$262 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 6/28. 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, Jun 8 - Mon, Jun 15
Multiple Airlines Logo
8:40 pm - 12:45 pm
SFO
-
GCM
14h 05m
1 stop
Multiple Airlines Logo
12:25 pm - 12:40 pm
GCM
-
SFO
26h 15m
1 stop
$557Multiple Airlines
Sun, Nov 1 - Sun, Nov 8
Southwest Logo
6:00 pm - 12:35 pm
SFO
-
GCM
15h 35m
2 stops
Southwest Logo
1:30 pm - 7:50 am
GCM
-
SFO
21h 20m
2 stops
$608Southwest
Wed, Jun 3 - Tue, Jun 9
JetBlue Logo
8:40 pm - 12:45 pm
SFO
-
GCM
14h 05m
1 stop
JetBlue Logo
2:05 pm - 12:33 am
GCM
-
SFO
12h 28m
1 stop
$625JetBlue
Fri, Sep 25 - Mon, Sep 28
Air Canada Logo
4:30 pm - 11:30 am
SFO
-
GCM
17h 00m
1 stop
Air Canada Logo
12:25 pm - 10:20 am
GCM
-
SFO
23h 55m
2 stops
$655Air Canada
Fri, Aug 21 - Wed, Aug 26
Delta Logo
4:05 pm - 11:39 am
SFO
-
GCM
17h 34m
1 stop
Delta Logo
1:04 pm - 9:58 pm
GCM
-
SFO
10h 54m
1 stop
$663Delta
Fri, Jun 19 - Mon, Jun 22
American Airlines Logo
3:37 pm - 10:22 am
SFO
-
GCM
16h 45m
1 stop
American Airlines Logo
5:12 pm - 10:53 am
GCM
-
SFO
19h 41m
1 stop
$664American Airlines
Thu, Sep 24 - Mon, Sep 28
Air Canada Logo
7:35 pm - 11:30 am
SFO
-
GCM
37h 55m
2 stops
Air Canada Logo
12:25 pm - 6:41 pm
GCM
-
SFO
32h 16m
2 stops
$665Air Canada
Thu, Jul 9 - Tue, Jul 14
American Airlines Logo
9:49 pm - 11:00 am
SFO
-
GCM
11h 11m
1 stop
American Airlines Logo
12:02 pm - 10:28 pm
GCM
-
SFO
12h 26m
2 stops
$668American Airlines
Wed, Jul 1 - Tue, Jul 7
American Airlines Logo
6:56 pm - 11:25 am
SFO
-
GCM
14h 29m
2 stops
American Airlines Logo
12:02 pm - 10:34 pm
GCM
-
SFO
12h 32m
1 stop
$673American Airlines
Thu, Sep 3 - Tue, Sep 8
American Airlines Logo
11:40 pm - 11:30 am
SFO
-
GCM
9h 50m
1 stop
American Airlines Logo
12:30 pm - 1:29 pm
GCM
-
SFO
26h 59m
1 stop
$681American Airlines
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 December, when tickets cost $350 (return) on average. On the other hand, the most expensive months are August and May, when the average cost of round-trip tickets is $623 and $532 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 12% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 15 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$262
Best time to beat the crowds with an average 22% drop in price.
Most popular time to fly with an average 5% 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 9751 reviews
6.6Food
7.3Comfort
8.1Crew
7.1Entertainment
7.7Boarding
Airline reviews

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.

2.0 MediocreCatie, May 2026
SFO - BOS
Read more United Airlines reviews

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.

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.

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.

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.

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

Great price, easy check in, love the free drinks and snacks, and nice crew. The only negative part was waiting for your seat assignment 5 minutes before boarding, and the seats are a bit uncomfortable.

What a great flight. Seats were more comfortable than other airlines. Flight was full but very easy to navigate. No stress no drama

Flight was quick, less time than expected, and the attendants all friendly and helpful. We had paid extra for more leg room and were very comfortable. Haven't flown JetBlue in quite a while. Glad to be back!

All airline travel outside of First or Business class is an ordeal to be endured. This trip was ok, small o, small k.

TV was broken and could not shut it off. The flicking was bother me and gave me a headache. The WiFi wouldn’t work correctly, I was able to text but not search the web or surf social media. The plane itself had a lot of wear and tear it is due for an update.

JetBlue not only has the most comfortable planes, but also used to have the best customer service. Lorie Wright, the lady at the gate was very rude not only to me, but to other passengers as well. Her colleague, the gentleman was also not very friendly. They both were acting like they were doing passengers a favor. The crew on board was very nice.

Flight was on time and smooth. Customer service was decent

The space between seat rows seemed to be larger than other airlines. I didn’t check their food or entertainment since I slept most of the way. They do seem to have a lot of options for purchase though.

Kayak sucked. You gave me a confirmation number that was not useable by the jet blue system. Nor did you send any check in emails. I’ll not be using your site again. Nice work.

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 from San Francisco to the Cayman Islands

Information on your arrival and departure airports