$137 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 5/16. 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$519
Santo Domingo
Santo Domingo2 stops$502
Montego Bay
Montego Bay2 stops$392
Oranjestad
Oranjestad1 stop$477
Nassau
Nassau1 stop$498
Kingston
Kingston1 stop$564
Simpson Bay
Simpson Bay1 stop$475
Providenciales
Providenciales1 stop$539
Port of Spain
Port of Spain1 stop$567
Bridgetown
Bridgetown1 stop$472
George Town
George Town1 stop$472
Willemstad
Willemstad1 stop$448
Puerto Plata
Puerto Plata2 stops$517
Aguadilla
Aguadilla2 stops$506
St. John's
St. John's1 stop$700
Punta Cana
Punta Cana1 stop$519
Santo Domingo
Santo Domingo2 stops$502
Montego Bay
Montego Bay2 stops$392
Oranjestad
Oranjestad1 stop$477
Nassau
Nassau1 stop$498
Kingston
Kingston1 stop$564
Simpson Bay
Simpson Bay1 stop$475
Providenciales
Providenciales1 stop$539
Port of Spain
Port of Spain1 stop$567
Bridgetown
Bridgetown1 stop$472
George Town
George Town1 stop$472
Willemstad
Willemstad1 stop$448
Puerto Plata
Puerto Plata2 stops$517
Aguadilla
Aguadilla2 stops$506
St. John's
St. John's1 stop$700

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

Thu, May 7 - Thu, May 14
American Airlines Logo
7:20 pm - 12:35 pm
SAN
-
STT
14h 15m
2 stops
American Airlines Logo
12:25 pm - 10:00 pm
STT
-
SAN
12h 35m
2 stops
$316American Airlines
Wed, Aug 26 - Tue, Sep 1
American Airlines Logo
10:45 pm - 3:52 pm
SAN
-
STT
14h 07m
2 stops
American Airlines Logo
1:49 pm - 10:19 am
STT
-
SAN
23h 30m
2 stops
$321American Airlines
Thu, May 14 - Mon, May 18
United Airlines Logo
8:45 pm - 3:43 pm
SAN
-
STT
15h 58m
2 stops
United Airlines Logo
1:22 pm - 8:04 pm
STT
-
SAN
9h 42m
1 stop
$381United Airlines
Tue, Apr 28 - Fri, May 1
United Airlines Logo
4:21 pm - 3:10 pm
SAN
-
MBJ
20h 49m
2 stops
United Airlines Logo
2:40 pm - 9:25 pm
MBJ
-
SAN
8h 45m
1 stop
$392United Airlines
Sun, Jul 19 - Thu, Jul 23
Delta Logo
6:10 pm - 3:20 pm
SAN
-
STT
18h 10m
2 stops
Delta Logo
3:33 pm - 10:57 pm
STT
-
SAN
10h 24m
1 stop
$398Delta
Thu, May 28 - Thu, Jun 4
Delta Logo
3:45 pm - 11:26 am
SAN
-
MBJ
17h 41m
2 stops
Delta Logo
4:59 pm - 9:43 am
MBJ
-
SAN
18h 44m
1 stop
$407Delta
Fri, May 8 - Mon, May 11
Copa Airlines Logo
10:00 pm - 12:08 pm
SAN
-
AUA
11h 08m
1 stop
Copa Airlines Logo
7:19 am - 6:30 pm
AUA
-
SAN
14h 11m
1 stop
$477Copa Airlines
Mon, Jun 15 - Sat, Jun 20
Copa Airlines Logo
10:00 pm - 12:18 pm
SAN
-
CUR
11h 18m
1 stop
Copa Airlines Logo
3:39 pm - 6:40 pm
CUR
-
SAN
30h 01m
1 stop
$508Copa Airlines
Mon, Sep 21 - Mon, Oct 5
JetBlue Logo
9:30 pm - 5:55 pm
SAN
-
SDQ
17h 25m
1 stop
JetBlue Logo
7:22 pm - 9:17 am
SDQ
-
SAN
16h 55m
1 stop
$509JetBlue
Thu, May 28 - Tue, Jun 2
JetBlue Logo
1:41 pm - 3:36 am
SAN
-
SDQ
10h 55m
1 stop
JetBlue Logo
3:11 am - 12:31 pm
SDQ
-
SAN
12h 20m
1 stop
$520JetBlue
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 72 hours 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 72 hours 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 $440, 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 $418 (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.

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 32% 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$137
Best time to beat the crowds with an average 25% drop in price.
Most popular time to fly with an average 8% 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
DeltaOverall score based on 8409 reviews
7.9Comfort
8.5Crew
7.8Entertainment
8.1Boarding
7.2Food
Airline reviews

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!

10.0 ExcellentTeresa, Apr 2026
SMF - LAX
Read more Delta reviews

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.

Flight late, the waited for a long time for “personal” to arrive at gate to dock the plane in Rochester. So annoying. This flight was expected, why aren’t personel available for the jet bridge?

My recent experience was excellent on Delta! I flew with Delta Comfort and I was really comfortable in my seat. I enjoyed the in-flight service. The flight attendants were so friendly and hospitable. I love the snack on the flight as well. This was my first time flying on Delta and I will definitely consider flying with them again.

