$137 Find Cheap Flights from Caribbean to San Diego - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to San Diego departing on 11/25. 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.
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Cheap Flights from Caribbean to San Diego

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Caribbean to San Diego 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 Caribbean to San Diego

Wed, Oct 21 - Sat, Oct 24
American Airlines Logo
2:54 pm - 11:33 pmSJU  San Juan Luis Munoz Marin Intl-SAN San Diego
11h 39m1 stop Chicago O'Hare Intl
American Airlines Logo
6:20 am - 10:57 pmSAN  San Diego-SJU San Juan Luis Munoz Marin Intl
13h 37m1 stop Philadelphia
$274American Airlines
Wed, Oct 21 - Sat, Oct 24
American Airlines Logo
2:18 pm - 11:38 pmSJU  San Juan Luis Munoz Marin Intl-SAN San Diego
12h 20m2 stops Miami Dallas/Fort Worth
American Airlines Logo
9:25 pm - 3:01 pmSAN  San Diego-SJU San Juan Luis Munoz Marin Intl
14h 36m1 stop Charlotte Douglas
$274American Airlines
Wed, Sep 2 - Mon, Sep 14
JetBlue Logo
12:56 pm - 7:35 pmSJU  San Juan Luis Munoz Marin Intl-SAN San Diego
9h 39m1 stop Atlanta Hartsfield-Jackson
JetBlue Logo
9:59 pm - 12:03 pmSAN  San Diego-SJU San Juan Luis Munoz Marin Intl
11h 04m1 stop New York John F Kennedy Intl
$307JetBlue
Wed, Sep 2 - Sat, Sep 5
JetBlue Logo
1:19 pm - 11:43 pmSJU  San Juan Luis Munoz Marin Intl-SAN San Diego
13h 24m1 stop New York John F Kennedy Intl
JetBlue Logo
10:25 pm - 11:46 amSAN  San Diego-SJU San Juan Luis Munoz Marin Intl
10h 21m1 stop Atlanta Hartsfield-Jackson
$340JetBlue
Wed, Sep 30 - Tue, Oct 6
United Airlines Logo
1:00 am - 11:35 amSJU  San Juan Luis Munoz Marin Intl-SAN San Diego
13h 35m2 stops Newark Los Angeles
United Airlines Logo
8:00 am - 8:38 pmSAN  San Diego-SJU San Juan Luis Munoz Marin Intl
9h 38m1 stop Houston George Bush Intcntl
$406United Airlines
Wed, Sep 30 - Tue, Oct 6
United Airlines Logo
1:00 am - 11:35 amSJU  San Juan Luis Munoz Marin Intl-SAN San Diego
13h 35m2 stops Newark Los Angeles
United Airlines Logo
6:15 am - 8:38 pmSAN  San Diego-SJU San Juan Luis Munoz Marin Intl
11h 23m2 stops Los Angeles Houston George Bush Intcntl
$406United Airlines
Thu, Feb 4 - Mon, Feb 22
Delta Logo
2:15 pm - 11:45 pmSJU  San Juan Luis Munoz Marin Intl-SAN San Diego
13h 30m1 stop New York John F Kennedy Intl
Delta Logo
10:30 pm - 2:05 pmSAN  San Diego-SJU San Juan Luis Munoz Marin Intl
11h 35m1 stop Detroit Metropolitan Wayne County
$406Delta
Fri, Oct 9 - Tue, Oct 13
Southwest Logo
6:00 am - 6:55 pmSJU  San Juan Luis Munoz Marin Intl-SAN San Diego
15h 55m1 stop Tampa
Southwest Logo
6:15 am - 11:05 pmSAN  San Diego-SJU San Juan Luis Munoz Marin Intl
13h 50m1 stop Baltimore/Washington
$406Southwest
Wed, Sep 2 - Wed, Sep 9
Southwest Logo
6:00 am - 4:15 pmSJU  San Juan Luis Munoz Marin Intl-SAN San Diego
13h 15m1 stop Baltimore/Washington
Southwest Logo
9:15 am - 10:05 pmSAN  San Diego-SJU San Juan Luis Munoz Marin Intl
9h 50m1 stop Orlando
$434Southwest
Thu, Sep 10 - Mon, Sep 14
Delta Logo
1:55 pm - 11:34 pmAUA  Oranjestad Reina Beatrix-SAN San Diego
12h 39m1 stop New York John F Kennedy Intl
Delta Logo
9:59 pm - 12:40 pmSAN  San Diego-AUA Oranjestad Reina Beatrix
11h 41m1 stop New York John F Kennedy Intl
$634Delta
Useful Info

Good to know

Low season

January

Cheapest flight

$137
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly with an average 14% increase in price.
Flight from San Juan to San Diego

FAQs for booking flights from Caribbean to San Diego

  • How does KAYAK find such low prices on flights from Caribbean to San Diego?

    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 Caribbean to San Diego.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Caribbean to San Diego?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to San Diego from 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 Caribbean to San Diego?

    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 to San Diego with an airline and back to Caribbean with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Caribbean to San Diego?

    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 to San Diego from 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 Caribbean to San Diego

 
Need help choosing which airline to fly with from Caribbean to San Diego? 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 4218 reviews
7.0Food
8.1Boarding
8.0Comfort
7.5Entertainment
8.6Crew
Airline reviews

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

2.0 MediocreAnonymous, Jan 2026
Read more Southwest reviews

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

The flight crew was extremely rude and especially not helpful when our flight was delayed.

Delays delays delays. Late taking off, late landing, wait for a gate, etc.

First time traveling on Southwest since bag fees were implemented. Usual good service. Just more expensive now.

Plane late from DC to Austin 30 minutes. Crew made up much of the time enroute to San Diego.

Our first flight was so delayed that we had 10 mins to board the next one. We requested if the flight attendant could allow us off there plane first and they denied our request even though I have seen this done before. Luck was on our side that we didn’t miss our next flight.

Everything was great except for the in-flight wifi that wasn't working.

It was great! The new boeing has much more space and charging ports!

Took a little longer than normal, but the process is clear and easy to understand.

Baggage check in would have been better if the service clerk told the other clerk that she was merging her two long lines of customers with her line so she could move luggage. Instead she only told the customers. When I told the agent and ask if she could direct who is next in line so we weren’t trying to cut in front of each other she said it’s not her problem and she can’t work three lines. I was shocked. Understood that they were working more than their share but some organization so the customers aren’t getting upset at each other would have gone a long way

Both of my flights to and from JFK experienced significant delays. Most notably, my first flight was delayed by six hours due to crew members being affected by delays on a previous flight. While I understand that disruptions can occur, Delta’s staffing and operational planning should include sufficient contingency measures to handle situations like this rather than placing the full burden of those delays on customers. Additionally, the $12 meal voucher offered as compensation was inadequate, particularly given the high cost of food and beverages at the airport. Considering the length of the delay and the substantial inconvenience caused, I believe more meaningful compensation would have been appropriate.

Crew was real good, flight was smooth and came in early.

Gate agent rushed to fill hot jetway with crowd so it took over 12 minutes to go from gate to plane. Just like a discount airline Pooly prepared cabin and third time that claim of rough air prevented any cabin service. Friends on a Southwest flight at similar time had service.

Not a "Delta" issue, but a JFK issue: We booked a connecting flight with 3 1/2 hours between to clearn immigration and customs. Our inbound flight (BCN to JFK) was on the taxiway 45 minutes which ate into our layover time. Immigtration was insanely quick with the CBP MPC app; however, clearing TSA (again, after we were ALREADY cleared in Spain on the inbound international flight) took over 95 minutes. This left us with 10 minutes before boarding the connecting flight (JFK to SAN) to walk to the far end of Terminal 4 and try to find food. We didn't find any food that could promise to serve us in under 10 minutes so we boarded the Delta flight after coming off a plance and an 8-hour flight knowing that we wouldn't be served any food on the next 5 1/2 hour flight. I feel like Delta needs to put pressure on the JFK TSA to open more screening stations (by our count, we saw only 5 scanners open and a line of - as we said - over 90 minutes. The insult is that we WERE ALREADY SCREENED through TSA, but as you come off one flight into the USA, you have to go through the whole process again. It seems like if you have a connecting flight, there should be a way to pass through immigration and customs without needing to return through TSA.

Rough day of travel all the way around. Wrong info given to us multiple times and mistakes in their booking making our trip 10 hours longer than planned. I’m bummed because I fly Delta all the time and love them. Mistakes happen. Just bummed that this was a rare trip our whole family was traveling together.

It was good until there was a 3 hour delay because there was not any pilots to fly the plane.

Everything was very good other than I had selected a specific seat when I booked the flight and they changed it once I checked-in the day before my flight. I was still in first class but lost my aisle seat for a window seat. Being tall, the aisle offers more comfort so I always select an aisle seat.

