$121 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 3/2. 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$419
Montego Bay
Montego Bay1 stop$425
Oranjestad
Oranjestad1 stop$509
Nassau
Nassau1 stop$402
Kingston
Kingston1 stop$546
Simpson Bay
Simpson Bay1 stop$395
Providenciales
Providenciales2 stops$456
Port of Spain
Port of Spain1 stop$350
Bridgetown
Bridgetown1 stop$429
George Town
George Town2 stops$390
Willemstad
Willemstad1 stop$525
St. John's
St. John's1 stop$745
Puerto Plata
Puerto Plata1 stop$544
Aguadilla
Aguadilla2 stops$316
Punta Cana
Punta Cana1 stop$387
Santo Domingo
Santo Domingo1 stop$419
Montego Bay
Montego Bay1 stop$425
Oranjestad
Oranjestad1 stop$509
Nassau
Nassau1 stop$402
Kingston
Kingston1 stop$546
Simpson Bay
Simpson Bay1 stop$395
Providenciales
Providenciales2 stops$456
Port of Spain
Port of Spain1 stop$350
Bridgetown
Bridgetown1 stop$429
George Town
George Town2 stops$390
Willemstad
Willemstad1 stop$525
St. John's
St. John's1 stop$745
Puerto Plata
Puerto Plata1 stop$544
Aguadilla
Aguadilla2 stops$316

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, Mar 3 - Wed, Mar 11
United Airlines Logo
5:55 pm - 12:00 pm
SAN
-
STT
14h 05m
2 stops
United Airlines Logo
12:02 pm - 11:40 pm
STT
-
SAN
14h 38m
2 stops
$246United Airlines
Tue, Mar 3 - Wed, Mar 11
American Airlines Logo
9:57 pm - 3:47 pm
SAN
-
STT
13h 50m
2 stops
American Airlines Logo
2:43 pm - 10:23 pm
STT
-
SAN
10h 40m
1 stop
$256American Airlines
Mon, Mar 23 - Tue, Mar 31
American Airlines Logo
10:43 pm - 3:40 pm
SAN
-
STT
13h 57m
1 stop
American Airlines Logo
3:40 pm - 8:39 am
STT
-
SAN
19h 59m
2 stops
$308American Airlines
Mon, Mar 23 - Mon, Mar 30
Delta Logo
10:30 pm - 2:45 pm
SAN
-
STT
13h 15m
1 stop
Delta Logo
3:00 pm - 11:09 pm
STT
-
SAN
11h 09m
1 stop
$310Delta
Tue, Mar 24 - Mon, Mar 30
Delta Logo
9:55 pm - 1:47 pm
SAN
-
STT
12h 52m
1 stop
Delta Logo
3:00 pm - 11:09 pm
STT
-
SAN
11h 09m
1 stop
$334Delta
Wed, Apr 29 - Thu, May 7
United Airlines Logo
7:40 pm - 3:43 pm
SAN
-
STT
17h 03m
2 stops
United Airlines Logo
1:22 pm - 8:04 pm
STT
-
SAN
9h 42m
1 stop
$336United Airlines
Sun, Apr 19 - Sat, Apr 25
JetBlue Logo
8:30 pm - 2:42 pm
SAN
-
SDQ
15h 12m
1 stop
JetBlue Logo
5:50 am - 8:04 pm
SDQ
-
SAN
17h 14m
1 stop
$429JetBlue
Mon, Apr 13 - Sat, Apr 25
JetBlue Logo
8:25 pm - 2:42 pm
SAN
-
SDQ
15h 17m
1 stop
JetBlue Logo
5:50 am - 8:04 pm
SDQ
-
SAN
17h 14m
1 stop
$439JetBlue
Wed, May 6 - Thu, May 14
Southwest Logo
10:40 pm - 2:55 pm
SAN
-
PLS
13h 15m
2 stops
Southwest Logo
3:50 pm - 8:30 am
PLS
-
SAN
19h 40m
2 stops
$456Southwest
Wed, May 6 - Thu, May 14
Southwest Logo
10:40 pm - 2:55 pm
SAN
-
PLS
13h 15m
2 stops
Southwest Logo
3:50 pm - 7:15 am
PLS
-
SAN
18h 25m
2 stops
$471Southwest
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 $420 (return) on average. On the other hand, the most expensive months are December and June, when the average cost of round-trip tickets is $697 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 3 weeks before departure, which saves you about 26% 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$121
Best time to beat the crowds with an average 25% drop in price.
Most popular time to fly with an average 3% increase in price.
Flight from San Diego to Saint Thomas Island

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 11874 reviews
7.0Entertainment
8.5Crew
7.1Food
7.8Comfort
8.1Boarding
Airline reviews

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.

10.0 ExcellentPhilip, Feb 2026
SAN - TPA
Read more Alaska Airlines reviews

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.

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!!

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.

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.

It was nt delta. It was aeromexo. Service was awful. They served a very small drink and NO snack for a 3hr and 35min flight. Then for the first 30 min of the flight is was talk and talk over head interruption the movie/ show i picked to watch.

Delta One is extraordinary. I fly business when somebody hires me. I just wonder why there is such a chasm between business class and the insanely inhumane and nonsensical coach. The seats are not large enough to fit even my tiny wife. We fly 10% of what we did because we don’t want to pay 5-10 k but for $400 it’s unbearable. It seems like the accountants took over and made stupid decisions. Screw in 20 extra seats and make it so unbearable that people fly 90% less. Just put the damn price up and put some proper chairs in. But business, yay.

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.

Check-in and in-flight staff were better than average. The seat was a fair size but too hard and not enough padding. The cushion/pillow provided is poor (thin and seems to be disposable ,it provides no effective cushioning or support). Food was OK-ish but no choice of inflight snacks and no easy place to get drinks other than water (I could ask for juice by intruding into the staff area at the back of the plane) Entertainment was very good actually. Overall better than I expected from a US-based airline (sorry!) but compared to ANA or Singapore it was so-so. (I live in Japan so they are my comparative airlines)

Terrible. Our first time back on United for 10 years, the seats in Polaris class are small and uncomfortable. They have squished too many people in to get more $$$. The staff are not friendly and not wanting to accommodate. I asked for two salads rather than a main meal and was advised no we wont do that. Then asked what I would like for breakfast and given something else anyway. I will not be flying United International anytime soon.

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.

Flight was delayed for 2 hours, then last minute the change to on time. The satélite location is far and a nightmare to get to.

We flew in first class. The crew did not offer drinks before the flight took off, but they treated us well during the flight. The food was excellent. There was actually too much food served, but it was nice to have all the options.

For a 5 1/2 hour flite i considered the "business class" to be subpar. The seats were just ok, no amenities, really nothing more than a long domestic flight. Frankly disappointed.

It would be nice to have some low carb options in the snacks.

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.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports