$138 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 2/17. 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

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Everything you should know

Cheapest round-trip
$351
Typical prices: $477-$552
Alaska Airlines
Sat 2/14Wed 2/18
SJU - SJC • 1 stop
Cheapest one-way
$147
Typical prices: $185-$271
Multiple Airlines
Tue 2/17
SJU - SJC • 3 stops
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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

Sat, Feb 14 - Wed, Feb 18
Alaska Airlines Logo
7:30 am - 9:29 pm
SJU
-
SJC
17h 59m1 stop
Alaska Airlines Logo
6:00 am - 11:32 pm
SJC
-
SJU
13h 32m1 stop
$351Alaska Airlines
Sat, Feb 14 - Wed, Feb 18
Alaska Airlines Logo
7:30 am - 9:29 pm
SJU
-
SJC
17h 59m1 stop
Alaska Airlines Logo
12:45 pm - 11:32 pm
SJC
-
SJU
30h 47m2 stops
$423Alaska Airlines
Thu, Jan 22 - Sun, Jan 25
United Airlines Logo
3:35 pm - 1:38 pm
NAS
-
SJC
49h 03m2 stops
United Airlines Logo
4:00 pm - 3:22 pm
SJC
-
NAS
20h 22m2 stops
$461United Airlines
Wed, Jan 14 - Thu, Jan 22
Alaska Airlines Logo
7:07 am - 1:42 pm
SJU
-
SJC
10h 35m1 stop
Alaska Airlines Logo
6:00 am - 10:26 pm
SJC
-
SJU
12h 26m1 stop
$463Alaska Airlines
Sat, Feb 14 - Wed, Feb 18
Alaska Airlines Logo
7:30 am - 10:56 pm
SJU
-
SJC
19h 26m2 stops
Alaska Airlines Logo
12:45 pm - 11:32 pm
SJC
-
SJU
30h 47m2 stops
$495Alaska Airlines
Thu, Jan 22 - Sat, Jan 24
United Airlines Logo
2:50 pm - 1:39 pm
GCM
-
SJC
25h 49m2 stops
United Airlines Logo
4:00 pm - 1:45 pm
SJC
-
GCM
42h 45m2 stops
$501United Airlines
Thu, Jan 22 - Mon, Jan 26
United Airlines Logo
5:06 pm - 1:39 pm
PLS
-
SJC
23h 33m2 stops
United Airlines Logo
4:00 pm - 1:17 pm
SJC
-
PLS
18h 17m2 stops
$543United Airlines
Wed, Mar 18 - Tue, Mar 24
Delta Logo
3:30 pm - 12:54 pm
BGI
-
SJC
24h 24m2 stops
Delta Logo
7:48 pm - 2:20 pm
SJC
-
BGI
15h 32m2 stops
$758Delta
Thu, Jan 22 - Mon, Jan 26
Air Canada Logo
4:10 pm - 8:56 pm
BGI
-
SJC
32h 46m2 stops
Air Canada Logo
8:40 am - 2:35 pm
SJC
-
BGI
25h 55m2 stops
$1,038Air Canada
Wed, Mar 18 - Tue, Mar 24
American Airlines Logo
7:20 am - 10:32 pm
BGI
-
SJC
18h 12m3 stops
American Airlines Logo
4:20 pm - 3:14 pm
SJC
-
BGI
19h 54m2 stops
$2,955American Airlines
Useful Info

Good to know

Low seasonOctober
Cheapest flight$147
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly and prices are also 19% 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 11054 reviews
7.2Comfort
7.5Boarding
6.5Food
8.0Crew
6.9Entertainment
Airline reviews

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

2.0 MediocreAnonymous, Nov 2025
DCA - LAX
Read more American Airlines reviews

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

We are too tired and frustrated to comment politely at this point

The business class seats are dated and uncomfortable. The space is bare minimum and there is absolutely no privacy. For $4K, this is not what I expect.

The flight crew was rude. We were in first class and no one even offered water until an hour after we were in the air. Horrible experience

Great. Quick and quiet and east. The breakfast choices were a welcome surprise!

The stewardess hit me with the food kart twice on the head and didn't say I'm sorry once. The same stewardess gave me a warm Apple Juice with No ice. The Flight was delayed for Departure 6 times, starting from 2:36pm, finally taking off 7:50pm. I was late picking up my child from the sitter by 3 hours.

Did not get the seat I selected and paid for.

Everything you need to know for your flight to San Jose

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

San Jose (SJC)