSJU-SJO
3h 15mnonstop
$212Avianca
Find Deal
Thu, Aug 21 - Sun, Aug 24
Copa Airlines Logo
8:11 am - 10:19 pmSJO-SJU
12h 08m1 stop
Copa Airlines Logo
5:32 am - 9:58 amSJU-SJO
6h 26m1 stop
$216Copa Airlines
Find Deal
Thu, Sep 18 - Sun, Sep 21
Copa Airlines Logo
9:17 am - 10:21 pmSJO-SJU
11h 04m2 stops
Copa Airlines Logo
5:31 am - 9:04 amSJU-SJO
5h 33m1 stop
$221Copa Airlines
Find Deal
Sat, Sep 6 - Fri, Sep 12
Spirit Airlines Logo
12:19 pm - 1:55 amSJO-SDQ
11h 36m1 stop
Spirit Airlines Logo
2:53 am - 11:14 amSDQ-SJO
10h 21m1 stop
$389Spirit Airlines
Find Deal
Sat, Sep 13 - Thu, Sep 18
Spirit Airlines Logo
12:19 pm - 1:55 amSJO-SDQ
11h 36m1 stop
Spirit Airlines Logo
2:53 am - 11:14 amSDQ-SJO
10h 21m1 stop
$405Spirit Airlines
Find Deal
Thu, Oct 9 - Mon, Oct 13
American Airlines Logo
1:00 pm - 8:50 pmSJO-NAS
5h 50m1 stop
American Airlines Logo
7:45 am - 12:00 pmNAS-SJO
6h 15m1 stop
$582American Airlines
Find Deal
Mon, Dec 1 - Sun, Dec 7
American Airlines Logo
4:55 pm - 10:20 amSJO-MBJ
16h 25m1 stop
American Airlines Logo
1:05 pm - 7:35 pmMBJ-SJO
7h 30m1 stop
$591American Airlines
Find Deal
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 Santo Domingo, at $160 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 $160.

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 $735, 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 $185 (return) on average. On the other hand, the most expensive months are December and January, when the average cost of round-trip tickets is $410 and $404 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. For the absolute cheapest price, our data suggests you should book 11 weeks before departure.


Good to know

Low seasonJune
High seasonJanuary
Cheapest flight$124
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly with an average 4% 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.

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.
7.5
ArajetOverall score based on 28 reviews
5.7Entertainment
7.4Comfort
8.2Crew
7.6Boarding
6.5Food
Airline reviews

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

8.0 ExcellentGralyn Michelle, Oct 2024SDQ - YYZ
Read more Arajet reviews

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

Had to go through security at the gate again. Had to take off shoes and go through the whole thing again even though we have global entry. They asked us to check in items bought at duty free during our layover and since we checked our luggage at the original departure airport, they forced us to check in a small backpack. None of this ever happened with other airlines. In addition, no vegetarian food option and no snacks during a 7 hr flight. Luggage limits are unusually small. This is unacceptable. Will NEVER fly Copa again and will tell friends and family to avoid this airline.

Seats not reclining, no vegetarian food option, no snacks. 7.5 hr flight should have been more comfortable. Luggage limits are unusually small. Will never fly Copa again and will tell friends and family to avoid this airline.

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.

We had a five hour layover in the way home from Colombia. I read the "bout your flight" email carefully before we checked bags. We had to go through security right at the gate. Almost lost our ground coffee because that airport only allows 16 ounce of coffee and we had 18. I've been to 48 countries and never heard of a coffee restriction. I can't follow a rule I don't know about. I requested they bring our coffee to our checked luggage. Instead tey gate checked our bag for free. Back to planning transfers in Dallas I guess

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.

Placed us in the last rear row of the plane so could not recline seats because of the rear wall, and also made it more of a tight space when the passenger in front reclined their seat. While understand seat assignments, every passenger should be afforded a reclining seat. The odor control scent from the restrooms was overwhelming strong. My wife and I could not deal with it, and she suffered a terrible headache as a result. I kept getting hit by the crew since I was on the ilse seat. No apologies, nothing. They made me feel like I was supposed to take the beating for a 3 hr flight.

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.

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....

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.

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.

Awkward carry on process. Forced to check all carry on. No overhead space of worthiness. Left delayed, but made up the time. Crew was amicable.

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.

from Boston to Washington was good but return to Boston was terrible, Gate was changed and plane was so uncomfortable, I thought it would crash 🙈🤦‍♀️ also when I showed my bording pass they didn't know where to send me and finally gave me direction and at the plane they said to find free seat somewhere😬🤦‍♀️🫣

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

great experience. minimal lines at BWI. at DFW they got a long haul 787 boarded in 30 minutes

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 chicken that was served in business class was cold!

Flight to Bogotá delayed by 3 h Missed connection from Bogotá to Guayaquil. Avianca unable to bring us to Baltra on time Overall delay 36h. We missed boat departure from galagos. Overall 10 day trip needed to be cancelled. Avianca was completely un-professional.

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.

A few years ago long flights 6 hours or so used to have video screens and they offered ear phones. The food cart used to come and drinks. Now absolutely nothing. Avianca is as bad as Spirit Airlines. Avianca will now be my last choice when booking my next flight.

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

Excellent flight and one of the smoothest landing I’ve ever experienced

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.

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

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

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.

The flight, the pilot, the flight crew, and the ground personnel were all great, despite the sudden and lengthy FAA Ground Stop in Boston, which SPIRIT obviously had nothing to do with and no control over.

I mean, it’s Spirit. But it was frustrating to have our flight canceled, get bumped to a later flight, and then Spirit was unwilling to check our bag until 4 hours before our flight… tell us we could not sit in the waiting area’s chairs… and really negative experience getting checked in and dropping the bag.

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

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