$183 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 10/5. 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

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
Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 22% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
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$579
Santo Domingo
Santo Domingo3 stops$532
Montego Bay
Montego Bay1 stop$569
Oranjestad
Oranjestad2 stops$648
Nassau
Nassau1 stop$425
Simpson Bay
Simpson Bay2 stops$802
Kingston
Kingston3 stops$665
Providenciales
Providenciales1 stop$518
Port of Spain
Port of Spain2 stops$614
Bridgetown
Bridgetown1 stop$638
George Town
George Town1 stop$533
Willemstad
Willemstad2 stops$798
St. John's
St. John's2 stops$770
Puerto Plata
Puerto Plata2 stops$555
Aguadilla
Aguadilla2 stops$641
Punta Cana
Punta Cana2 stops$579
Santo Domingo
Santo Domingo3 stops$532
Montego Bay
Montego Bay1 stop$569
Oranjestad
Oranjestad2 stops$648
Nassau
Nassau1 stop$425
Simpson Bay
Simpson Bay2 stops$802
Kingston
Kingston3 stops$665
Providenciales
Providenciales1 stop$518
Port of Spain
Port of Spain2 stops$614
Bridgetown
Bridgetown1 stop$638
George Town
George Town1 stop$533
Willemstad
Willemstad2 stops$798
St. John's
St. John's2 stops$770
Puerto Plata
Puerto Plata2 stops$555
Aguadilla
Aguadilla2 stops$641

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

Tue, Oct 28 - Thu, Oct 30
Delta Logo
4:37 pm - 11:56 amSJC-SJU
16h 19m2 stops
Delta Logo
12:46 pm - 10:58 pmSJU-SJC
13h 12m1 stop
$275Delta
Find Deal
Sun, Sep 28 - Wed, Oct 1
Frontier Logo
12:26 pm - 9:52 amSJC-SJU
18h 26m2 stops
Frontier Logo
12:28 am - 1:14 pmSJU-SJC
15h 46m2 stops
$331Frontier
Find Deal
Mon, Oct 27 - Tue, Oct 28
American Airlines Logo
1:18 pm - 1:45 pmSJC-SJU
21h 27m2 stops
American Airlines Logo
5:00 pm - 12:20 pmSJU-SJC
22h 20m2 stops
$346American Airlines
Find Deal
Sat, Oct 25 - Sat, Nov 1
American Airlines Logo
3:15 pm - 11:06 amSJC-SJU
16h 51m2 stops
American Airlines Logo
1:50 pm - 10:20 amSJU-SJC
23h 30m2 stops
$351American Airlines
Find Deal
Sun, Oct 26 - Thu, Oct 30
Southwest Logo
4:25 pm - 9:05 amSJC-SJU
13h 40m2 stops
Southwest Logo
5:50 am - 4:00 pmSJU-SJC
13h 10m1 stop
$390Southwest
Find Deal
Wed, Oct 1 - Wed, Oct 8
Southwest Logo
6:35 am - 10:45 pmSJC-SJU
13h 10m2 stops
Southwest Logo
6:10 am - 6:05 pmSJU-SJC
14h 55m1 stop
$400Southwest
Find Deal
Mon, Jan 12 - Wed, Jan 14
Alaska Airlines Logo
5:53 am - 10:14 pmSJC-SJU
12h 21m1 stop
Alaska Airlines Logo
7:20 am - 10:59 pmSJU-SJC
19h 39m2 stops
$426Alaska Airlines
Find Deal
Mon, Sep 29 - Fri, Oct 3
Spirit Airlines Logo
4:16 pm - 8:56 pmSJC-SJU
25h 40m3 stops
Spirit Airlines Logo
11:59 am - 10:45 amSJU-SJC
25h 46m3 stops
$439Spirit Airlines
Find Deal
Mon, Sep 29 - Fri, Oct 3
Spirit Airlines Logo
4:16 pm - 2:11 pmSJC-SJU
18h 55m3 stops
Spirit Airlines Logo
10:42 am - 10:45 amSJU-SJC
27h 03m2 stops
$496Spirit Airlines
Find Deal
Wed, Dec 31 - Tue, Jan 6
Alaska Airlines Logo
5:55 pm - 11:26 pmSJC-SJU
25h 31m2 stops
Alaska Airlines Logo
4:15 pm - 4:44 pmSJU-SJC
28h 29m2 stops
$498Alaska Airlines
Find Deal
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 $410, 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 September, when tickets cost $334 (return) on average. On the other hand, the most expensive months are June and December, when the average cost of round-trip tickets is $633 and $597 respectively.

What’s the cheapest day of the week to fly from San Jose to Caribbean Islands?

The average price of all round-trip flights from San Jose to Caribbean Islands clicked on KAYAK for each day over the last 12 months.

Your flight ticket price will generally be cheaper if you fly to Caribbean Islands on a Sunday and more expensive on a Friday. On your return trip to San Jose, you should consider flying back on a Wednesday, and avoid Sundays for better deals.

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 3 weeks before departure, which saves you about 13% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 7 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$183
Best time to beat the crowds with an average 19% drop in price.
Most popular time to fly with an average 20% increase in price.
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.

  • What is the cheapest time of day to fly to Caribbean Islands?

    The cheapest time of day to fly to Caribbean Islands is generally in the afternoon, when round-trip flights cost $487 on average. Morning departures are around 4% cheaper than evening flights, on average. The most expensive time of day to fly to Caribbean Islands is generally in the evening, which is peak travel time and where the average cost of a ticket is $597.

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 7954 reviews
7.9Entertainment
8.2Boarding
8.5Crew
7.3Food
7.9Comfort
Airline reviews

Flight delayed for two and half hours and then canceled altogether due to mechanical issues. No mechanic onsite to fix so had to send one from LAX.

2.0 MediocreAnonymous, Sep 2025SNA - SEA
Read more Delta reviews

Flight delayed for two and half hours and then canceled altogether due to mechanical issues. No mechanic onsite to fix so had to send one from LAX.

My husband upgraded our seats and I don't know if it was due to the type of planet was or if they didn't upgrade our seats. We were supposed to be in I believe comfort seats and they were just as tight as any other seat- no leg room and we are very tall people but at least it wasn't extremely cold. My husband did put in a complaint about our seating because he paid extra and if we would have known that the space and the tightness would have been the same, we just would have gotten the emergency row emergency row seats that we normally get. We love Delta but both our flights coming home we're not good. Oh I forgot to mention that on our flight to Hawaii our luggage wheels got broke and we had to purse new luggage on vacation then we never had this problem so we didn't know protocol and reported it after we got home only for them to tell is we only had 24hrs to report the damage. Not sure what was going on with Delta this vacation trip.

Crew was excellent. Comfort seats not as nice as other kinds of planes.

It was a great flight and the stewards and stewardess were all kind and accommodating!! The seats were comfortable and entertainment screen excellent!

There are 4 flights in consecutive gates with about the same departure time. Two flights were boarding at the same time. One was delayed or boarding would be happening at the same time. I am not sure what Delta and LAX need to do to have a better layout at the end of Terminal 2

There was a security issue at the airport and we were unable to land. We circled endlessly and then landed at another airfield for fuel. We then circled the airport again, almost landed but didn’t fully touch down before circling again. I am thankful to the crew for keeping us safe- the issue was the airline and staff at the airport getting us seats on our connecting flights. That part was hours of searching for someone and getting in double my steps.

Most aspects were good however if they assign boarding zones they ought to enforce them or why bother? My luggage from SAN-JFK-MAD was lost in NY so I without my main bag for two days upon arrival in Spain. They were helpful in tracking it and eventually delivered it to my hotel. The flub was because of a delay upon arrival in NYC. I had booked 2 1/2 hours between flights but we had to hold on the taxiway for an hour after landing while waiting for a clear gate which likely caused the baggage error.

Excellent flight, the planes were newer, they did a nice job with boarding, great service overall.

It would be nice if was given wires ear buds. Overall was a good experience was able to sleep on the plane

737-800 in first class was pretty dumpy. Seat had an uncomfortable angle, storage under the seat was blocked so even my very modest backpack didn't fit, power outlet was flaky. Weird tiny seat pockets that couldn't hold a gallon ziploc bag, emesis bag missing, etc. etc. No in-flight service due to turbulence. Crew was excellent, boarding was smooth despite a full flight.

The entertainment package was vast and the selections were very current. Keep updating it was great.

The seat was so hard my tailbone was aching The crew was kind of a b**** because I made a joke that I didn't care if they close the door I total c*** when she was trying to f****** act like she was mad at me because I said that The flight was bumpy. Sure you didnt have control over that.

4 hours late, including over +1 hour waiting in plane to take off. Baggage left behind too.

While waiting to claim my checked luggage, I discovered the airline had lost it. After a long wait and inquiries, I discovered it was on another flight. Fortunately, the airline finally sent my luggage home.

Was not able to watch most shows on the entertainment site. They would not load

Our flight was 1.5 hours delayed. There was no weather for the inbound flight, so I don't understand why. This meant a VERY late arrival and only a quick nap before my morning flight.

Delayed flight, so I switched fights to SFO to Phoenix , Phoenix to DSM. Excellent service through American Airlines

AA re-routed flight from HNL to LAX due to delay. My group of 3 with reserved seats in row 9 was broken up, with one assigned to a middle seat, another in the last row of the plane. Not happy. No explanation to the delay. No apologies. No compensation. Would have been nice to be offered an Admiral Club admission or a voucher for the extra 3 hours of layover in LAX. Could not hear the boarding gate announcements in LAX. Adjacent gate was boarding at the same time. Loud speakers were competing against each other. Barely made my boarding group.

Almost a 6 hour flight and the only food option is a cheese plate… and chips. Also how is it there are no options for texting on American. I’ll be going back to delta and united.

Bad food, small seats that didn’t recline. I thought I was buying a quantas ticket so I feel like I got scammed

Spirit Airlines was ok but TRAVELHELPDESK, the 3rd party travel agent IS A JOKE! VERY RUDE CUSTOMER AGENTS ont he phone. NO HELP AT ALL. But the airlines was ok.

No frills - because you get what you pay for. The crew was amazing!! I had plenty of room to spread out because the flight was half full. Which made it easy to sleep.

The staff was very very rude in Las Vegas when boarding the flight. When presenting the boarding ticket. Las Vegas flight, it was hot and stuffy, it smelled really bad.

Dear All, I have harassment and accident with the flight attendant . This is my phone to talk 8168073567, please, leave phone message . Regards Emily,

Flight was on time but the amount of noise from several children and the kicking of my seat the entire flight was overwhelming.

Unbelievable check in horrible. Asked to print tickets at the gate after a delay

check in at security was a hassle being scanned. Spirit employees were helpful and professional.

Had a issue with catching flight due to airline, was unable to board flight

I liked how cheap it was but both my flights were delayed heavily

It was okay delay was long but I made it

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.