$131 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 8/18. 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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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$453
Santo Domingo
Santo Domingo1 stop$507
Montego Bay
Montego Bay1 stop$417
Oranjestad
Oranjestad1 stop$589
Nassau
Nassau1 stop$410
Kingston
Kingston1 stop$574
Simpson Bay
Simpson Bay1 stop$431
Providenciales
Providenciales1 stop$468
Port of Spain
Port of Spain2 stops$444
Bridgetown
Bridgetown1 stop$555
George Town
George Town1 stop$481
Willemstad
Willemstad1 stop$431
Aguadilla
Aguadilla2 stops$481
Puerto Plata
Puerto Plata1 stop$642
St. John's
St. John's1 stop$778
Punta Cana
Punta Cana1 stop$453
Santo Domingo
Santo Domingo1 stop$507
Montego Bay
Montego Bay1 stop$417
Oranjestad
Oranjestad1 stop$589
Nassau
Nassau1 stop$410
Kingston
Kingston1 stop$574
Simpson Bay
Simpson Bay1 stop$431
Providenciales
Providenciales1 stop$468
Port of Spain
Port of Spain2 stops$444
Bridgetown
Bridgetown1 stop$555
George Town
George Town1 stop$481
Willemstad
Willemstad1 stop$431
Aguadilla
Aguadilla2 stops$481
Puerto Plata
Puerto Plata1 stop$642
St. John's
St. John's1 stop$778

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

vie., ago. 21 - sáb., ago. 29
American Airlines Logo
9:36 pm - 1:40 pm
SAN
-
STT
13h 04m
1 stop
American Airlines Logo
4:42 pm - 11:08 pm
STT
-
SAN
9h 26m
1 stop
$316American Airlines
mié., sep. 9 - mié., sep. 16
American Airlines Logo
11:15 am - 12:51 pm
SAN
-
STT
22h 36m
2 stops
American Airlines Logo
1:41 pm - 8:56 am
STT
-
SAN
22h 15m
2 stops
$321American Airlines
mié., nov. 11 - jue., nov. 19
Delta Logo
10:10 pm - 5:20 pm
SAN
-
SJU
15h 10m
1 stop
Delta Logo
1:55 pm - 9:41 pm
SJU
-
SAN
11h 46m
1 stop
$386Delta
jue., oct. 1 - sáb., oct. 10
United Airlines Logo
10:20 pm - 1:45 pm
SAN
-
SJU
12h 25m
1 stop
United Airlines Logo
1:00 am - 9:49 am
SJU
-
SAN
11h 49m
1 stop
$390United Airlines
jue., ago. 13 - jue., ago. 20
Southwest Logo
9:25 am - 11:50 pm
SAN
-
SJU
11h 25m
2 stops
Southwest Logo
8:55 pm - 11:00 am
SJU
-
SAN
17h 05m
2 stops
$410Southwest
mar., ago. 25 - mié., sep. 16
Delta Logo
3:00 pm - 11:42 am
SAN
-
NAS
17h 42m
2 stops
Delta Logo
12:55 pm - 11:52 pm
NAS
-
SAN
13h 57m
2 stops
$414Delta
lun., nov. 9 - mié., nov. 18
United Airlines Logo
10:30 pm - 1:41 pm
SAN
-
SJU
11h 11m
1 stop
United Airlines Logo
2:05 am - 3:30 pm
SJU
-
SAN
17h 25m
2 stops
$414United Airlines
dom., ago. 16 - dom., ago. 23
Southwest Logo
7:55 pm - 10:55 am
SAN
-
SJU
12h 00m
2 stops
Southwest Logo
9:25 pm - 11:00 am
SJU
-
SAN
16h 35m
2 stops
$415Southwest
mié., ago. 26 - dom., ago. 30
Copa Airlines Logo
10:00 pm - 2:36 pm
SAN
-
CUR
13h 36m
1 stop
Copa Airlines Logo
7:31 pm - 6:30 pm
CUR
-
SAN
25h 59m
1 stop
$431Copa Airlines
mié., ago. 26 - dom., ago. 30
Copa Airlines Logo
10:00 pm - 2:36 pm
SAN
-
CUR
13h 36m
1 stop
Copa Airlines Logo
7:31 pm - 6:30 pm
CUR
-
SAN
25h 59m
1 stop
$440Copa Airlines
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?