My flight was canceled on Sunday. Rebooking took three hours. Had to pay for accommodations another night. New flight was delayed for 5 hours, all that was sent was a 12 dollar food voucher, which doesn’t tell you how to use it. Then when we landed we had to sit on the plane for an hour before we could get off.

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

Entire experience from check in to landing was amazing the flight crew was excellent and friendly. Seats were comfortable.

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.

Copa staff at PTY and one particular crew member were unhelpful & rude.

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

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

Due to cancellation of connecting flight (Lufthansa) I didn’t fly with United

It was a red-eye, but the flight felt surprisingly quick. The seats were very comfortable, and that made resting much easier. I also want to thank the gentleman seated next to me, who graciously moved so my mom could sit beside me. We slept almost the entire way. The cabin crew was respectful in not disturbing us, while also being courteous and professional throughout. Thank you, United.

Boarding was again a "free for all". We were boarding group 4, and almost the entire plane was able to board before us. It's a shame that someone who follows the rules, gets the short end of the stick. Not fair.

It was perfect! I've never flown with United before, but I definitely will in the future

I had a cancelled flight because of technical issues going to my destination, and a delayed flight coming home. All told it wasn’t a total bust.

The business class seat is exceptional. I wish the food is more palatable.

the entire flight felt off. The crew seemed uninterested and disengaged. The food service was really bad - overcooked, bland, weird food service. They actually woke us up to serve chicken wraps in the middle of the night, after dinner and before breakfast. Made no sense. Ultimately, I was glad they did though, because the breakfast had been held for so long it was inedible. Eggs, potatoes, sausage - all disgusting. We were asked to "honor" the lavatories for premium customers and stay in our own cabin: this was also strange. So people in economy didn't pay enough to use the closest toilet to them??? It's a toilet. All in all, not the experience I have come to expect from United Airlines. The return flight from Paris to SFO was better, btw.

They delayed the flight from 9:00 to 11:55 At 11:45 they canceled the flight. I paid a premium price for the tickets with poor service

My flight was canceled a few hours before boarding. I was rebooked on Copa airlines and missed an important meeting .

Business class seats felt very cramped compared to other airlines.

Entertainment and wifi were very sub-par - audio issues and no wifi

We were delayed and had to circle due to weather and had to divert for fuel. While I understand that you can’t control the weather I would have appreciated knowing that the crew wasn’t going to run out of hours and then having to spend the night in the Raleigh airport.

Messy plane that was falling apart Small screens that didn't work

I was traveling with two small kids and our TV s were the only ones not working. Informed the flight attendant who did nothing about them.

They forced me to check my hand luggage at the gate.

I specifically choose not to check bags to ensure I can proceed directly to ground transportation upon arrival. However, due to a recurring lack of cabin space, I was again forced to gate-check my rolling luggage after going through my luggage to take out electronics and batteries. This practice unilaterally changes the service agreement made at the time of purchase. JetBlue needs to find a better way to manage overhead space that honors the carry-on baggage allowance.

Still hasn’t left. Why are you asking how it was?

Flight was good wish there were more snacks options for such a long flight but stewardesses were very pleasant as was flight crew.

I was denied a plastic fork to eat my food and was told plastic forks are for paying customers who buy Jet Blue’s food. So I had to make a utensil out of a cup so nourish my body. Like a refugee. Because decency is dead.

I was especially impressed without efficiently the crew got passengers on and off. One of the stewards was slightly gruff, I thought. No big deal but that's what I noticed.

The SFO Lounge crew were amazing. The bartender Faris was great. Thanks!

Friendly crew is the only nice thing. Seats uncomfortable. Food and snacks horrible. Movies were the same as the first 10 hour flight two weeks before

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.

Good flight, seated and had a water within 5 minutes. Crew was hospitable.

We left at 1030 am pacific from LA and supposed to land at 7 pm Eastern in NY. They made a detour, stopped in Philadelphia and didn’t land till 1130 PM Eastern!!! Worst flight experience with no pilot communication with no explanation as to what was going on. Everyone was very frustrated to say the least.

I cancelled my ticket less than 24 hours deadline but I didn’t get refunded.

Flight boarded from Gate 159B, the farthest gate in the LAX Bradley Terminal. While the flight operated on time, the first class cabin attendant made no recognition of my being an Advantage Executive Platinum member.

The flight itself was excellent but the gate attendant made me check my carryon since she said it was an inch too big. I’ve had no problems with this carryon on recent flights on Qantas, Delta, Austrian, Southwest Airlines even though the overhead bins are the same size. there were other carryons in the bins that also looked larger than mine and there was room left in the bins for more. When I picked up my carryon from baggage claim one of the wheels had broken off.

I was in last row so that is never great bc the person in front of me leaned his seat all the way back into me.

The experience at checkin for my American Airlines flight from Sacramento to LAX was very good including the assistance I received in getting my bags checked in and boarding passes printed. Was pleasantly surprised the my bags were checked through all the way to my destination at Clark International Airport in Angeles, Philippines.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports