$130 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 2/14. 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$387
Santo Domingo
Santo Domingo1 stop$415
Montego Bay
Montego Bay1 stop$450
Oranjestad
Oranjestad1 stop$491
Nassau
Nassau1 stop$373
Kingston
Kingston1 stop$502
Simpson Bay
Simpson Bay1 stop$395
Providenciales
Providenciales1 stop$460
Port of Spain
Port of Spain1 stop$440
Bridgetown
Bridgetown1 stop$501
George Town
George Town1 stop$430
Willemstad
Willemstad1 stop$513
St. John's
St. John's1 stop$783
Puerto Plata
Puerto Plata1 stop$582
Aguadilla
Aguadilla1 stop$389
Punta Cana
Punta Cana1 stop$387
Santo Domingo
Santo Domingo1 stop$415
Montego Bay
Montego Bay1 stop$450
Oranjestad
Oranjestad1 stop$491
Nassau
Nassau1 stop$373
Kingston
Kingston1 stop$502
Simpson Bay
Simpson Bay1 stop$395
Providenciales
Providenciales1 stop$460
Port of Spain
Port of Spain1 stop$440
Bridgetown
Bridgetown1 stop$501
George Town
George Town1 stop$430
Willemstad
Willemstad1 stop$513
St. John's
St. John's1 stop$783
Puerto Plata
Puerto Plata1 stop$582
Aguadilla
Aguadilla1 stop$389

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, May 4 - Fri, May 8
Delta Logo
9:45 pm - 11:50 am
SAN
-
SJU
11h 05m
1 stop
Delta Logo
1:10 pm - 11:43 pm
SJU
-
SAN
13h 33m
1 stop
$316Delta
Thu, Apr 2 - Wed, Apr 8
Multiple Airlines Logo
6:45 am - 11:07 am
SAN
-
SJU
25h 22m
1 stop
Multiple Airlines Logo
1:11 pm - 7:52 am
SJU
-
SAN
21h 41m
2 stops
$329Multiple Airlines
Thu, Apr 30 - Sat, May 9
JetBlue Logo
11:05 am - 2:39 am
SAN
-
SJU
12h 34m
1 stop
JetBlue Logo
11:20 pm - 9:15 am
SJU
-
SAN
12h 55m
1 stop
$330JetBlue
Sun, Apr 12 - Fri, Apr 17
United Airlines Logo
8:39 pm - 12:34 pm
SAN
-
SJU
12h 55m
2 stops
United Airlines Logo
1:40 pm - 10:30 pm
SJU
-
SAN
11h 50m
1 stop
$336United Airlines
Mon, Feb 9 - Fri, Feb 13
American Airlines Logo
10:25 pm - 9:57 am
SAN
-
NAS
8h 32m
1 stop
American Airlines Logo
4:36 pm - 10:59 pm
NAS
-
SAN
9h 23m
1 stop
$373American Airlines
Tue, May 19 - Tue, Jun 2
JetBlue Logo
8:30 pm - 2:42 pm
SAN
-
SDQ
15h 12m
1 stop
JetBlue Logo
8:50 am - 6:58 pm
SDQ
-
SAN
13h 08m
1 stop
$415JetBlue
Fri, May 15 - Wed, May 20
Southwest Logo
10:30 pm - 12:05 pm
SAN
-
NAS
10h 35m
1 stop
Southwest Logo
8:45 am - 7:35 pm
NAS
-
SAN
13h 50m
1 stop
$416Southwest
Mon, Feb 9 - Thu, Feb 12
United Airlines Logo
6:00 pm - 12:59 pm
SAN
-
PUJ
14h 59m
2 stops
United Airlines Logo
2:05 pm - 10:35 pm
PUJ
-
SAN
12h 30m
1 stop
$419United Airlines
Mon, Feb 9 - Fri, Feb 13
American Airlines Logo
4:47 pm - 10:53 am
SAN
-
NAS
15h 06m
2 stops
American Airlines Logo
4:36 pm - 10:59 pm
NAS
-
SAN
9h 23m
1 stop
$421American Airlines
Wed, Apr 29 - Thu, May 7
Southwest Logo
8:50 pm - 12:10 pm
SAN
-
GCM
13h 20m
2 stops
Southwest Logo
1:05 pm - 7:15 am
GCM
-
SAN
20h 10m
2 stops
$501Southwest
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 $431 (return) on average. On the other hand, the most expensive months are December and June, when the average cost of round-trip tickets is $688 and $584 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 4 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$132
Best time to beat the crowds with an average 25% drop 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
Alaska AirlinesOverall score based on 11792 reviews
7.8Comfort
8.1Boarding
7.1Food
8.5Crew
7.0Entertainment
Airline reviews

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.

4.0 OkayJerry, Jan 2026
SAN - ORD
Read more Alaska Airlines reviews

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.

Again, very smooth and all of the Alaska folks were great. They continue to meet all my needs.

The whole experience went smoothly with no hitches along the way.

My Alaska Airlines return flight, although worked out in the end, didn't start off well. The initial plane that my family and I boarded was grounded because of a mishap that happened to one of the engines and everyone on board had to disembark the plane. Thankfully we were accommodated with a another plane but our initial flight was supposed to have departed at 11 pm San Diego time for Orlando but instead we ended up leaving at 1:40 am San Diego time. All Passengers were informed that part of the delay was that the plane had to be inspected by the captain, the food had to be stocked and the individuals responsible for fueling the plane left for the evening and had to be summoned to return to fill up our. The Alaska Airlines crew at the airport and on the plane were awesome and apologetic. I know that the crew wasn't responsible for the mishap of the engine but I think in the future the airline should offer a complimentary drink or (1) item of food other than pretzels, nuts or chips to all passengers since we're not to blame for the extreme set backs. The airline in general is good and I recommend to all flyers.

Late leaving so threatened our connection in Vegas to Seattle. We did make up time and made our connection.

Dropping off of the checked bags took way longer than it should have. The agent for the pre-tagged and ready to drop off line was gone and didn't come back for about 15 minutes. The other bag check lines were barely moving. Agents were standing around and not much was getting done. Everything else about the flight was great.

Was late but $50 voucher was great benefit of the summit card.

See previous. It was the flight from Honolulu to Kapalua that was cancelled.

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.

Great flight but super high price. Glad it was a business trip and not personal

3 hour delay. Had to change plans and was still delayed.

We got exit row seats both flights. Everything was running on time

The boarding and seat assignment system no longer works for me, but I know it is being replaced. Otherwise, I am good with the overall experience.

The lead steward kept singing about "San Francisco" and hotel California---more annoying than humorous....needs work. Flight was smooth and on time.

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.

Delta’s staff is unmatched. From the gate agents, to the pilots, to the flight attendants… all top of the industry.

The flight was delayed for about 2 hrs. Other than it, it was good.

I am extremely disappointed that delta internal pilot manuals now refer to the Gulf of Mexico as the “gulf of America”. You can bow down to the Orange turd on your own. I will never fly delta again

No lunch on a x-country flight scheduled for 10:50 am departure, arrived 5+ hrs later. That requires a black box label before you pay for the tickets. Worst, when I checked in online, it's specifically said that lunch was served on his flight for economy Plus passengers.

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.

The food was terrible this time. Otherwise pleasant, quiet, on-time.

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

The flight crew where really good. Better then the crew from BNE to SFO

Food should be changed in menu Many muslims travels in this airlime they need to add one Halal meal

left on time, reasonable boarding process arrived early luggage came out quickly

Some flight attendants were great others were cranky. Seats were very tight and sitting on an aisle was very hard as the carts and people walking constantly bumped shoulder and arm.

It was great with United overall except for two things. 1) It was a 5-hour flight and we were with kids, so we were asking for extra snacks. They were extremely reticent to dole them out even though there wasn't any meal and the kids were starting to hit their limit towards the end. 2) Baggage didn't arrive until 80 minutes after we landed.

I’m so sorry, I can’t remember her name, I believe it was Dimpti. She was stellar, also a mature Asian flight attendant, lots of flowers in her hair, just as amazing! But literally the crew was AWESOME . Only downside is there weren’t any charging outlets. Maybe I needed to ask a flight attendant , but it would’ve been nice to have one easily accessible.

I boarded flight UA#1318 at Sacramento International Airport going back to Houston TX. The flight was scheduled at 5:10am. I was able to check in virtually using the United Airlines app. When I entered the airport, there was no one outside assisting with checked bags as it was for Delta Airlines. Immediately upon entering, there was a LONG, EXTREMELY LONG line to the kiosks to get boarding passes. I stand in line to get boarding passes then had to move to ANOTHER EXTREMELY LONG line to get my bags checked in. While standing in this line, we noticed an agent taking customers to 3 at a time to her station to check their bags in. Lucky for me, she called me back, checked my bags for me and I was on my way. I then encountered another long line at the TSA check and to avoid I ending up having to sign up for CLEAR to bypass it. So glad, I did.,...Both of my flights were great with no issues, butthe check in progress at Bush Airport was so much smoother. Check-in at SMF airport needs to be anaylzed and corrected. Do better United, I know you can....thanks

Pushed back only to get deplaned due to a tire damaged by ground crew. They did at least go pretty fast. The bathrooms should be banned under the Geneva convention. No room to even sit straight on the toilet. The under-seat entertainment units block what little leg room there is.

The entertainment options were at best, fair. It was exactly the same as my outbound flight. It would have been more entertaining if there were some series from Apple TV, HBO, Showtime or other carriers for me to catch up with.

The flight was on time and arrived early. The crew were friendly and helpful.

While I didn’t watch much tv I would have liked a few more options of TV series from Apple TV or hbo max ..

Overall experience was great. Flights were almost on time in departing and we arrived at our destination as scheduled. No issues with amenities or flight crew. Everything went well as as expected. Will fly again with American Airlines in the future!

The flight was very smooth and the meal in business class was great.

I requested a low sodium meal. Reason being, I take medicine for high blood pressure and I wear compression socks on long flights to help with leg swelling. Having less sodium in meals really helps me feel better on long flights. I received my initial low sodium meal after takeoff. Just before landing, the crew came through with the meal cart and offered me what was being served. I said no thank you and then noticed my low sodium meal in the meal cart, with my name and seat assignment on it. I motioned to the crew member, but he grabbed the meal cart and proceeded to move to the rear of the aircraft. He didn’t see me or other passengers who had attempted to get this attention. He was more concerned about completing meal service since we were due to land in under 45 minutes. I pressed the call light five times from my seat to receive help, but no crew member responded to me. So, I didn’t receive a second meal, one that I requested (the low sodium option). This led me to have a migraine from only eating one meal on an 11-hour flight. This is why I’m not a fan of flying US-based airlines overseas. The crew members continue to show the absolute worst customer service experience. I would not recommend flying American for overseas flights.

Not great. Booked Extra seats and got nothing extra at all. It’s basically a big budget airline.

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!

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports