$186 Find Cheap Flights from San Diego to the Cayman Islands - Compare and Save

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 9/15. 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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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

Sun, Sep 13 - Sat, Sep 19
Delta Logo
9:45 pm - 11:40 am
SAN
-
GCM
11h 55m
1 stop
Delta Logo
1:05 pm - 9:19 pm
GCM
-
SAN
10h 14m
1 stop
$477Delta
Sun, Sep 13 - Sat, Sep 19
American Airlines Logo
7:15 pm - 11:27 am
SAN
-
GCM
14h 12m
2 stops
American Airlines Logo
12:36 pm - 8:18 am
GCM
-
SAN
21h 42m
2 stops
$482American Airlines
Thu, Sep 10 - Mon, Sep 14
American Airlines Logo
10:27 pm - 11:27 am
SAN
-
GCM
11h 00m
1 stop
American Airlines Logo
12:36 pm - 8:59 am
GCM
-
SAN
22h 23m
1 stop
$490American Airlines
Tue, Sep 1 - Tue, Sep 8
American Airlines Logo
10:45 pm - 11:00 am
SAN
-
GCM
10h 15m
1 stop
American Airlines Logo
12:00 pm - 10:00 pm
GCM
-
SAN
12h 00m
1 stop
$503American Airlines
Tue, Sep 1 - Tue, Sep 8
American Airlines Logo
10:20 pm - 1:10 pm
SAN
-
GCM
12h 50m
2 stops
American Airlines Logo
2:10 pm - 10:25 am
GCM
-
SAN
22h 15m
2 stops
$508American Airlines
Tue, Sep 15 - Mon, Sep 21
American Airlines Logo
10:27 pm - 11:27 am
SAN
-
GCM
11h 00m
1 stop
American Airlines Logo
12:36 pm - 8:59 am
GCM
-
SAN
22h 23m
1 stop
$517American Airlines
Sun, Dec 13 - Tue, Dec 22
American Airlines Logo
12:55 pm - 12:10 pm
SAN
-
GCM
20h 15m
1 stop
American Airlines Logo
3:45 pm - 10:55 pm
GCM
-
SAN
10h 10m
1 stop
$518American Airlines
Sun, Aug 9 - Tue, Aug 18
American Airlines Logo
10:26 pm - 11:27 am
SAN
-
GCM
11h 01m
1 stop
American Airlines Logo
12:00 pm - 10:00 pm
GCM
-
SAN
12h 00m
1 stop
$529American Airlines
Sun, Aug 9 - Tue, Aug 18
American Airlines Logo
10:45 pm - 11:00 am
SAN
-
GCM
10h 15m
1 stop
American Airlines Logo
12:30 pm - 8:12 am
GCM
-
SAN
21h 42m
2 stops
$534American Airlines
Mon, Jan 4 - Mon, Jan 11
American Airlines Logo
7:30 pm - 11:57 am
SAN
-
GCM
13h 27m
2 stops
American Airlines Logo
8:45 am - 9:58 pm
GCM
-
SAN
16h 13m
2 stops
$553American 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.

What is the cheapest month to fly from San Diego 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 Diego 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 Diego to the Cayman Islands is August, when tickets cost $0 (return) on average. On the other hand, the most expensive months are November and June, when the average cost of round-trip tickets is $850 and $701 respectively.

Good to know

Low season

September

Cheapest flight

$186
Best time to beat the crowds with an average 19% drop in price.
Most popular time to fly and prices are also 9% 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 10013 reviews
7.1Entertainment
8.1Crew
7.7Boarding
6.6Food
7.3Comfort
Airline reviews

Service was professional and quick. Premium economy seat was comfortable given the class

10.0 ExcellentDavid, Jun 2026
SAN - LAX
Read more United Airlines reviews

Service was professional and quick. Premium economy seat was comfortable given the class

The staff was extremely helpful and friendly at all times! They went above and beyond to get us into an earlier flight in San Diego to make our connection in SFO possible, because our original flight did actually not make it! I did so much appreciate the UA team and how they made this possible. We also didn’t have seats together on the long flight to Singapore, but they found us seats together last moment with no additional cost! Nobody sat next to us, so that we were able to sleep! Thanks to UA for improving their service and Underpricer for booking this trip! Please be careful: 1,5 hrs for transfer in San Francisco might not be enough time in the future

Over 2.5 hour maintenance delay on first morning flight with no acknowledgement, compensation or even gesture of good will. Aircraft had overnighted at airport so issue should have been addressed prior to boarding. Over 3.5 hours before first slow and deliberate beverage service.

Complimentary light meal would be appreciated. But great flight crew service on all legs

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

I was in first class. The outlets at my seat did not work. The plane was shabby and run down. I had prepurchsed a day subscription for internet that was not redeemable. I had to repurchase the internet for my flight and then it didn’t work anyway. Quite disappointed in what was supposed to be the launch of a great vacation.

As usual, United scheduling is completely misleading. A 54-minute layover at O’Hare is too short to make a lot of connections, especially since the flight landed “on time” but had to wait on the taxiway 15 minutes for a gate to open up. Then it takes another 10 minutes to exit the plane before one can run to another concourse to catch a connecting flight.

Flight was ok. Unfortunately it was a Boeing 737, which is a cramped / tight airplane. I prefer the Airbus as they are a more comfortable flight experience.

We were traveling as a family of 5 and they refused to seat us together. There were entire rows open, and my 13 year old daughter had to sit alone. Ridiculous!

Do not like the feeling of being in the basic economy. Everyone should feel good no matter what.

Well, true to American Airlines, both of my flights were delayed. But it’s a good thing that American is so consistently incompetent because if the first flight was delayed in the second flight was on time then I might’ve had a problem..

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.

The entertainment package was vast and the selections were very current. Keep updating it was great.

The seat was so hard my tailbone was aching The crew was kind of a b**** because I made a joke that I didn't care if they close the door I total c*** when she was trying to f****** act like she was mad at me because I said that The flight was bumpy. Sure you didnt have control over that.

Cramped seats. FAA should make airlines have more legroom, for even short people complain

Flight was full, and would have preferred an aisle seat, but due to getting a late ticket ,the seat I had was adequate. The flight crew were very help full and hard working. Food and drink were excellent for the 11hr flight. Overall I was pleased with flight, and would recommend British Airways again.

The plane was late and then sat on the runway for almost 45 minutes before taking off.

Had to wait on pilot and crew to depart and had to wait to arrive at the gate because they only had 2 crews working. Delays, delays....Planes just keep getting smaller and tighter and they nickle and dime for everything. When will an airline actually wake up and make flying more enjoyable?

I paid for what I got which was cheap, I brought my own entertainment. I knew what to expect, so I could be prepared. If you’re flying economy, check in early like me. I have no problems with my flight, was on time, staff were friendly, and overall good experience.

Multiple maintenance delays and the missed and rebooked connection changed gates at least 6 times including one which had us walking 20 minutes to another terminal and then back again. Seated our family of three in different middle seats throughout the plane and then there was an empty seat next to me. Very long travel day which I would have never agreed to if I knew the itinerary would be changed at 5 am, 2 hours before takeoff.

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

Information on your arrival and departure airports