$156 Find Cheap Flights from San Diego to Caribbean Islands

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 Islands departing on 6/15. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Caribbean Islands

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from San Diego to Caribbean Islands.
These are the airlines KAYAK users have selected most often from within our search results in flight searches from San Diego to Caribbean Islands.
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Flight Deals

Cheap Flights from San Diego to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$520
Santo Domingo
Santo Domingo1 stop$502
Montego Bay
Montego Bay1 stop$412
Oranjestad
Oranjestad1 stop$611
Nassau
Nassau1 stop$498
Kingston
Kingston1 stop$564
Simpson Bay
Simpson Bay1 stop$475
Providenciales
Providenciales1 stop$681
Port of Spain
Port of Spain3 stops$650
Bridgetown
Bridgetown1 stop$568
George Town
George Town1 stop$489
Willemstad
Willemstad1 stop$430
Aguadilla
Aguadilla2 stops$486
Puerto Plata
Puerto Plata1 stop$662
St. John's
St. John's1 stop$776
Punta Cana
Punta Cana1 stop$520
Santo Domingo
Santo Domingo1 stop$502
Montego Bay
Montego Bay1 stop$412
Oranjestad
Oranjestad1 stop$611
Nassau
Nassau1 stop$498
Kingston
Kingston1 stop$564
Simpson Bay
Simpson Bay1 stop$475
Providenciales
Providenciales1 stop$681
Port of Spain
Port of Spain3 stops$650
Bridgetown
Bridgetown1 stop$568
George Town
George Town1 stop$489
Willemstad
Willemstad1 stop$430
Aguadilla
Aguadilla2 stops$486
Puerto Plata
Puerto Plata1 stop$662
St. John's
St. John's1 stop$776

Book Cheap San Diego to Caribbean Islands 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 Islands 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 Islands

Sun, Aug 23 - Fri, Aug 28
American Airlines Logo
9:10 pm - 2:59 pm
SAN
-
STT
14h 49m
1 stop
American Airlines Logo
1:49 pm - 8:12 am
STT
-
SAN
21h 23m
2 stops
$316American Airlines
Sat, Aug 29 - Fri, Sep 4
American Airlines Logo
10:45 pm - 3:52 pm
SAN
-
STT
14h 07m
1 stop
American Airlines Logo
4:42 pm - 10:49 pm
STT
-
SAN
9h 07m
1 stop
$341American Airlines
Thu, Aug 13 - Thu, Aug 20
Delta Logo
9:40 pm - 11:46 am
SAN
-
SJU
11h 06m
1 stop
Delta Logo
2:59 pm - 11:00 pm
SJU
-
SAN
11h 01m
1 stop
$386Delta
Sat, Sep 5 - Wed, Sep 9
United Airlines Logo
9:45 pm - 12:54 pm
SAN
-
SJU
12h 09m
1 stop
United Airlines Logo
3:00 pm - 9:25 pm
SJU
-
SAN
9h 25m
1 stop
$390United Airlines
Wed, Oct 28 - Fri, Nov 6
United Airlines Logo
6:30 am - 8:26 pm
SAN
-
SJU
10h 56m
2 stops
United Airlines Logo
7:45 am - 1:47 pm
SJU
-
SAN
10h 02m
1 stop
$393United Airlines
Sun, Jul 12 - Fri, Sep 4
Delta Logo
10:30 pm - 3:34 pm
SAN
-
MBJ
15h 04m
1 stop
Delta Logo
1:14 pm - 9:19 pm
MBJ
-
SAN
10h 05m
1 stop
$412Delta
Fri, Jun 5 - Thu, Jun 11
JetBlue Logo
8:44 pm - 12:02 pm
SAN
-
SJU
12h 18m
1 stop
JetBlue Logo
8:30 am - 7:30 pm
SJU
-
SAN
14h 00m
1 stop
$420JetBlue
Wed, Aug 26 - Sun, Aug 30
Copa Airlines Logo
8:58 pm - 2:36 pm
SAN
-
CUR
14h 38m
1 stop
Copa Airlines Logo
7:31 pm - 6:30 pm
CUR
-
SAN
25h 59m
1 stop
$430Copa Airlines
Mon, Sep 21 - Mon, Oct 5
Copa Airlines Logo
9:03 pm - 11:42 am
SAN
-
SDQ
11h 39m
1 stop
Copa Airlines Logo
8:47 am - 6:30 pm
SDQ
-
SAN
12h 43m
1 stop
$502Copa Airlines
Sat, Jun 6 - Sat, Jun 13
JetBlue Logo
9:10 pm - 12:30 pm
SAN
-
AUA
12h 20m
1 stop
JetBlue Logo
2:35 pm - 9:10 am
AUA
-
SAN
21h 35m
1 stop
$624JetBlue
Booking Insights

KAYAK's insights & trends for San Diego to Caribbean Islands flights

Get data-powered insights and trends into flights from San Diego to Caribbean Islands to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest San Diego to Caribbean Islands flight route?

Data is based on round-trip flight searches on KAYAK over the past month.

The cheapest ticket to Caribbean Islands 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.

Can I save money by flying with a layover from San Diego to Caribbean Islands?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $442, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from San Diego to Caribbean Islands?

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 Islands, 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 Islands is June, when tickets cost $150 (return) on average. On the other hand, the most expensive months are September and August, when the average cost of round-trip tickets is $238 and $228 respectively.

How far in advance should I book a flight from San Diego to Caribbean Islands?

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 Islands, 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 Islands, you should book around 5 weeks before departure, which saves you about 29% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 21 weeks before departure.

Good to know

Low seasonOctober
Cheapest flight$156
Best time to beat the crowds with an average 26% 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 Islands flights

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

    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 Islands.

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

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

    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 Islands 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 Islands?

    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 Islands 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 Islands

 
See real verified KAYAK customer reviews for airlines flying from San Diego to Caribbean Islands. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from San Diego to Caribbean Islands? 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.
7.9
DeltaOverall score based on 8454 reviews
8.5Crew
7.2Food
7.8Comfort
7.8Entertainment
8.1Boarding
Airline reviews

While they turned off most cabin lights to allow people to sleep, I was bothered by how bright the side lights still were. It was still quite bright for me in a window seat, when I wish I could have slept!

10.0 ExcellentTeresa, Apr 2026
SMF - LAX
Read more Delta reviews

While they turned off most cabin lights to allow people to sleep, I was bothered by how bright the side lights still were. It was still quite bright for me in a window seat, when I wish I could have slept!

Generally on time departures and arrivals, clean planes, sky miles membership provides great benefits (complimentary upgrades, etc).

N Everything was perfect from boarding to assistance to baggage in Tampa

Loved the crew! Sucks that we went from 1 hour and 8 minute layover to a 3 hour layover. But weather sucks like that.

Fast, lovely scenery, great info on the Delta flight screen about landmarks we were flying over. Great landing!

Long flight but comfortable and not freezing as I have experienced on Hawaiian flights to the islands. They gave us blankets just in case. Nice touch.

I took seat 15A in anticipation of window seat, there is no window.

Flight late, the waited for a long time for “personal” to arrive at gate to dock the plane in Rochester. So annoying. This flight was expected, why aren’t personel available for the jet bridge?

My recent experience was excellent on Delta! I flew with Delta Comfort and I was really comfortable in my seat. I enjoyed the in-flight service. The flight attendants were so friendly and hospitable. I love the snack on the flight as well. This was my first time flying on Delta and I will definitely consider flying with them again.

My flight was canceled on Sunday. Rebooking took three hours. Had to pay for accommodations another night. New flight was delayed for 5 hours, all that was sent was a 12 dollar food voucher, which doesn’t tell you how to use it. Then when we landed we had to sit on the plane for an hour before we could get off.

Boarding was a mess, they call all priority members without distinction so gold, platinum, silver were all mixed together in a long line which defeats the purpose

Entire experience from check in to landing was amazing the flight crew was excellent and friendly. Seats were comfortable.

Boarding was confusing from staff telling going to preboard and than to group 1 Airplane was not cooling at the beginning

Avoid at all costs. My wife had to stay back on a connecting flight as her parents flight was delayed. 10 days later on the way back they cancelled all our flights. We had to rebook all four of us on the next days flight.

Friendly crew, good food options, food not the best and seats not as comfy but that’s typical.

The food is terrible I ask for water never got transport my mother we’re late and my sister from Lima was the worst waiting to long for wheelchair

Copa staff at PTY and one particular crew member were unhelpful & rude.

There should be a warning regarding the quality of the aircraft on the website as we reserve the tickets. There was no TV or any type of screen onboard. The wifi they offer is good for nothing. Traveling 9 hours straight with kids and no type of entetainment was horrible. I wish I had been informed prior so I could buy a ticket with another airline. The food was a joke too. A very tiny portion per passenger. They also charged $100 per checked bag. With United I used to pay $60. So, fair to say that I wont be flying Copa anymore. Their aircraft was super old, outdated, no entertainment, with nearly no onboard food.

I always enjoy flying Copa. There are very few airlines where I can enjoy a comfortable sleep in-flight. The snacks weren't the best, but they sufficed. The in-flight entertainment was fantastic, and I crossed another movie off my watch list.

Very strict carry on rules meant most of the plane had to gate check their luggage. As is often the case had things that were broken because of this, but I appreciated not being charged to gate check. Otherwise good flight and great crew once on the plane

My flight time was changed without any notification to me which ruined my time sensitive plans so I ended up completely changing my travel plans and no reimbursement.

No screens or meal options. Freezing cold. Dirty seats. Left late.

I liked that my son and I were reseated next to each other (we had different bookings). I liked that it was a directg flight and mostly on time. I liked that you provided pillows and blankets. Flight attendants were generally courteous. The messaging through wifi did not work well. The food was not good. Seats are very narrow and I felt slightly claustraphobic in the window seat.

Some crew were unfriendly or in some cases just straight up rude.

Booked through Kayak Business, had a seat in middle and towards back due to booking rate, not comfortable.

Outstanding service, efficient & friendly crew, flight was safe, comfortable & on time

United Airline crews were very friendly and very attentive. 12 hours flight was gone like in a shorter one.

Food was surprisingly delicious. Space in the seat is horrible when the seating front is reclined. Movie offerings were terrible. Crew was friendly and helpful.

Flight itself excellent, but delayed so missed connection & got to destination 2 hrs later

Due to cancellation of connecting flight (Lufthansa) I didn’t fly with United

All airline travel outside of First or Business class is an ordeal to be endured. This trip was ok, small o, small k.

TV was broken and could not shut it off. The flicking was bother me and gave me a headache. The WiFi wouldn’t work correctly, I was able to text but not search the web or surf social media. The plane itself had a lot of wear and tear it is due for an update.

JetBlue not only has the most comfortable planes, but also used to have the best customer service. Lorie Wright, the lady at the gate was very rude not only to me, but to other passengers as well. Her colleague, the gentleman was also not very friendly. They both were acting like they were doing passengers a favor. The crew on board was very nice.

Flight was on time and smooth. Customer service was decent

The space between seat rows seemed to be larger than other airlines. I didn’t check their food or entertainment since I slept most of the way. They do seem to have a lot of options for purchase though.

Kayak sucked. You gave me a confirmation number that was not useable by the jet blue system. Nor did you send any check in emails. I’ll not be using your site again. Nice work.

Direct tv did not work on flight Short flight so no good service offered Arrived early to destination and had to wait for gate to open. Deplaned LATER than if we arrived on time!! Poor planning Jet blue has had something go wrong on every flight I’ve taken with them in last five years. Terribly run airline

Given us a free miles or free flight for waiting for 9 hours I didn’t get home till 5am in the morning and I was supposed to be home at 9:30 touch down.

Excellent price. Everything on time. two bad parts. Kayak said I couldn't sign in for the flight online, but I got an email at the same time from Jet Blue and they let me sign in online. Second bad part was that, although I had provided my known traveler number, neither of my boarding passes, for this flight and the previous one, had TSA pre-check showing.

Jet blue was great But the Jayak system Wasa pure nightmare and wasted so much of my time and energy by not giving me a way to access jet blue to check in the flight back I didn’t even get the number confirmation code 24 hours before. Because I didn’t receive the email with the confirmation code I could NoT CHECk IN. I spoke to a kayak third party and they informed me I could not carry a carry on, on the flight which caused me so much extra stress it was just too much. You can be sure I will not be using it recommending your site. Again.

Premium Economy Good crew, good service, excellent food. Seat back screen just not bright enough.

The crew was very attentive through out the flight. Seats were comfortable, nice flight bag with pillow and blanket. Food was okay, since it was a overnight flight seemed to go by fast.

Left early arrived early..right amount of talking from pilots..of course had to love the biscuit and water!

Boarding gate at LAX was too crowded—two gates next to one another

On time departure and early arrival. Flight attendant very nice.

The business class layout of chairs was weired. You are sitting directly across stranger.,

The SFO Lounge crew were amazing. The bartender Faris was great. Thanks!

Friendly crew is the only nice thing. Seats uncomfortable. Food and snacks horrible. Movies were the same as the first 10 hour flight two weeks before

Was not able to do a online check-in because the American Airlines system doesn't store our visa or other passport information, allowing us to have a trouble-free check-in. We were forced to have to check-in at the counter which Changes are upgrade status given that we were not able to check in much earlier.

Good flight, seated and had a water within 5 minutes. Crew was hospitable.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports