$172 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 5/30. 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 Cana2 stops$524
Santo Domingo
Santo Domingo2 stops$611
Montego Bay
Montego Bay2 stops$518
Oranjestad
Oranjestad2 stops$668
Nassau
Nassau2 stops$516
Kingston
Kingston1 stop$794
Simpson Bay
Simpson Bay2 stops$673
Providenciales
Providenciales2 stops$476
Port of Spain
Port of Spain2 stops$669
Bridgetown
Bridgetown2 stops$807
George Town
George Town1 stop$462
Willemstad
Willemstad2 stops$813
Puerto Plata
Puerto Plata2 stops$773
St. John's
St. John's2 stops$907
Aguadilla
Aguadilla2 stops$866
Punta Cana
Punta Cana2 stops$524
Santo Domingo
Santo Domingo2 stops$611
Montego Bay
Montego Bay2 stops$518
Oranjestad
Oranjestad2 stops$668
Nassau
Nassau2 stops$516
Kingston
Kingston1 stop$794
Simpson Bay
Simpson Bay2 stops$673
Providenciales
Providenciales2 stops$476
Port of Spain
Port of Spain2 stops$669
Bridgetown
Bridgetown2 stops$807
George Town
George Town1 stop$462
Willemstad
Willemstad2 stops$813
Puerto Plata
Puerto Plata2 stops$773
St. John's
St. John's2 stops$907
Aguadilla
Aguadilla2 stops$866

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

Sat, May 2 - Sat, May 9
American Airlines Logo
6:10 am - 11:02 pm
SJC
-
SJU
13h 52m
2 stops
American Airlines Logo
11:59 pm - 10:10 am
SJU
-
SJC
13h 11m
1 stop
$346American Airlines
Wed, Aug 19 - Wed, Aug 26
American Airlines Logo
7:11 pm - 1:35 pm
SJC
-
SJU
15h 24m
2 stops
American Airlines Logo
8:00 am - 10:25 pm
SJU
-
SJC
17h 25m
2 stops
$351American Airlines
Mon, Aug 17 - Fri, Aug 21
American Airlines Logo
7:11 pm - 2:10 pm
SJC
-
SJU
15h 59m
2 stops
American Airlines Logo
6:00 am - 4:41 pm
SJU
-
SJC
13h 41m
2 stops
$366American Airlines
Wed, Sep 9 - Wed, Sep 23
Southwest Logo
10:30 pm - 2:30 pm
SJC
-
SJU
13h 00m
1 stop
Southwest Logo
11:50 am - 8:30 pm
SJU
-
SJC
11h 40m
2 stops
$411Southwest
Mon, Aug 17 - Fri, Aug 21
Southwest Logo
10:30 pm - 12:50 pm
SJC
-
SJU
11h 20m
1 stop
Southwest Logo
5:00 am - 3:20 pm
SJU
-
SJC
13h 20m
2 stops
$426Southwest
Sun, Apr 12 - Tue, Apr 21
Delta Logo
10:50 pm - 12:00 pm
SJC
-
GCM
11h 10m
1 stop
Delta Logo
1:25 pm - 8:47 am
GCM
-
SJC
21h 22m
2 stops
$462Delta
Sun, Apr 12 - Tue, Apr 21
Delta Logo
10:50 pm - 12:00 pm
SJC
-
GCM
11h 10m
1 stop
Delta Logo
1:25 pm - 9:45 pm
GCM
-
SJC
10h 20m
1 stop
$467Delta
Tue, Apr 28 - Tue, May 5
United Airlines Logo
3:45 pm - 12:30 pm
SJC
-
GCM
18h 45m
2 stops
United Airlines Logo
1:35 pm - 1:28 pm
GCM
-
SJC
25h 53m
2 stops
$492United Airlines
Tue, Apr 28 - Tue, May 5
United Airlines Logo
8:45 am - 11:45 am
SJC
-
GCM
25h 00m
2 stops
United Airlines Logo
1:35 pm - 12:00 pm
GCM
-
SJC
24h 25m
1 stop
$499United Airlines
Wed, May 13 - Sun, May 17
JetBlue Logo
10:00 pm - 12:40 pm
SJC
-
PLS
11h 40m
1 stop
JetBlue Logo
2:05 pm - 10:55 pm
PLS
-
SJC
11h 50m
1 stop
$617JetBlue
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 January, when tickets cost $300 (return) on average. On the other hand, the most expensive months are December and October, when the average cost of round-trip tickets is $615 and $555 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 18 weeks before departure.

Good to know

Low seasonFebruary
Cheapest flight$172
Best time to beat the crowds with an average 27% drop in price.
Most popular time to fly and prices are also 12% lower on average.
Flight from San Jose to Montego Bay

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 4318 reviews
7.5Entertainment
8.0Comfort
8.1Boarding
8.6Crew
7.0Food
Airline reviews

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.

8.0 ExcellentTobin, Mar 2026
SJC - BUR
Read more Southwest reviews

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

Flight boarded late after announcing on time boarding. Flight arrived only a little late despite late departure. Had trouble connecting to WiFi

The Southwest experience has definitely taken a dive from its early days. You can no longer deferentiate from other airlines. Air travel is too expensive. Southwest is no longer budget friendly. They have lost me as a loyal customer.

The charges were ridiculous for an hour flight and the turbulence was very scary.

The seats are now more narrow. I paid for front row the seats in the front are even more narrow than before.

The wifi on the plane is great. The only issue that I have is that I prefer an aisle seat and on my trips this week, I was either in the middle or window. If we can work to secure aisle seating, I will be thrilled. Nice trip.

Great flight but super high price. Glad it was a business trip and not personal

3 hour delay. Had to change plans and was still delayed.

We got exit row seats both flights. Everything was running on time

I was in first class and literally the men behind me were so aggressively loud I moved myself to economy. This has become so common on Delta - people using audio without headphones, and men on 12am / late night flights drinking and yelling to talk to each other which prevents anyone around them from resting. Pretty crazy to have to move from first to economy (poorer service, less comfort...). Wild wild. Looking into other airlines.

Flight was delayed by 3-hours and their fix was… complimentary pretzels.

The crew, and fellow passengers, were super gracious and kind. There seemed to be plenty of bin space even though the plane was full. It’s nice to get a glass of wine with dinner in Premiere seating, and there was a lot of food.

Everything I mentioned earlier - the airbus was more comfortable indeed and the experience was further enhanced.

The plane was an older model, so it wasn’t as comfortable as others. The flight attendants were not helpful during onboarding. It was a full flight so there was chaos finding space for baggage.

Awesome! On time flight, early arrival, and a complimentary upgrade!

It was nt delta. It was aeromexo. Service was awful. They served a very small drink and NO snack for a 3hr and 35min flight. Then for the first 30 min of the flight is was talk and talk over head interruption the movie/ show i picked to watch.

Delta One is extraordinary. I fly business when somebody hires me. I just wonder why there is such a chasm between business class and the insanely inhumane and nonsensical coach. The seats are not large enough to fit even my tiny wife. We fly 10% of what we did because we don’t want to pay 5-10 k but for $400 it’s unbearable. It seems like the accountants took over and made stupid decisions. Screw in 20 extra seats and make it so unbearable that people fly 90% less. Just put the damn price up and put some proper chairs in. But business, yay.

Delta’s staff is unmatched. From the gate agents, to the pilots, to the flight attendants… all top of the industry.

The flight was delayed for about 2 hrs. Other than it, it was good.

The 777’s economy seat’s legroom was more tolerable than expected. I appreciate the reclining mechanism which slides the seat forward to minimize cannibalizing the space behind. The food was terrible: very salty.

Seats are uncomfortable. This has been a trend in the industry for decades. Trying to fit more seats on each plane to increase profits at the expense of the passenger.

Staff were good. My seat was in need of repair, but for a short flight was not problematic. Usual basic snack and drink setup that you'll find on any US carrier. Over, a decent, basic flight.

Complimentary light meal would be appreciated. But great flight crew service on all legs

Flight delayed for more than 16 hrs and no effort was spent to provide an alternate

We had turbulence ever 1/2 hr or so and the captains announcements were SOOOO LOUD

Women boarding passengers at the gate was absolutely rude and disrespectful of passengers. The flight attendant was absolutely delightful! Smiling and connected with the passengers. So happy. The seats are cramped and uncomfortable but I guess that’s just the way it is Communication regarding flight was excellent

it was a very short flight so my expectations were low.

Entertainment kept turning itself off. Gave up on watching a movie.

Very disappointing given gate agent behavior. Filed a formal complaint with United.

Dloght delayed by 2.5 hrs . Common theme in my last four american floghts

They are rarely on time! Very hard to plan your travels when flights or connections keep getting delayed.

My seat was assigned last row behind restrooms No legroom’s I’m very Pettit Still was not comfortable Food choice was excellent

The worst Airline ever. They centered my second flight and leave me in NY. They don’t have any representatives at the airport and they don’t respond to calls. Basically I got stuck. I will never purchase through there again.

The chicken wrap was tiny ($13 for what looked like a 1/3 of a normal wrap?) and disgusting.

Mediocre would be best description. Food bland. Seat biz class uncomfortable to sleep. Crew never dimmed lights completely in an overnight flight to Europe. Would avoid AA if possible.

Small plane, poor meal choices for first class, bad terminal and boarding experience at LAX

Massimo, flight attendant was very authentic, attentive - wonderful. Food/wrap was just okay.

Experience was great. The best part is the free Wi-Fi connection which helps me to work on the flight

The flight was fine. It's the satellite terminal that supports American eagle flights is what sucks. There is only one food option and everything there is way overpriced. I mean I know it's airport pricing, but it's even crazier than that. I bought a sandwich in a plastic container for $18.

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.

Got to LAX at 3:20 am, the counter personnel did not start to check in bags till 3:40 am. I patiently waited at the priority check in line as they started to take people from the general line. After about 15 minutes of waiting, I approached the lady exactly in front of the priority line and asked her if they would be taking people from the priority line or if I would need to switch to waiting in the general line. She responded “yes”, I then asked her yes to what? And she yelled back at me loudly “I SAID YES!” Needless to say, I waited at the end of the line of the general line. I could have been told the priority line would not be called upon and could have queued in the general line ahead of many people that arrived to cue after I did

Terrible they canceled the flight very sheepishly and ended up costing me 1200 dollars and kayak and xcover are doing nothing

No free snacks or drinks. Freezing. Uncomfortable. No plugs or entertainment. If you fly to LA the make you change terminals with a slow bus. Awful trip that took forever. Terrible airline- maybe the worst I’ve ever flown.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports