$124 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 1/10. 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$360
Santo Domingo
Santo Domingo1 stop$430
Montego Bay
Montego Bay1 stop$452
Oranjestad
Oranjestad1 stop$498
Nassau
Nassau1 stop$363
Kingston
Kingston1 stop$628
Simpson Bay
Simpson Bay1 stop$451
Providenciales
Providenciales1 stop$561
Port of Spain
Port of Spain1 stop$349
Bridgetown
Bridgetown1 stop$431
George Town
George Town2 stops$496
Willemstad
Willemstad1 stop$514
St. John's
St. John's1 stop$583
Puerto Plata
Puerto Plata2 stops$557
Aguadilla
Aguadilla2 stops$385
Punta Cana
Punta Cana1 stop$360
Santo Domingo
Santo Domingo1 stop$430
Montego Bay
Montego Bay1 stop$452
Oranjestad
Oranjestad1 stop$498
Nassau
Nassau1 stop$363
Kingston
Kingston1 stop$628
Simpson Bay
Simpson Bay1 stop$451
Providenciales
Providenciales1 stop$561
Port of Spain
Port of Spain1 stop$349
Bridgetown
Bridgetown1 stop$431
George Town
George Town2 stops$496
Willemstad
Willemstad1 stop$514
St. John's
St. John's1 stop$583
Puerto Plata
Puerto Plata2 stops$557
Aguadilla
Aguadilla2 stops$385

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

Tue, Jan 27 - Sat, Jan 31
American Airlines Logo
10:45 pm - 1:08 pmSAN-SJU
10h 23m1 stop
American Airlines Logo
7:07 am - 10:50 pmSJU-SAN
19h 43m1 stop
$328American Airlines
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Thu, Jan 1 - Sun, Jan 11
Frontier Logo
4:47 pm - 7:56 pmSAN-SJU
23h 09m2 stops
Frontier Logo
2:29 am - 7:37 pmSJU-SAN
21h 08m2 stops
$330Frontier
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Thu, Feb 26 - Mon, Mar 2
JetBlue Logo
12:40 pm - 2:47 amSAN-SJU
10h 07m1 stop
JetBlue Logo
6:10 am - 2:23 pmSJU-SAN
12h 13m1 stop
$336JetBlue
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Fri, Jan 23 - Sun, Feb 1
JetBlue Logo
9:00 pm - 2:56 pmSAN-SJU
13h 56m1 stop
JetBlue Logo
6:05 am - 2:18 pmSJU-SAN
12h 13m1 stop
$343JetBlue
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Mon, May 4 - Fri, May 8
Southwest Logo
9:35 pm - 10:35 amSAN-SJU
10h 00m2 stops
Southwest Logo
6:50 am - 3:50 pmSJU-SAN
12h 00m2 stops
$344Southwest
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Sun, Apr 19 - Thu, Apr 30
Delta Logo
9:40 pm - 1:46 pmSAN-NAS
13h 06m1 stop
Delta Logo
1:05 pm - 8:48 pmNAS-SAN
10h 43m1 stop
$365Delta
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Mon, Apr 20 - Fri, May 1
Delta Logo
9:40 pm - 1:23 pmSAN-NAS
12h 43m2 stops
Delta Logo
1:05 pm - 11:43 pmNAS-SAN
13h 38m1 stop
$369Delta
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Fri, Jan 9 - Fri, Jan 16
United Airlines Logo
7:52 pm - 1:33 pmSAN-NAS
14h 41m2 stops
United Airlines Logo
12:55 pm - 9:28 pmNAS-SAN
11h 33m1 stop
$385United Airlines
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Sun, Jan 11 - Sun, Jan 18
United Airlines Logo
6:55 pm - 11:53 amSAN-NAS
13h 58m2 stops
United Airlines Logo
4:25 pm - 9:20 amNAS-SAN
19h 55m2 stops
$389United Airlines
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Fri, Jan 2 - Wed, Jan 7
Southwest Logo
8:50 pm - 2:25 pmSAN-PLS
14h 35m2 stops
Southwest Logo
2:40 pm - 9:25 amPLS-SAN
21h 45m2 stops
$617Southwest
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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 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 $441 (return) on average. On the other hand, the most expensive months are December and June, when the average cost of round-trip tickets is $684 and $585 respectively.

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

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

Your flight ticket price will generally be cheaper if you fly to Caribbean on a Saturday and more expensive on a Sunday. On your return trip to San Diego, you should consider flying back on a Thursday, and avoid Mondays for better deals.

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 3 weeks before departure, which saves you about 22% 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$124
Best time to beat the crowds with an average 25% drop in price.
Most popular time to fly with an average 46% 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.

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

    The cheapest time of day to fly to Caribbean 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 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

 
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
Alaska AirlinesOverall score based on 11373 reviews
7.8Comfort
8.5Crew
8.1Boarding
7.0Entertainment
7.1Food
Airline reviews

I truly appreciated the kindness and attentiveness of the staff and flight attendants. They did their best to be prompt with departure times to San Diego and back to New York! Alaska Airlines ... you are awesome!!

10.0 ExcellentAnonymous, Nov 2025SAN - JFK
Read more Alaska Airlines reviews

I truly appreciated the kindness and attentiveness of the staff and flight attendants. They did their best to be prompt with departure times to San Diego and back to New York! Alaska Airlines ... you are awesome!!

I've never flied them before but liked them. Weather was bad so a little scarey but they did a great job landing.

I recently traveled with my service animal, and before boarding, a gate agent kindly arranged for me to have an empty seat next to me to give my dog more space. However, once on board, a male crew member spoke to me in a rude and loud tone, insisting my dog stay on the floor or my lap—even after I explained what the gate agent had approved. His tone and behavior were unprofessional and made me feel uncomfortable in front of other passengers. I understand and respect airline policies, but I would appreciate if this could be reviewed to ensure better awareness and sensitivity toward passengers traveling with service animals. Thank you for your understanding.

Check in online didn't accept my confirmation number so i could only check in with assistance at the airport and ended up with s creepy middle seat.

It was the most expensive Alaska Airlines ticket I’ve ever purchased. I had a middle seat with no legroom or space compared to any other middle seat I’ve hadThere was a silver box under the seat that took up 70% of my legroom on the most narrow 737 max the crew flat out would not help they would not help with bags they would not help with garbage there was no coffee,It was definitely not one of my better experiences on Alaska.

Sitting on the ground for 2 hours waiting for a gate wasn't fun.

It was a great experience, friendly staff and good snacks

Very mediocre, and disappointing for the price of the ticket

My flight wait is 3 hours delayed due to Unknown reason. We waited a very long time in the tarmac. Our flight 24 was scheduled @ 7, therefore we left my house at 330 to park our car. We were at the gate @ 530, then we were told at 6a that it will be late , we boarded at 930 but did not take off until 1015. Therefore my arranged pick up in JFK was cancelled because of no show. Before all these I got an email offers of changing my flight to a different date which I took a day earlier. I will never again take Alaska Airlines, very Inefficient and Disappointing.

Such great crew, from checkin to the plane. So friendly and helpful, I was genuinely impressed.

San Diego airport is brand new, spacious, airy and very smooth checkin at SW baggage drop.

Crew could have been friendlier, maybe I'm spoiled by SW crews. In flight wifi was good. Would be nice to have more food offerings on a 4 plus hour flight

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

Sacrament staff are always polite and helpful. Airport is easy to maneuver and boarding is straightforward.

As always, the entire Southwest experience was wonderful, from online booking to flight to baggage retrieval. Very grateful.

The weather could have been better. There was a 40 minute ATC delay in SFO because of marine fog and a micro cell storm delayed landing and take-off at Nashville. The gate was changed 5 minutes from boarding from gate B3 to gate C23 at Nashville airport.

The cabin was quiet for the redeye flight. The area was clean. The staff was great. The 787 Max was in good condition. Drawbacks were that the seat widths were tight for some passengers. The seat padding was at best average and for a long flight uncomfortable.

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

No trays in our seats, we sat in first row, purchased a business class fare. Had to hold our drinks and snack in our hands. No plugs for our cell phones. Had to pay for it a drink cocktail each. Seats so uncomfortable.

Flight wasn’t even full, but too many carry-ons caused us to run out of bin space. New bag fee has folks who would usually check their bags carrying on. Watching Southwest morph into Spirit/Frontier is so sad to watch

Our flight from SFO to MSP was right on time on 11/15/2025. No delays. As we approached MSP at about 8 pm, we circled in the air until 8:40 pm so I don't call that efficient for MSP. I think the captain should announce the delay and why. (as if we all don't know that we are just circling around the area, slowing down, speeding up, slowing down.) Thank you. Marilyn Fischer

Staff were friendly and happy. Delta could make sure passengers that don't have the app know of changes. Without Kayak I would not have known about the change of gate or the delay. Kayak was faster to notify me.

The flight used a B767 with a very old interior from before 2014. The entertainment system did not work at all during the flight despite attempts to reset the system. It was like they flew this route just to be competitive.

Delayed flight (1hour) plus a long layover after an overnight flight with no backup plane available.

Flight delayed for two and half hours and then canceled altogether due to mechanical issues. No mechanic onsite to fix so had to send one from LAX.

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.

from SFO-> FRA flight, AVML meal was significantly less compared to regular meal, especially no Desert, no Bread, no sides.

This was an older airplane. The cabin was constantly warm to hot throughout the 10 hour flight and there were no vents to personalize air flow. Also since it was an older plane, the material and comfort of the chairs were very uncomfortable. I left my flight with major soreness on my tailbone.

Older aircraft, no meal, only food was for purchase. Not impressed United.

Not pleasant trip cross country when the entertainment and WiFi system not working. No entertainment for entirety of route. Staff was rather nonchalant in that they dismissed the problem due to age of plane. It would have been nice to know this up front so I could have come prepared to read or download movies before boarding Coincidentally or not, there was a similar issue with the entertainment system on my previous flight I took on my fist leg of the trip. There are no seat TVs, so you must rely on the app when it works. United can do better. Also, what use it it to pay for boarding group 2 when half of the passengers are in the same line as you?

My experience on this United Airlines flight was highly uncomfortable, primarily due to two issues: Cabin Temperature: The temperature on the Boeing 737 MAX 8 was unacceptably high, feeling consistently around 80 degrees throughout the flight. This made sleeping impossible and significantly detracted from the experience. Seating Arrangement: Being stuck in a middle seat for a six-and-a-half-hour overnight flight compounded the discomfort. Moving forward, I will always purchase a seat assignment to avoid this situation.

Premium Plus is a really good idea for longer flights

Same as last comment. Food sucks. Quality. Not surprising most people have no clue about nourishment Clearly

The flight attendants were great, I joked with one I can’t remember her name, a blond, really sweet. I thought it was run well very professional. This was great i survived Spirit, I know for which I speak.

We were in business class. the angled seats in that class do not have a real window view & the placement of the controls are bad. But we knew that. But the food options were mediocre. The taste was fine, but the size was for a child. It’s just really feels like United is skimping on everything. Even when we were in the Polaris lounge they did not have diet sodas. They said they were out no Coke zero no Diet Coke, etc. I do not think the portion of nuts they serve on the plane could get any smaller. Really a minimal service and offer for what you’re paying for in business.

I was in first class. The outlets at my seat did not work. The plane was shabby and run down. I had prepurchsed a day subscription for internet that was not redeemable. I had to repurchase the internet for my flight and then it didn’t work anyway. Quite disappointed in what was supposed to be the launch of a great vacation.

Horrible. Both legs of my flight were delayed more than 6 hours. No compensation, no screens on the plane, and the plane was not clean.

The flight was smooth, the pilot kept us informed about delays and we arrived more of less on time

The flight was flawless and we even arrived between 20 and 25 minutes early!

Always seated jammed in rear of aircraft Admirals Club food at DFW terminal D was absolute worst food experience and I pay $600/year to eat this dried out junk

Mostly good. Flight was crowded but Airline personnel were very friendly & accommodating. It would be good to have savory snacks rather than just sweet Biscoff cookies.

It was a red eye flight, so no meals were provided, but it was fine with snacks. The seats felt cramped and almost too narrow.

Very crowded flight but what can you expect these days?? Crew was accommodating.

The seats in economy were appeared to be quite thin and lack sufficient cushioning to be comfortable. Perhaps it was my seating position but the plane seemed notably load.

The entertainment package was vast and the selections were very current. Keep updating it was great.

The seat was so hard my tailbone was aching The crew was kind of a b**** because I made a joke that I didn't care if they close the door I total c*** when she was trying to f****** act like she was mad at me because I said that The flight was bumpy. Sure you didnt have control over that.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports