$98 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 8/5. 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

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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Flights Deals

Best Caribbean Islands Flight Deals from San Diego

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana2 stops$376
Santo Domingo
Santo Domingo1 stop$427
Montego Bay
Montego Bay1 stop$411
Oranjestad
Oranjestad1 stop$523
Nassau
Nassau1 stop$437
Kingston
Kingston2 stops$470
Simpson Bay
Simpson Bay3 stops$534
Providenciales
Providenciales2 stops$559
Port of Spain
Port of Spain2 stops$524
Bridgetown
Bridgetown2 stops$578
George Town
George Town1 stop$496
Willemstad
Willemstad2 stops$522
St. John's
St. John's1 stop$752
Aguadilla
Aguadilla2 stops$420
Punta Cana
Punta Cana2 stops$376
Santo Domingo
Santo Domingo1 stop$427
Montego Bay
Montego Bay1 stop$411
Oranjestad
Oranjestad1 stop$523
Nassau
Nassau1 stop$437
Kingston
Kingston2 stops$470
Simpson Bay
Simpson Bay3 stops$534
Providenciales
Providenciales2 stops$559
Port of Spain
Port of Spain2 stops$524
Bridgetown
Bridgetown2 stops$578
George Town
George Town1 stop$496
Willemstad
Willemstad2 stops$522
St. John's
St. John's1 stop$752
Aguadilla
Aguadilla2 stops$420

Cheap Flights from San Diego to Caribbean Islands

 
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

Sat, Aug 30 - Thu, Sep 4
Spirit Airlines Logo
1:17 pm - 2:17 pmSAN-SJU
22h 00m2 stops
Spirit Airlines Logo
2:53 pm - 6:10 pmSJU-SAN
30h 17m2 stops
$221Spirit Airlines
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Mon, Nov 3 - Thu, Nov 13
United Airlines Logo
8:40 pm - 12:49 pmSAN-SJU
12h 09m2 stops
United Airlines Logo
2:05 am - 10:05 amSJU-SAN
12h 00m1 stop
$241United Airlines
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Sun, Sep 7 - Wed, Sep 17
American Airlines Logo
10:42 pm - 3:52 pmSAN-SJU
14h 10m1 stop
American Airlines Logo
4:43 pm - 9:27 amSJU-SAN
19h 44m1 stop
$243American Airlines
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Mon, Sep 29 - Fri, Oct 3
Delta Logo
5:05 pm - 1:16 pmSAN-SJU
17h 11m2 stops
Delta Logo
12:58 pm - 8:25 pmSJU-SAN
10h 27m1 stop
$275Delta
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Mon, Nov 3 - Fri, Nov 14
Southwest Logo
6:40 am - 1:25 amSAN-SJU
14h 45m1 stop
Southwest Logo
6:10 am - 5:55 pmSJU-SAN
15h 45m1 stop
$281Southwest
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Tue, Sep 9 - Wed, Sep 17
American Airlines Logo
10:32 pm - 3:52 pmSAN-SJU
14h 20m1 stop
American Airlines Logo
4:43 pm - 9:27 amSJU-SAN
19h 44m1 stop
$301American Airlines
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Mon, Nov 3 - Fri, Nov 14
Southwest Logo
8:05 pm - 10:25 amSAN-SJU
10h 20m2 stops
Southwest Logo
6:10 am - 5:55 pmSJU-SAN
15h 45m1 stop
$327Southwest
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Tue, Sep 16 - Wed, Sep 24
Delta Logo
9:52 pm - 11:25 amSAN-MBJ
11h 33m1 stop
Delta Logo
1:25 pm - 8:26 pmMBJ-SAN
9h 01m1 stop
$411Delta
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Thu, Aug 14 - Wed, Aug 20
JetBlue Logo
8:30 pm - 9:03 amSAN-NAS
9h 33m1 stop
JetBlue Logo
10:07 am - 6:57 pmNAS-SAN
11h 50m1 stop
$437JetBlue
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Fri, Jul 25 - Wed, Jul 30
JetBlue Logo
8:30 pm - 9:04 amSAN-NAS
9h 34m1 stop
JetBlue Logo
10:07 am - 6:55 pmNAS-SAN
11h 48m1 stop
$587JetBlue
Find Deal
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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.

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 $1,035, 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 September, when tickets cost $417 (return) on average. On the other hand, the most expensive months are December and June, when the average cost of round-trip tickets is $724 and $584 respectively.

What’s the cheapest day of the week to fly from San Diego to Caribbean Islands?

The average price of all round-trip flights from San Diego to Caribbean Islands clicked on KAYAK for each day over the last 12 months.

For San Diego to Caribbean Islands, Saturday is the cheapest day to fly on average and Sunday is the most expensive. Flying from Caribbean Islands back to San Diego, the best deals are generally found on Thursday, with Monday being the most expensive.

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 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 20 weeks before departure.


Good to know

Low seasonOctober
High seasonDecember
Cheapest flight$98
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly with an average 44% 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.

  • What is the cheapest time of day to fly to Caribbean Islands?

    The cheapest time of day to fly to Caribbean Islands is generally in the afternoon, when round-trip flights cost $485 on average. On average, there is no price difference when choosing to fly in the morning or the evening on this flight route. The most expensive time of day to fly to Caribbean Islands is generally in the evening, which is peak travel time and where the average cost of a ticket is $569.

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.
8.0
DeltaOverall score based on 7951 reviews
8.5Crew
7.3Food
7.9Comfort
8.2Boarding
7.9Entertainment
Airline reviews

My husband upgraded our seats and I don't know if it was due to the type of planet was or if they didn't upgrade our seats. We were supposed to be in I believe comfort seats and they were just as tight as any other seat- no leg room and we are very tall people but at least it wasn't extremely cold. My husband did put in a complaint about our seating because he paid extra and if we would have known that the space and the tightness would have been the same, we just would have gotten the emergency row emergency row seats that we normally get. We love Delta but both our flights coming home we're not good. Oh I forgot to mention that on our flight to Hawaii our luggage wheels got broke and we had to purse new luggage on vacation then we never had this problem so we didn't know protocol and reported it after we got home only for them to tell is we only had 24hrs to report the damage. Not sure what was going on with Delta this vacation trip.

4.0 OkayMrs., Jul 2025LAX - RDU
Read more Delta reviews

My husband upgraded our seats and I don't know if it was due to the type of planet was or if they didn't upgrade our seats. We were supposed to be in I believe comfort seats and they were just as tight as any other seat- no leg room and we are very tall people but at least it wasn't extremely cold. My husband did put in a complaint about our seating because he paid extra and if we would have known that the space and the tightness would have been the same, we just would have gotten the emergency row emergency row seats that we normally get. We love Delta but both our flights coming home we're not good. Oh I forgot to mention that on our flight to Hawaii our luggage wheels got broke and we had to purse new luggage on vacation then we never had this problem so we didn't know protocol and reported it after we got home only for them to tell is we only had 24hrs to report the damage. Not sure what was going on with Delta this vacation trip.

Crew was excellent. Comfort seats not as nice as other kinds of planes.

It was a great flight and the stewards and stewardess were all kind and accommodating!! The seats were comfortable and entertainment screen excellent!

There are 4 flights in consecutive gates with about the same departure time. Two flights were boarding at the same time. One was delayed or boarding would be happening at the same time. I am not sure what Delta and LAX need to do to have a better layout at the end of Terminal 2

There was a security issue at the airport and we were unable to land. We circled endlessly and then landed at another airfield for fuel. We then circled the airport again, almost landed but didn’t fully touch down before circling again. I am thankful to the crew for keeping us safe- the issue was the airline and staff at the airport getting us seats on our connecting flights. That part was hours of searching for someone and getting in double my steps.

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.

Excellent flight, the planes were newer, they did a nice job with boarding, great service overall.

It would be nice if was given wires ear buds. Overall was a good experience was able to sleep on the plane

737-800 in first class was pretty dumpy. Seat had an uncomfortable angle, storage under the seat was blocked so even my very modest backpack didn't fit, power outlet was flaky. Weird tiny seat pockets that couldn't hold a gallon ziploc bag, emesis bag missing, etc. etc. No in-flight service due to turbulence. Crew was excellent, boarding was smooth despite a full flight.

Delta flight was on time, seats were comfortable, and crew was nice.

Everything was great. Only thing that could’ve made it better was buy on board options for hot food, but the snacks were decent. The flight attendants were great. I had no complaints. I was able to make it to my destination safely

Boarded plane and then delayed 1.5 hours while on the plane

Horrific. They missed my connecting flight to San Diego. I didn’t get there until Monday at 9am when I had a mandatory court settlement conference scheduled at 6am since we had parties on the east coast. This caused many issues. All because United apparently forgot to hold the doors open until my flight landed that only had a 10 minute delay. This was the last flight to Southern California. So I couldn’t even rent a car to finish the trip. United cannot be trusted when traveling on specific days and times since weather didn’t have anything to do with the delays.

Really good 😊 the woman at the gate entrance was a little rude checking in our carry-on but i dont think she worked for the airline, she worked for the airport at sacramento, other than that amazing.

it was so bad. I tried to board my flight from vancouver to saskatoon. And to my surprise they did not board me cause the flight was changed and no email was send to me. and on my boarding pass which i got from seattle says different flight. I did not knew anyone from Vancouver, air canada crew was rude, i asked for today flight but they were rude and i had early morning dental appointment in saskatoon. I was so much in pain and my whole day is wasted today. and i suffered alot. They did provide me hotel but they did not provide me any food. I am really really disappointed first time had so bad experience with air canada. I may think twice to book it again. If i can get any reply or any composition that would be great. Thanks

Very comfortable (upgraded to business class). The audio on my screen didn’t work, but I managed to play the audio through my phone while watching the screen.

The food was the worst I’ve had on any flight I’ve ever been on.

I was supposed to be on business class at first class from Denver back to Miami due to weather changes. I missed my connection and it’s put on a flight to Fort Lauderdale. Instead of honoring my business class/1st class ticket, they put me in coach, but there were two first class seats open. I think it’s absolutely disgusting that I paid for first class $1300 ticket and they put me in economy and they had to open seats available and I have still not been refunded the difference. I ended up having to eat a snack box instead of the meal I was supposed to get and did not get home till 2 AM so I think that’s a little pathetic that I had to live off crackers for dinner And my poor dog ate some cheese and salami. Oh yes, apparently when they switched me to the new flight they forgot to mention I had a service dog

Flight was late as pilot crew had to land at different airport in their previous flight. Passengers boarded and had to wait for pilots inside plane. Series of incomplete and unnecessary announcements by an annoying voice, rather than complete, informative announcements.

Breakfast was not loaded at SFO due to catering company change. Seems like a major airline at a major hub would have thought of something else or warned passengers to pick up food before boarding a 3 hour flight.

I especially liked the lead crew officer. His boarding and safety announcements were made with a bit of novelty and humor. The flight also left the gate 10 minutes early and we landed about 20 minutes early… It was a delightful flight…

There were mutliple delays. There was inconsistent, delayed, and poor communication regarding the delays.

flight was delayed for hours with no explanation. The plane was a very old aircraft.

Spend hours delayed with no food, water anything sitting on the aieplane with no ability to eat or use the restroom. My entire experience was the absolute worst. I will never fly jet Blue again.

It would have been nice if they had offered more than one set of snacks

Seats were not too comfortable; it was impossible to locate the underseat power outlet.

You get what you pay for with JetBlue. Every little thing costs more, you are nickel and dimed until the end. Entertainment doesn’t function. Flight attendants do the bare minimum.

The check in and boarding process was a bit of a cluster. Two people at the counter to check in, three random lines that nobody knew which was for what, and people kept getting shuffled from one line to another for no apparent reason because then they’d get shuffled back and end up getting out further back in the line than they were originally. I only had to hand my already checked bag over and it took 45 minutes. I was never assigned a seat so when I tried to board I was pulled out of line again while someone had to try to manually assign me a seat. During the flight I got up to go to the bathroom, and there was an attendant in the aisle offering pillows etc and it was a 30 min wait unbuckled standing by the bathrooms because she said I couldn’t go past her. First and last time flying jet blue to be honest.

Communication since no reason or explanation was given for 3 hrs delay

The flight departed more than 1 hour late. Leg room is bigger than most airlines

AA re-routed flight from HNL to LAX due to delay. My group of 3 with reserved seats in row 9 was broken up, with one assigned to a middle seat, another in the last row of the plane. Not happy. No explanation to the delay. No apologies. No compensation. Would have been nice to be offered an Admiral Club admission or a voucher for the extra 3 hours of layover in LAX. Could not hear the boarding gate announcements in LAX. Adjacent gate was boarding at the same time. Loud speakers were competing against each other. Barely made my boarding group.

Almost a 6 hour flight and the only food option is a cheese plate… and chips. Also how is it there are no options for texting on American. I’ll be going back to delta and united.

Bad food, small seats that didn’t recline. I thought I was buying a quantas ticket so I feel like I got scammed

The chair cushions may need an upgrade. I have been noticing they are so worn out, thin so you’d sit in a dip 😄. Other than that, all was an enjoyable trip. Thanks AA!

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.

Eventless. It was a good flight and good crew. Can’t complaint.

Very helpful ground crew after an earlier flight delay and being rebooked on a different flight.

British Airways staff are very polite and willing to help.

The plane was late and then sat on the runway for almost 45 minutes before taking off.

It was okay delay was long but I made it

I have never flown Spirit it was much better than anticipated!

Staff was very friendly. They attended to people nicely and reprimanded, in a professional way, to those who wouldn’t listen. AC wasn’t working on the flight waiting to depart in Burbank, so it was uncomfortable for a while since the flight was delayed but then better before take off.

Good on that leg. When I arrived in Detroit I had to wait over an hour for luggage.

First off, i received an e-mail to allow me to check in for our flight. I folllowed the link, when it came to the seat selection, I was unable to select any "free" seats ( meaning without any additional charge) because everything was " unavailable". My Husband and I were ttavelling with our 3 children hence, i wanted to be assured that we were all seated next to each other. I tried 3 times and everytime I click the selection it said " error loading". What the system wants is for me to buy the seats ( anywhere from $25 to $50 dollars each passenger) like I did on our flight bound to L.A. I called customer service and the guy was unhelpful all he kept repeating was to come really early at the airport and we will be assigned seats there. Imagine my anxiety!!! Spirit says they are a budget airline but they are actually the opposite!! And just before our flight, the flight attendant KEPT announcing/ selling the seats that were not purchased for a cheaper price!! Like it was a bidding/ bargaining game! This was our first and last time to fly Spirit.

The crew was very nice. I would like to see them offer basic refreshments just like a soda and pretzels, etc. for free.

Good experience except for the drunk woman who was with a child. Sad

Too many time late and postponed No electrical power for my electric devices

Spirit is by far the worst airline to travel with, period. Seats are cardboard, flight attendants need anger management and if you ask for water, you’re basically a criminal. I don’t care how much it costs but I will travel with an airline who actually cares about their customers. Oh and one more thing, the next time your gate agent puts his foot on someone’s baggage's scale, I hope they get what’s coming next, a viral video of your scams. You suck Spirit, do better.

I mean, it’s Spirit. But it was frustrating to have our flight canceled, get bumped to a later flight, and then Spirit was unwilling to check our bag until 4 hours before our flight… tell us we could not sit in the waiting area’s chairs… and really negative experience getting checked in and dropping the bag.

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