$250 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 9/18. 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

Sat, Oct 3 - Sat, Oct 10
Air Canada Logo
7:35 pm - 11:30 am
SFO
-
GCM
37h 55m
2 stops
Air Canada Logo
12:25 pm - 3:21 pm
GCM
-
SFO
28h 56m
2 stops
$563Air Canada
Mon, Jun 22 - Fri, Jun 26
Southwest Logo
6:10 pm - 11:55 am
SFO
-
GCM
15h 45m
2 stops
Southwest Logo
12:50 pm - 12:10 am
GCM
-
SFO
13h 20m
2 stops
$634Southwest
Thu, Aug 13 - Wed, Aug 19
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
Thu, Jul 9 - Tue, Jul 14
American Airlines Logo
6:55 pm - 11:00 am
SFO
-
GCM
14h 05m
2 stops
American Airlines Logo
2:41 pm - 10:28 pm
GCM
-
SFO
9h 47m
1 stop
$668American Airlines
Sat, Oct 10 - Sat, Oct 17
Air Canada Logo
6:25 pm - 11:30 am
SFO
-
GCM
39h 05m
2 stops
Air Canada Logo
12:25 pm - 3:21 pm
GCM
-
SFO
28h 56m
2 stops
$669Air Canada
Wed, Jul 1 - Thu, Jul 9
American Airlines Logo
11:59 pm - 4:10 pm
SFO
-
GCM
14h 11m
1 stop
American Airlines Logo
12:02 pm - 10:28 pm
GCM
-
SFO
12h 26m
2 stops
$673American Airlines
Thu, Sep 3 - Tue, Sep 8
American Airlines Logo
12:31 pm - 11:27 am
SFO
-
GCM
20h 56m
1 stop
American Airlines Logo
12:30 pm - 8:56 am
GCM
-
SFO
22h 26m
2 stops
$685American Airlines
Thu, Sep 3 - Tue, Sep 8
American Airlines Logo
12:31 pm - 11:27 am
SFO
-
GCM
20h 56m
1 stop
American Airlines Logo
12:30 pm - 10:57 am
GCM
-
SFO
24h 27m
1 stop
$698American Airlines
Fri, Jul 17 - Sat, Jul 25
United Airlines Logo
11:59 pm - 3:35 pm
SFO
-
GCM
13h 36m
1 stop
United Airlines Logo
4:45 pm - 12:05 am
GCM
-
SFO
9h 20m
1 stop
$708United Airlines
Mon, Jun 29 - Mon, Jul 6
American Airlines Logo
11:49 pm - 11:30 am
SFO
-
GCM
9h 41m
1 stop
American Airlines Logo
5:10 pm - 10:24 am
GCM
-
SFO
19h 14m
1 stop
$722American 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 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$250
Best time to beat the crowds with an average 25% drop in price.
Most popular time to fly with an average 1% 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 9778 reviews
6.6Food
7.3Comfort
8.1Crew
7.1Entertainment
7.7Boarding
Airline reviews

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

2.0 MediocreAnonymous, May 2026
SFO - TPA
Read more United Airlines reviews

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

United Airline crews were very friendly and very attentive. 12 hours flight was gone like in a shorter one.

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!

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.,

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.

I was seated next to an autistic child who was out of control and had a child behind me kicking my seat for most of the trip. I will never fly JetBlue again. Ever. I don't care how cheap it is. It's terrible.

Boarding process was terrible. No assigned seat until the gate, then a long line to get seat assignment.

This was the first flight I've taken since pre-pandemic. I was pleased with how orderly the boarding and disembarking went. The seats were comfortable. I loved that there was no "first class'. The attendants and passengers I met were all very friendly and welcoming.

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

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