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

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?

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 $445, 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 $165 (return) on average. On the other hand, the most expensive months are June and September, when the average cost of round-trip tickets is $238 and $238 respectively.

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 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 21 weeks before departure.

Good to know

Low seasonOctober
Cheapest flight$131
Best time to beat the crowds with an average 27% 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.

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
SouthwestOverall score based on 4235 reviews
8.0Comfort
8.1Boarding
8.6Crew
7.5Entertainment
7.0Food
Airline reviews

Was fine, delayed and feels like southwest is always late

6.0 GoodAnonymous, Jun 2026
SMF - LAS
Read more Southwest reviews

Was fine, delayed and feels like southwest is always late

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

Delayed flight, lack of information, boarding process is a mess as is the carryon luggage causing issues when leaving the plane….just a poor experience.

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

The crew was very kind and made going to Hawaii relaxing and fun to look forward to! Thank you Southwest for a pleasant flight!

Terrible. Even though there’s assigned seating now, they are still the slowest boarding airline of anyone.

It was good from LAX to Phoenix, But the connection in Phoenix to Tulsa was not that great. The staff on both flights were great. The choice of free entertainment was ok nothing to brag about. The 45 min delay because of some electrical issue wasn't great from Phoenix to Tulsa. We sat there with hardly any air, The seat I had was between windows so the side of the plane pushed in on you. My being a bigger man it then made the seating area uncomfortable. The seats on the plane had no power to connect to recharge your phone or anything. I would recommend that they should look into a slot or clamp to hold your phone to enjoy while watching the entertainment choices hands-free. Also make it possible to raise the inner seat by the window be able to raise the arm rest up to make more room for larger people to set more comfortably. I would also say other then that stop price gouging the airfare or nickel and diming everything. Not fair for people having to fly for emergencies and be paying for higher prices due to the season or holidays. Your making your money either way and the cost of flying is still going to be the same regardless if there's 100 people or 200 people.

Southwest was greaat! The most expensive but the least upsetting for those we were flying to see.

Boarding was easy. The seats are small and fairly uncomfortable

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

Flight delayed four separate times. I’m now one hour hours late to landing.

Checkin was good, fllight ws good. Onlly complaint is lack of foot on 6 hour flight from Seattle to Boston. Snacks were flimsy - chips and cookies. could have offered something more substantial for such a long flight. I know you can buy food in airport but for the price you pay for a ticket, they should step up for the passengers.

Long story short, it was one of the better flight experiences I've had in some time when compared with other airlines.

While they turned off most cabin lights to allow people to sleep, I was bothered by how bright the side lights still were. It was still quite bright for me in a window seat, when I wish I could have slept!

Generally on time departures and arrivals, clean planes, sky miles membership provides great benefits (complimentary upgrades, etc).

N Everything was perfect from boarding to assistance to baggage in Tampa

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

Fast, lovely scenery, great info on the Delta flight screen about landmarks we were flying over. Great landing!

Long flight but comfortable and not freezing as I have experienced on Hawaiian flights to the islands. They gave us blankets just in case. Nice touch.

I took seat 15A in anticipation of window seat, there is no window.

They didn’t have any headphones for the entertainment screen and their USB port didn’t accommodate a USB-C for more modern phones. The food was just ok. The staff was friendly but the seats were very uncomfortable for a full flight.

I had to run from the end of terminal one to the end of terminal two to make the connecting flight....probably a kilometer. No electric carts were available. I'm 76 and literally had to run to make the connection at the last minute. The connecting time was absolutely unrealistic. When Last Call was announced, I tried to get other Copa gate staff to call Gate 221 to let them know I was on my way, but they said no. I came within 1 minute of missing the flight.

Boarding was a mess, they call all priority members without distinction so gold, platinum, silver were all mixed together in a long line which defeats the purpose

Boarding was confusing from staff telling going to preboard and than to group 1 Airplane was not cooling at the beginning

Avoid at all costs. My wife had to stay back on a connecting flight as her parents flight was delayed. 10 days later on the way back they cancelled all our flights. We had to rebook all four of us on the next days flight.

Friendly crew, good food options, food not the best and seats not as comfy but that’s typical.

Seats were awful. Media should have been included for such a long flight.

There should be a warning regarding the quality of the aircraft on the website as we reserve the tickets. There was no TV or any type of screen onboard. The wifi they offer is good for nothing. Traveling 9 hours straight with kids and no type of entetainment was horrible. I wish I had been informed prior so I could buy a ticket with another airline. The food was a joke too. A very tiny portion per passenger. They also charged $100 per checked bag. With United I used to pay $60. So, fair to say that I wont be flying Copa anymore. Their aircraft was super old, outdated, no entertainment, with nearly no onboard food.

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

I was promised by United Airline (operated by ANA) that I will be seated together with my kids as I am the only adult flying with two minors. We did not get seats together in our 11 hours flight from LA to Tokyo. When asked at the gate, ANA representative said United Airline should have informed them that there is a parent flying with two minors. He said they can’t do anything in the system as the flight is full. He ask me to ask passengers next to me and the kids if they are willing to change seats. This is ridiculous! However, I went in the flight and asked other passages but no one willing to change seats. 11 hours and we were seating separately. I was very disappointed with this. It made things super inconvenient for me.

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

It was perfect! United Airlines staff was extremely caring, super friendly and professional

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.

United has maintenance issues and can then never recover. No operations ability and simple issues always turn into multiple hours long cascading delays. Worst airline on earth.

I paid for a confirmed upgraded aisle seat and was moved to a center seat in the back of the plane at the last minute.

Horrifying Almost 2 million miles. Bring your own food and drink. One coffee or drink every three hours. Have to order meals on app more than 24 hours ahead Tiny and dirty bathrooms

Flight was delayed but more than 90 minutes. This caused me to miss my available windows for pick-up by a friend. I had to pay $125 for an uber back home from the airport which was an added expense that I had not budgeted for my trip. Staff was friendly.

Seat pitch is horrible especially on the 15 hour flight. Gate crew at SFO was Outstanding. The flight crew was also great.

Luggage did not make it onto my plane. Business seats were economy with empty row seat. Just horrible experience. Why would the company allow for transfers that don’t give employees enough time to transfer luggages??

The gate experience at LAX was abysmal (same for the arrival experience two days prior). Despite the LAX -> SAT schedule of two flights daily, our departure gate was at a smaller hub that we had to be bussed to from Terminal 4. Fortunately, I arrived at LAX extra early and had time to spare, but if I had not known, I might have missed my flight. I looked at the LAX airport map in the AA app and there was no indication of the additional boarding process. Lastly the gate area we were bussed to was crowded with limited food and beverage options. On flight, the fight attendant was hospitable and attentive, the flight was smooth, and AA's free (and working) wifi for AA members were all on the positive side.

Our flight from JFK to Madrid was delayed. We had to go from one side of the Madrid airport (Terminal 4s to the far end of terminal 4 - Gate K98) to our gate in less than 30 minutes. Put passport control and security/baggage check and that’s very hard unless you’re Usain Bolt. I called Iberia Airlines and the telephone customer service told me that I was going to have to pay to re-book. Luckily the help desk in the airport (who was dealing with dozens of people from the same JFK-Madrid flight) did not charge us extra to reschedule to a flight 8 hours later. They also gave us a voucher for breakfast and lunch. Glad the actual person at the airport had some actual sense.

For an long range economy flight I feel more space and more meal options need to be offered for flights over 5 hours

Take-off delayed an hour because of a missing flight officer, so,arrived in Charlotte lates causing many passengers to miss connections. Otherwise a very good flight, safe and comfortable, with an excellent professional crew.

The flight from LA to Chicago was smooth and service was very good overall.

B-class on an old plane with antiquated amenities and poor service. Landed in Rome w/o bag that didn’t make the connection (plenty of time in London). Bag will come to hotel NOT the day it lands but the following night!! Still waiting for bag…BA had nothing to offer in support and couldn’t even tell me their comp, told to submit receipts and then I’ll learn what is or isn’t covered.

Ontario airport boarding was very easy to park and access, is clean and TSA took 10 minutes total. Check-in was a breeze and cruise was very nice.

It's a long flight and that is always difficult. I was comfortable and well. The movies available were great and the crew was good.

Premium Economy Good crew, good service, excellent food. Seat back screen just not bright enough.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports