$193 Find Cheap Flights from San Jose to Caribbean

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from San Jose to Caribbean 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 San Jose to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$612
Santo Domingo
Santo Domingo2 stops$673
Montego Bay
Montego Bay2 stops$527
Oranjestad
Oranjestad2 stops$708
Nassau
Nassau2 stops$560
Kingston
Kingston1 stop$736
Simpson Bay
Simpson Bay1 stop$570
Providenciales
Providenciales2 stops$686
Port of Spain
Port of Spain2 stops$810
Bridgetown
Bridgetown2 stops$919
George Town
George Town2 stops$682
Willemstad
Willemstad1 stop$931
Aguadilla
Aguadilla2 stops$920
Puerto Plata
Puerto Plata2 stops$735
St. John's
St. John's2 stops$872
Punta Cana
Punta Cana1 stop$612
Santo Domingo
Santo Domingo2 stops$673
Montego Bay
Montego Bay2 stops$527
Oranjestad
Oranjestad2 stops$708
Nassau
Nassau2 stops$560
Kingston
Kingston1 stop$736
Simpson Bay
Simpson Bay1 stop$570
Providenciales
Providenciales2 stops$686
Port of Spain
Port of Spain2 stops$810
Bridgetown
Bridgetown2 stops$919
George Town
George Town2 stops$682
Willemstad
Willemstad1 stop$931
Aguadilla
Aguadilla2 stops$920
Puerto Plata
Puerto Plata2 stops$735
St. John's
St. John's2 stops$872

Book Cheap San Jose to Caribbean Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from San Jose to Caribbean 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 San Jose to Caribbean

Mon, Aug 10 - Fri, Aug 14
Delta Logo
5:05 pm - 1:30 pm
SJC
-
SJU
17h 25m
2 stops
Delta Logo
1:06 pm - 10:41 pm
SJU
-
SJC
12h 35m
1 stop
$386Delta
Fri, Aug 7 - Tue, Aug 18
Delta Logo
4:30 pm - 11:46 am
SJC
-
SJU
16h 16m
2 stops
Delta Logo
7:30 am - 9:45 pm
SJU
-
SJC
17h 15m
2 stops
$414Delta
Wed, Oct 14 - Wed, Oct 21
United Airlines Logo
6:37 pm - 12:34 pm
SJC
-
SJU
14h 57m
2 stops
United Airlines Logo
2:00 pm - 9:04 pm
SJU
-
SJC
10h 04m
1 stop
$433United Airlines
Sun, Sep 20 - Fri, Sep 25
Southwest Logo
8:15 pm - 10:55 am
SJC
-
SJU
11h 40m
2 stops
Southwest Logo
5:00 am - 3:20 pm
SJU
-
SJC
13h 20m
2 stops
$440Southwest
Wed, Aug 5 - Fri, Aug 14
Delta Logo
4:30 pm - 11:46 am
SJC
-
SJU
16h 16m
2 stops
Delta Logo
1:06 pm - 9:45 pm
SJU
-
SJC
11h 39m
2 stops
$441Delta
Tue, Sep 29 - Thu, Oct 1
United Airlines Logo
6:37 pm - 11:57 am
SJC
-
SJU
14h 20m
2 stops
United Airlines Logo
2:00 pm - 9:04 pm
SJU
-
SJC
10h 04m
1 stop
$476United Airlines
Mon, May 25 - Thu, May 28
American Airlines Logo
7:24 pm - 9:39 am
SJC
-
SJU
11h 15m
2 stops
American Airlines Logo
6:00 am - 6:34 pm
SJU
-
SJC
15h 34m
2 stops
$480American Airlines
Wed, Jul 1 - Mon, Jul 6
American Airlines Logo
11:24 pm - 4:14 pm
SJC
-
MBJ
14h 50m
1 stop
American Airlines Logo
5:17 pm - 10:50 am
MBJ
-
SJC
19h 33m
2 stops
$530American Airlines
Wed, Oct 14 - Wed, Oct 21
Southwest Logo
9:45 pm - 1:15 pm
SJC
-
NAS
12h 30m
2 stops
Southwest Logo
2:10 pm - 9:55 pm
NAS
-
SJC
10h 45m
2 stops
$560Southwest
Mon, Jun 22 - Fri, Jun 26
JetBlue Logo
10:00 pm - 11:56 am
SJC
-
MBJ
11h 56m
1 stop
JetBlue Logo
2:37 pm - 10:57 pm
MBJ
-
SJC
10h 20m
1 stop
$653JetBlue
Booking Insights

