$258 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 7/22. 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 Town2 stops$593
Cayman Brac
Cayman Brac2 stops$1,326
George Town
George Town2 stops$593
Cayman Brac
Cayman Brac2 stops$1,326

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, Nov 4 - Mon, Nov 9
Southwest Logo
2:20 pm - 12:35 pm
SFO
-
GCM
19h 15m
2 stops
Southwest Logo
1:30 pm - 9:45 am
GCM
-
SFO
23h 15m
2 stops
$593Southwest
Sat, Aug 22 - Sat, Aug 29
American Airlines Logo
11:40 pm - 11:30 am
SFO
-
GCM
9h 50m
1 stop
American Airlines Logo
3:17 pm - 11:10 pm
GCM
-
SFO
9h 53m
1 stop
$683American Airlines
Sat, Aug 22 - Sat, Aug 29
American Airlines Logo
4:31 pm - 11:00 am
SFO
-
GCM
16h 29m
2 stops
American Airlines Logo
11:55 am - 10:18 pm
GCM
-
SFO
12h 23m
2 stops
$688American Airlines
Wed, Nov 4 - Sun, Nov 8
American Airlines Logo
11:59 pm - 11:58 am
SFO
-
GCM
8h 59m
1 stop
American Airlines Logo
3:14 pm - 10:58 pm
GCM
-
SFO
10h 44m
1 stop
$693American Airlines
Wed, Nov 4 - Sun, Nov 8
American Airlines Logo
11:59 pm - 2:17 pm
SFO
-
GCM
11h 18m
2 stops
American Airlines Logo
1:00 pm - 10:58 pm
GCM
-
SFO
12h 58m
1 stop
$698American Airlines
Thu, Jul 16 - Sat, Jul 25
American Airlines Logo
6:55 pm - 11:00 am
SFO
-
GCM
14h 05m
2 stops
American Airlines Logo
3:15 pm - 8:53 am
GCM
-
SFO
19h 38m
1 stop
$703American Airlines
Wed, Jul 15 - Mon, Jul 20
Southwest Logo
9:10 pm - 11:55 am
SFO
-
GCM
12h 45m
2 stops
Southwest Logo
12:50 pm - 11:30 pm
GCM
-
SFO
12h 40m
2 stops
$713Southwest
Fri, Jul 31 - Wed, Aug 5
American Airlines Logo
11:49 pm - 3:03 pm
SFO
-
GCM
13h 14m
1 stop
American Airlines Logo
12:00 pm - 8:18 pm
GCM
-
SFO
10h 18m
1 stop
$732American Airlines
Thu, Jul 16 - Sat, Jul 25
American Airlines Logo
6:55 pm - 11:25 am
SFO
-
GCM
14h 30m
2 stops
American Airlines Logo
4:07 pm - 11:33 pm
GCM
-
SFO
9h 26m
1 stop
$737American Airlines
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
$1,326Multiple 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$258
Best time to beat the crowds with an average 14% drop in price.
Most popular time to fly with an average 49% 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 9889 reviews
7.3Comfort
6.6Food
8.1Crew
7.7Boarding
7.1Entertainment
Airline reviews

Lost one piece of luggage even though I checked in 2.5 hours before the flight

6.0 Goodmerrill, Jun 2026
SFO - MCO
Read more United Airlines reviews

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

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.

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.

The SFO Lounge crew were amazing. The bartender Faris was great. Thanks!

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

Dloght delayed by 2.5 hrs . Common theme in my last four american floghts

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.

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 from San Francisco to the Cayman Islands

Information on your arrival and departure airports