$193 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 7/9. 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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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

Wed, Sep 23 - Mon, Sep 28
United Airlines Logo
1:00 am - 11:59 am
SJU
-
SJC
13h 59m
2 stops
United Airlines Logo
6:37 pm - 12:34 pm
SJC
-
SJU
14h 57m
2 stops
$386United Airlines
Thu, Sep 24 - Mon, Sep 28
Southwest Logo
5:30 am - 1:00 pm
SJU
-
SJC
10h 30m
1 stop
Southwest Logo
10:30 pm - 12:50 pm
SJC
-
SJU
11h 20m
1 stop
$414Southwest
Thu, Oct 15 - Mon, Oct 19
United Airlines Logo
2:00 pm - 9:04 pm
SJU
-
SJC
10h 04m
1 stop
United Airlines Logo
6:37 pm - 11:57 am
SJC
-
SJU
14h 20m
2 stops
$491United Airlines
Wed, May 27 - Wed, Sep 2
Delta Logo
6:15 am - 5:02 pm
SJU
-
SJC
13h 47m
2 stops
Delta Logo
7:15 am - 10:23 pm
SJC
-
SJU
12h 08m
1 stop
$511Delta
Tue, Jun 30 - Sat, Jul 11
Alaska Airlines Logo
12:44 am - 1:41 pm
SJU
-
SJC
15h 57m
1 stop
Alaska Airlines Logo
6:00 am - 11:40 pm
SJC
-
SJU
14h 40m
1 stop
$523Alaska Airlines
Wed, May 27 - Wed, Sep 2
Delta Logo
6:15 am - 3:32 pm
SJU
-
SJC
12h 17m
2 stops
Delta Logo
7:00 am - 10:23 pm
SJC
-
SJU
12h 23m
2 stops
$539Delta
Thu, Oct 15 - Mon, Oct 19
Alaska Airlines Logo
6:00 am - 9:56 pm
SJU
-
SJC
18h 56m
1 stop
Alaska Airlines Logo
6:00 am - 11:33 pm
SJC
-
SJU
14h 33m
1 stop
$558Alaska Airlines
Mon, May 18 - Fri, May 22
American Airlines Logo
3:44 pm - 10:10 am
NAS
-
SJC
21h 26m
1 stop
American Airlines Logo
2:34 pm - 2:46 pm
SJC
-
NAS
21h 12m
1 stop
$685American Airlines
Fri, May 29 - Fri, Jun 5
Aeromexico Logo
11:01 am - 2:11 pm
SDQ
-
SJC
30h 10m
2 stops
Aeromexico Logo
11:41 am - 6:36 am
SJC
-
SDQ
39h 55m
2 stops
$737Aeromexico
Thu, Jun 11 - Mon, Jun 22
American Airlines Logo
7:01 am - 11:12 pm
POS
-
SJC
19h 11m
2 stops
American Airlines Logo
7:24 pm - 2:11 pm
SJC
-
POS
15h 47m
2 stops
$932American Airlines
Useful Info

Good to know

Low seasonJune
Cheapest flight$193
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly and prices are also 16% lower on average.
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 airline 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.
7.9
DeltaOverall score based on 8464 reviews
8.5Crew
7.9Comfort
8.1Boarding
7.8Entertainment
7.2Food
Airline reviews

Everything went smoothly, although the usual gripes about airline travel were still present: the boarding process is inefficient, the snack selection is limited, and so on. Since there was extra space on the flight, the gate agent rearranged many people's seats to put people on the aisles and windows, leaving the middle seats empty, as much as possible, which was pretty great.

10.0 ExcellentDavid, Apr 2026
DTW - SFO
Read more Delta reviews

Everything went smoothly, although the usual gripes about airline travel were still present: the boarding process is inefficient, the snack selection is limited, and so on. Since there was extra space on the flight, the gate agent rearranged many people's seats to put people on the aisles and windows, leaving the middle seats empty, as much as possible, which was pretty great.

While they turned off most cabin lights to allow people to sleep, I was bothered by how bright the side lights still were. It was still quite bright for me in a window seat, when I wish I could have slept!

One of the flight attendants was a little cranky. I appreciated the free wifi and plug to charge my laptop

WiFi didn’t work most of the time. The usb chargers would work only occasionally for 5 mins and wouldn’t charge after that. Had to keep trying repeatedly at each of the seats in the row.

The crew bent over backwards to thank us for flying and make us comfortable. The food service was quick and efficient. The Captain communicated and said goodbye and thank you as we departed. They really stood out!

Generally on time departures and arrivals, clean planes, sky miles membership provides great benefits (complimentary upgrades, etc).

my mom urmila patel needed a wheelchair which was not available on the curbside. she needed to walk almost 50 meters inside (at the risk of falling) and then had to wait in line to get a wheelchair (this is not ok). Once obtained she had to seat in it for 30-45 minutes for someone to take her in thru the checkin process (which was fairly smooth and easy). the lady who helped her with her checkin process was very courteous and helpful

Staff at the check-in counter were friendly, happy and helpful. They tagged our bags and sent us to “bag drop off” but were not very clear about where that was. The airport was busy we headed off in what we thought was the right direction until a gentleman waved us down and actually came after us. He was the baggage handler for Delta and recognized our “deer in the headlights “ look-he brought us to the right area (which was marked as the Southwest Airlines Drop Off) and sent us on our way. Wonderful guy, low key and working with a big smile on his face. Loved it. Loved him.

Arlene was a great flight attendant. I also liked how one of the other flight attendants gave us a heads up about snacks and asked everyone to remove their headphones when it was their turn to order. Good idea.

I haven’t flown economy in over 20 years but it was not bad. Room by my feet for my bag and seat was roomy enough. Surprised in a good way.

Everything you need to know for your flight to San Jose

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