$109 Find Cheap Flights from San Diego 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 Diego to Caribbean departing on 11/15. 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

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Cheap Flights from San Diego to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$424
Santo Domingo
Santo Domingo1 stop$386
Montego Bay
Montego Bay1 stop$461
Oranjestad
Oranjestad1 stop$520
Nassau
Nassau1 stop$407
Simpson Bay
Simpson Bay1 stop$453
Kingston
Kingston2 stops$452
Providenciales
Providenciales1 stop$499
Port of Spain
Port of Spain1 stop$491
Bridgetown
Bridgetown1 stop$497
George Town
George Town1 stop$496
Willemstad
Willemstad1 stop$514
St. John's
St. John's1 stop$585
Puerto Plata
Puerto Plata1 stop$548
Aguadilla
Aguadilla2 stops$385
Punta Cana
Punta Cana1 stop$424
Santo Domingo
Santo Domingo1 stop$386
Montego Bay
Montego Bay1 stop$461
Oranjestad
Oranjestad1 stop$520
Nassau
Nassau1 stop$407
Simpson Bay
Simpson Bay1 stop$453
Kingston
Kingston2 stops$452
Providenciales
Providenciales1 stop$499
Port of Spain
Port of Spain1 stop$491
Bridgetown
Bridgetown1 stop$497
George Town
George Town1 stop$496
Willemstad
Willemstad1 stop$514
St. John's
St. John's1 stop$585
Puerto Plata
Puerto Plata1 stop$548
Aguadilla
Aguadilla2 stops$385

Book Cheap San Diego 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 Diego 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 Diego to Caribbean

Tue, Feb 3 - Tue, Feb 10
United Airlines Logo
8:00 am - 9:26 pmSAN-SJU
9h 26m1 stop
United Airlines Logo
3:46 pm - 9:56 pmSJU-SAN
10h 10m1 stop
$295United Airlines
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Tue, Nov 11 - Tue, Nov 18
American Airlines Logo
6:35 am - 11:52 pmSAN-SJU
13h 17m1 stop
American Airlines Logo
6:25 am - 6:59 pmSJU-SAN
16h 34m1 stop
$300American Airlines
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Sat, Nov 8 - Wed, Nov 12
United Airlines Logo
8:00 am - 9:26 pmSAN-SJU
9h 26m1 stop
United Airlines Logo
2:05 am - 10:05 amSJU-SAN
12h 00m1 stop
$321United Airlines
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Tue, Mar 3 - Wed, Mar 4
American Airlines Logo
6:27 am - 10:35 pmSAN-SJU
12h 08m1 stop
American Airlines Logo
10:26 am - 10:15 pmSJU-SAN
15h 49m1 stop
$329American Airlines
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Sat, Jan 24 - Wed, Jan 28
Delta Logo
10:40 pm - 2:15 pmSAN-SJU
11h 35m1 stop
Delta Logo
7:30 am - 1:18 pmSJU-SAN
9h 48m1 stop
$348Delta
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Wed, Dec 3 - Thu, Dec 11
JetBlue Logo
9:05 pm - 12:35 pmSAN-SJU
11h 30m1 stop
JetBlue Logo
5:09 am - 12:47 pmSJU-SAN
11h 38m1 stop
$353JetBlue
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Sat, Nov 8 - Thu, Nov 13
JetBlue Logo
9:05 pm - 11:25 amSAN-SJU
10h 20m1 stop
JetBlue Logo
12:30 pm - 7:51 pmSJU-SAN
11h 21m1 stop
$398JetBlue
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Thu, Oct 30 - Tue, Nov 4
Delta Logo
7:10 am - 12:27 amSAN-SDQ
14h 17m1 stop
Delta Logo
7:05 am - 8:47 pmSDQ-SAN
17h 42m1 stop
$400Delta
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Tue, Dec 30 - Wed, Jan 14
Southwest Logo
8:30 am - 11:15 pmSAN-SJU
10h 45m1 stop
Southwest Logo
6:10 am - 2:20 pmSJU-SAN
12h 10m1 stop
$420Southwest
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Mon, Dec 15 - Thu, Dec 18
Southwest Logo
8:05 pm - 3:00 pmSAN-PUJ
14h 55m2 stops
Southwest Logo
4:05 pm - 7:15 amPUJ-SAN
19h 10m2 stops
$502Southwest
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Booking Insights

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

Get data-powered insights and trends into flights from San Diego 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 Diego to Caribbean?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from San Diego 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 Diego to Caribbean is January, when tickets cost $429 (return) on average. On the other hand, the most expensive months are December and June, when the average cost of round-trip tickets is $703 and $585 respectively.

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

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

Your flight ticket price will generally be cheaper if you fly to Caribbean on a Saturday and more expensive on a Sunday. On your return trip to San Diego, you should consider flying back on a Thursday, and avoid Mondays for better deals.

How far in advance should I book a flight from San Diego 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 Diego 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 Diego to Caribbean, you should book around 3 weeks before departure, which saves you about 21% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 26 weeks before departure.

Good to know

Low seasonOctober
Cheapest flight$109
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly with an average 47% increase in price.
Flight from San Diego to San Juan

FAQs - booking Caribbean flights

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

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

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

    The cheapest time of day to fly to Caribbean is generally in the afternoon, when round-trip flights cost $485 on average. On average, there is no price difference when choosing to fly in the morning or the evening on this flight route. The most expensive time of day to fly to Caribbean is generally in the evening, which is peak travel time and where the average cost of a ticket is $569.

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

 
Need help choosing which airline to fly with from San Diego 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
Alaska AirlinesOverall score based on 11102 reviews
7.0Entertainment
7.1Food
8.1Boarding
7.8Comfort
8.5Crew
Airline reviews

My flight wait is 3 hours delayed due to Unknown reason. We waited a very long time in the tarmac. Our flight 24 was scheduled @ 7, therefore we left my house at 330 to park our car. We were at the gate @ 530, then we were told at 6a that it will be late , we boarded at 930 but did not take off until 1015. Therefore my arranged pick up in JFK was cancelled because of no show. Before all these I got an email offers of changing my flight to a different date which I took a day earlier. I will never again take Alaska Airlines, very Inefficient and Disappointing.

10.0 ExcellentGRACE, Aug 2025SAN - JFK
Read more Alaska Airlines reviews

My flight wait is 3 hours delayed due to Unknown reason. We waited a very long time in the tarmac. Our flight 24 was scheduled @ 7, therefore we left my house at 330 to park our car. We were at the gate @ 530, then we were told at 6a that it will be late , we boarded at 930 but did not take off until 1015. Therefore my arranged pick up in JFK was cancelled because of no show. Before all these I got an email offers of changing my flight to a different date which I took a day earlier. I will never again take Alaska Airlines, very Inefficient and Disappointing.

Such great crew, from checkin to the plane. So friendly and helpful, I was genuinely impressed.

Seats extremely uncomfortable, no entertainment, no snacks, and when boarding, half of the passengers needed to check in the carry on luggage without any explanation.

The flight was jumping between being delayed and closer to schedule about 5 times. Alaska air website showed incorrect times while google had latest info. This panic was horrible to deal with.

I always heard this was a terrible airline but I was happy to experience otherwise. The seats were more comfortable than delta. They did board late and gate was a little chaotic, which is to be expected for a budget airline. I would definitely do it again for that price.

Very expensive for short flights. Can’t communicate with Alaska Air about passport issue at check-in. Also no replies to my text messages. Wanted to extend our vacation for two more days but this expensive flight ticket is called SAVER and I couldn’t make changes or cancel or get a credit even, so I paid another airline for the return trip. Extremely disappointed.

They canceled my flight then changed me $155 for the same flight the next day

Our flight time was drastically changed which caused us to lose a day of vacation

I like the new adjustable headrest. Unfortunately 2 crying children were in front of us. But it was the first time and not holding Alaska accountable for that. Alaska always seems to have everything in order professional but comfortable.

Very bad, terrible food and late by 2 hours. Then no to open aircraft doors

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

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

We were in business class. the angled seats in that class do not have a real window view & the placement of the controls are bad. But we knew that. But the food options were mediocre. The taste was fine, but the size was for a child. It’s just really feels like United is skimping on everything. Even when we were in the Polaris lounge they did not have diet sodas. They said they were out no Coke zero no Diet Coke, etc. I do not think the portion of nuts they serve on the plane could get any smaller. Really a minimal service and offer for what you’re paying for in business.

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.

We had to deboard 2 times due to maintenance issues. They changed the plane, and then we got deviated to LAX due to maibtenance issues on the other plane, had to sleep at LAX and los a full day.

From the first moment you interact with United Airlines, you can expect nothing less but extreme frustration. The baggage handler at the bag drop seems completely unbothered by the presence of customers waiting in line. No help was extended to load the baggage whatsoever. And if any of your bags is overweight by 0.01 pound they will make you re-distribute everything in your suitcase just to play power trip. When it was time to board no help was extended to customers to locate their seats. Moreover. It was a chaotic mess at the gate when it was unclear who should board first and everyone just bunched up, trying to get on the plane. I am sure the crew was doing their best to perform their jobs while being paid their wages however it shouldn’t be that hard to smile once or twice when you’re in the business if serving customers. It is a shame for the United States of America to have a flagship carrier of such low caliber. Our flight was also delayed by about an hour and a half due to further delays prior to our inbound flight. Being someone who has travelled for both business and leisure in Asia, Europe, and South America I have never experienced such poor quality of service.

I understand stuff happens, but plane failures are likely due to lack of maintenance. Additionally, air conditioning wasn't working, no snack/drink service, no WiFi. Fortunately, the crew was communicative and light-hearted. United grabbed another plane and we were able to get to our destination.

The pilots were late and it made us 1 hour late. The meat was tough and bok choy was also tough.

Stuck on tarmac for two hours plus a 5.5 hour flight. Rude flight attendant. And no meals, not even for purchase!

I learned that seating towards the end of plane that a line forms for the restroom and people use your chair as a hand railing, bumping your seat consistently. I was seated in the aisle. I think that next time if I am towards the back row I would want to sit in the middle or window seat.

The best airline I have ever travel , really good customer service, attention and service !!

United sent me a mileage plus number last year but that number is invalid so I can’t use it to check into flights or collect mileage. There is human to speak about the problem, only computers who keep asking me if I am using the correct email. It’s so frustrating and I cannot resolve it.

Always seated jammed in rear of aircraft Admirals Club food at DFW terminal D was absolute worst food experience and I pay $600/year to eat this dried out junk

Mostly good. Flight was crowded but Airline personnel were very friendly & accommodating. It would be good to have savory snacks rather than just sweet Biscoff cookies.

It was a red eye flight, so no meals were provided, but it was fine with snacks. The seats felt cramped and almost too narrow.

Very crowded flight but what can you expect these days?? Crew was accommodating.

The seats in economy were appeared to be quite thin and lack sufficient cushioning to be comfortable. Perhaps it was my seating position but the plane seemed notably load.

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

Plane was in bad shape. TV’s and WiFi didn’t work. Plane need a refresh. Not enough room for bags.

There was a fowl odour coming from the lavatory the entire flight

Everything was great. I liked the text updates so that I never miss a gate change & I have all the latest info.

I don’t usually fly budget airlines or airlines in the United States. It was as good as any other airline. The seats are comfortable and the airline attendants are not rude & surly. Very nice flight (s).

No internet on a flight over three hours in this age is criminal. Staff inattentive and dismissive

They have the most inexperienced / rude flight staff I’ve encountered

very difficult boarding process - aggressive passengers not the friendliest crew

WiFi was not eorkig (again) And the plane was from 1990 with the screens which were.not touch and most didn’t even work and if lucky could tune in tv

I paid extra for a seat closer to the front. The TV didn’t work at all for the entire flight. Would have been nice to know before I purchased an “upgraded “ seat

It was great. I had never flown on JetBlue before, but would be very happy to fly with them in the future.

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