$137 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 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

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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$519
Santo Domingo
Santo Domingo1 stop$496
Montego Bay
Montego Bay2 stops$392
Oranjestad
Oranjestad1 stop$477
Nassau
Nassau1 stop$489
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
Willemstad2 stops$448
Puerto Plata
Puerto Plata2 stops$517
Aguadilla
Aguadilla1 stop$506
St. John's
St. John's1 stop$700
Punta Cana
Punta Cana1 stop$519
Santo Domingo
Santo Domingo1 stop$496
Montego Bay
Montego Bay2 stops$392
Oranjestad
Oranjestad1 stop$477
Nassau
Nassau1 stop$489
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
Willemstad2 stops$448
Puerto Plata
Puerto Plata2 stops$517
Aguadilla
Aguadilla1 stop$506
St. John's
St. John's1 stop$700

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

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
Mon, May 4 - Fri, May 8
Multiple Airlines Logo
12:25 pm - 3:50 pm
SAN
-
SJU
24h 25m
2 stops
Multiple Airlines Logo
7:00 am - 11:44 am
SJU
-
SAN
31h 44m
1 stop
$322Multiple 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
Tue, Apr 28 - Tue, May 5
Southwest Logo
9:40 pm - 1:15 pm
SAN
-
NAS
12h 35m
2 stops
Southwest Logo
8:45 am - 4:10 pm
NAS
-
SAN
10h 25m
2 stops
$510Southwest
Fri, Jun 5 - Fri, Jun 12
JetBlue Logo
8:30 pm - 12:04 pm
SAN
-
PUJ
12h 34m
1 stop
JetBlue Logo
10:23 am - 7:28 pm
PUJ
-
SAN
12h 05m
1 stop
$530JetBlue
Mon, May 25 - Mon, Jun 1
Southwest Logo
8:25 pm - 1:35 pm
SAN
-
AUA
14h 10m
2 stops
Southwest Logo
2:35 pm - 7:45 am
AUA
-
SAN
20h 10m
2 stops
$553Southwest
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 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.

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 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?

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 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 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.
8.0
SouthwestOverall score based on 4329 reviews
8.6Crew
7.5Entertainment
7.0Food
8.0Comfort
8.1Boarding
Airline reviews

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

2.0 MediocreJames, Apr 2026
LAX - MCO
Read more Southwest reviews

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.

Good but I prefer choose your own seat. With the new assigned seats they should board from the back I see no advantage to this new boarding. Just like every other airline

Flight boarded late after announcing on time boarding. Flight arrived only a little late despite late departure. Had trouble connecting to WiFi

The Southwest experience has definitely taken a dive from its early days. You can no longer deferentiate from other airlines. Air travel is too expensive. Southwest is no longer budget friendly. They have lost me as a loyal customer.

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.

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

Luggage was severely damaged. Flight was late for several hours

The ticketing counter in SD was a mess. The lady handling the First-Class check-in seemed overwhelmed until a supervisor replaced her. It took almost 20 minutes to get once couple checked in, and then she started walking around the counters while 7 people just stood in line. Once her supervisor arrived, she announced she was going on break, never to engage with customers again.

No outlets, plugs, way to charge the phone or service and no food on one leg o the trip, but other than that, great. Loved WIFI, the flight, the crew, the pilots, the schedule, etc. Great job. My new favorite airline!

I had a problem with my reservation and no one could help me understand what happened. I booked my flight months ago and received a confirmation email. In the confirmation email, it said that the flight would depart at 3:15 p.m. A few hours before the flight, I tried to go online and check in, and suddenly it said that the flight was leaving an hour earlier. I had to rush to get to the airport and almost didn't make it. No one could help me understand why this happened, and I'm really concerned that it might happen in the future. I would appreciate some support in this matter.

It was a super old plane so the first class experience was just not luxurious

Good as usual. Just wished my seat was assigned at online check in. Thanks anyways

This was my first trip with Alaska Airlines (round trip DCA to San Diego). Despite a slight delay on the return flight, I feel compelled to post a RAVE review! I cannot praise the airline and the crew enough! Everyone was kind, professional, and courteous, every step of the way- excellent service, snacks, and entertainment! On both legs of the trip I inquired whether there were any free seating upgrades and my request were granted BOTH times! I’ve flown on other airlines where they won’t do that, even when those premium seats are empty. As a customer service professional myself, I can say I left my experience feeling like a valued customer and not just a number. I NEVER expected to praise an airline lol I’ll definitely go out of my way to fly with Alaska on future trips. Thank you for such an awesome experience!

I bought tickets MONTHS ago for a flight that left SAN at 14:30. That is what it says on our tickets. I was never notified of any time changes. During online check-in. I discovered the flight time had been changed to 15:45. This was unacceptable and had I been notified, I would have changed flights, or airlines. That departure time was unworkable with our plans. We called Alaska and asked for an explanation. They said flight time was changed 11/08/25. No proof of notification could be offered. We asked to be moved to an earlier flight. After much pleading, the rep said she would allow a “one time exception..” While I appreciate being moved, this was YOUR fault Alaska 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.

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.

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.

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

Information on your arrival and departure airports