KAYAK's insights & trends for San Jose to Caribbean flights

Get data-powered insights and trends into flights from San Jose to Caribbean to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest month to fly from San Jose to Caribbean?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from San Jose to Caribbean, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from San Jose to Caribbean is September, when tickets cost $128 (return) on average. On the other hand, the most expensive months are March and October, when the average cost of round-trip tickets is $465 and $388 respectively.

How far in advance should I book a flight from San Jose to Caribbean?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from San Jose to Caribbean, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from San Jose to Caribbean, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 24 weeks before departure.

Good to know

Low seasonFebruary
Cheapest flight$193
Best time to beat the crowds with an average 28% drop in price.
Most popular time to fly and prices are also 9% lower on average.
Flight from San Jose to San Juan

FAQs - booking Caribbean flights

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

    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 San Jose to Caribbean.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from San Jose to Caribbean?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from San Jose to 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 San Jose to Caribbean?

    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 from San Jose to Caribbean with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from San Jose to Caribbean?

    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 from San Jose to Caribbean up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 5 airlines serving from San Jose to Caribbean

 
Need help choosing which airline to fly with from San Jose to Caribbean? 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 4314 reviews
8.1Boarding
7.0Food
7.5Entertainment
8.0Comfort
8.6Crew
Airline reviews

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

10.0 Excellentlarry, Apr 2026
LGB - PHX
Read more Southwest reviews

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

Delayed flight, lack of information, boarding process is a mess as is the carryon luggage causing issues when leaving the plane….just a poor experience.

Comfortable. Easy. No problems. Just wish they had gf options for snacks.

The crew was very kind and made going to Hawaii relaxing and fun to look forward to! Thank you Southwest for a pleasant flight!

Terrible. Even though there’s assigned seating now, they are still the slowest boarding airline of anyone.

It was good from LAX to Phoenix, But the connection in Phoenix to Tulsa was not that great. The staff on both flights were great. The choice of free entertainment was ok nothing to brag about. The 45 min delay because of some electrical issue wasn't great from Phoenix to Tulsa. We sat there with hardly any air, The seat I had was between windows so the side of the plane pushed in on you. My being a bigger man it then made the seating area uncomfortable. The seats on the plane had no power to connect to recharge your phone or anything. I would recommend that they should look into a slot or clamp to hold your phone to enjoy while watching the entertainment choices hands-free. Also make it possible to raise the inner seat by the window be able to raise the arm rest up to make more room for larger people to set more comfortably. I would also say other then that stop price gouging the airfare or nickel and diming everything. Not fair for people having to fly for emergencies and be paying for higher prices due to the season or holidays. Your making your money either way and the cost of flying is still going to be the same regardless if there's 100 people or 200 people.

Southwest was greaat! The most expensive but the least upsetting for those we were flying to see.

Boarding was easy. The seats are small and fairly uncomfortable

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

Good but I prefer choose your own seat. With the new assigned seats they should board from the back I see no advantage to this new boarding. Just like every other airline

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!

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

N Everything was perfect from boarding to assistance to baggage in Tampa

Loved the crew! Sucks that we went from 1 hour and 8 minute layover to a 3 hour layover. But weather sucks like that.

Fast, lovely scenery, great info on the Delta flight screen about landmarks we were flying over. Great landing!

Long flight but comfortable and not freezing as I have experienced on Hawaiian flights to the islands. They gave us blankets just in case. Nice touch.

I took seat 15A in anticipation of window seat, there is no window.

Flight late, the waited for a long time for “personal” to arrive at gate to dock the plane in Rochester. So annoying. This flight was expected, why aren’t personel available for the jet bridge?

My recent experience was excellent on Delta! I flew with Delta Comfort and I was really comfortable in my seat. I enjoyed the in-flight service. The flight attendants were so friendly and hospitable. I love the snack on the flight as well. This was my first time flying on Delta and I will definitely consider flying with them again.

