$100 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 4/17. 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$361
Santo Domingo
Santo Domingo1 stop$429
Montego Bay
Montego Bay1 stop$352
Oranjestad
Oranjestad1 stop$541
Nassau
Nassau1 stop$401
Kingston
Kingston2 stops$509
Simpson Bay
Simpson Bay1 stop$415
Providenciales
Providenciales1 stop$436
Port of Spain
Port of Spain1 stop$440
Bridgetown
Bridgetown1 stop$442
George Town
George Town1 stop$398
Willemstad
Willemstad1 stop$566
St. John's
St. John's1 stop$750
Puerto Plata
Puerto Plata1 stop$544
Aguadilla
Aguadilla2 stops$393
Punta Cana
Punta Cana1 stop$361
Santo Domingo
Santo Domingo1 stop$429
Montego Bay
Montego Bay1 stop$352
Oranjestad
Oranjestad1 stop$541
Nassau
Nassau1 stop$401
Kingston
Kingston2 stops$509
Simpson Bay
Simpson Bay1 stop$415
Providenciales
Providenciales1 stop$436
Port of Spain
Port of Spain1 stop$440
Bridgetown
Bridgetown1 stop$442
George Town
George Town1 stop$398
Willemstad
Willemstad1 stop$566
St. John's
St. John's1 stop$750
Puerto Plata
Puerto Plata1 stop$544
Aguadilla
Aguadilla2 stops$393

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

Wed, Apr 29 - Wed, May 6
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
$204United Airlines
Wed, Apr 29 - Thu, May 7
United Airlines Logo
6:22 pm - 1:08 pm
SAN
-
STT
15h 46m
2 stops
United Airlines Logo
1:22 pm - 11:59 pm
STT
-
SAN
13h 37m
2 stops
$233United Airlines
Mon, Apr 27 - Fri, May 8
American Airlines Logo
7:20 pm - 4:15 pm
SAN
-
STT
17h 55m
2 stops
American Airlines Logo
2:05 pm - 8:15 am
STT
-
SAN
21h 10m
2 stops
$264American Airlines
Wed, Apr 29 - Thu, May 7
American Airlines Logo
7:20 pm - 10:47 am
SAN
-
STT
12h 27m
2 stops
American Airlines Logo
5:05 pm - 11:16 am
STT
-
SAN
21h 11m
1 stop
$265American Airlines
Wed, Apr 8 - Wed, Apr 15
Southwest Logo
6:20 am - 10:40 pm
SAN
-
SJU
13h 20m
1 stop
Southwest Logo
11:25 am - 9:30 pm
SJU
-
SAN
13h 05m
2 stops
$362Southwest
Tue, May 5 - Tue, May 12
Delta Logo
6:51 pm - 12:03 pm
SAN
-
NAS
14h 12m
2 stops
Delta Logo
1:20 pm - 11:42 pm
NAS
-
SAN
13h 22m
1 stop
$410Delta
Tue, Apr 14 - Tue, Apr 21
Southwest Logo
10:10 pm - 1:15 pm
SAN
-
NAS
12h 05m
1 stop
Southwest Logo
8:45 am - 7:35 pm
NAS
-
SAN
13h 50m
1 stop
$416Southwest
Wed, Apr 8 - Wed, Apr 15
Delta Logo
6:15 am - 4:45 pm
SAN
-
NAS
7h 30m
1 stop
Delta Logo
3:28 pm - 11:25 pm
NAS
-
SAN
10h 57m
1 stop
$426Delta
Tue, Apr 28 - Fri, May 1
JetBlue Logo
8:35 pm - 2:50 pm
SAN
-
SDQ
15h 15m
1 stop
JetBlue Logo
5:50 am - 8:04 pm
SDQ
-
SAN
17h 14m
1 stop
$461JetBlue
Fri, May 1 - Sat, May 9
JetBlue Logo
9:15 pm - 12:34 pm
SAN
-
SXM
12h 19m
1 stop
JetBlue Logo
4:40 pm - 9:53 am
SXM
-
SAN
20h 13m
1 stop
$467JetBlue
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 $419 (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 4 weeks before departure, which saves you about 25% 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$100
Best time to beat the crowds with an average 24% drop in price.
Most popular time to fly with an average 4% 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 11978 reviews
8.5Crew
7.1Food
8.1Boarding
7.0Entertainment
7.8Comfort
Airline reviews

Good as usual. Just wished my seat was assigned at online check in. Thanks anyways

8.0 ExcellentAnonymous, Mar 2026
SAN - MRY
Read more Alaska Airlines reviews

Good as usual. Just wished my seat was assigned at online check in. Thanks anyways

This was my first trip with Alaska Airlines (round trip DCA to San Diego). Despite a slight delay on the return flight, I feel compelled to post a RAVE review! I cannot praise the airline and the crew enough! Everyone was kind, professional, and courteous, every step of the way- excellent service, snacks, and entertainment! On both legs of the trip I inquired whether there were any free seating upgrades and my request were granted BOTH times! I’ve flown on other airlines where they won’t do that, even when those premium seats are empty. As a customer service professional myself, I can say I left my experience feeling like a valued customer and not just a number. I NEVER expected to praise an airline lol I’ll definitely go out of my way to fly with Alaska on future trips. Thank you for such an awesome experience!

I bought tickets MONTHS ago for a flight that left SAN at 14:30. That is what it says on our tickets. I was never notified of any time changes. During online check-in. I discovered the flight time had been changed to 15:45. This was unacceptable and had I been notified, I would have changed flights, or airlines. That departure time was unworkable with our plans. We called Alaska and asked for an explanation. They said flight time was changed 11/08/25. No proof of notification could be offered. We asked to be moved to an earlier flight. After much pleading, the rep said she would allow a “one time exception..” While I appreciate being moved, this was YOUR fault Alaska Airlines.

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.

The Southwest experience has definitely taken a dive from its early days. You can no longer deferentiate from other airlines. Air travel is too expensive. Southwest is no longer budget friendly. They have lost me as a loyal customer.

The charges were ridiculous for an hour flight and the turbulence was very scary.

The seats are now more narrow. I paid for front row the seats in the front are even more narrow than before.

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.

Flight was delayed by 3-hours and their fix was… complimentary pretzels.

The crew, and fellow passengers, were super gracious and kind. There seemed to be plenty of bin space even though the plane was full. It’s nice to get a glass of wine with dinner in Premiere seating, and there was a lot of food.

Everything I mentioned earlier - the airbus was more comfortable indeed and the experience was further enhanced.

The plane was an older model, so it wasn’t as comfortable as others. The flight attendants were not helpful during onboarding. It was a full flight so there was chaos finding space for baggage.

Awesome! On time flight, early arrival, and a complimentary upgrade!

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

Staff were good. My seat was in need of repair, but for a short flight was not problematic. Usual basic snack and drink setup that you'll find on any US carrier. Over, a decent, basic flight.

Complimentary light meal would be appreciated. But great flight crew service on all legs

Flight delayed for more than 16 hrs and no effort was spent to provide an alternate

We had turbulence ever 1/2 hr or so and the captains announcements were SOOOO LOUD

Women boarding passengers at the gate was absolutely rude and disrespectful of passengers. The flight attendant was absolutely delightful! Smiling and connected with the passengers. So happy. The seats are cramped and uncomfortable but I guess that’s just the way it is Communication regarding flight was excellent

it was a very short flight so my expectations were low.

Entertainment kept turning itself off. Gave up on watching a movie.

Very disappointing given gate agent behavior. Filed a formal complaint with United.

Crew was great (professional, attentive, prompt). Snacks for 4 hrs flight is deplorable.

Flight delayed. WiFi connectivity very poor if not existant. Last minute arrival forced me to run to catch my connection.

My seat was assigned last row behind restrooms No legroom’s I’m very Pettit Still was not comfortable Food choice was excellent

The worst Airline ever. They centered my second flight and leave me in NY. They don’t have any representatives at the airport and they don’t respond to calls. Basically I got stuck. I will never purchase through there again.

The chicken wrap was tiny ($13 for what looked like a 1/3 of a normal wrap?) and disgusting.

Mediocre would be best description. Food bland. Seat biz class uncomfortable to sleep. Crew never dimmed lights completely in an overnight flight to Europe. Would avoid AA if possible.

Small plane, poor meal choices for first class, bad terminal and boarding experience at LAX

Massimo, flight attendant was very authentic, attentive - wonderful. Food/wrap was just okay.

Experience was great. The best part is the free Wi-Fi connection which helps me to work on the flight

The flight was fine. It's the satellite terminal that supports American eagle flights is what sucks. There is only one food option and everything there is way overpriced. I mean I know it's airport pricing, but it's even crazier than that. I bought a sandwich in a plastic container for $18.

The flight was really crowded. Flight attendants were just ok.

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.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports