$244 Find Cheap Flights from San Diego 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 Diego to the Cayman Islands departing on 5/21. 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 Diego 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 Diego 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 Diego to the Cayman Islands

Mon, Mar 16 - Thu, Mar 19
American Airlines Logo
10:43 pm - 11:10 am
SAN
-
GCM
10h 27m
1 stop
American Airlines Logo
2:35 pm - 10:50 pm
GCM
-
SAN
10h 15m
1 stop
$451American Airlines
Mon, Mar 16 - Thu, Mar 19
American Airlines Logo
7:11 pm - 11:10 am
SAN
-
GCM
13h 59m
2 stops
American Airlines Logo
11:40 am - 10:59 pm
GCM
-
SAN
13h 19m
2 stops
$456American Airlines
Mon, Mar 16 - Thu, Mar 19
United Airlines Logo
10:30 pm - 12:15 pm
SAN
-
GCM
11h 45m
1 stop
United Airlines Logo
4:45 pm - 10:22 am
GCM
-
SAN
19h 37m
2 stops
$466United Airlines
Thu, Mar 26 - Mon, Mar 30
United Airlines Logo
5:50 pm - 3:30 pm
SAN
-
GCM
19h 40m
1 stop
United Airlines Logo
1:35 pm - 8:05 pm
GCM
-
SAN
8h 30m
1 stop
$486United Airlines
Sun, Mar 15 - Tue, Mar 17
United Airlines Logo
10:30 pm - 12:45 pm
SAN
-
GCM
12h 15m
1 stop
United Airlines Logo
4:45 pm - 10:40 am
GCM
-
SAN
19h 55m
2 stops
$490United Airlines
Sat, Apr 18 - Sat, Apr 25
American Airlines Logo
9:45 pm - 11:33 am
SAN
-
GCM
11h 48m
1 stop
American Airlines Logo
3:13 pm - 8:15 am
GCM
-
SAN
19h 02m
1 stop
$496American Airlines
Sun, Mar 15 - Thu, Mar 19
United Airlines Logo
10:30 pm - 12:45 pm
SAN
-
GCM
12h 15m
1 stop
United Airlines Logo
4:45 pm - 8:18 pm
GCM
-
SAN
29h 33m
1 stop
$497United Airlines
Sat, Apr 18 - Sat, Apr 25
American Airlines Logo
7:20 pm - 11:33 am
SAN
-
GCM
14h 13m
2 stops
American Airlines Logo
3:13 pm - 8:15 am
GCM
-
SAN
19h 02m
1 stop
$501American Airlines
Sun, Mar 29 - Wed, Apr 1
American Airlines Logo
7:52 pm - 10:40 am
SAN
-
GCM
12h 48m
2 stops
American Airlines Logo
3:15 pm - 11:59 pm
GCM
-
SAN
10h 44m
1 stop
$507American Airlines
Thu, Mar 26 - Mon, Mar 30
United Airlines Logo
5:50 pm - 3:30 pm
SAN
-
GCM
19h 40m
1 stop
United Airlines Logo
1:35 pm - 9:54 am
GCM
-
SAN
22h 19m
2 stops
$509United Airlines
Booking Insights

KAYAK's insights & trends for San Diego to the Cayman Islands flights

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

Which airlines provide the cheapest flights from San Diego to the Cayman Islands?

The cheapest round-trip price for the route for each airline clicked by KAYAK users in the last 72 hours.

In the past 3 days, the cheapest round-trip tickets from San Diego to the Cayman Islands were found on American Airlines ($451) and United Airlines ($466).

Good to know

Low seasonSeptember
Cheapest flight$244
Best time to beat the crowds with an average 21% drop in price.
Most popular time to fly and prices are also 3% lower on average.
Flight from San Diego to George Town

FAQs - booking Cayman Islands flights

  • How does KAYAK find such low prices on flights from San Diego 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 Diego 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 Diego to the Cayman Islands?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from San Diego 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 Diego 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 Diego 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 Diego 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 Diego 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 airlines flying from San Diego to the Cayman Islands

 
Need help choosing which airline to fly with from San Diego 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 9276 reviews
6.6Food
8.1Crew
7.7Boarding
7.3Comfort
7.1Entertainment
Airline reviews

Terrible. No customer service, no food, no drinks on a 6 hour premier economy booking.

2.0 MediocreAnonymous, Feb 2026
SFO - RDU
Read more United Airlines reviews

Terrible. No customer service, no food, no drinks on a 6 hour premier economy booking.

Check-in and in-flight staff were better than average. The seat was a fair size but too hard and not enough padding. The cushion/pillow provided is poor (thin and seems to be disposable ,it provides no effective cushioning or support). Food was OK-ish but no choice of inflight snacks and no easy place to get drinks other than water (I could ask for juice by intruding into the staff area at the back of the plane) Entertainment was very good actually. Overall better than I expected from a US-based airline (sorry!) but compared to ANA or Singapore it was so-so. (I live in Japan so they are my comparative airlines)

Terrible. Our first time back on United for 10 years, the seats in Polaris class are small and uncomfortable. They have squished too many people in to get more $$$. The staff are not friendly and not wanting to accommodate. I asked for two salads rather than a main meal and was advised no we wont do that. Then asked what I would like for breakfast and given something else anyway. I will not be flying United International anytime soon.

The food was terrible this time. Otherwise pleasant, quiet, on-time.

It was a pretty standard flight... until the almost hour and a half spent on the taxi way. I get that the weather has been poor but the delay had nothing to do with the weather and more to do with a plane with several issues tying up the gate. I get that that happens from time to time but this has been EVERY flight I've been on for the past 5 years and I fly 3 to 5 times a year. This isn't just United... it's American, it's Delta. It's an issue with the entire industry. I work for UPS and packages on a cargo plane get better service than people do these days. Anymore I HATE flying.

The flight crew where really good. Better then the crew from BNE to SFO

Food should be changed in menu Many muslims travels in this airlime they need to add one Halal meal

left on time, reasonable boarding process arrived early luggage came out quickly

Some flight attendants were great others were cranky. Seats were very tight and sitting on an aisle was very hard as the carts and people walking constantly bumped shoulder and arm.

It was great with United overall except for two things. 1) It was a 5-hour flight and we were with kids, so we were asking for extra snacks. They were extremely reticent to dole them out even though there wasn't any meal and the kids were starting to hit their limit towards the end. 2) Baggage didn't arrive until 80 minutes after we landed.

Flight was delayed for 2 hours, then last minute the change to on time. The satélite location is far and a nightmare to get to.

We flew in first class. The crew did not offer drinks before the flight took off, but they treated us well during the flight. The food was excellent. There was actually too much food served, but it was nice to have all the options.

For a 5 1/2 hour flite i considered the "business class" to be subpar. The seats were just ok, no amenities, really nothing more than a long domestic flight. Frankly disappointed.

It would be nice to have some low carb options in the snacks.

The entertainment options were at best, fair. It was exactly the same as my outbound flight. It would have been more entertaining if there were some series from Apple TV, HBO, Showtime or other carriers for me to catch up with.

The flight was on time and arrived early. The crew were friendly and helpful.

While I didn’t watch much tv I would have liked a few more options of TV series from Apple TV or hbo max ..

Overall experience was great. Flights were almost on time in departing and we arrived at our destination as scheduled. No issues with amenities or flight crew. Everything went well as as expected. Will fly again with American Airlines in the future!

The flight was very smooth and the meal in business class was great.

I requested a low sodium meal. Reason being, I take medicine for high blood pressure and I wear compression socks on long flights to help with leg swelling. Having less sodium in meals really helps me feel better on long flights. I received my initial low sodium meal after takeoff. Just before landing, the crew came through with the meal cart and offered me what was being served. I said no thank you and then noticed my low sodium meal in the meal cart, with my name and seat assignment on it. I motioned to the crew member, but he grabbed the meal cart and proceeded to move to the rear of the aircraft. He didn’t see me or other passengers who had attempted to get this attention. He was more concerned about completing meal service since we were due to land in under 45 minutes. I pressed the call light five times from my seat to receive help, but no crew member responded to me. So, I didn’t receive a second meal, one that I requested (the low sodium option). This led me to have a migraine from only eating one meal on an 11-hour flight. This is why I’m not a fan of flying US-based airlines overseas. The crew members continue to show the absolute worst customer service experience. I would not recommend flying American for overseas flights.

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

Information on your arrival and departure airports