$156 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 7/24. 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$458
Santo Domingo
Santo Domingo1 stop$492
Montego Bay
Montego Bay1 stop$412
Oranjestad
Oranjestad1 stop$611
Nassau
Nassau1 stop$487
Kingston
Kingston1 stop$664
Simpson Bay
Simpson Bay2 stops$527
Providenciales
Providenciales1 stop$686
Port of Spain
Port of Spain1 stop$730
Bridgetown
Bridgetown1 stop$563
George Town
George Town1 stop$494
Willemstad
Willemstad2 stops$533
Aguadilla
Aguadilla2 stops$656
Puerto Plata
Puerto Plata2 stops$652
St. John's
St. John's1 stop$732
Punta Cana
Punta Cana1 stop$458
Santo Domingo
Santo Domingo1 stop$492
Montego Bay
Montego Bay1 stop$412
Oranjestad
Oranjestad1 stop$611
Nassau
Nassau1 stop$487
Kingston
Kingston1 stop$664
Simpson Bay
Simpson Bay2 stops$527
Providenciales
Providenciales1 stop$686
Port of Spain
Port of Spain1 stop$730
Bridgetown
Bridgetown1 stop$563
George Town
George Town1 stop$494
Willemstad
Willemstad2 stops$533
Aguadilla
Aguadilla2 stops$656
Puerto Plata
Puerto Plata2 stops$652
St. John's
St. John's1 stop$732

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

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 22 - Fri, Aug 28
American Airlines Logo
12:32 pm - 3:52 pm
SAN
-
STT
24h 20m
1 stop
American Airlines Logo
1:49 pm - 8:12 am
STT
-
SAN
21h 23m
2 stops
$380American Airlines
Tue, Oct 20 - Tue, Oct 27
Delta Logo
5:00 pm - 11:56 am
SAN
-
SJU
15h 56m
2 stops
Delta Logo
1:06 pm - 11:45 pm
SJU
-
SAN
13h 39m
1 stop
$386Delta
Thu, Aug 27 - Mon, Aug 31
Southwest Logo
8:30 am - 10:15 pm
SAN
-
SJU
10h 45m
1 stop
Southwest Logo
5:00 am - 1:50 pm
SJU
-
SAN
11h 50m
2 stops
$406Southwest
Thu, Aug 13 - Wed, Aug 19
Delta Logo
9:40 pm - 3:34 pm
SAN
-
MBJ
15h 54m
1 stop
Delta Logo
1:09 pm - 11:00 pm
MBJ
-
SAN
11h 51m
1 stop
$412Delta
Sat, May 30 - Fri, Jun 5
JetBlue Logo
9:10 pm - 12:04 pm
SAN
-
SJU
11h 54m
1 stop
JetBlue Logo
7:00 am - 7:07 pm
SJU
-
SAN
15h 07m
1 stop
$420JetBlue
Mon, Aug 31 - Wed, Sep 2
JetBlue Logo
8:40 pm - 2:00 pm
SAN
-
SJU
14h 20m
1 stop
JetBlue Logo
8:30 am - 7:28 pm
SJU
-
SAN
13h 58m
1 stop
$425JetBlue
Thu, Aug 6 - Mon, Aug 10
United Airlines Logo
5:15 pm - 5:29 am
SAN
-
SJU
9h 14m
1 stop
United Airlines Logo
2:05 am - 11:35 am
SJU
-
SAN
12h 30m
2 stops
$427United Airlines
Fri, Jul 17 - Mon, Jul 20
United Airlines Logo
10:25 pm - 1:47 pm
SAN
-
NAS
12h 22m
2 stops
United Airlines Logo
4:58 pm - 9:24 pm
NAS
-
SAN
7h 26m
1 stop
$497United Airlines
Mon, Jun 29 - Thu, Jul 9
Southwest Logo
9:55 pm - 2:55 pm
SAN
-
PLS
14h 00m
1 stop
Southwest Logo
3:50 pm - 8:35 am
PLS
-
SAN
19h 45m
2 stops
$686Southwest
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 May, when tickets cost $140 (return) on average. On the other hand, the most expensive months are February and July, when the average cost of round-trip tickets is $194 and $191 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 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 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
SouthwestOverall score based on 4298 reviews
8.6Crew
7.5Entertainment
8.0Comfort
8.1Boarding
7.0Food
Airline reviews

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

10.0 Excellentlarry, Apr 2026
LGB - PHX
Read more Southwest reviews

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

Delayed flight, lack of information, boarding process is a mess as is the carryon luggage causing issues when leaving the plane….just a poor experience.

Comfortable. Easy. No problems. Just wish they had gf options for snacks.

The crew was very kind and made going to Hawaii relaxing and fun to look forward to! Thank you Southwest for a pleasant flight!

Terrible. Even though there’s assigned seating now, they are still the slowest boarding airline of anyone.

It was good from LAX to Phoenix, But the connection in Phoenix to Tulsa was not that great. The staff on both flights were great. The choice of free entertainment was ok nothing to brag about. The 45 min delay because of some electrical issue wasn't great from Phoenix to Tulsa. We sat there with hardly any air, The seat I had was between windows so the side of the plane pushed in on you. My being a bigger man it then made the seating area uncomfortable. The seats on the plane had no power to connect to recharge your phone or anything. I would recommend that they should look into a slot or clamp to hold your phone to enjoy while watching the entertainment choices hands-free. Also make it possible to raise the inner seat by the window be able to raise the arm rest up to make more room for larger people to set more comfortably. I would also say other then that stop price gouging the airfare or nickel and diming everything. Not fair for people having to fly for emergencies and be paying for higher prices due to the season or holidays. Your making your money either way and the cost of flying is still going to be the same regardless if there's 100 people or 200 people.

Southwest was greaat! The most expensive but the least upsetting for those we were flying to see.

Boarding was easy. The seats are small and fairly uncomfortable

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

Good but I prefer choose your own seat. With the new assigned seats they should board from the back I see no advantage to this new boarding. Just like every other airline

Alaska is by far the best airline to fly with 😍

More efficient with checking lines and boarding/checking bags when needed.

They were really helpful with every question and my kids had never been on a plane and the staff made them feel comfortable

I was on flight #3022 departed from San Diego, California to Medford, Oregon. I had Denise & Damaris as my flight attendants. I didn’t have much interaction with Damaris, but I did with Denise who had, this calm, cool collective voice when she spoke about the emergency exit plans before takeoff. I travel often and I’ve never met a flight attendant that can put you at ease. I felt she respects and takes pride in her position and more airlines need to adopt the integrity and respect that she has for Alaska Airlines. Debbie

All airlines should board planes back to front, instead of catering to higher priced tickets. The boarding groups are inefficient and delay takeoff time

Luggage was severely damaged. Flight was late for several hours

The ticketing counter in SD was a mess. The lady handling the First-Class check-in seemed overwhelmed until a supervisor replaced her. It took almost 20 minutes to get once couple checked in, and then she started walking around the counters while 7 people just stood in line. Once her supervisor arrived, she announced she was going on break, never to engage with customers again.

No outlets, plugs, way to charge the phone or service and no food on one leg o the trip, but other than that, great. Loved WIFI, the flight, the crew, the pilots, the schedule, etc. Great job. My new favorite airline!

I had a problem with my reservation and no one could help me understand what happened. I booked my flight months ago and received a confirmation email. In the confirmation email, it said that the flight would depart at 3:15 p.m. A few hours before the flight, I tried to go online and check in, and suddenly it said that the flight was leaving an hour earlier. I had to rush to get to the airport and almost didn't make it. No one could help me understand why this happened, and I'm really concerned that it might happen in the future. I would appreciate some support in this matter.

It was a super old plane so the first class experience was just not luxurious

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.

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

It was a red-eye, but the flight felt surprisingly quick. The seats were very comfortable, and that made resting much easier. I also want to thank the gentleman seated next to me, who graciously moved so my mom could sit beside me. We slept almost the entire way. The cabin crew was respectful in not disturbing us, while also being courteous and professional throughout. Thank you, United.

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

Information on your arrival and departure airports