$170 Find Cheap Flights from Caribbean 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 7/16. 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

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 20% 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.

Flights Deals
Useful Info
Flights Deals

Cheap Flights from Caribbean 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 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 to San Jose

Thu, Sep 25 - Tue, Sep 30
Delta Logo
12:55 pm - 10:58 pmSJU-SJC
13h 03m1 stop
Delta Logo
6:45 am - 10:08 pmSJC-SJU
12h 23m1 stop
$265Delta
Find Deal
Thu, Sep 25 - Tue, Sep 30
Delta Logo
12:55 pm - 10:58 pmSJU-SJC
13h 03m1 stop
Delta Logo
2:35 pm - 12:03 pmSJC-SJU
18h 28m2 stops
$275Delta
Find Deal
Thu, Jul 31 - Thu, Aug 7
Spirit Airlines Logo
4:05 pm - 10:36 amSTT-SJC
21h 31m2 stops
Spirit Airlines Logo
4:22 pm - 3:10 pmSJC-STT
19h 48m2 stops
$381Spirit Airlines
Find Deal
Mon, Jul 14 - Mon, Jul 21
Spirit Airlines Logo
1:37 am - 10:36 amSJU-SJC
35h 59m3 stops
Spirit Airlines Logo
4:22 pm - 12:02 pmSJC-SJU
16h 40m2 stops
$384Spirit Airlines
Find Deal
Tue, Jul 15 - Mon, Jul 21
Southwest Logo
6:30 am - 5:00 pmSJU-SJC
13h 30m1 stop
Southwest Logo
7:25 am - 11:05 pmSJC-SJU
12h 40m2 stops
$449Southwest
Find Deal
Tue, Jul 15 - Mon, Jul 21
Southwest Logo
6:30 am - 5:00 pmSJU-SJC
13h 30m1 stop
Southwest Logo
8:55 pm - 12:35 pmSJC-SJU
12h 40m1 stop
$479Southwest
Find Deal
Mon, Jul 21 - Tue, Jul 29
 Logo
12:59 am - 12:16 pmSJU-SJC
14h 17m1 stop
 Logo
6:30 am - 11:32 amSJC-SJU
26h 02m2 stops
Mon, Jul 14 - Mon, Jul 21
 Logo
12:59 am - 12:16 pmSJU-SJC
14h 17m1 stop
 Logo
4:22 pm - 12:02 pmSJC-SJU
16h 40m2 stops
Mon, Dec 8 - Sun, Dec 14
American Airlines Logo
8:09 am - 8:48 pmSJU-SJC
16h 39m1 stop
American Airlines Logo
5:58 am - 8:55 pmSJC-SJU
10h 57m1 stop
$629American Airlines
Find Deal
Mon, Jul 14 - Mon, Jul 21
American Airlines Logo
12:59 am - 9:10 amSJU-SJC
11h 11m2 stops
American Airlines Logo
11:38 am - 5:06 amSJC-SJU
14h 28m1 stop
$641American Airlines
Find Deal
Useful Info

Good to know

Low seasonSeptember
High seasonNovember
Cheapest flight$170
Best time to beat the crowds with an average 5% drop in price.
Most popular time to fly with an average 46% increase in price.
Flight from San Juan to San Jose

FAQs for booking flights from Caribbean to San Jose

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

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Caribbean 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 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 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 with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Caribbean 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 up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 3 airlines serving from Caribbean to San Jose

 
Need help choosing which airline to fly with from Caribbean 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.
8.0
SouthwestOverall score based on 4280 reviews
7.1Food
8.6Crew
7.6Entertainment
8.0Comfort
8.2Boarding
Airline reviews

It was a perfect flight in all aspects! Both legs!

10.0 ExcellentAnonymous, Apr 2025LGB - SMF
Read more Southwest reviews

It was a perfect flight in all aspects! Both legs!

Boarding process, crew were good. But the seats were so uncomfortable that was all I could focus on. I literally had to sit forward so that all 3 of us could fit in row. I will try to avoid Southwest in the future for any flights over 60 minutes.

Great flight, 47 passengers on a 180 seat plane. Stewardess was pleasant and cheerful.

Great experience flying Southwest. The crew was really kind and helpful, and very friendly with our toddler.

Plane late from DC to Austin 30 minutes. Crew made up much of the time enroute to San Diego.

Fine, but how to board on SW versus othrr airlines, is just lame. Goood staff though and all was solid otherwise.

Was as expected. Crowed planes. Too many carryons delaying takeoff. But the ride only took an hour and saved me a lot of time SFO is a not a great airport.

Was as expected. Crowed planes. Too many carryons delaying takeoff. But the ride only took an hour and saved me a lot of time SFO is a hell hole of an airport. It is the new LaGuardia. Everything Cobbled together. Security gates closed. Terri directional signage

I will be flying again Southwest Airlines. Friendly crew, comfortable and affordable.

The plane arrived 25 minutes late, and the Wi-Fi was slower than it usually is.

5 hours of delay that could've been much shorter if Delta had taken the 1 hour delay they imposed on the flight before boarding to run any of the plane checks required for flight to find the hydraulic issue that required nearly 3 hours to fix. $24 of meal credit buys a sandwich and a soft drink. Poor communication within the terminal about what gate we'd be re-boarding from and when we'd be re-boarding.

The entertainment and wifi mostly didn't work on this flight.

Terrible entertainment system - kept freezing and audio kept cutting out. Snacks were mediocre at best for a 5 hour flight.

I am still upset that my bag was lost on a recent trip to Rome ; we were inconvenienced and out €150 Euros ; delta has refused to reimburse us

This had nothing to do with Delta… The flights were on time and flawless. The service was excellent. We purchased seats in (aisle/middle) comfort plus since this was a cross country flight. Unfortunately, the woman seated at the window was 300+ pounds and, as might be expected, covered up about a third of the middle seat also. there was absolutely nothing that Delta could have done about that… I just don’t know what the answer should be. If you purchase a seat, you should should be able to use the entire seat and not just the portion that someone else is not sitting/oozing in. Disappointing…there should be something that could be done….I'm just not sure what solution could be.

I love the free WiFi!! Crew was nice. Bathroom was decent. First time flying delta in a long time and I enjoyed it. Will definitely look into booking with Delta more but I think Delta is a little more expensive than the other airlines.

Seats are much much more comfortable than United, which is what I usually fly

If I pay extra for "comfort+" I expect leg room where I can stretch my legs. I was seated with an attendant's seat blocking my feet. Knee space was fine but my feet had less room than the non-"comfort+" seats. Also, don't go cheap on food when you have flights of 3+ hours. It's insulting.

Only one side of the heafphone jack work. Crew was friendly and helpful.

Great. Flight departed early and arrived early. Deplaning and baggage claim ww were quick.

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.

Bigger seats. Board back to front! Disembark front to back!

Extraordinary service in business class, and very good breakfast and snacks. A really lovely flight.

This flight didn’t happen because AA agents didn’t let us board the flight

Plane was pretty clean, staff was friendly and helpful, flight left about on time arrived early. Took a long time to board and get off the plane - carry on items didn't have enough room so people had to move all around to find places.

The service and food needs to improve to catch up with other international flights

Everything you need to know for your flight to San Jose

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

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.