$161 Find Cheap Flights from San Francisco to Caribbean Islands - 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 Islands departing on 9/14. 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.
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Cheap Flights from San Francisco to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$512
Santo Domingo
Santo Domingo1 stop$530
Montego Bay
Montego Bay1 stop$552
Oranjestad
Oranjestad1 stop$586
Nassau
Nassau2 stops$511
Kingston
Kingston1 stop$596
Simpson Bay
Simpson Bay1 stop$524
Providenciales
Providenciales1 stop$640
Port of Spain
Port of Spain1 stop$707
Bridgetown
Bridgetown1 stop$642
George Town
George Town1 stop$664
Willemstad
Willemstad1 stop$516
Castries
Castries2 stops$1,281
Aguadilla
Aguadilla1 stop$430
Puerto Plata
Puerto Plata1 stop$686
St. John's
St. John's1 stop$632
Punta Cana
Punta Cana1 stop$512
Santo Domingo
Santo Domingo1 stop$530
Montego Bay
Montego Bay1 stop$552
Oranjestad
Oranjestad1 stop$586
Nassau
Nassau2 stops$511
Kingston
Kingston1 stop$596
Simpson Bay
Simpson Bay1 stop$524
Providenciales
Providenciales1 stop$640
Port of Spain
Port of Spain1 stop$707
Bridgetown
Bridgetown1 stop$642
George Town
George Town1 stop$664
Willemstad
Willemstad1 stop$516
Castries
Castries2 stops$1,281
Aguadilla
Aguadilla1 stop$430
Puerto Plata
Puerto Plata1 stop$686
St. John's
St. John's1 stop$632

Book Cheap San Francisco 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 Francisco 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 Francisco to Caribbean Islands

Sun, Oct 18 - Thu, Oct 22
JetBlue Logo
9:45 pm - 3:29 pm
SFO
-
SJU
14h 44m
1 stop
JetBlue Logo
2:35 pm - 11:17 pm
SJU
-
SFO
11h 42m
1 stop
$425JetBlue
Tue, Aug 18 - Tue, Aug 25
Multiple Airlines Logo
10:35 pm - 2:16 pm
SFO
-
SJU
12h 41m
1 stop
Multiple Airlines Logo
5:00 pm - 11:51 pm
SJU
-
SFO
9h 51m
1 stop
$426Multiple Airlines
Sun, Aug 9 - Fri, Aug 14
Frontier Logo
10:18 pm - 2:16 pm
SFO
-
SJU
12h 58m
1 stop
Frontier Logo
7:10 am - 10:54 pm
SJU
-
SFO
42h 44m
2 stops
$440Frontier
Tue, Aug 4 - Wed, Aug 12
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
$512Frontier
Wed, Nov 11 - Tue, Nov 17
Copa Airlines Logo
7:36 pm - 6:22 pm
SFO
-
CUR
18h 46m
1 stop
Copa Airlines Logo
3:34 pm - 11:12 pm
CUR
-
SFO
11h 38m
1 stop
$516Copa Airlines
Fri, Aug 28 - Thu, Sep 10
American Airlines Logo
11:30 pm - 3:39 pm
SFO
-
CUR
13h 09m
2 stops
American Airlines Logo
4:57 pm - 10:12 am
CUR
-
SFO
20h 15m
2 stops
$520American Airlines
Sat, Sep 12 - Fri, Sep 18
American Airlines Logo
9:54 pm - 3:31 pm
SFO
-
CUR
14h 37m
1 stop
American Airlines Logo
2:41 pm - 11:59 pm
CUR
-
SFO
12h 18m
1 stop
$529American Airlines
Sun, Oct 25 - Wed, Nov 4
Copa Airlines Logo
8:36 pm - 2:11 am
SFO
-
SDQ
26h 35m
1 stop
Copa Airlines Logo
12:45 pm - 11:12 pm
SDQ
-
SFO
14h 27m
1 stop
$530Copa Airlines
Mon, Aug 24 - Mon, Aug 31
Delta Logo
4:05 pm - 2:14 pm
SFO
-
UVF
19h 09m
1 stop
Delta Logo
3:34 pm - 11:58 pm
UVF
-
SFO
11h 24m
1 stop
$536Delta
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
Booking Insights

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

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

Can I save money by flying with a layover from San Francisco 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 $659, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from San Francisco 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 Francisco 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 Francisco to Caribbean Islands is August, when tickets cost $184 (return) on average. On the other hand, the most expensive months are July and March, when the average cost of round-trip tickets is $2,766 and $1,787 respectively.

How far in advance should I book a flight from San Francisco 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 Francisco 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 Francisco to Caribbean Islands, 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$161
Best time to beat the crowds with an average 11% 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 Islands flights

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

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

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

 
See real verified KAYAK customer reviews for airlines flying from San Francisco 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 Francisco 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.
7.8
DeltaOverall score based on 8459 reviews
8.5Crew
7.8Entertainment
7.8Comfort
7.2Food
8.1Boarding
Airline reviews

Crew was absolutely fantastic and we’re so welcoming and friendly ❤️

10.0 ExcellentRachel, Jul 2026
SFO - SLC
Read more Delta reviews

Crew was absolutely fantastic and we’re so welcoming and friendly ❤️

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

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!

Delta’s staff is unmatched. From the gate agents, to the pilots, to the flight attendants… all top of the industry.

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

Excellent flight, the planes were newer, they did a nice job with boarding, great service overall.

Thank you for not flipping the plane on the run way. You guys get a 5 star rating for the flight!!!

Boarding is, as it always is… horrible. Gate lice. Slow moving zones. Too many people with carry ons

New boarding doesn't make sense. Filling front first is slow.

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.

It would have been better if they don't separate families in seating. We were seated in the aile row in the middle of a family of four. It would have been better if they they seat the family of four together than separated.

It was good, plane is a bit older so seats are somewhat flat

Very good flight and crew Food was a surprise on a short flight

Biggest issue was that they only had two restrooms in the back of the aircraft. Too many people for only two restrooms. The trash was overflowing and there was paper on the floor too. Long lines in the isle to use it. Food was also a bit meh. They don’t offer snacks with drinks, so you might want to buy a snack to hold you off on a longer trip, since the meals are very small.

Everything was smooth and crew was very polite and friendly.

I like that they served a mail, I’m not sure about the in-flight entertainment. I didn’t really check. staff helped me with my luggage. Smooth boarding smooth takeoff smooth flight

The seats had plenty of leg room and the staff were very nice.

Copa performed as expected for the amount of money I was willing to spend for the flight; it wasn’t exceptional but it was not bad in any way either. The crew was good; friendly and straightforward. The food was airplane food, so no expectations there and the entertainment was lacking but that was my fault for owning an IPhone with a charging port that’s not compatible with the rest of the world. I’d fly Copa again.

Left my bags in origin city on a business class ticket , spent about 2-3 days in the same clothes plus the flight .

It was a short, comfortable flight. It did leave an hour late due to the pilot having to be replaced (family emergency) but that didn’t inconvenience myself & my friend. The situation was explained, eventually.

Excellent communication from the staff. We actually arrived early. Very friendly and professional staff.

No extra snacks were available. Meals quality is terrible. Crew was not friendly.

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

Over the course of 7 months of travel, I can count on my hand the number of times the flight has departed on time. Majority of the instances have been related to non-weather reasons. Would not recommend flying this Airline

The food was okay and the space in business class was smaller than we had to Singapore.

The plane was spartan, the seats not that comfortable. It was like flying a super low budget airline. They charged for coffee!!! I have never, ever experienced that before.

I had no problems but the changing of planes that I was supposed to be on was confusing. Maybe it would be helpful to let people know your flight changed. Not everyone understands airports or how flying works.

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

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.

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.

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

Seats were great, the staff was great, and the food was about the best I've had on a plane, and is especially the best of any US-based carrier I've flown. Free Wi-Fi was also great.

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).

It was good. I’m very disappointed that they don’t give commentary ear pods for the movie. I forgot mine at home

Rude crew member. She seemed annoyed at me without me saying a single word. Also loudly admonished me for having my bag next to my seat instead of tucked away before landing. Just telling me to put it away and guiding me without giving me a lecture would have been enough.

Too many long delays with JetBlue. Worst major airline that serves JFK but unfortunately I keep going back because of the prices.

Little snafu at boarding. Staff communicated with gate poorly. Flight attendant was rude making disembark early. This was an older mint class. Needs an overhaul for sure. Food was good. The male flight attendant was really nice.

I really liked the way snacks and drinks were available throughout the flight!!! The flight attendants were also all fantastic!

Always like Jet Blue! It seems, however, that people are getting bigger & seats are getting smaller! We had a very full flight and I couldn't get an aisle seat like I always do. I wish there were more leg room. People sitting next to me were very nice though so it was fine to disturb them if I needed to use the restroom. Otherwise the flight was fine but a bit long.

None of the in flight Direct TV worked. A better selection of Shows would have been better. The baggage was s low. Otherwise we enjoyed our flight!

the staff was very helpful and the airline was very good.

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports