$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 3/17. 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 San Jose

Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 23% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Everything you should know

Cheapest round-trip
$422
Delta
Tue 2/24Wed 3/4
PLS - SJC • 2 stops
Cheapest one-way
$211
Typical prices: $180-$336
Multiple Airlines
Tue 3/17
SJU - SJC • 3 stops
Start a new search
KAYAK searches 100s of sites at once to find you the best travel deals.
We hope you love your trip to San Jose!
Flight Deals
Useful Info
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

Tue, Feb 24 - Wed, Mar 4
Delta Logo
2:10 pm - 12:52 pm
PLS
-
SJC
25h 42m
2 stops
Delta Logo
10:35 pm - 2:25 pm
SJC
-
PLS
12h 50m
1 stop
$422Delta
Sat, Feb 14 - Wed, Feb 18
American Airlines Logo
6:33 am - 6:45 pm
SJU
-
SJC
16h 12m
2 stops
American Airlines Logo
6:00 am - 11:31 pm
SJC
-
SJU
13h 31m
1 stop
$462American Airlines
Sat, Feb 14 - Wed, Feb 18
American Airlines Logo
7:33 am - 6:45 pm
SJU
-
SJC
15h 12m
2 stops
American Airlines Logo
6:00 am - 11:34 pm
SJC
-
SJU
13h 34m
2 stops
$482American Airlines
Wed, Feb 25 - Sat, Feb 28
Alaska Airlines Logo
7:33 am - 6:37 pm
SJU
-
SJC
15h 04m
2 stops
Alaska Airlines Logo
10:24 am - 3:11 pm
SJC
-
SJU
24h 47m
2 stops
$570Alaska Airlines
Wed, Feb 25 - Sat, Feb 28
Alaska Airlines Logo
7:33 am - 10:56 pm
SJU
-
SJC
43h 23m
2 stops
Alaska Airlines Logo
12:45 pm - 3:11 pm
SJC
-
SJU
22h 26m
2 stops
$580Alaska Airlines
Thu, Feb 26 - Mon, Mar 2
United Airlines Logo
5:20 pm - 9:05 pm
PUJ
-
SJC
31h 45m
2 stops
United Airlines Logo
8:50 am - 12:59 pm
SJC
-
PUJ
24h 09m
2 stops
$618United Airlines
Thu, Feb 26 - Mon, Mar 2
United Airlines Logo
12:56 pm - 9:05 pm
PUJ
-
SJC
36h 09m
2 stops
United Airlines Logo
8:50 am - 6:18 pm
SJC
-
PUJ
29h 28m
1 stop
$637United Airlines
Wed, Jul 1 - Wed, Jul 8
Southwest Logo
2:35 pm - 7:00 am
STT
-
SJC
19h 25m
2 stops
Southwest Logo
7:40 pm - 1:50 pm
SJC
-
STT
15h 10m
2 stops
$732Southwest
Sun, Mar 15 - Sun, Mar 22
British Airways Logo
2:35 pm - 10:16 am
CUR
-
SJC
22h 41m
2 stops
British Airways Logo
4:20 pm - 1:35 pm
SJC
-
CUR
18h 15m
2 stops
$886British Airways
Sun, Mar 29 - Thu, Apr 2
Southwest Logo
1:35 pm - 7:00 am
PUJ
-
SJC
20h 25m
2 stops
Southwest Logo
9:35 pm - 2:30 pm
SJC
-
PUJ
13h 55m
2 stops
$962Southwest
Useful Info

Good to know

Low seasonOctober
Cheapest flight$211
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly and prices are also 18% 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.
7.2
American AirlinesOverall score based on 11213 reviews
8.0Crew
6.4Food
6.9Entertainment
7.5Boarding
7.2Comfort
Airline reviews

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

10.0 ExcellentRobert, Jan 2026
AKL - LAX
Read more American Airlines reviews

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.

We were told the flight was delayed 5 times, then it was moved to the next day.

The experience with American Airlines was good, although the Philippines Airlines flight was much better (better seats, better food, better entertainment options, overall better). Again, the MIA to LAX flight was fine, but nothing in comparison to the comfort and accommodations of the Philippines Airlines flight from LAX to MNL.

Loved the crew . Absolutely no complaints. Except for luggage lost

Wish some foods provided rather than just biscuit/cookie for flight more than 2 hours

Everything you need to know for your flight to San Jose

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