$269 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 6/5. 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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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

Mon, May 4 - Thu, May 7
JetBlue Logo
11:05 pm - 12:45 pm
SFO
-
GCM
11h 40m
1 stop
JetBlue Logo
2:05 pm - 11:51 pm
GCM
-
SFO
11h 46m
1 stop
$463JetBlue
Mon, May 4 - Thu, May 7
JetBlue Logo
11:05 pm - 12:45 pm
SFO
-
GCM
11h 40m
1 stop
JetBlue Logo
2:05 pm - 11:51 pm
GCM
-
SFO
11h 46m
1 stop
$522JetBlue
Mon, Apr 27 - Wed, May 6
Southwest Logo
5:40 pm - 12:10 pm
SFO
-
GCM
16h 30m
2 stops
Southwest Logo
1:05 pm - 11:35 pm
GCM
-
SFO
12h 30m
2 stops
$546Southwest
Fri, May 15 - Tue, May 26
JetBlue Logo
10:45 pm - 12:19 pm
SFO
-
GCM
11h 34m
1 stop
JetBlue Logo
2:05 pm - 12:33 am
GCM
-
SFO
12h 28m
1 stop
$548JetBlue
Fri, May 15 - Tue, May 26
JetBlue Logo
10:45 pm - 12:19 pm
SFO
-
GCM
11h 34m
1 stop
JetBlue Logo
2:05 pm - 12:33 am
GCM
-
SFO
12h 28m
1 stop
$550JetBlue
Mon, May 4 - Fri, May 8
Southwest Logo
9:15 pm - 12:10 pm
SFO
-
GCM
12h 55m
2 stops
Southwest Logo
1:05 pm - 11:45 pm
GCM
-
SFO
12h 40m
2 stops
$570Southwest
Mon, May 4 - Thu, May 7
JetBlue Logo
10:35 am - 12:45 pm
SFO
-
GCM
24h 10m
2 stops
JetBlue Logo
2:05 pm - 11:51 pm
GCM
-
SFO
11h 46m
1 stop
$571JetBlue
Mon, May 4 - Thu, May 7
JetBlue Logo
7:00 am - 12:45 pm
SFO
-
GCM
27h 45m
2 stops
JetBlue Logo
2:05 pm - 11:51 pm
GCM
-
SFO
11h 46m
1 stop
$595JetBlue
Fri, May 15 - Tue, May 26
JetBlue Logo
10:45 pm - 12:19 pm
SFO
-
GCM
11h 34m
1 stop
JetBlue Logo
2:05 pm - 12:33 am
GCM
-
SFO
12h 28m
1 stop
$613JetBlue
Mon, Jul 13 - Fri, Jul 17
Southwest Logo
9:10 pm - 11:50 am
SFO
-
GCM
12h 40m
2 stops
Southwest Logo
12:45 pm - 11:25 pm
GCM
-
SFO
12h 40m
2 stops
$618Southwest
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 $531 (return) on average. On the other hand, the most expensive months are December and March, when the average cost of round-trip tickets is $1,100 and $714 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 10% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 7 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$269
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly with an average 8% 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 9546 reviews
7.7Boarding
8.1Crew
7.1Entertainment
6.6Food
7.3Comfort
Airline reviews

It was perfect! I've never flown with United before, but I definitely will in the future

10.0 ExcellentAnonymous, Apr 2026
SFO - LAS
Read more United Airlines reviews

It was perfect! I've never flown with United before, but I definitely will in the future

the entire flight felt off. The crew seemed uninterested and disengaged. The food service was really bad - overcooked, bland, weird food service. They actually woke us up to serve chicken wraps in the middle of the night, after dinner and before breakfast. Made no sense. Ultimately, I was glad they did though, because the breakfast had been held for so long it was inedible. Eggs, potatoes, sausage - all disgusting. We were asked to "honor" the lavatories for premium customers and stay in our own cabin: this was also strange. So people in economy didn't pay enough to use the closest toilet to them??? It's a toilet. All in all, not the experience I have come to expect from United Airlines. The return flight from Paris to SFO was better, btw.

They delayed the flight from 9:00 to 11:55 At 11:45 they canceled the flight. I paid a premium price for the tickets with poor service

The 777’s economy seat’s legroom was more tolerable than expected. I appreciate the reclining mechanism which slides the seat forward to minimize cannibalizing the space behind. The food was terrible: very salty.

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.

They forced me to check my hand luggage at the gate.

I specifically choose not to check bags to ensure I can proceed directly to ground transportation upon arrival. However, due to a recurring lack of cabin space, I was again forced to gate-check my rolling luggage after going through my luggage to take out electronics and batteries. This practice unilaterally changes the service agreement made at the time of purchase. JetBlue needs to find a better way to manage overhead space that honors the carry-on baggage allowance.

Still hasn’t left. Why are you asking how it was?

Flight was good wish there were more snacks options for such a long flight but stewardesses were very pleasant as was flight crew.

I was denied a plastic fork to eat my food and was told plastic forks are for paying customers who buy Jet Blue’s food. So I had to make a utensil out of a cup so nourish my body. Like a refugee. Because decency is dead.

I was especially impressed without efficiently the crew got passengers on and off. One of the stewards was slightly gruff, I thought. No big deal but that's what I noticed.

Absolutely horrible. Flight was delayed 4 hours and they had no clue what was going on.

Onboard functioning wide-variety entertainment on a budget and having an open pantry is nice. Seats are not comfortable but go provide plenty of legroom for a 6'2" 260lbs man.

Even though the weather made a lot of flights become cancelled Jet Blue made the flight that was supposed to leave at 9 pm and we left at 12:15 am and I was so grateful- Thanks to the Senior Jet Blue Staff who made those decisions

Worst customer service ever experienced on the planet, dirty plane, no communication, and severe delays

We left at 1030 am pacific from LA and supposed to land at 7 pm Eastern in NY. They made a detour, stopped in Philadelphia and didn’t land till 1130 PM Eastern!!! Worst flight experience with no pilot communication with no explanation as to what was going on. Everyone was very frustrated to say the least.

I cancelled my ticket less than 24 hours deadline but I didn’t get refunded.

Flight boarded from Gate 159B, the farthest gate in the LAX Bradley Terminal. While the flight operated on time, the first class cabin attendant made no recognition of my being an Advantage Executive Platinum member.

The flight itself was excellent but the gate attendant made me check my carryon since she said it was an inch too big. I’ve had no problems with this carryon on recent flights on Qantas, Delta, Austrian, Southwest Airlines even though the overhead bins are the same size. there were other carryons in the bins that also looked larger than mine and there was room left in the bins for more. When I picked up my carryon from baggage claim one of the wheels had broken off.

I was in last row so that is never great bc the person in front of me leaned his seat all the way back into me.

The experience at checkin for my American Airlines flight from Sacramento to LAX was very good including the assistance I received in getting my bags checked in and boarding passes printed. Was pleasantly surprised the my bags were checked through all the way to my destination at Clark International Airport in Angeles, Philippines.

Terrible planning. And even worse gate agents. Absolutely rude behavior.

Flight was scheduled at 11:26am but they keep Delaying until midnight. They waited at airport restless.

Rough flight No beverage service due to turbulence Bottom Seat cushion was non existent

Not good. One of my luggage is missing. And until now they can’t find it

Everything you need to know for your flight from San Francisco to the Cayman Islands

Information on your arrival and departure airports