$267 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 7/17. 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 Town2 stops$631
Cayman Brac
Cayman Brac2 stops$1,324
Little Cayman
Little Cayman2 stops$1,484
George Town
George Town2 stops$631
Cayman Brac
Cayman Brac2 stops$1,324
Little Cayman
Little Cayman2 stops$1,484

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, Jul 29 - Tue, Aug 4
Multiple Airlines Logo
4:30 pm - 9:15 pm
SFO
-
GCM
26h 45m
2 stops
Multiple Airlines Logo
11:30 am - 10:25 am
GCM
-
SFO
24h 55m
2 stops
$631Multiple Airlines
Thu, Jul 9 - Wed, Jul 15
Southwest Logo
10:50 pm - 11:55 am
SFO
-
GCM
11h 05m
2 stops
Southwest Logo
12:50 pm - 11:30 pm
GCM
-
SFO
12h 40m
2 stops
$654Southwest
Thu, Sep 3 - Tue, Sep 8
American Airlines Logo
9:35 pm - 11:00 am
SFO
-
GCM
11h 25m
1 stop
American Airlines Logo
2:10 pm - 11:53 pm
GCM
-
SFO
11h 43m
1 stop
$673American Airlines
Thu, Sep 3 - Tue, Sep 8
American Airlines Logo
5:00 pm - 11:27 am
SFO
-
GCM
16h 27m
2 stops
American Airlines Logo
2:10 pm - 10:12 am
GCM
-
SFO
22h 02m
2 stops
$678American Airlines
Thu, Jul 9 - Tue, Jul 14
American Airlines Logo
9:49 pm - 11:00 am
SFO
-
GCM
11h 11m
1 stop
American Airlines Logo
12:33 pm - 10:48 pm
GCM
-
SFO
12h 15m
1 stop
$683American Airlines
Thu, Jul 9 - Tue, Jul 14
American Airlines Logo
11:49 pm - 11:00 am
SFO
-
GCM
9h 11m
1 stop
American Airlines Logo
12:02 pm - 12:43 am
GCM
-
SFO
14h 41m
2 stops
$688American Airlines
Wed, Jul 15 - Wed, Jul 22
American Airlines Logo
6:55 pm - 11:25 am
SFO
-
GCM
14h 30m
2 stops
American Airlines Logo
12:02 pm - 10:28 pm
GCM
-
SFO
12h 26m
2 stops
$693American Airlines
Sun, Oct 11 - Sun, Oct 18
American Airlines Logo
7:36 pm - 12:35 pm
SFO
-
GCM
14h 59m
2 stops
American Airlines Logo
3:30 pm - 11:42 am
GCM
-
SFO
22h 12m
1 stop
$704American Airlines
Mon, Jul 6 - Mon, Jul 13
Southwest Logo
10:50 pm - 11:55 am
SFO
-
GCM
11h 05m
2 stops
Southwest Logo
12:50 pm - 9:35 pm
GCM
-
SFO
10h 45m
2 stops
$705Southwest
Sun, Aug 16 - Sat, Aug 22
Multiple Airlines Logo
4:40 pm - 3:25 pm
SFO
-
CYB
20h 45m
2 stops
Multiple Airlines Logo
2:10 pm - 8:40 am
CYB
-
SFO
20h 30m
2 stops
$1,324Multiple 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 June and August, when the average cost of round-trip tickets is $649 and $623 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 1 week before departure. For the absolute cheapest price, our data suggests you should book 15 weeks before departure.

Good to know

Low seasonSeptember
Cheapest flight$267
Best time to beat the crowds with an average 27% drop in price.
Most popular time to fly with an average 51% 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 9861 reviews
7.1Entertainment
7.3Comfort
7.7Boarding
8.1Crew
6.7Food
Airline reviews

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

10.0 ExcellentClaudia, Jun 2026
SFO - SIN
Read more United Airlines reviews

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.

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.

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.

Ontario airport boarding was very easy to park and access, is clean and TSA took 10 minutes total. Check-in was a breeze and cruise was very nice.

It's a long flight and that is always difficult. I was comfortable and well. The movies available were great and the crew was good.

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!

They lost my luggage and refuse to help. Terrible airline. I've never experienced worse customer service in my life. Pretty much just told me too bad that I lost all my luggage, not caring that I am stuck in Europe for 2 weeks with absolutely nothing.

You should have had Wifi to make it much enjoyable.

The flight out was delayed from 3:40pm to 5pm and again to 8pm. We boarded after 5pm, had to disembark because they could not get the Engine started, then we switched gates and got a new plane and did not board until after 8pm.

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

Information on your arrival and departure airports