My flight was canceled on Sunday. Rebooking took three hours. Had to pay for accommodations another night. New flight was delayed for 5 hours, all that was sent was a 12 dollar food voucher, which doesn’t tell you how to use it. Then when we landed we had to sit on the plane for an hour before we could get off.

Some crew were unfriendly or in some cases just straight up rude.

Booked through Kayak Business, had a seat in middle and towards back due to booking rate, not comfortable.

Outstanding service, efficient & friendly crew, flight was safe, comfortable & on time

United Airline crews were very friendly and very attentive. 12 hours flight was gone like in a shorter one.

Food was surprisingly delicious. Space in the seat is horrible when the seating front is reclined. Movie offerings were terrible. Crew was friendly and helpful.

Flight itself excellent, but delayed so missed connection & got to destination 2 hrs later

Due to cancellation of connecting flight (Lufthansa) I didn’t fly with United

It was a red-eye, but the flight felt surprisingly quick. The seats were very comfortable, and that made resting much easier. I also want to thank the gentleman seated next to me, who graciously moved so my mom could sit beside me. We slept almost the entire way. The cabin crew was respectful in not disturbing us, while also being courteous and professional throughout. Thank you, United.

Boarding was again a "free for all". We were boarding group 4, and almost the entire plane was able to board before us. It's a shame that someone who follows the rules, gets the short end of the stick. Not fair.

It was perfect! I've never flown with United before, but I definitely will in the future

Boarding gate at LAX was too crowded—two gates next to one another

On time departure and early arrival. Flight attendant very nice.

The business class layout of chairs was weired. You are sitting directly across stranger.,

The SFO Lounge crew were amazing. The bartender Faris was great. Thanks!

Friendly crew is the only nice thing. Seats uncomfortable. Food and snacks horrible. Movies were the same as the first 10 hour flight two weeks before

Was not able to do a online check-in because the American Airlines system doesn't store our visa or other passport information, allowing us to have a trouble-free check-in. We were forced to have to check-in at the counter which Changes are upgrade status given that we were not able to check in much earlier.

Good flight, seated and had a water within 5 minutes. Crew was hospitable.

We left at 1030 am pacific from LA and supposed to land at 7 pm Eastern in NY. They made a detour, stopped in Philadelphia and didn’t land till 1130 PM Eastern!!! Worst flight experience with no pilot communication with no explanation as to what was going on. Everyone was very frustrated to say the least.

I cancelled my ticket less than 24 hours deadline but I didn’t get refunded.

Flight boarded from Gate 159B, the farthest gate in the LAX Bradley Terminal. While the flight operated on time, the first class cabin attendant made no recognition of my being an Advantage Executive Platinum member.

My flight was delayed then put back on time then cancelled and they automatically rebooked me to another flight but that flight was going to make me late to a concert i had planned for. Flight was at 10am concert was at 7pm from Burbank to Las Vegas so I allowed enough time but the flight that was rebooked was too late so I talked with the desk and they were able to get me on an afternoon flight. Thank goodness. That was stressful for a moment. I want to thank the person who helped me get to my show on time. Concert tickets are very expensive and the show was amazing. Hopefully my flight home will be smooth.

We were delayed and the bag charge fees are very expensive.

Horrible airline .. my flight was cancel , the only offer to flight next day was no good for me , representative from spirit advise everybody to buy the new ticket from southwest airline and spirit will pay back the money we spend on new ticket but after we did this they don’t want to pay us back , .. customer service is not help anybody Chat text messages it is horrible also , robots can’t answer and help u with anything … I send the complains to head quarter in Miami and department of transportation

My flight was delayed by over an hour and the turbulance was horrible.

I was double booked for my ticket- they have record of it and admitted to their error but wouldn’t let me board until I paid once again for the fare- have documentation of their mistake -

I cannot effectively rate the food and drink as I had not. Otherwise, the trip was fine. The seats were nice, the crew was fine. They could smile once in a while. They all look like they were mad.

They cancelled the flight due to crew unavailability. The next day they cancelled the flight again.

For the price of the fare, there really isn’t much to complain about.

A Spirit agent caused me to miss my flight. The company has not responded for request of refund. Stay away from Spirit.

I arrived two hours early, and at 9:20 I was still queuing for security.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports