$115 Find Cheap Flights from San Diego to Caribbean - Compare and Save

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 9/19. 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 Diego to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$540
Santo Domingo
Santo Domingo1 stop$502
Montego Bay
Montego Bay1 stop$432
Oranjestad
Oranjestad2 stops$558
Nassau
Nassau1 stop$494
Kingston
Kingston1 stop$572
Simpson Bay
Simpson Bay1 stop$495
Providenciales
Providenciales1 stop$531
Port of Spain
Port of Spain2 stops$444
Bridgetown
Bridgetown1 stop$734
George Town
George Town2 stops$498
Willemstad
Willemstad1 stop$431
Aguadilla
Aguadilla2 stops$422
Puerto Plata
Puerto Plata1 stop$670
St. John's
St. John's2 stops$803
Punta Cana
Punta Cana1 stop$540
Santo Domingo
Santo Domingo1 stop$502
Montego Bay
Montego Bay1 stop$432
Oranjestad
Oranjestad2 stops$558
Nassau
Nassau1 stop$494
Kingston
Kingston1 stop$572
Simpson Bay
Simpson Bay1 stop$495
Providenciales
Providenciales1 stop$531
Port of Spain
Port of Spain2 stops$444
Bridgetown
Bridgetown1 stop$734
George Town
George Town2 stops$498
Willemstad
Willemstad1 stop$431
Aguadilla
Aguadilla2 stops$422
Puerto Plata
Puerto Plata1 stop$670
St. John's
St. John's2 stops$803

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

Mon, Aug 24 - Tue, Aug 25
American Airlines Logo
10:45 pm - 2:38 pm
SAN
-
SJU
12h 53m
2 stops
American Airlines Logo
12:55 am - 8:58 am
SJU
-
SAN
11h 03m
1 stop
$257American Airlines
Wed, Sep 9 - Fri, Sep 18
United Airlines Logo
6:15 am - 8:38 pm
SAN
-
SJU
11h 23m
2 stops
United Airlines Logo
7:00 am - 5:26 pm
SJU
-
SAN
13h 26m
2 stops
$262United Airlines
Tue, Oct 20 - Tue, Oct 27
Delta Logo
7:10 pm - 11:56 am
SAN
-
SJU
13h 46m
2 stops
Delta Logo
7:00 am - 6:46 pm
SJU
-
SAN
14h 46m
2 stops
$276Delta
Tue, Aug 11 - Fri, Aug 28
United Airlines Logo
8:00 am - 8:38 pm
SAN
-
SJU
9h 38m
1 stop
United Airlines Logo
2:20 pm - 9:25 pm
SJU
-
SAN
10h 05m
1 stop
$285United Airlines
Fri, Aug 21 - Fri, Aug 28
American Airlines Logo
10:45 pm - 3:52 pm
SAN
-
STT
14h 07m
2 stops
American Airlines Logo
3:43 pm - 8:50 am
STT
-
SAN
20h 07m
2 stops
$316American Airlines
Fri, Sep 18 - Tue, Sep 29
Delta Logo
10:25 pm - 3:34 pm
SAN
-
MBJ
15h 09m
1 stop
Delta Logo
12:59 pm - 11:34 pm
MBJ
-
SAN
12h 35m
1 stop
$432Delta
Mon, Aug 17 - Fri, Aug 21
Southwest Logo
10:40 pm - 12:15 pm
SAN
-
NAS
10h 35m
2 stops
Southwest Logo
1:10 pm - 9:55 pm
NAS
-
SAN
11h 45m
2 stops
$498Southwest
Fri, Aug 21 - Fri, Aug 28
Southwest Logo
8:00 pm - 1:20 pm
SAN
-
STT
14h 20m
2 stops
Southwest Logo
2:35 pm - 11:25 pm
STT
-
SAN
11h 50m
2 stops
$508Southwest
Sun, Aug 9 - Mon, Aug 17
JetBlue Logo
8:40 pm - 3:30 pm
SAN
-
AUA
15h 50m
1 stop
JetBlue Logo
6:00 pm - 7:29 pm
AUA
-
SAN
28h 29m
1 stop
$617JetBlue
Fri, Sep 18 - Fri, Sep 25
JetBlue Logo
9:30 pm - 1:00 pm
SAN
-
PLS
12h 30m
1 stop
JetBlue Logo
2:25 pm - 9:17 am
PLS
-
SAN
21h 52m
1 stop
$657JetBlue
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 San Diego to Caribbean flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Caribbean 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.

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 September, when tickets cost $141 (return) on average. On the other hand, the most expensive months are April and February, when the average cost of round-trip tickets is $204 and $194 respectively.

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 5 weeks before departure, which saves you about 34% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 11 weeks before departure.

Good to know

Low seasonOctober
Cheapest flight$115
Best time to beat the crowds with an average 28% drop in price.
Most popular time to fly with an average 5% increase in price.
Flight from San Diego to Saint Thomas Island

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.

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.
7.9
Alaska AirlinesOverall score based on 12589 reviews
8.5Crew
7.0Food
8.1Boarding
7.0Entertainment
7.8Comfort
Airline reviews

Orderly boarding; engaged, attentive and detailed flight crew. Late out of the gate but time recovered during flight; super landing and deplaning.

10.0 ExcellentMark, Jun 2026
SAN - DEN
Read more Alaska Airlines reviews

Orderly boarding; engaged, attentive and detailed flight crew. Late out of the gate but time recovered during flight; super landing and deplaning.

My flight was several times rescheduled and then finally canceled.

Short trip, was nice to have a drink on the short flight still.

Flight got delayed like 5 times, then they put and ada passenger in the back of the plane.

Flight delayed no communication. The gate was changed so many times.

Alaska is by far the best airline to fly with 😍

More efficient with checking lines and boarding/checking bags when needed.

They were really helpful with every question and my kids had never been on a plane and the staff made them feel comfortable

I was on flight #3022 departed from San Diego, California to Medford, Oregon. I had Denise & Damaris as my flight attendants. I didn’t have much interaction with Damaris, but I did with Denise who had, this calm, cool collective voice when she spoke about the emergency exit plans before takeoff. I travel often and I’ve never met a flight attendant that can put you at ease. I felt she respects and takes pride in her position and more airlines need to adopt the integrity and respect that she has for Alaska Airlines. Debbie

All airlines should board planes back to front, instead of catering to higher priced tickets. The boarding groups are inefficient and delay takeoff 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.

There was over a 9 hour delay for one thing after another. A toilet problem, they had to change the brakes, they had to refuel, three pilots times out, etc. We had to sit on the plane at the gate for over 5 hours with no air.

Unfortunately it was not a good experience. There was a rude stewardess.

No problems with the flight, my issue is with the terminal at SAN airport. I’ve never seen a dirtier, worse equipped terminal. No power plugs worked, but you could of course buy a fuel rod battery from the kiosk (seemingly the only thing that worked).

Usually reliable SWA worked out fine for my quick business trip to Phoenix.

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.

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.

Delta flight was great from the check in all the way to arrival. However, I had a very bad experience. I requested a wheelchair and the wheelchair employee that went to pick me up from the plane in Boston to bring me to the baggage claims told me I have to pay him. I was under the impression that it was a free service and I usually give tips but the person forced me to pay and since I said no because I was upset with his demand when my daughter walked in to pick me up he demanded payment from my daughter who paid him thinking maybe now it is a charged service.

There was a loud squeaky sound the whole time we were flying.

The landing was bad and the hostess came two times and i was sleeping but when she served the person that nexts to me I woke up and she didn’t even asked me if I need any drink or snacks two times!!!!

Waited 3 hours on a plane to de-ice due to manpower issues. Waited another hour and a half once we landed because of a gate issue. Missed my connections. Created. A total of 13 hours of delay.

Like most domestic flights in the US, you are basically on your own with this airline when it comes to food, so be sure to purchase meals and drinks ahead of time or expect to arrive starving and dehydrated (like I was).

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.

As usual, United scheduling is completely misleading. A 54-minute layover at O’Hare is too short to make a lot of connections, especially since the flight landed “on time” but had to wait on the taxiway 15 minutes for a gate to open up. Then it takes another 10 minutes to exit the plane before one can run to another concourse to catch a connecting flight.

Flight was ok. Unfortunately it was a Boeing 737, which is a cramped / tight airplane. I prefer the Airbus as they are a more comfortable flight experience.

We were traveling as a family of 5 and they refused to seat us together. There were entire rows open, and my 13 year old daughter had to sit alone. Ridiculous!

Do not like the feeling of being in the basic economy. Everyone should feel good no matter what.

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.

Had to wait on pilot and crew to depart and had to wait to arrive at the gate because they only had 2 crews working. Delays, delays....Planes just keep getting smaller and tighter and they nickle and dime for everything. When will an airline actually wake up and make flying more enjoyable?

I paid for what I got which was cheap, I brought my own entertainment. I knew what to expect, so I could be prepared. If you’re flying economy, check in early like me. I have no problems with my flight, was on time, staff were friendly, and overall good experience.

Multiple maintenance delays and the missed and rebooked connection changed gates at least 6 times including one which had us walking 20 minutes to another terminal and then back again. Seated our family of three in different middle seats throughout the plane and then there was an empty seat next to me. Very long travel day which I would have never agreed to if I knew the itinerary would be changed at 5 am, 2 hours before takeoff.

Not too impressed with them to be honest. They had forgotten my gf meal, despite the fact that the app had notified me that it was sorted. Apparently there is a ‘glitch’ in the system, according to one of the stewardesses, and has been for a while. Also the legroom in economy is way too small (and I’m a slight person) and are very uncomfortable. An extra Internal flight I booked via the app, had not even given me the option to order a meal, so was unaware of that and left without food on a 9 hr. flight !! Don’t think I’ll use AA again after this.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports