$173 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 9/23. 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

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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

Fri, Sep 19 - Wed, Sep 24
Delta Logo
12:58 pm - 10:55 pmSJU-SJC
12h 57m2 stops
Delta Logo
7:00 am - 10:00 pmSJC-SJU
12h 00m2 stops
$265Delta
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Thu, Sep 18 - Sun, Sep 21
Southwest Logo
5:50 am - 3:50 pmSJU-SJC
13h 00m1 stop
Southwest Logo
8:55 pm - 12:40 pmSJC-SJU
12h 45m1 stop
$333Southwest
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Wed, Sep 10 - Sat, Sep 13
Spirit Airlines Logo
3:19 pm - 8:00 pmSJU-SJC
31h 41m3 stops
Spirit Airlines Logo
11:40 am - 1:43 pmSJC-SJU
23h 03m2 stops
$351Spirit Airlines
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Fri, Sep 19 - Wed, Sep 24
Spirit Airlines Logo
11:59 am - 7:20 amSJU-SJC
22h 21m3 stops
Spirit Airlines Logo
8:15 am - 1:53 pmSJC-SJU
26h 38m3 stops
$377Spirit Airlines
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Thu, Sep 25 - Tue, Sep 30
American Airlines Logo
6:10 am - 9:05 pmSJU-SJC
17h 55m2 stops
American Airlines Logo
12:45 pm - 12:47 pmSJC-SJU
21h 02m2 stops
$381American Airlines
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Wed, Sep 10 - Sat, Sep 13
American Airlines Logo
6:10 am - 4:41 pmSJU-SJC
13h 31m2 stops
American Airlines Logo
2:08 pm - 12:50 pmSJC-SJU
19h 42m2 stops
$414American Airlines
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Wed, Sep 24 - Tue, Sep 30
United Airlines Logo
1:05 am - 10:24 pmSJU-SJC
24h 19m2 stops
United Airlines Logo
6:30 am - 11:57 pmSJC-SJU
14h 27m2 stops
$529United Airlines
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Tue, Sep 16 - Wed, Sep 24
United Airlines Logo
1:05 am - 12:05 pmSJU-SJC
14h 00m2 stops
United Airlines Logo
6:30 am - 11:57 pmSJC-SJU
14h 27m2 stops
$537United Airlines
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Thu, Aug 28 - Thu, Sep 4
 Logo
5:30 pm - 11:44 amNAS-SJC
21h 14m3 stops
 Logo
6:00 am - 10:30 amSJC-NAS
25h 30m3 stops
Thu, Aug 28 - Thu, Sep 4
 Logo
8:30 am - 10:58 pmNAS-SJC
17h 28m2 stops
 Logo
6:00 am - 10:30 amSJC-NAS
25h 30m3 stops
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Good to know

Low seasonSeptember
Cheapest flight$173
Best time to beat the crowds with an average 5% drop in price.
Most popular time to fly and prices are also 13% 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 10000 reviews
7.5Boarding
6.9Entertainment
8.0Crew
7.2Comfort
6.5Food
Airline reviews

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

10.0 ExcellentBrendan, Jul 2025ORD - SNA
Read more American Airlines reviews

Amazing food, great staff, with one noticable detail missing ...but no seat entertainment in any of aircraft ...I am not a fan

Boarding gate in Honolulu was staffed with a great clerk with a soothing voice despite the flight delay of over an hour. Flight attendants in the plane were all grumpy, not pleasant looking bunch. Their sour attitude showed throughout the flight. Inly able to get a select few movies started. Most of the movie links in the “free entertainment” did not work.

I flew Business Class. Rory, one of the Cabin stewards, was attentive, explained the menu, provided appropriate drinks. was

This was a horrible experience. For a first class experience, my chair was held together by 3M tape - and I have a photo. The crew weren’t very attentive, somewhat dismissive and forgot my drink and snack, the chair reclined about 3 inches on a 6-hour cross country flight. I was also not informed that there was no lounge available in Newark airport because of renovations, so all around this was one of the worst experiences and I would actively avoid both American and Alaska Air going forward.

Boarding was very efficient. Everyone got on board and we got on our way very quickly. It was frustrating that the entertainment app was not functioning properly. I was not able to activate some of the movies offered. The crew on this flight appears to be pretty grumpy. They had no smile on their faces. I felt like they were doing us a favor for being there.

Loved the staff, boarding and drink options! Wish the comfort of the seat could have been better nevertheless

Honestly, I haven’t flown American in years, probably due to the pandemic and my being unable to travel for certain periods in the last two years, but it was a good experience to dig out or obtain a new American Airlines account after many years of traveling for business with American in the past.

Long 5 hour and 45 min flight and only one drink service and cookie snack

One bottle of water and a package of cookies for comfort plus. We had to literally beg a flight attendant for an extra bottle of water later in the flight due to feeling dehydrated.

Flight boarded from Gate 39 at OGG, the farthest gate in the terminal. There were no Hawaiian themed amenities for the flight. The first class service was mediocre at best; I received not special welcome or recognition as an executive platinum member of American Advantage program. The flight attendants were more concerned with their cell phones than saying "thank you" to the passengers as we disembarked. Fortunately, the flight arrived at LAX a few minutes early.

Everything you need to know for your flight to San Jose

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

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