$133 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 4/28. 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 Cana2 stops$338
Santo Domingo
Santo Domingo1 stop$452
Montego Bay
Montego Bay2 stops$336
Oranjestad
Oranjestad1 stop$485
Nassau
Nassau1 stop$470
Kingston
Kingston1 stop$564
Simpson Bay
Simpson Bay1 stop$445
Providenciales
Providenciales2 stops$530
Port of Spain
Port of Spain1 stop$508
Bridgetown
Bridgetown1 stop$472
George Town
George Town1 stop$435
Willemstad
Willemstad1 stop$429
Puerto Plata
Puerto Plata1 stop$630
St. John's
St. John's1 stop$835
Aguadilla
Aguadilla1 stop$486
Punta Cana
Punta Cana2 stops$338
Santo Domingo
Santo Domingo1 stop$452
Montego Bay
Montego Bay2 stops$336
Oranjestad
Oranjestad1 stop$485
Nassau
Nassau1 stop$470
Kingston
Kingston1 stop$564
Simpson Bay
Simpson Bay1 stop$445
Providenciales
Providenciales2 stops$530
Port of Spain
Port of Spain1 stop$508
Bridgetown
Bridgetown1 stop$472
George Town
George Town1 stop$435
Willemstad
Willemstad1 stop$429
Puerto Plata
Puerto Plata1 stop$630
St. John's
St. John's1 stop$835
Aguadilla
Aguadilla1 stop$486

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, Apr 20 - Thu, Apr 23
Delta Logo
5:00 pm - 1:51 pm
SAN
-
STT
17h 51m
2 stops
Delta Logo
1:59 pm - 11:25 pm
STT
-
SAN
12h 26m
1 stop
$310Delta
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 - 9:55 pm
STT
-
SAN
12h 30m
2 stops
$316American Airlines
Wed, May 6 - Thu, May 14
United Airlines Logo
6:05 pm - 12:20 pm
SAN
-
STT
15h 15m
2 stops
United Airlines Logo
1:22 pm - 8:04 pm
STT
-
SAN
9h 42m
1 stop
$320United Airlines
Wed, Apr 29 - Thu, May 7
American Airlines Logo
7:20 pm - 11:35 am
SAN
-
STT
13h 15m
2 stops
American Airlines Logo
1:15 pm - 8:50 pm
STT
-
SAN
10h 35m
1 stop
$321American Airlines
Thu, May 7 - Thu, May 14
United Airlines Logo
9:45 pm - 12:20 pm
SAN
-
STT
11h 35m
1 stop
United Airlines Logo
1:22 pm - 9:25 pm
STT
-
SAN
11h 03m
1 stop
$332United Airlines
Mon, Apr 27 - Thu, May 7
Delta Logo
9:45 pm - 1:51 pm
SAN
-
STT
13h 06m
1 stop
Delta Logo
3:01 pm - 11:27 pm
STT
-
SAN
11h 26m
1 stop
$357Delta
Wed, Sep 16 - Tue, Sep 22
JetBlue Logo
9:30 pm - 5:55 pm
SAN
-
SDQ
17h 25m
1 stop
JetBlue Logo
6:45 am - 8:01 pm
SDQ
-
SAN
16h 16m
1 stop
$452JetBlue
Sat, Apr 25 - Sat, May 9
JetBlue Logo
9:15 pm - 1:56 pm
SAN
-
SDQ
13h 41m
1 stop
JetBlue Logo
5:01 am - 8:04 pm
SDQ
-
SAN
18h 03m
1 stop
$468JetBlue
Mon, Apr 27 - Mon, May 4
Southwest Logo
10:40 pm - 1:15 pm
SAN
-
NAS
11h 35m
2 stops
Southwest Logo
2:10 pm - 10:55 pm
NAS
-
SAN
11h 45m
2 stops
$502Southwest
Wed, Apr 22 - Fri, May 1
Southwest Logo
10:40 pm - 2:55 pm
SAN
-
PLS
13h 15m
2 stops
Southwest Logo
3:50 pm - 10:55 am
PLS
-
SAN
22h 05m
2 stops
$530Southwest
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 27% 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$133
Best time to beat the crowds with an average 24% drop in price.
Most popular time to fly with an average 3% 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 4337 reviews
8.1Boarding
7.5Entertainment
8.0Comfort
8.6Crew
7.0Food
Airline reviews

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.

10.0 ExcellentAnthony & Kathy, Mar 2026
LAX - PHX
Read more Southwest reviews

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.

The wifi on the plane is great. The only issue that I have is that I prefer an aisle seat and on my trips this week, I was either in the middle or window. If we can work to secure aisle seating, I will be thrilled. Nice trip.

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.

The room for legs is adequate for a 6’ tall man and the flight was comfortable. The cabin is clean and the crew is very friendly and pleasant.

Worst first/business class I have ever flown after 75 years on planes. Barely acceptable seats, terrible food, uninterested attendants, unavailable WiFi. I’ll never fly this airline again.

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.

I was in first class and literally the men behind me were so aggressively loud I moved myself to economy. This has become so common on Delta - people using audio without headphones, and men on 12am / late night flights drinking and yelling to talk to each other which prevents anyone around them from resting. Pretty crazy to have to move from first to economy (poorer service, less comfort...). Wild wild. Looking into other airlines.

Flight was delayed by 3-hours and their fix was… complimentary pretzels.

The crew, and fellow passengers, were super gracious and kind. There seemed to be plenty of bin space even though the plane was full. It’s nice to get a glass of wine with dinner in Premiere seating, and there was a lot of food.

Everything I mentioned earlier - the airbus was more comfortable indeed and the experience was further enhanced.

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.

OK, we were delayed and had to de plane and reboard.

The 777’s economy seat’s legroom was more tolerable than expected. I appreciate the reclining mechanism which slides the seat forward to minimize cannibalizing the space behind. The food was terrible: very salty.

Seats are uncomfortable. This has been a trend in the industry for decades. Trying to fit more seats on each plane to increase profits at the expense of the passenger.

Staff were good. My seat was in need of repair, but for a short flight was not problematic. Usual basic snack and drink setup that you'll find on any US carrier. Over, a decent, basic flight.

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.

Terrible planning. And even worse gate agents. Absolutely rude behavior.

Flight was scheduled at 11:26am but they keep Delaying until midnight. They waited at airport restless.

Rough flight No beverage service due to turbulence Bottom Seat cushion was non existent

Not good. One of my luggage is missing. And until now they can’t find it

My 9:50AM flight was delayed to 3:40PM "due to incoming aircraft delay". No aircraft is "delayed" that long. Found out once we did board (after several changes in times) that the aircraft had a maintenance issue and we had to wait for another aircraft. Just tell us that. The aircraft we did get was old and the seats need to be updated. I have been traveling for several weeks with AA and you should refresh your entertainment content as frequent flyers have gone through most of your new content. I have Celiac and a shellfish allergy and continue to have struggles with meals on business and first class flights. Please keep this in mind. Sorry - was a long travel day yesterday and a bit cranky this morning with my experience comments. Still an AA fan.

Delay after delay with little communication then AA lost my luggage and at airport would not assist just said scan this QR code to track your luggage and submit a claim. However QR code provided did not work so have to go back to airport

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports