$170 Find Cheap Flights from San Francisco to the Cayman 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 Francisco to the Cayman Islands departing on 4/22. 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 the Cayman Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
George Town
George Town1 stop$469
Cayman Brac
Cayman Brac2 stops$1,702
George Town
George Town1 stop$469
Cayman Brac
Cayman Brac2 stops$1,702

Book Cheap San Francisco to the Cayman 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 the Cayman 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 the Cayman Islands

Wed, Apr 29 - Tue, May 5
JetBlue Logo
11:05 pm - 12:45 pm
SFO
-
GCM
11h 40m
1 stop
JetBlue Logo
2:05 pm - 11:56 pm
GCM
-
SFO
11h 51m
1 stop
$469JetBlue
Sun, Apr 19 - Tue, Apr 21
Southwest Logo
9:15 pm - 12:10 pm
SFO
-
GCM
12h 55m
2 stops
Southwest Logo
1:05 pm - 11:35 pm
GCM
-
SFO
12h 30m
2 stops
$472Southwest
Mon, Apr 27 - Tue, May 5
JetBlue Logo
11:05 pm - 12:39 pm
SFO
-
GCM
11h 34m
1 stop
JetBlue Logo
2:05 pm - 11:56 pm
GCM
-
SFO
11h 51m
1 stop
$480JetBlue
Wed, Apr 15 - Wed, Apr 22
Southwest Logo
7:15 pm - 12:10 pm
SFO
-
GCM
14h 55m
2 stops
Southwest Logo
1:05 pm - 11:35 pm
GCM
-
SFO
12h 30m
2 stops
$487Southwest
Tue, Apr 28 - Tue, May 5
Southwest Logo
9:15 pm - 12:10 pm
SFO
-
GCM
12h 55m
2 stops
Southwest Logo
1:05 pm - 11:35 pm
GCM
-
SFO
12h 30m
2 stops
$517Southwest
Fri, May 15 - Tue, May 26
JetBlue Logo
11:05 pm - 1:00 pm
SFO
-
GCM
11h 55m
1 stop
JetBlue Logo
2:05 pm - 10:17 am
GCM
-
SFO
22h 12m
1 stop
$521JetBlue
Sat, Apr 18 - Sat, Apr 25
Multiple Airlines Logo
4:15 pm - 10:55 am
SFO
-
GCM
16h 40m
1 stop
Multiple Airlines Logo
2:10 pm - 11:56 pm
GCM
-
SFO
11h 46m
1 stop
$524Multiple Airlines
Tue, Apr 14 - Mon, Apr 20
Multiple Airlines Logo
10:38 pm - 4:05 pm
SFO
-
GCM
15h 27m
2 stops
Multiple Airlines Logo
1:50 pm - 12:45 pm
GCM
-
SFO
24h 55m
1 stop
$541Multiple Airlines
Fri, May 15 - Tue, May 26
JetBlue Logo
11:05 pm - 1:00 pm
SFO
-
GCM
11h 55m
1 stop
JetBlue Logo
2:05 pm - 10:17 am
GCM
-
SFO
22h 12m
1 stop
$542JetBlue
Fri, Apr 17 - Fri, Apr 24
JetBlue Logo
8:00 am - 12:50 pm
SFO
-
GCM
26h 50m
1 stop
JetBlue Logo
3:05 pm - 9:23 am
GCM
-
SFO
20h 18m
1 stop
$543JetBlue
Booking Insights

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

Get data-powered insights and trends into flights from San Francisco to the Cayman Islands 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 the Cayman 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 the Cayman 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 the Cayman Islands is September, when tickets cost $530 (return) on average. On the other hand, the most expensive months are December and June, when the average cost of round-trip tickets is $1,191 and $691 respectively.

How far in advance should I book a flight from San Francisco to the Cayman 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 the Cayman 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 the Cayman 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 18 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$170
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly with an average 4% increase in price.
Flight from San Francisco to George Town

FAQs - booking Cayman Islands flights

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

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from San Francisco to the Cayman 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 the Cayman 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 the Cayman 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 the Cayman 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 the Cayman Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 3 airlines serving from San Francisco to the Cayman Islands

 
Need help choosing which airline to fly with from San Francisco to the Cayman 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.
7.4
United AirlinesOverall score based on 9388 reviews
7.7Boarding
6.6Food
8.1Crew
7.3Comfort
7.1Entertainment
Airline reviews

Seats are uncomfortable. This has been a trend in the industry for decades. Trying to fit more seats on each plane to increase profits at the expense of the passenger.

6.0 GoodAnonymous, Mar 2026
SFO - DEN
Read more United Airlines reviews

Seats are uncomfortable. This has been a trend in the industry for decades. Trying to fit more seats on each plane to increase profits at the expense of the passenger.

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.

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

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.

Terrible. No customer service, no food, no drinks on a 6 hour premier economy booking.

The flight crew where really good. Better then the crew from BNE to SFO

Food should be changed in menu Many muslims travels in this airlime they need to add one Halal meal

I have to congratulate Kayak (and Dylan the Chatdeal agent) because because when we decided extended our trip in Florida by two days, there were many direct flights oprions back to Boston available on the Friday we wanted to fly on the JetBlue website, but once I canceled the original JetBlue flight on their website, those direct return options disappeared immediatley! I think it's a game JetBlue plays. . Luckily, I checked Kayak and they had a direct flight that wasn't appearing on JetBlue's website and so I booked it, and we were able to fly home direct through the Kayak booking when JetBlue was offering nothing (even though I have been a True Blue member for 20 years, and also am a Mosaic member). So much for loyalty- their algorithm for booking is like a shell game. JetBlue used to be a good company but now they're worse than anyone. Also I was originally booked this trip to Florida, two months before the departure date, I booked the trip on JetBlue's website and then after the payment part, they said there was a problem and that I needed to do the booking again, so when I immediately went to rebook , the price had gone up 30%! I called them and it sounded like they had heard this so many times before and the guy told me to check back in 10 minutes and the price would be back to where it was when I was booking- it but it never was. How could the price go up 30% in one minute two months before the flight???? They're playing a game with their customers. Anyways, I booked a cheaper flight then at a less convenient time. So fast forward two months the night before the 7 AM flight, they sent me an email at midnight when I was sleeping to let me know that my flight at 7 AM had been canceled. The only thing they offered was a flight that night from from a different airport (Providence) to a different airport in Florida (West Palm Beach) or a flight two days later. No compensation, nothing. They couldn't of tried to get another plane to the Boston airport? They had all night to do it. I passed on their ridiculous options and flew with Delta and it was a great experience. Of course, I had to pay a lot more booking on the same day, but JetBlue doesn't care. I put in a lengthy complaint with the agent who assured me someone would get back to me by email within three days and I haven't heard a thing. JetBlue used to be a good company but now they're among the worst. The only thing they still have is decent legroom, but the corporate bean counters will probably start taking that away too.

We were made to wait in the airport for six hours for a flight that was ultimately canceled.

Both flights were significantly delayed. The flight experience itself was great.

My flight got delayed and eventually canceled, then rescheduled. I and several others had a connection from Boston to Paris and asked several times if we would make it. They assured us we would and then rebooked us mid flight without our consent and closed doors early even though they said they communicated we were a bit delayed. We got stranded in Boston and I opted with being rebooked for a different connection to France since they refused to pay for a Hotel. I've now been in Europe for 5 days and still haven't recieved my bags. There was absolutely no urgency for the fact that I'm in a foreign country with absolutely no change of clothes or any of my medication. Such an overwhelming and frustrating experience.

Automated scanning was slow and somewhat haphazard. Too many people were unfamiliar with the tech and were forced to learn on the fly. The hands off approach of the gate staff made it more uncomfortable. This needs work. Overall the flight and cabin crew were excellent.

The crew for the flight was A+ top notch. They were friendly and professional and made the flight a very relaxing and enjoable.

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.

No included food for a 5 hour flight and the entertainment was only accessible if you had wired headphones (not provided). Otherwise though, great and smooth flying and customer service.

Crew were fantastic and so catering and wonderful! Full score for the entire crew!

Because of weather and mechanical issues our flight was 4 hours late. The only compensation offered to us was a meal voucher to be used only at Boston Airport and only on the day issued. But by the time it was offered to us all the restaurants were closed, so there was no way to use that offer.

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 from San Francisco to the Cayman Islands

Information on your arrival and departure airports