Flight diverted in SD. Later take off in Seattle by 1.3hrs

Was a great smooth flight from Detroit to San Diego.

The boarding process was terrible especially with an indirect flight Chicago to Seattle to San Diego was terrible talking about we overbooked a flight idk if I’d take this airline ever again we got off our flight from Chicago to Seattle and we traveled for business and they told us our connecting flight was over booked and their was no seats asking people to take a delayed next flight and they don’t tell anyone coughing to wear masks seats 30A-B were terrible during the flight no one wants to sit next to people coughing all around I don’t want to be sick traveling for work or get sick anytime it’s very upsetting the staff doesn’t take this stuff serious to tell them to wear masks when they see people coughing and sneezing

the seat has a problem. the back had a hole.

Old 757 with poor entertainment system. United no longer partners with United for free text and email. O'Hara an absolute disaster! Limited gates clauses two hour delay. Unfortunately this appears to be the norm.

Delayed 2 hours while stuck on the aircraft. If the luggage was properly loaded the first time we probably wouldn’t have been delayed at all

UA594 was delayed multiple times. I ended up getting picked up so I can make it in time for work 6AM on Monday, 7/6/2026

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.

Was a pain having to leave the plane and reboard but glad the plane was fixed

Connecting flights were poor,especially in Naples.our Lufthansa air bus was a joke.way too small for that long of a flight.no room at all.couldn’t even get out of the seats to move around or go to the bathrooms.we thought we were getting an actual air bus,double decker.i will never fly that long in a plane like that again.kind of misleading to call it an air bus.we actually had more room on our buses that we used.

For a 22 minute flight all you expect is for it to be safe and comfortable

Lost connnection had to stayON in Chicago Was a mess

Booked economy through United - air canada treated it as standby and was almost refused boarding.

Awful! We boarded and then sat on the plane for 50 mins before having to deplane due to a maintenance issue which should have been addressed before boarding. Then we had to change terminals as there was no other plane for us at the current terminal. Then we waited another 2 and a half hours to board again only to wait for 50 mins on the plane again for the snacks to be brought from the broken plane. And once we were on the flight we still only got the complimentary cookie and soda or water. No food vouchers provided even though we had waited over 3 hours for our flight.

The seat when "flat" was not flat and pad was too thin to cover it.

Delayed for mechanical and no updates on what was happening and how long the delay might be.

We are too tired and frustrated to comment politely at this point

My flight was delayed for several hours. Sitting at gate 16 for several hours, I got a text from Kayak the gate changed to 9 before it was announced. Very bad communication at each gate from American Airlines employees. I received 10 notifications of delay from Kayak. My vacation started off horrible! I will write to American Airlines corporate office also.

The service and food needs to improve to catch up with other international flights

The flight crew was fantastic! Which the seats had a small TV.

also wi-fi never worked attendant said satellite coverage is spotty over water ..... but we were over land!

They attended to my needs as I couldn't walk and they provided a wheelchair for me.q

This time my flight was smooth and uneventful. They started boarding even earlier than it was scheduled. I was pleasantly surprised. Thank you!

A more comfortable seat. Padding would be really helpful but I've read the airlines don't want customers to be satisfied with economy seats.

Everything was good except checking bags . I had paid for two bags but it didn’t show so we had to do it again while people waited and we were struggling to get to our flight

Flight delayed 4 times on a non-stop from BOS to SFO. Then when landed in SFO had to wait for 30 mins for a gate AT 3:30AM.

The security line at JFK was one of the longest I’ve ever experienced - probably 45 minutes. I don’t know if JetBlue has control over it, but it detracted from the overall experience. Entertainment had good options, but the volume control was a bit small to tap on and the screen had a fair amount of interference blips. Clearer picture would have been better.

Whole experience was poor. Delayed 2 hours. Lied about the delays. Was all jet blues fault and tried to blame on air traffic control. Sent out other let trips and wouldn't allow people to switch aircraft.

It was fine for what it was. It’s not luxury travel but it was efficient, for the most part. Having my carry-on transferred into luggage however, was unwelcome.

Great price, easy check in, love the free drinks and snacks, and nice crew. The only negative part was waiting for your seat assignment 5 minutes before boarding, and the seats are a bit uncomfortable.

It took an hour to get my bag after landing. Not exaggerating

Everything was good instead change the gates! I missed my first flight because it was changed the gate and I didn’t know!

almost 4 hour delay as they over booked and had to wait for 8-10 volunteers to agree to travel next day.

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