$184 Find Cheap Flights from San Francisco to Caribbean - 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 from San Francisco to Caribbean departing on 9/15. 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

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Cheap Flights from San Francisco to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$502
Santo Domingo
Santo Domingo1 stop$520
Montego Bay
Montego Bay1 stop$536
Oranjestad
Oranjestad1 stop$594
Nassau
Nassau1 stop$535
Kingston
Kingston1 stop$596
Simpson Bay
Simpson Bay1 stop$557
Providenciales
Providenciales2 stops$549
Port of Spain
Port of Spain1 stop$721
Bridgetown
Bridgetown1 stop$630
George Town
George Town2 stops$593
Willemstad
Willemstad1 stop$516
Castries
Castries2 stops$1,138
Aguadilla
Aguadilla1 stop$441
Puerto Plata
Puerto Plata1 stop$685
St. John's
St. John's1 stop$632
Punta Cana
Punta Cana1 stop$502
Santo Domingo
Santo Domingo1 stop$520
Montego Bay
Montego Bay1 stop$536
Oranjestad
Oranjestad1 stop$594
Nassau
Nassau1 stop$535
Kingston
Kingston1 stop$596
Simpson Bay
Simpson Bay1 stop$557
Providenciales
Providenciales2 stops$549
Port of Spain
Port of Spain1 stop$721
Bridgetown
Bridgetown1 stop$630
George Town
George Town2 stops$593
Willemstad
Willemstad1 stop$516
Castries
Castries2 stops$1,138
Aguadilla
Aguadilla1 stop$441
Puerto Plata
Puerto Plata1 stop$685
St. John's
St. John's1 stop$632

Book Cheap San Francisco 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 Francisco 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 Francisco to Caribbean

Wed, Aug 12 - Wed, Aug 19
Southwest Logo
5:50 am - 9:05 pm
SFO
-
SJU
12h 15m
2 stops
Southwest Logo
5:15 am - 1:50 pm
SJU
-
SFO
11h 35m
2 stops
$416Southwest
Tue, Sep 1 - Sat, Sep 5
Multiple Airlines Logo
10:35 pm - 2:16 pm
SFO
-
SJU
12h 41m
1 stop
Multiple Airlines Logo
9:55 pm - 9:11 am
SJU
-
SFO
14h 16m
1 stop
$421Multiple Airlines
Mon, Oct 5 - Wed, Oct 14
JetBlue Logo
11:59 pm - 3:56 pm
SFO
-
SJU
12h 57m
1 stop
JetBlue Logo
2:35 pm - 11:17 pm
SJU
-
SFO
11h 42m
1 stop
$428JetBlue
Wed, Aug 12 - Wed, Aug 19
JetBlue Logo
10:57 am - 11:18 pm
SFO
-
SJU
9h 21m
1 stop
JetBlue Logo
4:58 pm - 11:50 pm
SJU
-
SFO
9h 52m
1 stop
$454JetBlue
Tue, Aug 4 - Tue, Aug 11
Frontier Logo
10:10 pm - 2:21 pm
SFO
-
PUJ
13h 11m
1 stop
Frontier Logo
3:31 pm - 7:13 pm
PUJ
-
SFO
30h 42m
1 stop
$502Frontier
Mon, Jul 27 - Tue, Aug 4
Frontier Logo
11:00 pm - 2:21 pm
SFO
-
PUJ
12h 21m
1 stop
Frontier Logo
3:31 pm - 7:13 pm
PUJ
-
SFO
30h 42m
1 stop
$522Frontier
Sun, Dec 13 - Wed, Dec 23
American Airlines Logo
12:25 am - 2:37 pm
SFO
-
CUR
10h 12m
1 stop
American Airlines Logo
5:46 pm - 11:17 am
CUR
-
SFO
21h 31m
1 stop
$529American Airlines
Mon, Dec 14 - Wed, Dec 23
American Airlines Logo
6:15 pm - 2:44 pm
SFO
-
CUR
16h 29m
2 stops
American Airlines Logo
5:46 pm - 11:17 am
CUR
-
SFO
21h 31m
1 stop
$533American Airlines
Wed, Sep 2 - Wed, Sep 9
Delta Logo
4:05 pm - 2:14 pm
SFO
-
UVF
19h 09m
2 stops
Delta Logo
3:32 pm - 11:57 pm
UVF
-
SFO
11h 25m
1 stop
$541Delta
Wed, Sep 2 - Wed, Sep 9
Delta Logo
10:00 pm - 2:14 pm
SFO
-
UVF
13h 14m
1 stop
Delta Logo
3:32 pm - 11:57 pm
UVF
-
SFO
11h 25m
1 stop
$587Delta
Booking Insights

KAYAK's insights & trends for San Francisco to Caribbean flights

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

What is the cheapest month to fly from San Francisco to Caribbean?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from San Francisco 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 Francisco to Caribbean is September, when tickets cost $134 (return) on average. On the other hand, the most expensive months are May and November, when the average cost of round-trip tickets is $966 and $850 respectively.

How far in advance should I book a flight from San Francisco 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 Francisco 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 Francisco to Caribbean, you should book around 3 weeks before departure, which saves you about 14% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 26 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$184
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly with an average 20% increase in price.
Flight from San Francisco to San Juan

FAQs - booking Caribbean flights

  • How does KAYAK find such low prices on flights from San Francisco 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 Francisco to Caribbean.

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

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

 
Need help choosing which airline to fly with from San Francisco 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.
7.8
DeltaOverall score based on 8424 reviews
8.1Boarding
7.8Comfort
8.5Crew
7.8Entertainment
7.2Food
Airline reviews

Very good flight. Crew was great. No issues and we even arrived early.

10.0 ExcellentAnonymous, Jun 2026
SAN - DTW
Read more Delta reviews

Very good flight. Crew was great. No issues and we even arrived early.

Be on time? When not on time a circling for over an hour offer more than 1 bag of chips to the passengers? It was a 7 hour flight by the time we got done.

Flight delayed four separate times. I’m now one hour hours late to landing.

Checkin was good, fllight ws good. Onlly complaint is lack of foot on 6 hour flight from Seattle to Boston. Snacks were flimsy - chips and cookies. could have offered something more substantial for such a long flight. I know you can buy food in airport but for the price you pay for a ticket, they should step up for the passengers.

Long story short, it was one of the better flight experiences I've had in some time when compared with other airlines.

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!

Lost one piece of luggage even though I checked in 2.5 hours before the flight

It was perfect! United Airlines staff was extremely caring, super friendly and professional

United has maintenance issues and can then never recover. No operations ability and simple issues always turn into multiple hours long cascading delays. Worst airline on earth.

I paid for a confirmed upgraded aisle seat and was moved to a center seat in the back of the plane at the last minute.

Horrifying Almost 2 million miles. Bring your own food and drink. One coffee or drink every three hours. Have to order meals on app more than 24 hours ahead Tiny and dirty bathrooms

Easy of boarding, helpfully staff at check in, surprisingly comfortable seating

Lost of requested seat assignments. Lost my husband's meal choice

My service dog and I were asked to deplane just before they closed the door - clearly very last minute they couldn’t find the documentation that I have filled out many many times before that is for flying service animals. I purposely purchase 3seats (a whole row) since he is large and not all passengers want to sit next to a dog on a cross country flight. The plane departed with my husband on it!!! They made me fill out a hard copy of the same form and had to reschedule me on a later flight where they could find 3 seats together!! I’ve done this so many times before - clearly the error was on their part in a technology glitch - but really people - do better!! Very traumatic - and my husband had to wait for us when he landed ….so bad. Poor pup was confused and tired.

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.

Flight was delayed multiple times without giving any particular reason and the only thing that was communicated was that 'Aircraft is getting ready'. I was stuck at SFO airport for 15 hours and finally took Southwest Airlines flight back home to Dallas.

I was not clear if food was offered or not.

Agency very bad had to cancelled my booking too many changes in the flight changed my flight to 1 week

Luggage did not make it onto my plane. Business seats were economy with empty row seat. Just horrible experience. Why would the company allow for transfers that don’t give employees enough time to transfer luggages??

The gate experience at LAX was abysmal (same for the arrival experience two days prior). Despite the LAX -> SAT schedule of two flights daily, our departure gate was at a smaller hub that we had to be bussed to from Terminal 4. Fortunately, I arrived at LAX extra early and had time to spare, but if I had not known, I might have missed my flight. I looked at the LAX airport map in the AA app and there was no indication of the additional boarding process. Lastly the gate area we were bussed to was crowded with limited food and beverage options. On flight, the fight attendant was hospitable and attentive, the flight was smooth, and AA's free (and working) wifi for AA members were all on the positive side.

Our flight from JFK to Madrid was delayed. We had to go from one side of the Madrid airport (Terminal 4s to the far end of terminal 4 - Gate K98) to our gate in less than 30 minutes. Put passport control and security/baggage check and that’s very hard unless you’re Usain Bolt. I called Iberia Airlines and the telephone customer service told me that I was going to have to pay to re-book. Luckily the help desk in the airport (who was dealing with dozens of people from the same JFK-Madrid flight) did not charge us extra to reschedule to a flight 8 hours later. They also gave us a voucher for breakfast and lunch. Glad the actual person at the airport had some actual sense.

For an long range economy flight I feel more space and more meal options need to be offered for flights over 5 hours

Take-off delayed an hour because of a missing flight officer, so,arrived in Charlotte lates causing many passengers to miss connections. Otherwise a very good flight, safe and comfortable, with an excellent professional crew.

The flight from LA to Chicago was smooth and service was very good overall.

B-class on an old plane with antiquated amenities and poor service. Landed in Rome w/o bag that didn’t make the connection (plenty of time in London). Bag will come to hotel NOT the day it lands but the following night!! Still waiting for bag…BA had nothing to offer in support and couldn’t even tell me their comp, told to submit receipts and then I’ll learn what is or isn’t covered.

The flight was delayed 14 hours and communication was very poor. No one seemed to know what was happening and the gate agent was trying to help people for several flights. She was by herself trying to help 100s of people.

Domestic flights are good. Just stay away from international travel

Flight left 2 hours late with no explanation as to the delay

The aircraft was fine, it’s was just the service. The flight got canceled several times and that was very inconvenient for my 69 years old mom.

My checked in luggage cost was $59, almost ticket price. The first 13 rows were empty, but fly attendant did not alow women with little boy change her middle sit, sweet boy was crying, I am so sorry for mother and passengers. At the end of the flight the cabin became impossible cold. Only good was timing of departure and early landing, but it suppose to be normal.

Seamless flight, didn’t feel like five hours at all very smooth ride. Watched two good movies didn’t even realize I was on a plane. The staff were extremely nice and helpful.

I tried to book a flight with Jet Blue. Your third party company hijacked my attempt with a website that looked like I was booking with Jet Blue. I realized it when I paid. I tried to cancel and was told by a man in India that there were no refunds. $735 stolen, Thanks Kayak!

It was inexplicably canceled and we are stuck in LA, haven't gotten home and it has been an inconvenience having lost work (on unpaid leave for my husband).

I like everything. Blythe at DCA is the absolute best!

JetBlue worker, Blythe, was so amazing at the DCA counter. If it wasn’t for her, I’m not sure we would’ve made it through. Please thank her!

Crew was kind of grumpy and there was no beverage service at all. Sodas were $4. Disappointing.

There weren't enough employees at check in took awhile to get bags checked. There wasn't a wheel chair for me, I was sent to someone who turns out to work for a different airline, if My flight hadn't been delayed I probably would have missed my flight as it was, by the time I arrived at my gate, they started boarding in about 15 minutes. I don't know who took me to my gate, definitely was not the normal people who take passengers to the gate. I'm guessing she may have been in a management position. I wish I knew her name, she went beyond to help me. With that said everyone was kind, and were doing the best they could. So, I choose to say it was an Adventure, stressful start, but good. In the end went well. The situation was not only difficult for passengers but the employee's.

The staff at the check in counter was so rude. Made you feel Incompetent

Frontier scheduled a 40 minute connection in DEN. What they failed to mention was that they “close the doors” 20 mins prior to departure, which means you only have 20 mins. Not enough time. Possibly against DOT regulations. Filing complaint.

Flight was scheduled at 9:40pm. Got delayed to 10 am, the next day. crazy

The bag check, flight check-in, and onboard experience convinced my wife and me that we will actively go out of our way to avoid flying Frontier Airlines in the future. At bag check, we were informed that check-in could only be completed via the Frontier mobile app. Unfortunately, the app was extremely frustrating—sending us through repetitive, confusing loops that repeatedly forced us to decline add-on services with nearly every click. While most airline apps upsell, this one felt intentionally exhausting. As the process dragged on, we became genuinely concerned that my phone battery would die before check-in could be completed. We approached the bag check staff—who were standing together talking—and explained both our frustration and our predicament. They laughed. Later, my wife described the interaction as “gaslighting,” which felt accurate. We were then informed it would cost $25 per person simply to have our boarding passes printed. From that point forward, the tone of the experience was consistently hostile. The bag check employees were condescending and combative, behaving more like bullies than customer service staff. Unfortunately, that same attitude continued onboard. One flight attendant argued with me when I attempted to stow my backpack in the overhead bin. I explained that we had each paid $75 to check our bags specifically so we would not need to use carry-on space and could have adequate legroom. She demanded to see my ticket, pointed out that it said “no carry-on”—which I acknowledged—and I reiterated that this was precisely why we paid to check our bags. Her response was, “I don’t make the rules.” She then walked away, but not before asking if I “truly wanted to fly back to Chicago today?”—an unnecessary and unmistakable threat. It is also worth noting that despite booking our tickets together in the same transaction, we were not seated together. Upon our return to Chicago—where we could once again sit together—we compared onboard experiences. We both remarked on how unhappy the flight attendants appeared and how each of us was separately asked whether we would like to purchase a beverage. We declined. At no point was water mentioned as an option, leaving us with the clear impression that even water came at a cost—or that complimentary water, if available at all, was deliberately left unmentioned. Overall, the experience was shocking and deeply disappointing, but it was also a profound learning experience—one we will not forget and will not repeat. -Steve

They didn’t offer a water, even after I asked

Remind customers of the need to have passport or new ID for boarding.

The flight never took off and we spent 7 hours at the airport

It was ok. It was expensive to check 2 bags ($75.00 per bag), and then it took a long time to wait for shuttle to take us from one terminal to the terminal where the plane was taking off at LAX. And all of this for a flight where we had to pay for any food or drink that was not water.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports