$189 Find Cheap Flights from Caribbean Islands to San Jose

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to San Jose departing on 4/9. 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.
1 adult
1 adult, Economy, 0 bags

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Flight Deals

Cheap Flights from Caribbean Islands to San Jose

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Caribbean Islands to San Jose 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 Caribbean Islands to San Jose

Thu, Apr 16 - Mon, Apr 20
Delta Logo
2:45 pm - 9:45 pm
SJU
-
SJC
10h 00m
1 stop
Delta Logo
6:00 pm - 12:52 pm
SJC
-
SJU
15h 52m
2 stops
$419Delta
Tue, Apr 28 - Thu, Apr 30
American Airlines Logo
5:45 am - 6:36 pm
SJU
-
SJC
15h 51m
2 stops
American Airlines Logo
2:02 pm - 4:32 am
SJC
-
SJU
11h 30m
1 stop
$444American Airlines
Mon, May 4 - Mon, May 11
American Airlines Logo
11:59 pm - 10:10 am
SJU
-
SJC
13h 11m
1 stop
American Airlines Logo
7:09 pm - 9:13 am
SJC
-
SJU
11h 04m
2 stops
$445American Airlines
Sat, May 2 - Sat, May 9
American Airlines Logo
11:38 am - 10:59 pm
SJU
-
SJC
14h 21m
2 stops
American Airlines Logo
2:02 pm - 4:32 am
SJC
-
SJU
11h 30m
1 stop
$472American Airlines
Thu, Apr 23 - Mon, Apr 27
Alaska Airlines Logo
11:59 pm - 10:10 am
SJU
-
SJC
13h 11m
1 stop
Alaska Airlines Logo
6:00 am - 11:02 pm
SJC
-
SJU
14h 02m
1 stop
$474Alaska Airlines
Mon, May 4 - Mon, May 11
Southwest Logo
6:50 am - 10:25 pm
SJU
-
SJC
18h 35m
2 stops
Southwest Logo
8:35 pm - 10:35 am
SJC
-
SJU
11h 00m
2 stops
$531Southwest
Wed, Sep 9 - Mon, Sep 14
United Airlines Logo
12:15 am - 12:04 pm
BQN
-
SJC
14h 49m
2 stops
United Airlines Logo
6:37 pm - 11:09 pm
SJC
-
BQN
25h 32m
2 stops
$711United Airlines
Sat, May 2 - Sat, May 9
United Airlines Logo
6:00 am - 9:32 pm
SDQ
-
SJC
18h 32m
2 stops
United Airlines Logo
2:33 pm - 11:55 am
SJC
-
SDQ
18h 22m
2 stops
$725United Airlines
Thu, Apr 23 - Fri, May 1
Aeromexico Logo
11:02 am - 1:18 pm
SDQ
-
SJC
53h 16m
2 stops
Aeromexico Logo
4:00 pm - 6:25 am
SJC
-
SDQ
11h 25m
2 stops
$739Aeromexico
Tue, Apr 14 - Thu, Apr 23
Aeromexico Logo
11:02 am - 10:01 pm
SDQ
-
SJC
37h 59m
2 stops
Aeromexico Logo
6:45 am - 6:25 am
SJC
-
SDQ
20h 40m
2 stops
$789Aeromexico
Useful Info

Good to know

Low seasonOctober
Cheapest flight$237
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly and prices are also 22% lower on average.
Flight from San Juan to San Jose

FAQs for booking flights from Caribbean Islands to San Jose

  • How does KAYAK find such low prices on flights from Caribbean Islands to San Jose?

    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 Caribbean Islands to San Jose.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Caribbean Islands to San Jose?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to San Jose from 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 Caribbean Islands to San Jose?

    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 San Jose with an airline and back to Caribbean Islands with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Caribbean Islands to San Jose?

    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 San Jose from Caribbean Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airline flying from Caribbean Islands to San Jose

 
Need help choosing which airline to fly with from Caribbean Islands to San Jose? 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.
7.1
American AirlinesOverall score based on 11488 reviews
6.4Food
7.5Boarding
7.2Comfort
6.9Entertainment
7.9Crew
Airline reviews

Smooth flight. From the early boarding and all were on board before departure time and arrived early in ONT. Great crew. Thank you!!!!

10.0 ExcellentFraxys, Feb 2026
DFW - ONT
Read more American Airlines reviews

Smooth flight. From the early boarding and all were on board before departure time and arrived early in ONT. Great crew. Thank you!!!!

The flight was significantly delayed for 6.5 hours because of snow. There was no communication once the plane returned to the gate regarding when the flight would resume. Other flights were departing while our flight was being unloaded for reasons unknown. Our flight also seemed out of the queue regarding further deicing, refueling, and waiting to Taxi to the runway.

They are always late and seats was also not having working charger

did not have enough meal for first class passengers so offer us snack

We were upgraded to Business Class. So comfortable with great service and food options

The flight was completely full. Crew was not happy. Everyone was rude and brusque. Travelling with an arm in a cast and seating in the first row of economy cabin (in front of the separation) I needed help retrieving my tray for the meal. A staff member literally threw the tray on my lap, without helping to take out the tray. Boarding was messy, with 300 people waiting in an encloses space with low ceiling. I will try to avoid AA next time I have a long flight.

The comfort of Business Class made this trip far more comfortable. I was indeed surprised when I asked one of the flight attendant to help me set up my "bed", she responded that "We don't make beds in Business Class any longer...only First Class" I believe her name was Giselle, but I'm not certain. She did instruct me how to adjust the seat, place the hooded cover and I clearly understood how to place the blanket and the cover. Additionally, the meal I was served (a beef dish) was almost inedible. The beef was tough and odd tasting. I didn't mention it as I was hoping to quickly settle down and try to get some sleep.

Amazing I love American. I’ll never fly anyone else if I can help it.

Everything about the flight was lovely. My only suggestion would be to offer a few more options of tv series from Apple TV or HBO.

After the door had been closed, the cockpit makes an announcement that catering is running late and it is not the airline's fault. It is their fault in the sense that we had to sit for 2 hours or more when we could have stayed in the terminal. Poor communications between catering and airline. This caused a young man to lose his temper and he went storming out hitting objects. He had complained to the gate agent that he had already waited at the gate 7 hours and when can the airplane leave? Airilnes do a poor job of explaining delays, maintenance issues, etc. whereas being truthful may gain more sympathy or understanding.

Everything you need to know for your flight to San Jose

Information on the airport you'll fly into in San Jose