$186 Find Cheap Flights from San Jose to Caribbean Islands

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 Islands departing on 8/22. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Caribbean Islands

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from San Jose to Caribbean Islands, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from San Jose to Caribbean Islands, as well as popular online travel agencies
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Flight Deals

Cheap Flights from San Jose to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana2 stops$705
Santo Domingo
Santo Domingo2 stops$663
Montego Bay
Montego Bay2 stops$397
Oranjestad
Oranjestad2 stops$708
Nassau
Nassau1 stop$556
Kingston
Kingston1 stop$736
Simpson Bay
Simpson Bay2 stops$700
Providenciales
Providenciales2 stops$943
Port of Spain
Port of Spain2 stops$789
George Town
George Town2 stops$797
Willemstad
Willemstad2 stops$856
Aguadilla
Aguadilla2 stops$768
St. John's
St. John's2 stops$902
Punta Cana
Punta Cana2 stops$705
Santo Domingo
Santo Domingo2 stops$663
Montego Bay
Montego Bay2 stops$397
Oranjestad
Oranjestad2 stops$708
Nassau
Nassau1 stop$556
Kingston
Kingston1 stop$736
Simpson Bay
Simpson Bay2 stops$700
Providenciales
Providenciales2 stops$943
Port of Spain
Port of Spain2 stops$789
George Town
George Town2 stops$797
Willemstad
Willemstad2 stops$856
Aguadilla
Aguadilla2 stops$768
St. John's
St. John's2 stops$902

Book Cheap San Jose to Caribbean Islands 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 Islands 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 Islands

Sun, Aug 23 - Sat, Aug 29
Delta Logo
6:30 am - 10:29 pm
SJC
-
SJU
12h 59m
1 stop
Delta Logo
6:48 am - 7:25 pm
SJU
-
SJC
15h 37m
2 stops
$386Delta
Sat, Aug 1 - Mon, Aug 31
American Airlines Logo
2:23 pm - 1:09 pm
SJC
-
MBJ
20h 46m
2 stops
American Airlines Logo
2:37 pm - 10:48 am
MBJ
-
SJC
22h 11m
2 stops
$397American Airlines
Sun, Aug 30 - Sat, Sep 5
American Airlines Logo
7:12 pm - 2:51 pm
SJC
-
SJU
16h 39m
2 stops
American Airlines Logo
7:05 am - 6:30 pm
SJU
-
SJC
14h 25m
2 stops
$440American Airlines
Wed, Aug 12 - Sun, Aug 16
Southwest Logo
8:00 am - 10:00 pm
SJC
-
SJU
11h 00m
2 stops
Southwest Logo
5:30 am - 1:15 pm
SJU
-
SJC
10h 45m
1 stop
$455Southwest
Sun, Aug 23 - Sat, Aug 29
Delta Logo
6:30 am - 10:29 pm
SJC
-
SJU
12h 59m
1 stop
Delta Logo
12:56 pm - 9:58 pm
SJU
-
SJC
12h 02m
1 stop
$466Delta
Wed, Aug 12 - Sun, Aug 16
Southwest Logo
10:30 pm - 2:30 pm
SJC
-
SJU
13h 00m
1 stop
Southwest Logo
5:30 am - 1:15 pm
SJU
-
SJC
10h 45m
1 stop
$494Southwest
Fri, Jun 19 - Fri, Jun 26
United Airlines Logo
6:37 pm - 3:10 pm
SJC
-
MBJ
18h 33m
2 stops
United Airlines Logo
4:12 pm - 1:24 pm
MBJ
-
SJC
23h 12m
2 stops
$505United Airlines
Mon, Jun 1 - Fri, Jun 5
United Airlines Logo
6:37 pm - 12:34 pm
SJC
-
SJU
14h 57m
2 stops
United Airlines Logo
1:00 am - 1:24 pm
SJU
-
SJC
15h 24m
2 stops
$542United Airlines
Mon, Jun 22 - Fri, Jun 26
JetBlue Logo
10:00 pm - 1:12 pm
SJC
-
MBJ
13h 12m
1 stop
JetBlue Logo
2:37 pm - 10:57 pm
MBJ
-
SJC
10h 20m
1 stop
$553JetBlue
Thu, May 21 - Tue, May 26
JetBlue Logo
10:00 pm - 12:00 pm
SJC
-
AUA
11h 00m
1 stop
JetBlue Logo
3:25 pm - 10:55 pm
AUA
-
SJC
10h 30m
1 stop
$844JetBlue
Booking Insights

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

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

Can I save money by flying with a layover from San Jose to Caribbean Islands?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $483, prices are generally cheapest when you fly direct.

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

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 Islands, 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 Islands is August, when tickets cost $176 (return) on average. On the other hand, the most expensive months are March and December, when the average cost of round-trip tickets is $758 and $500 respectively.

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

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 Islands, 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 Islands, 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$186
Best time to beat the crowds with an average 29% drop in price.
Most popular time to fly and prices are also 2% lower on average.
Flight from San Jose to San Juan

FAQs - booking Caribbean Islands flights

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

    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 Islands.

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

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

    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 Islands 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 Islands?

    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 Islands 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 San Jose to Caribbean Islands

 
See real verified KAYAK customer reviews for airlines flying from San Jose to Caribbean Islands. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from San Jose to Caribbean Islands? 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 8458 reviews
7.9Comfort
7.8Entertainment
8.5Crew
8.1Boarding
7.2Food
Airline reviews

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!

10.0 ExcellentTeresa, Apr 2026
SMF - LAX
Read more Delta reviews

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.

The crew was very attentive through out the flight. Seats were comfortable, nice flight bag with pillow and blanket. Food was okay, since it was a overnight flight seemed to go by fast.

Left early arrived early..right amount of talking from pilots..of course had to love the biscuit and water!

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.

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 Islands

Information on your arrival and departure airports