$262 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 6/11. 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

Thu, Nov 12 - Sun, Nov 15
Southwest Logo
10:35 pm - 12:35 pm
SAN
-
GCM
11h 00m
1 stop
Southwest Logo
1:30 pm - 11:40 pm
GCM
-
SAN
13h 10m
2 stops
$494Southwest
Thu, Nov 12 - Sun, Nov 15
Southwest Logo
10:35 pm - 12:35 pm
SAN
-
GCM
11h 00m
1 stop
Southwest Logo
1:30 pm - 8:00 pm
GCM
-
SAN
9h 30m
1 stop
$522Southwest
Fri, Jun 19 - Sat, Jun 27
American Airlines Logo
6:45 pm - 10:22 am
SAN
-
GCM
13h 37m
1 stop
American Airlines Logo
2:17 pm - 9:48 pm
GCM
-
SAN
9h 31m
1 stop
$564American Airlines
Fri, Jun 19 - Sat, Jun 27
United Airlines Logo
6:55 pm - 12:30 pm
SAN
-
GCM
15h 35m
2 stops
United Airlines Logo
1:35 pm - 9:24 pm
GCM
-
SAN
9h 49m
1 stop
$595United Airlines
Mon, Jul 13 - Sun, Jul 19
American Airlines Logo
9:25 pm - 11:25 am
SAN
-
GCM
12h 00m
1 stop
American Airlines Logo
5:10 pm - 8:16 am
GCM
-
SAN
17h 06m
2 stops
$618American Airlines
Fri, Jun 19 - Sat, Jun 27
United Airlines Logo
4:07 pm - 1:30 pm
SAN
-
GCM
19h 23m
2 stops
United Airlines Logo
4:45 pm - 10:49 pm
GCM
-
SAN
32h 04m
2 stops
$635United Airlines
Mon, Jul 13 - Sun, Jul 19
American Airlines Logo
6:45 pm - 1:36 pm
SAN
-
GCM
16h 51m
1 stop
American Airlines Logo
5:10 pm - 11:12 am
GCM
-
SAN
20h 02m
1 stop
$636American Airlines
Thu, Nov 19 - Fri, Nov 27
Air Canada Logo
11:50 am - 12:00 pm
SAN
-
GCM
21h 10m
1 stop
Air Canada Logo
1:10 pm - 10:53 am
GCM
-
SAN
24h 43m
1 stop
$1,001Air Canada
Thu, Nov 12 - Sun, Nov 15
Multiple Airlines Logo
6:01 pm - 12:00 pm
SAN
-
GCM
38h 59m
3 stops
Multiple Airlines Logo
1:10 pm - 5:06 pm
GCM
-
SAN
30h 56m
3 stops
$1,046Multiple Airlines
Thu, Nov 19 - Fri, Nov 27
Air Canada Logo
11:50 am - 12:00 pm
SAN
-
GCM
21h 10m
1 stop
Air Canada Logo
1:10 pm - 1:04 pm
GCM
-
SAN
26h 54m
2 stops
$1,105Air Canada
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 October, 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 $736 and $701 respectively.

Good to know

Low seasonSeptember
Cheapest flight$262
Best time to beat the crowds with an average 26% drop in price.
Most popular time to fly and prices are also 7% 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 9768 reviews
7.3Comfort
7.7Boarding
6.6Food
7.1Entertainment
8.1Crew
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

Flight was delayed but more than 90 minutes. This caused me to miss my available windows for pick-up by a friend. I had to pay $125 for an uber back home from the airport which was an added expense that I had not budgeted for my trip. Staff was friendly.

Seat pitch is horrible especially on the 15 hour flight. Gate crew at SFO was Outstanding. The flight crew was also great.

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.

Late plane. Only one crew on the ground so we b had to wait for Denver flight to come in, board, and depart. At 78 yrs of age I was not pleased trying to get my connection. What really made me angry was the notification you sent me to hurry up or I would miss my connection. Why tell me to hurry up when you got me in late. It was not a good way of treating customers.

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.

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.,

The SFO Lounge crew were amazing. The bartender Faris was great. Thanks!

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

Information on your arrival and departure airports