$139 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 5/29. 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.
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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.

Recent round-trip flight deals from Caribbean to San Jose

KAYAK's recommended round-trip deals from the most popular airlines that fly from Caribbean to San Jose.
Discover the best prices for you by selecting your travel dates on KAYAK.
Spirit Airlines Logo
4:05 pm - 10:05 amSJU-SJC
21h 00m2 stops
Spirit Airlines Logo
4:28 pm - 11:31 amSJC-SJU
16h 03m2 stops
$302Spirit Airlines
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Wed, May 28 - Wed, Jun 4
Delta Logo
1:06 pm - 10:50 pmSJU-SJC
12h 44m1 stop
Delta Logo
10:25 pm - 1:10 pmSJC-SJU
11h 45m1 stop
$304Delta
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Fri, Aug 8 - Sun, Aug 10
 Logo
3:35 pm - 3:33 pmSDQ-SJC
26h 58m2 stops
 Logo
4:33 pm - 2:35 pmSJC-SDQ
19h 02m2 stops
Tue, Jun 3 - Fri, Jun 6
 Logo
3:35 pm - 11:29 pmSDQ-SJC
34h 54m3 stops
 Logo
6:00 am - 2:35 pmSJC-SDQ
29h 35m2 stops
Tue, Jun 3 - Fri, Jun 6
United Airlines Logo
1:40 pm - 8:50 pmSJU-SJC
10h 10m1 stop
United Airlines Logo
2:30 pm - 5:30 amSJC-SJU
12h 00m2 stops
$487United Airlines
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Wed, May 28 - Wed, Jun 4
United Airlines Logo
2:05 am - 11:50 amSJU-SJC
12h 45m1 stop
United Airlines Logo
2:30 pm - 5:30 amSJC-SJU
12h 00m2 stops
$539United Airlines
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Tue, May 27 - Wed, Jun 4
American Airlines Logo
6:15 am - 9:25 pmSJU-SJC
18h 10m1 stop
American Airlines Logo
6:00 am - 5:06 amSJC-SJU
20h 06m1 stop
$599American Airlines
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Sat, Jun 14 - Sun, Jun 22
American Airlines Logo
12:59 am - 12:23 pmSJU-SJC
14h 24m1 stop
American Airlines Logo
6:00 am - 5:06 amSJC-SJU
20h 06m1 stop
$643American Airlines
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Mon, Jun 9 - Sun, Jun 15
Alaska Airlines Logo
6:30 am - 9:44 pmSJU-SJC
18h 14m1 stop
Alaska Airlines Logo
12:10 pm - 5:12 amSJC-SJU
14h 02m1 stop
$673Alaska Airlines
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Thu, May 15 - Mon, May 19
Alaska Airlines Logo
6:15 am - 8:51 pmSJU-SJC
17h 36m3 stops
Alaska Airlines Logo
6:17 pm - 11:25 pmSJC-SJU
26h 08m2 stops
$1,637Alaska Airlines
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Sat, Jun 14 - Sat, Jun 21
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Good to know

Low seasonMarch
High seasonNovember
Cheapest flight$139
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly with an average 57% 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.

Top airlines flying 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 4294 reviews
8.2Boarding
8.0Comfort
7.1Food
7.6Entertainment
8.6Crew
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.

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.

They separated our seats and moved us to the back of the plane. Hundreds of dollars and thousands of miles used and this was my platinum member experience.

Since it wasn’t a Delta flight, I was not able to sit with my group and there was no entertainment.

Three adults, three children. They did not give us seats together. Two seats together, in row 23, one in 13, one in 14, one in 10, and one in 17. When we got on the plane, the crew tried to ask people to move but basically threw up their hands. One person moved so we had two pairs of seats together. The 1.5 year old sat on a parent's lap (despite having paid for his own seat).

the fight attendants were great and i appreciated that they had season 1 of The Wire from HBO as a viewing option

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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