$279 Find Cheap Flights from San Francisco to Grand Cayman

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 Grand Cayman departing on 6/5. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Grand Cayman

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from San Francisco to Grand Cayman, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from San Francisco to Grand Cayman, as well as popular online travel agencies
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Flight Deals

Book Cheap San Francisco to Grand Cayman 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 Grand Cayman 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 Grand Cayman

Tue, May 26 - Mon, Jun 1
Southwest Logo
3:55 pm - 12:10 pm
SFO
-
GCM
18h 15m
2 stops
Southwest Logo
1:05 pm - 11:45 pm
GCM
-
SFO
12h 40m
2 stops
$490Southwest
Fri, May 15 - Tue, May 26
Southwest Logo
9:15 pm - 3:00 pm
SFO
-
GCM
15h 45m
2 stops
Southwest Logo
1:05 pm - 10:45 pm
GCM
-
SFO
11h 40m
2 stops
$516Southwest
Fri, May 15 - Tue, May 26
JetBlue Logo
10:45 pm - 12:19 pm
SFO
-
GCM
11h 34m
1 stop
JetBlue Logo
2:05 pm - 12:33 am
GCM
-
SFO
12h 28m
1 stop
$542JetBlue
Wed, May 6 - Wed, May 13
Southwest Logo
7:15 pm - 12:10 pm
SFO
-
GCM
14h 55m
2 stops
Southwest Logo
1:05 pm - 10:45 pm
GCM
-
SFO
11h 40m
2 stops
$549Southwest
Wed, Aug 12 - Mon, Aug 17
Air Canada Logo
4:30 pm - 11:25 am
SFO
-
GCM
16h 55m
1 stop
Air Canada Logo
12:25 pm - 12:32 pm
GCM
-
SFO
26h 07m
1 stop
$571Air Canada
Wed, Jun 3 - Mon, Jun 8
Southwest Logo
7:15 pm - 11:50 am
SFO
-
GCM
14h 35m
2 stops
Southwest Logo
12:45 pm - 9:35 pm
GCM
-
SFO
10h 50m
2 stops
$575Southwest
Wed, May 27 - Sun, May 31
Multiple Airlines Logo
12:52 pm - 9:15 pm
SFO
-
GCM
30h 23m
2 stops
Multiple Airlines Logo
7:00 am - 4:41 pm
GCM
-
SFO
35h 41m
2 stops
$577Multiple Airlines
Sun, May 24 - Thu, May 28
Southwest Logo
7:45 pm - 12:10 pm
SFO
-
GCM
14h 25m
2 stops
Southwest Logo
1:05 pm - 10:25 pm
GCM
-
SFO
11h 20m
2 stops
$586Southwest
Wed, Aug 12 - Mon, Aug 17
Air Canada Logo
4:30 pm - 11:25 am
SFO
-
GCM
16h 55m
1 stop
Air Canada Logo
12:25 pm - 11:21 am
GCM
-
SFO
24h 56m
2 stops
$587Air Canada
Tue, May 26 - Tue, Jun 2
Multiple Airlines Logo
10:15 pm - 11:35 am
SFO
-
GCM
35h 20m
2 stops
Multiple Airlines Logo
1:45 pm - 12:20 pm
GCM
-
SFO
24h 35m
1 stop
$594Multiple Airlines
Booking Insights

KAYAK's insights & trends for San Francisco to Grand Cayman flights

Get data-powered insights and trends into flights from San Francisco to Grand Cayman to help you find the cheapest flights, the best time to fly and much more.

Can I save money by flying with a layover from San Francisco to Grand Cayman?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $628, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from San Francisco to Grand Cayman?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from San Francisco to Grand Cayman, 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 Grand Cayman is September, when tickets cost $531 (return) on average. On the other hand, the most expensive months are December and June, when the average cost of round-trip tickets is $1,100 and $722 respectively.

How far in advance should I book a flight from San Francisco to Grand Cayman?

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 Grand Cayman, 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 Grand Cayman, you should book around 3 weeks before departure, which saves you about 10% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 7 weeks before departure.

Good to know

Low seasonJanuary
Cheapest flight$279
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly with an average 9% increase in price.
Flight from San Francisco to George Town

FAQs - booking Grand Cayman flights

  • How does KAYAK find such low prices on flights from San Francisco to Grand Cayman?

    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 Grand Cayman.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from San Francisco to Grand Cayman?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from San Francisco to Grand Cayman 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 Grand Cayman?

    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 Grand Cayman 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 Grand Cayman?

    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 Grand Cayman 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 Grand Cayman

 
See real verified KAYAK customer reviews for airlines flying from San Francisco to Grand Cayman. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from San Francisco to Grand Cayman? 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 9637 reviews
7.1Entertainment
6.6Food
7.3Comfort
7.7Boarding
8.1Crew
Airline reviews

Flight itself excellent, but delayed so missed connection & got to destination 2 hrs later

8.0 ExcellentSandra, Apr 2026
SFO - FCO
Read more United Airlines reviews

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.

Boarding was again a "free for all". We were boarding group 4, and almost the entire plane was able to board before us. It's a shame that someone who follows the rules, gets the short end of the stick. Not fair.

It was perfect! I've never flown with United before, but I definitely will in the future

the entire flight felt off. The crew seemed uninterested and disengaged. The food service was really bad - overcooked, bland, weird food service. They actually woke us up to serve chicken wraps in the middle of the night, after dinner and before breakfast. Made no sense. Ultimately, I was glad they did though, because the breakfast had been held for so long it was inedible. Eggs, potatoes, sausage - all disgusting. We were asked to "honor" the lavatories for premium customers and stay in our own cabin: this was also strange. So people in economy didn't pay enough to use the closest toilet to them??? It's a toilet. All in all, not the experience I have come to expect from United Airlines. The return flight from Paris to SFO was better, btw.

They delayed the flight from 9:00 to 11:55 At 11:45 they canceled the flight. I paid a premium price for the tickets with poor service

The 777’s economy seat’s legroom was more tolerable than expected. I appreciate the reclining mechanism which slides the seat forward to minimize cannibalizing the space behind. The food was terrible: very salty.

Seats are uncomfortable. This has been a trend in the industry for decades. Trying to fit more seats on each plane to increase profits at the expense of the passenger.

Staff were good. My seat was in need of repair, but for a short flight was not problematic. Usual basic snack and drink setup that you'll find on any US carrier. Over, a decent, basic flight.

Crew was very friendly. Did not like being jammed in the back middle seat. Don’t understand why I can not select an aisle for free based on first come first serve. Also first time I’ve been on a flight which attempted land then circled Detroit airport multiple times.

Terrible. There was a lot of misleading information regarding ticketing, seat upgrades, & boarding group. I also expect my seat will recline. I have back problems & it is very painful for me of the seat doesn’t recline. In addition, when I choose a fare that allows me a carry-on bag, I expect to be able to carry it on. Not be forced to check it. Thos happened on my flight to MCO & back to Boston. Not sure I will ever fly JetBlue again. Further I bought the ticket through hat deal. I will NEVER do that again. They were incapable of providing an accurate record locator # for either leg of the trip. I had to call them before each flight with me VERY stressed about whether I would actually be able to get on my flight. Who does that? Who books flight & then FAILS to give an accurate record locator? Twice!

The flight was delayed 4 hours and the JetBlue people at the counter kept lying to us and telling us it was due to weather however all other flights were going in and out of NY and FL. Then they lied that the plane had to stop to refuel. Then they lied and said the plane needed a tire change. JetBlue is the worst. Then they gave a lot of people meal vouchers however I didn’t know they did that and they didn’t offer anything to me.

My experience with Jet Blue was wonderful. My experience with Kayak sucked and will never use again.

Jet Blue has excellent everything, Friendly customer service and staff, clean aircraft’s and is always on time.

Entertainment and wifi were very sub-par - audio issues and no wifi

We were delayed and had to circle due to weather and had to divert for fuel. While I understand that you can’t control the weather I would have appreciated knowing that the crew wasn’t going to run out of hours and then having to spend the night in the Raleigh airport.

Messy plane that was falling apart Small screens that didn't work

I was traveling with two small kids and our TV s were the only ones not working. Informed the flight attendant who did nothing about them.

They forced me to check my hand luggage at the gate.

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.

We left at 1030 am pacific from LA and supposed to land at 7 pm Eastern in NY. They made a detour, stopped in Philadelphia and didn’t land till 1130 PM Eastern!!! Worst flight experience with no pilot communication with no explanation as to what was going on. Everyone was very frustrated to say the least.

I cancelled my ticket less than 24 hours deadline but I didn’t get refunded.

Flight boarded from Gate 159B, the farthest gate in the LAX Bradley Terminal. While the flight operated on time, the first class cabin attendant made no recognition of my being an Advantage Executive Platinum member.

The flight itself was excellent but the gate attendant made me check my carryon since she said it was an inch too big. I’ve had no problems with this carryon on recent flights on Qantas, Delta, Austrian, Southwest Airlines even though the overhead bins are the same size. there were other carryons in the bins that also looked larger than mine and there was room left in the bins for more. When I picked up my carryon from baggage claim one of the wheels had broken off.

Everything you need to know for your flight to Grand Cayman

Information on your arrival and departure airports