$111 Find Cheap Flights from San Diego 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 Diego to Caribbean Islands departing on 1/9. 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 Diego to Caribbean Islands.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from San Diego to Caribbean Islands.
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Flight Deals

Cheap Flights from San Diego to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$398
Santo Domingo
Santo Domingo1 stop$436
Montego Bay
Montego Bay1 stop$436
Oranjestad
Oranjestad1 stop$498
Nassau
Nassau1 stop$400
Kingston
Kingston1 stop$459
Simpson Bay
Simpson Bay1 stop$453
Providenciales
Providenciales1 stop$488
Port of Spain
Port of Spain1 stop$546
Bridgetown
Bridgetown1 stop$541
George Town
George Town2 stops$490
Willemstad
Willemstad1 stop$514
St. John's
St. John's1 stop$630
Puerto Plata
Puerto Plata1 stop$511
Aguadilla
Aguadilla2 stops$322
Punta Cana
Punta Cana1 stop$398
Santo Domingo
Santo Domingo1 stop$436
Montego Bay
Montego Bay1 stop$436
Oranjestad
Oranjestad1 stop$498
Nassau
Nassau1 stop$400
Kingston
Kingston1 stop$459
Simpson Bay
Simpson Bay1 stop$453
Providenciales
Providenciales1 stop$488
Port of Spain
Port of Spain1 stop$546
Bridgetown
Bridgetown1 stop$541
George Town
George Town2 stops$490
Willemstad
Willemstad1 stop$514
St. John's
St. John's1 stop$630
Puerto Plata
Puerto Plata1 stop$511
Aguadilla
Aguadilla2 stops$322

Book Cheap San Diego 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 Diego 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 Diego to Caribbean Islands

Tue, Dec 2 - Tue, Dec 16
American Airlines Logo
9:42 am - 12:44 amSAN-SJU
11h 02m2 stops
American Airlines Logo
6:00 am - 3:48 pmSJU-SAN
13h 48m2 stops
$334American Airlines
Find Deal
Thu, Apr 23 - Thu, Apr 30
United Airlines Logo
6:15 am - 8:38 pmSAN-SJU
11h 23m1 stop
United Airlines Logo
7:45 am - 3:30 pmSJU-SAN
10h 45m1 stop
$335United Airlines
Find Deal
Tue, Dec 2 - Wed, Dec 10
American Airlines Logo
12:27 pm - 12:44 amSAN-SJU
8h 17m1 stop
American Airlines Logo
11:00 am - 11:00 pmSJU-SAN
16h 00m1 stop
$337American Airlines
Find Deal
Tue, Mar 31 - Tue, Apr 7
Delta Logo
9:40 pm - 3:40 pmSAN-PUJ
15h 00m1 stop
Delta Logo
1:45 pm - 11:55 pmPUJ-SAN
13h 10m1 stop
$398Delta
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Wed, Apr 1 - Tue, Apr 7
JetBlue Logo
8:50 pm - 9:30 amSAN-NAS
9h 40m1 stop
JetBlue Logo
12:12 pm - 7:44 pmNAS-SAN
10h 32m1 stop
$400JetBlue
Find Deal
Tue, Mar 31 - Tue, Apr 7
Delta Logo
7:30 pm - 12:25 pmSAN-PUJ
13h 55m2 stops
Delta Logo
1:45 pm - 11:55 pmPUJ-SAN
13h 10m1 stop
$402Delta
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Mon, Mar 16 - Sat, Mar 21
JetBlue Logo
9:22 pm - 10:35 amSAN-NAS
10h 13m1 stop
JetBlue Logo
10:17 am - 7:34 pmNAS-SAN
12h 17m1 stop
$407JetBlue
Find Deal
Fri, Apr 24 - Sun, Apr 26
Copa Airlines Logo
9:16 pm - 10:40 amSAN-PUJ
10h 24m1 stop
Copa Airlines Logo
5:43 am - 6:10 pmPUJ-SAN
15h 27m1 stop
$423Copa Airlines
Find Deal
Wed, Apr 29 - Sun, May 3
Copa Airlines Logo
9:16 pm - 1:09 pmSAN-SDQ
12h 53m1 stop
Copa Airlines Logo
6:00 am - 6:10 pmSDQ-SAN
15h 10m1 stop
$436Copa Airlines
Find Deal
Sun, Mar 1 - Sat, Mar 7
United Airlines Logo
10:15 pm - 12:59 pmSAN-PUJ
10h 44m1 stop
United Airlines Logo
12:56 pm - 8:33 pmPUJ-SAN
11h 37m1 stop
$478United Airlines
Find Deal
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.

Can I save money by flying with a layover from San Diego 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 $395, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from San Diego 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 Diego 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 Diego to Caribbean Islands is October, when tickets cost $441 (return) on average. On the other hand, the most expensive months are December and June, when the average cost of round-trip tickets is $681 and $585 respectively.

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

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

For San Diego to Caribbean Islands, Saturday is the cheapest day to fly on average and Sunday is the most expensive. Flying from Caribbean Islands back to San Diego, the best deals are generally found on Thursday, with Monday being the most expensive.

How far in advance should I book a flight from San Diego 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 Diego 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 Diego to Caribbean Islands, 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$111
Best time to beat the crowds with an average 25% drop in price.
Most popular time to fly with an average 7% increase in price.
Flight from San Diego to San Juan

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.

  • 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 $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 Islands 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 Islands

 
See real verified KAYAK customer reviews for airlines flying from San Diego 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 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
DeltaOverall score based on 8009 reviews
7.9Entertainment
7.3Food
7.9Comfort
8.5Crew
8.1Boarding
Airline reviews

Staff were friendly and happy. Delta could make sure passengers that don't have the app know of changes. Without Kayak I would not have known about the change of gate or the delay. Kayak was faster to notify me.

8.0 ExcellentJulie, Oct 2025LAX - SFO
Read more Delta reviews

Staff were friendly and happy. Delta could make sure passengers that don't have the app know of changes. Without Kayak I would not have known about the change of gate or the delay. Kayak was faster to notify me.

The flight used a B767 with a very old interior from before 2014. The entertainment system did not work at all during the flight despite attempts to reset the system. It was like they flew this route just to be competitive.

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.

I always enjoy flying Copa. There are very few airlines where I can enjoy a comfortable sleep in-flight. The snacks weren't the best, but they sufficed. The in-flight entertainment was fantastic, and I crossed another movie off my watch list.

Very strict carry on rules meant most of the plane had to gate check their luggage. As is often the case had things that were broken because of this, but I appreciated not being charged to gate check. Otherwise good flight and great crew once on the plane

Simply as follows:- First, there was no vegetarian option for the meal Second, only 2 washrooms for the entire economy class.

I liked the meatloaf the chicken was awful but the plane was on time and got there and the staff was nice.

They were super friendly bumped me up to exit row free of charge, All flight legs were on time

Boarding was quick & efficient; they gave boarding groups due priority; staff & air crew were very cordial and helpful, pleasant flight.

We had a great flight just wished they had a tv so we can see a movie that would of made my trip excellent.

Great experience with a crew always thinking in the passenger

Very happy with my flight. I would definitely recommend it.

Did upgrade, travel in business it was great (more room I could sleep)

Older aircraft, no meal, only food was for purchase. Not impressed United.

Not pleasant trip cross country when the entertainment and WiFi system not working. No entertainment for entirety of route. Staff was rather nonchalant in that they dismissed the problem due to age of plane. It would have been nice to know this up front so I could have come prepared to read or download movies before boarding Coincidentally or not, there was a similar issue with the entertainment system on my previous flight I took on my fist leg of the trip. There are no seat TVs, so you must rely on the app when it works. United can do better. Also, what use it it to pay for boarding group 2 when half of the passengers are in the same line as you?

My experience on this United Airlines flight was highly uncomfortable, primarily due to two issues: Cabin Temperature: The temperature on the Boeing 737 MAX 8 was unacceptably high, feeling consistently around 80 degrees throughout the flight. This made sleeping impossible and significantly detracted from the experience. Seating Arrangement: Being stuck in a middle seat for a six-and-a-half-hour overnight flight compounded the discomfort. Moving forward, I will always purchase a seat assignment to avoid this situation.

Premium Plus is a really good idea for longer flights

Same as last comment. Food sucks. Quality. Not surprising most people have no clue about nourishment Clearly

The flight attendants were great, I joked with one I can’t remember her name, a blond, really sweet. I thought it was run well very professional. This was great i survived Spirit, I know for which I speak.

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.

The flight was smooth, the pilot kept us informed about delays and we arrived more of less on time

The flight was flawless and we even arrived between 20 and 25 minutes early!

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.

Checking In on JetBlue site was impossible. It hung up on REAL ID. Even my Global Entry did not help. Luckily, on Kayak site it was a breeze. Entire flight the temperature was COLD! Otherwise the crew was great!

The flight was two hours late due to a computer fault and resulting maintenance. Nothing was offered as compensation beyond bottles of water during the time we were deplaned and waiting in the terminal.

Very pleasant flight attendants. Gate crew rather loud chatting with each other.

Four plus hour flight delay in New York caused us to take off after 11:30pm. We didn’t arrive at our hotel until five hours after check in. Started the trip off feeling exhausted.

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

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports