$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 7/15. 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$623
Cayman Brac
Cayman Brac2 stops$1,096
Little Cayman
Little Cayman2 stops$1,340
George Town
George Town1 stop$623
Cayman Brac
Cayman Brac2 stops$1,096
Little Cayman
Little Cayman2 stops$1,340

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

Fri, Nov 13 - Sat, Nov 21
Air Canada Logo
10:45 pm - 12:00 pm
SFO
-
GCM
10h 15m
1 stop
Air Canada Logo
1:10 pm - 11:04 am
GCM
-
SFO
24h 54m
1 stop
$623Air Canada
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 - 12:35 am
GCM
-
SFO
13h 45m
2 stops
$644Southwest
Mon, Jul 6 - Fri, Jul 10
Southwest Logo
5:40 pm - 11:55 am
SFO
-
GCM
16h 15m
2 stops
Southwest Logo
12:50 pm - 12:15 am
GCM
-
SFO
13h 25m
2 stops
$661Southwest
Fri, Nov 13 - Sat, Nov 21
American Airlines Logo
5:00 pm - 11:58 am
SFO
-
GCM
15h 58m
2 stops
American Airlines Logo
3:14 pm - 12:35 am
GCM
-
SFO
12h 21m
2 stops
$668American Airlines
Thu, Jul 9 - Tue, Jul 14
American Airlines Logo
10:05 pm - 11:25 am
SFO
-
GCM
11h 20m
1 stop
American Airlines Logo
12:02 pm - 8:20 pm
GCM
-
SFO
10h 18m
1 stop
$673American Airlines
Thu, Jul 9 - Tue, Jul 14
American Airlines Logo
6:55 pm - 11:25 am
SFO
-
GCM
14h 30m
2 stops
American Airlines Logo
12:02 pm - 12:43 am
GCM
-
SFO
14h 41m
2 stops
$678American Airlines
Thu, Jul 23 - Fri, Jul 31
Multiple Airlines Logo
10:10 pm - 4:05 pm
SFO
-
GCM
15h 55m
2 stops
Multiple Airlines Logo
11:25 am - 8:48 am
GCM
-
SFO
23h 23m
2 stops
$680Multiple Airlines
Wed, Sep 2 - Sun, Sep 6
American Airlines Logo
11:40 pm - 11:27 am
SFO
-
GCM
9h 47m
1 stop
American Airlines Logo
12:30 pm - 10:40 pm
GCM
-
SFO
12h 10m
1 stop
$683American Airlines
Wed, Sep 2 - Sun, Sep 6
American Airlines Logo
11:40 pm - 11:27 am
SFO
-
GCM
9h 47m
1 stop
American Airlines Logo
12:30 pm - 12:11 am
GCM
-
SFO
13h 41m
2 stops
$688American Airlines
Fri, Nov 13 - Sat, Nov 21
Multiple Airlines Logo
6:12 pm - 1:20 pm
SFO
-
CYB
16h 08m
2 stops
Multiple Airlines Logo
7:10 am - 9:44 pm
CYB
-
SFO
17h 34m
2 stops
$1,096Multiple 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 50% 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 9808 reviews
7.3Comfort
7.1Entertainment
7.7Boarding
8.1Crew
6.6Food
Airline reviews

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.

2.0 MediocreAnonymous, Jun 2026
SFO - HND
Read more United Airlines reviews

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.

Some crew were unfriendly or in some cases just straight up rude.

Outstanding service, efficient & friendly crew, flight was safe, comfortable & on time

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.

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!

Nice plane, clean, wifi available and movies. All the flight attendants were courteous.

The gate attendant in Boston had a high raspy voice and spoke much too fast to be understood. Not pleasant.

The flight was delayed for more than 3 hours the flight attendant was so angry, it was my first flight with JetBlue but i don’t think I flight with them again.

First the flt was delayed over 2 hrs bc of plane mechanics that should have been handled better! No text or email was sent so only found out at the airport so there we sat for 5 hours! THATS RIDICULOUS! The gate area was filthy! No agents showed up till hr before so no additional info was given-waited online for 15 mins while the gate agent chatted and got together then given last seat in back of plane!! No priority for senior or anything-took attendants over 2hrs to serve drinks and snack-WHY are they not served together? By time snack came needed another drink! Worst service in my life!

Since we started at syr the service, crews, and flights were just excellent

All the TV screens in my rows was non functional . The map shown for an international route was antiqued..

It was fine for what it was. It’s not luxury travel but it was efficient, for the most part. Having my carry-on transferred into luggage however, was unwelcome.

We had better-than-average leg room and I loved the access to shows and movies. During boarding, we could not hear the agent even though we were close to the boarding door, which was kind of scary when we realized that half of the passengers had already boarded. Also, the entertainment was awesome, but I could not hear the movie as well as I would have liked, because my headphones were crappy. It would have been better if I could connect my own ear buds via Bluetooth or if JetBlue provided headphones.

On time, friendly attendants, quick wheelchair assistance and help checking in bags. Also appreciated change in seats, more forward to make it easier for my 97 year old mother to board and exit the plane. Thank you, JetBlue!

Flight did not have onboard charging and TV screen flickering.

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

Information on your arrival and departure airports