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Cheap Flights from San Diego to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Punta Cana
Punta Cana1 stop$550
Santo Domingo
Santo Domingo1 stop$532
Montego Bay
Montego Bay1 stop$513
Nassau
Nassau1 stop$552
Kingston
Kingston1 stop$578
Providenciales
Providenciales2 stops$692
Port of Spain
Port of Spain1 stop$513
Bridgetown
Bridgetown1 stop$561
George Town
George Town1 stop$532
Aguadilla
Aguadilla2 stops$558
Puerto Plata
Puerto Plata1 stop$637
St. John's
St. John's1 stop$819
Punta Cana
Punta Cana1 stop$550
Santo Domingo
Santo Domingo1 stop$532
Montego Bay
Montego Bay1 stop$513
Nassau
Nassau1 stop$552
Kingston
Kingston1 stop$578
Providenciales
Providenciales2 stops$692
Port of Spain
Port of Spain1 stop$513
Bridgetown
Bridgetown1 stop$561
George Town
George Town1 stop$532
Aguadilla
Aguadilla2 stops$558
Puerto Plata
Puerto Plata1 stop$637
St. John's
St. John's1 stop$819
Booking Insights

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

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

What is the cheapest San Diego to Caribbean Islands flight route?

The cheapest ticket to Caribbean Islands from San Diego found in the last 5 days was to San Juan, at $380 round-trip. The most popular route is from San Diego (SAN) to San Juan Luis Munoz Marin Intl Airport (SJU), and the cheapest round-trip airline ticket found on this route in the last 5 days was $380.

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

No, with an average price for the route of $465, prices are generally cheapest when you fly direct.

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

The cheapest month for flights from San Diego to Caribbean Islands is May, when tickets cost $558 (return) on average. On the other hand, the most expensive months are December and June, when the average cost of round-trip tickets is $809 and $747 respectively.

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

To get a below average price on the flight from San Diego to Caribbean Islands, you should book around 5 weeks before departure, which saves you about 31% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 22 weeks before departure.

Good to know

Low season

November
Most popular time to fly with an average 7% increase in price.

FAQs - booking Caribbean Islands flights

  • How does KAYAK find such low prices on flights from San Diego 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 Diego to Caribbean Islands.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from San Diego 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 Diego 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 Diego 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 Diego 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 Diego 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 5 airlines serving from San Diego to Caribbean Islands

 
Need help choosing which airline to fly with from San Diego 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
SouthwestOverall score based on 4213 reviews
8.1Boarding
7.5Entertainment
7.0Food
8.6Crew
8.0Comfort
Airline reviews

I liked how it boarded fast. I do not like how the seats are just too narrow, and I’m not a big person.

6.0 GoodRobert, Oct 2026
Read more Southwest reviews

I liked how it boarded fast. I do not like how the seats are just too narrow, and I’m not a big person.

had to check bag at gate when there was still overhead bin space. As usual the WIFI didn't really work.

Red eye from San Diego. Temperature of the cabin was way too warm and the air duct flowed very little air.

Great job Southwest! My family doesn't fly often but we felt safe the whole time.

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

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 boarding and seat assignment system no longer works for me, but I know it is being replaced. Otherwise, I am good with the overall experience.

San Diego airport is brand new, spacious, airy and very smooth checkin at SW baggage drop.

No trays in our seats, we sat in first row, purchased a business class fare. Had to hold our drinks and snack in our hands. No plugs for our cell phones. Had to pay for it a drink cocktail each. Seats so uncomfortable.

The only issue is that the plane was HOT. This was not the case on my first flight so not sure why, but thankfully I had a portable fan with me. Everything else was great!

Seats were old and very uncomfortable. Coach seating is way too tight

Flight was delayed at airport with large backlog and WiFi was spotty

Flight was delayed from San Diego due to being overweight for weather conditions. We missed our connecting flight to our final destination due to the delay, as well as the connecting flight leaving before the scheduled departure time. We missed the connection within 10 - 15 minutes. We were booked on a later flight arriving 7 hours later. There were 7 passengers sharing the same originating and connecting flight.

Horrible, mismanaged ground issue resulting in a long delayed, next flight left early, waiting extra 7 hours in the airport, screen did not work

The internet on these planes stinks. Need to get starlink

Very good flight. Crew was great. No issues and we even arrived early.

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

Delayed flight (1hour) plus a long layover after an overnight flight with no backup plane available.

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

We where skipped for this flight will not head to Panama until tonight..

It would have been better if they don't separate families in seating. We were seated in the aile row in the middle of a family of four. It would have been better if they they seat the family of four together than separated.

It was good, plane is a bit older so seats are somewhat flat

Very good flight and crew Food was a surprise on a short flight

Biggest issue was that they only had two restrooms in the back of the aircraft. Too many people for only two restrooms. The trash was overflowing and there was paper on the floor too. Long lines in the isle to use it. Food was also a bit meh. They don’t offer snacks with drinks, so you might want to buy a snack to hold you off on a longer trip, since the meals are very small.

Everything was smooth and crew was very polite and friendly.

I like that they served a mail, I’m not sure about the in-flight entertainment. I didn’t really check. staff helped me with my luggage. Smooth boarding smooth takeoff smooth flight

The seats had plenty of leg room and the staff were very nice.

Copa performed as expected for the amount of money I was willing to spend for the flight; it wasn’t exceptional but it was not bad in any way either. The crew was good; friendly and straightforward. The food was airplane food, so no expectations there and the entertainment was lacking but that was my fault for owning an IPhone with a charging port that’s not compatible with the rest of the world. I’d fly Copa again.

Left my bags in origin city on a business class ticket , spent about 2-3 days in the same clothes plus the flight .

Entertainment was great. Seats were good. They did not have my pre-ordered hot food product available but did comp me something cold in place of the item.

Food was good. Clean aircraft. But why do the airlines make the seats so narrow?! Your executives should have ride in a seat so restrictive for 11 hours and see how miserable it is! When.we got to MUC they changed my boarding gate 3 times for my next flight!!!!

Flight was on time, clean, etc. Despite connecting to your wi fi I was unable to use your app to watch entertainment.

The back to back mechanical delays from Denver to San Diego and then on my return flight from Denver to Great Falls it added extra time both ways

Service was professional and quick. Premium economy seat was comfortable given the class

The staff was extremely helpful and friendly at all times! They went above and beyond to get us into an earlier flight in San Diego to make our connection in SFO possible, because our original flight did actually not make it! I did so much appreciate the UA team and how they made this possible. We also didn’t have seats together on the long flight to Singapore, but they found us seats together last moment with no additional cost! Nobody sat next to us, so that we were able to sleep! Thanks to UA for improving their service and Underpricer for booking this trip! Please be careful: 1,5 hrs for transfer in San Francisco might not be enough time in the future

Over 2.5 hour maintenance delay on first morning flight with no acknowledgement, compensation or even gesture of good will. Aircraft had overnighted at airport so issue should have been addressed prior to boarding. Over 3.5 hours before first slow and deliberate beverage service.

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

The food was terrible this time. Otherwise pleasant, quiet, on-time.

I was in first class. The outlets at my seat did not work. The plane was shabby and run down. I had prepurchsed a day subscription for internet that was not redeemable. I had to repurchase the internet for my flight and then it didn’t work anyway. Quite disappointed in what was supposed to be the launch of a great vacation.

I was truly shocked at how poor this flight went. The crew was not friendly during the checking process. The asked for people to gate check and were rude about it. They didn't handle my luggage with care. When I got to my seat I noticed a large section of the ceiling vent area was, no joke, TAPED TOGETHER WITH CLEAR PACKING TAPE! To add insult to injury, the back rest button was disabled on my seat and all the seats I could see. The wifi, never connected for me, despite troubleshooting it for a while. I did everything from restarting my wifi/phone to forgetting the network and restarting the app. But that didn't stop the mandatory 2 ads from playing every single time. Even the bags took over 45 mins to arrive at the carousel. Everything about this flight was a flop and I am beginning to notice that some of these events are becoming a trend. Perhaps it's time I switch loyalty programs.

Had to pay for WiFi, delayed start, and sat on the runway forever.

More space for economy, and the bathroom size is only for people with size XS

Well, true to American Airlines, both of my flights were delayed. But it’s a good thing that American is so consistently incompetent because if the first flight was delayed in the second flight was on time then I might’ve had a problem..

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.

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.

Cramped seats. FAA should make airlines have more legroom, for even short people complain

Flight was full, and would have preferred an aisle seat, but due to getting a late ticket ,the seat I had was adequate. The flight crew were very help full and hard working. Food and drink were excellent for the 11hr flight. Overall I was pleased with flight, and would recommend British Airways again.

The plane was late and then sat on the runway for almost 45 minutes before taking off.

More options for your flight to Caribbean Islands

Complete your trip to Caribbean Islands with a hotel stay or car rental