$145 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 4/25. 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, Mar 15 - Tue, Mar 24
United Airlines Logo
8:50 pm - 12:45 pm
SAN
-
GCM
13h 55m
2 stops
United Airlines Logo
4:45 pm - 10:22 am
GCM
-
SAN
19h 37m
2 stops
$400United Airlines
Sun, Mar 15 - Tue, Mar 24
American Airlines Logo
10:30 pm - 1:35 pm
SAN
-
GCM
13h 05m
1 stop
American Airlines Logo
3:30 pm - 10:30 pm
GCM
-
SAN
9h 00m
1 stop
$471American Airlines
Mon, Mar 16 - Thu, Mar 19
JetBlue Logo
9:05 pm - 12:56 pm
SAN
-
GCM
13h 51m
2 stops
JetBlue Logo
2:40 pm - 7:52 pm
GCM
-
SAN
31h 12m
1 stop
$513JetBlue
Sun, Apr 26 - Sun, May 3
Southwest Logo
10:30 pm - 12:10 pm
SAN
-
GCM
11h 40m
1 stop
Southwest Logo
12:50 pm - 8:25 pm
GCM
-
SAN
9h 35m
1 stop
$530Southwest
Sun, Apr 26 - Sun, May 3
Southwest Logo
9:35 pm - 12:10 pm
SAN
-
GCM
12h 35m
2 stops
Southwest Logo
12:50 pm - 8:25 pm
GCM
-
SAN
9h 35m
1 stop
$535Southwest
Tue, Apr 14 - Sun, Apr 19
American Airlines Logo
12:53 pm - 1:10 pm
SAN
-
GCM
22h 17m
1 stop
American Airlines Logo
2:10 pm - 8:38 am
GCM
-
SAN
20h 28m
2 stops
$544American Airlines
Mon, Mar 16 - Thu, Mar 19
American Airlines Logo
1:37 pm - 11:10 am
SAN
-
GCM
19h 33m
1 stop
American Airlines Logo
7:45 am - 10:50 pm
GCM
-
SAN
17h 05m
1 stop
$547American Airlines
Mon, Mar 16 - Thu, Mar 19
American Airlines Logo
10:43 pm - 1:35 pm
SAN
-
GCM
12h 52m
2 stops
American Airlines Logo
11:40 am - 10:59 pm
GCM
-
SAN
13h 19m
2 stops
$552American 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
$555American Airlines
Wed, Apr 15 - Sun, Apr 19
United Airlines Logo
7:40 pm - 12:30 pm
SAN
-
GCM
14h 50m
2 stops
United Airlines Logo
1:35 pm - 8:05 pm
GCM
-
SAN
8h 30m
1 stop
$558United 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 United Airlines ($400) and American Airlines ($471).

Good to know

Low seasonSeptember
Cheapest flight$145
Best time to beat the crowds with an average 22% drop in price.
Most popular time to fly and prices are also 4% 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 9342 reviews
6.6Food
8.1Crew
7.1Entertainment
7.3Comfort
7.7Boarding
Airline reviews

We had turbulence ever 1/2 hr or so and the captains announcements were SOOOO LOUD

8.0 ExcellentAnonymous, Feb 2026
SFO - HKG
Read more United Airlines reviews

We had turbulence ever 1/2 hr or so and the captains announcements were SOOOO LOUD

Women boarding passengers at the gate was absolutely rude and disrespectful of passengers. The flight attendant was absolutely delightful! Smiling and connected with the passengers. So happy. The seats are cramped and uncomfortable but I guess that’s just the way it is Communication regarding flight was excellent

it was a very short flight so my expectations were low.

Entertainment kept turning itself off. Gave up on watching a movie.

Very disappointing given gate agent behavior. Filed a formal complaint with United.

Crew was great (professional, attentive, prompt). Snacks for 4 hrs flight is deplorable.

Flight delayed. WiFi connectivity very poor if not existant. Last minute arrival forced me to run to catch my connection.

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.

Experience was great. The best part is the free Wi-Fi connection which helps me to work on the flight

The flight was fine. It's the satellite terminal that supports American eagle flights is what sucks. There is only one food option and everything there is way overpriced. I mean I know it's airport pricing, but it's even crazier than that. I bought a sandwich in a plastic container for $18.

The flight was really crowded. Flight attendants were just ok.

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 ..

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

Information on your arrival and departure airports