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Find cheap flights from San José to Caribbean Islands from $139

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 6/26. 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
0 bags
Sat 6/15
Sat 6/22

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Best Caribbean Islands Flight Deals

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

Punta Cana
Punta Cana1 stop$392
Montego Bay
Montego Bay1 stop$356
Santo Domingo
Santo Domingo1 stop$243
Oranjestad
Oranjestad1 stop$328
Nassau
Nassau1 stop$380
Kingston
Kingston1 stop$440
Willemstad
Willemstad1 stop$312

Good to know

Low season

November

High season

January

Cheapest flight

$139
Best time to beat the crowds with an average 0% drop in price.
Most popular time to fly and prices are also 2% lower on average.
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 to Caribbean Islands from San José 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 to Caribbean Islands with an airline and back to San José 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 to Caribbean Islands from San José up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top 5 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.
7.8
Copa AirlinesOverall score based on 2707 reviews
8.3Crew
8.1Boarding
7.3Food
7.7Comfort
7.2Entertainment
Airline reviews
Pros: "Nothing. This airline is awful in every way imaginable."
Cons: "We booked tickets to Costa Rica with Copa and they just changed our flights to two days later than the booking. They didn’t even bother to inform us of the change we only found out because we booked through Kayak and they let us know. Apparently Copa expects you to frequently check your booking just in case they’ve changed anything and don’t feel the need to inform their customers of any changes they make. Then we were told we could get a Copa voucher to use for other Copa flights for having to cancel our booking and rebook with another airline as a 48 hour change to our flight made flying with Copa not doable for us. But the website kept telling us we had a voucher that was sent to our email but despite repeated attempts it never came through. And spent hours trying to get through to someone on the phone to sort it out with no success ever getting through. My advice. NEVER EVER FLY WITH COPA."
2.0 MediocreSebastian, Mar 2021SJO - PTY
Read more about Copa Airlines reviews
Pros: "Nothing. This airline is awful in every way imaginable."
Cons: "We booked tickets to Costa Rica with Copa and they just changed our flights to two days later than the booking. They didn’t even bother to inform us of the change we only found out because we booked through Kayak and they let us know. Apparently Copa expects you to frequently check your booking just in case they’ve changed anything and don’t feel the need to inform their customers of any changes they make. Then we were told we could get a Copa voucher to use for other Copa flights for having to cancel our booking and rebook with another airline as a 48 hour change to our flight made flying with Copa not doable for us. But the website kept telling us we had a voucher that was sent to our email but despite repeated attempts it never came through. And spent hours trying to get through to someone on the phone to sort it out with no success ever getting through. My advice. NEVER EVER FLY WITH COPA."
Pros: "Both of my flights were on time which i know sounds basic but all of the flights i’ve catched from SJO to X were late and this time my connection in Panama was only 1h15 and we got there earlier, so that was nice!"
Cons: "A bunch of seats were free and we were mostly sat all together (3 person next to each other).. With the covid situation i think it could be good to be more separate if possible"
Pros: "Crew and i ohhh ver all copa experience."
Cons: "Nothing. I am now a loyal Copa flier. Any of my trips to Latin America I will consider flying with Copa"
Pros: "Everything has gone very well."
Cons: "The food (egg) made me get a little bit sick but it wasn’t a big deal."
Pros: "Food was good"
Cons: "Different movie, more leg room but I'm tall so that is with any plane."
Pros: "Everything was great as usual. Copa is an excellent airline."
Pros: "The crew wasnt nice"
Cons: "The organisation. Letting know to people about the documents required to access in a country by email in advance."
Pros: "Very quick, friendly service."
Cons: "WiFi on the plane would have made it an A+ experience."
Cons: "They tend to be very sensationalist with the people sitting on the exit road. It would be nice to have some food for the people that are vegetarian, something; just don’t ignore them and continue walking. This happened in both flights. Not even chips. Nothing."
Cons: "The airline forced my wife to check her carry on AND THEN LOST IT."

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.

The good thing is the flight was on time and the crew was really nice. They can work better the arriving with staff

I don't think anyone actually reads these comments, so I won't spend much time on this submission. If you want to talk, you know how to reach me. The D/FW manager of Avianca (self-identified), Juan Calderon, insisted I buy an onward ticket from San Salvador even though I have diplomatic status in El Salvador and live here. It cost me $1,393 and Mr Calderon would not let me make the ticked flexible so I could get a refund. He went out of his way to be rude to me. He gave me seat 32K -- windowless window seat in the last row and did not offer to let me upgrade even though there were plenty of seats. I have flown well over a million miles in my life and this is the worst experience I have ever had. I would like a refund on the ticket I was forced to buy. Just awful!

It is better at the jfk than my home country. It was very easy and everything was on time.

There is no food. There is no in-inflight entertainment. The seats are cardboard. The airline is a living hellscape.

They could offer food and drink without having to pay extra for it,

Every food and beverage has to be paid and the seat was not confortable. They even gave water.

Wasn’t able to take the trip and no one could help me with a refund or rescheduling

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

50% of flights book with Avanca have issues either reschedualed cancelled and their actions further supports their poorly managed airline do not use them only if there is no other options

Delayed almost 4 hours for a 45 minute flight with no explanation.

Ac was broken so we deplaned, waited 2 hours, taxiing for takeoff they said the plane would not fly so we went back to the gate and got a new plane which took another hour. In all a 4 hour delay for an 80 min flight.

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.😀

On the new 319 NEO? seatback entertainment system did not work even when the flight attendant rebooted it. At least I had my cell phone to connect with wifi.

I can say I will not be taking this airline again any time soon. Seat were uncomfortable and too tight. Lack of chair screen and little overhead space.

Cut off carry ons, had to check, got on and there was plenty of bin space. Disappointing.

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.

Horrible! Got stuck in Jackson Hole and the plane kept delaying every 30 min until they finally cancelled the flight. Other airlines were busy flying out and American had cancelled. Horrible experience, we had to switch to United to get out of there!

2 gate changes, several announced delays, not enough room and seats at the gate. Many had to stand while waiting. The actual flight was fine.

Some of the crew members were rude for no good reason

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

I would like more Details about the bags or think s like guitars

First the good, everyone was friendly and efficient. Flight was smooth and plane was very clean and new. Now the bad, seats have almost no padding on your behind. I was in exit row so I had tons of leg room for a 6' 2" bean pole with long legs. Everything was extra - water, soda, snacks everything besides oxygen. Ya get what you pay for, and my flight was cheap as you could ever want it, so no worries. They dont really bother you about carry-on size, I brought a descent sized backpack and they didnt even check.

Flying on Spirit Airline is a penny-pinching beat down.

I like the price. I did not like the seats: very little space and not reclining.

MY FLIGHT GOT CANCELED AND I HAD TO BUY ANOTHER TICKET FROM DELTA TO GET HOME SO I COULD GET BACK TO WORK!!!! SPIRIT SUCKS!! I WILL NEVER USE THEM AGAIN!!

Pack light and enjoy the quick boarding and early departure and arrivals.

Flight was delayed 2+ hours missed a concert because of it…

Well those seats! Man! On a short flight tolerable but too stiff and lack of cushioning make a longer flight uncomfortable. Good leg room tho, but I’m only 5’3”….

There was no WiFi available and trying to check baggage with the automated system never works with my Florida IDENTIFICATION

The flight was delayed. The boarding process disorganized. Poor communication regarding the delays. We were sitting on the runway in Boston for over 1-hr. Again very poor communication regarding the status. Bags didn’t arrive after almost 2-hr wait. I gave up and went home without my bag and had to return to the airport to pick it up the next day. Very exhausting experience!

Book cheap flights from San José to Caribbean Islands

Recent round-trip flight deals

7/26Fri
1 stopCopa Airlines
14h 13mSJO-SDQ
8/4Sun
1 stopCopa Airlines
15h 48mSDQ-SJO
$243
10/24Thu
nonstopArajet
3h 00mSJO-SDQ
10/27Sun
nonstopArajet
3h 00mSDQ-SJO
$244
8/1Thu
nonstopArajet
3h 00mSJO-SDQ
8/5Mon
nonstopArajet
3h 00mSDQ-SJO
$257
6/25Tue
1 stopCopa Airlines
4h 33mSJO-STI
7/2Tue
1 stopCopa Airlines
4h 58mSTI-SJO
$259
6/2Sun
1 stopSpirit Airlines
15h 40mSJO-SJU
6/10Mon
1 stopSpirit Airlines
17h 31mSJU-SJO
$282
6/21Fri
1 stopSpirit Airlines
9h 39mSJO-SJU
6/25Tue
1 stopSpirit Airlines
17h 31mSJU-SJO
$298
5/19Sun
1 stopAvianca
12h 06mSJO-AUA
5/25Sat
1 stopAvianca
8h 40mAUA-SJO
$357
5/28Tue
1 stopAvianca
15h 15mSJO-CUR
6/4Tue
1 stopAvianca
17h 25mCUR-SJO
$358
6/3Mon
2 stopsAmerican Airlines
26h 24mSJO-NAS
6/7Fri
1 stopAmerican Airlines
14h 10mNAS-SJO
$531
6/6Thu
1 stopAmerican Airlines
26h 15mSJO-MBJ
6/10Mon
1 stopAmerican Airlines
34h 20mMBJ-SJO
$604

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Recent one-way flight deals

6/26Wed
nonstopArajet
3h 00mSJO-SDQ
$139
5/22Wed
nonstopArajet
3h 00mSJO-SDQ
$140
6/5Wed
1 stopJetBlue
10h 44mSJO-SJU
$174
6/7Fri
2 stopsCopa Airlines
23h 46mSJO-SDQ
$178
5/31Fri
1 stopSpirit Airlines
11h 19mSJO-SJU
$183
6/18Tue
1 stopAvianca
12h 06mSJO-AUA
$190
6/18Tue
1 stopAvianca
12h 06mSJO-AUA
$191
6/7Fri
1 stopSpirit Airlines
9h 39mSJO-SJU
$193
5/24Fri
1 stopAvianca
7h 41mSJO-SJU
$197
7/19Fri
1 stopCopa Airlines
5h 35mSJO-SDQ
$221

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Last minute flights from San José to Caribbean Islands

Last minute flight, train and bus deals

5/19Sun
multi-stopCopa Airlines
8h 32mSJO-SDQ
5/24Fri
multi-stopCopa Airlines
5h 34mSDQ-SJO
$243
5/17Fri
multi-stopCopa Airlines
23h 46mSJO-SDQ
5/19Sun
multi-stopCopa Airlines
6h 21mSDQ-SJO
$284
5/20Mon
nonstopArajet
3h 00mSJO-SDQ
5/22Wed
nonstopArajet
3h 00mSDQ-SJO
$336
5/19Sun
multi-stopAvianca
12h 06mSJO-AUA
5/25Sat
multi-stopAvianca
8h 40mAUA-SJO
$357
5/18Sat
nonstopArajet
3h 00mSJO-SDQ
5/25Sat
nonstopArajet
3h 00mSDQ-SJO
$370
5/19Sun
multi-stopSpirit Airlines
12h 08mSJO-PUJ
5/25Sat
multi-stopSpirit Airlines
8h 13mPUJ-SJO
$392
5/18Sat
multi-stopSpirit Airlines
11h 27mSJO-STI
5/21Tue
multi-stopSpirit Airlines
10h 33mSTI-SJO
$398
5/19Sun
multi-stopAvianca
12h 06mSJO-AUA
5/25Sat
multi-stopAvianca
22h 05mAUA-SJO
$437
5/19Sun
multi-stopAmerican Airlines
17h 45mSJO-NAS
5/21Tue
multi-stopAmerican Airlines
10h 04mNAS-SJO
$525
5/19Sun
multi-stopAmerican Airlines
17h 36mSJO-NAS
5/21Tue
multi-stopAmerican Airlines
10h 04mNAS-SJO
$530

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San José - Caribbean Islands Flights

Departure:

San José (SJO)Costa Rica

Return flight deals:

Caribbean Islands - San José

Cabin classes:

$1,974
$502
$506
$78