$196 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 1/22. 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

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

Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 22% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Bundle and saveSave money when you bundle your flight + hotel.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
Flight Deals

Cheap Flights from San Diego to the Cayman Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
George Town
George Town1 stop$496
George Town
George Town1 stop$496

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

Tue, Dec 2 - Mon, Dec 8
American Airlines Logo
10:23 pm - 12:01 pmSAN-GCM
10h 38m1 stop
American Airlines Logo
8:45 am - 11:00 pmGCM-SAN
17h 15m1 stop
$496American Airlines
Find Deal
Tue, Dec 2 - Mon, Dec 8
American Airlines Logo
10:23 pm - 2:42 pmSAN-GCM
13h 19m2 stops
American Airlines Logo
1:25 pm - 11:00 pmGCM-SAN
12h 35m1 stop
$500American Airlines
Find Deal
Wed, Dec 3 - Mon, Dec 8
American Airlines Logo
12:43 pm - 2:24 pmSAN-GCM
22h 41m1 stop
American Airlines Logo
3:45 pm - 11:00 pmGCM-SAN
10h 15m1 stop
$509American Airlines
Find Deal
Tue, Dec 2 - Mon, Dec 8
American Airlines Logo
10:23 pm - 2:42 pmSAN-GCM
13h 19m2 stops
American Airlines Logo
8:45 am - 10:21 pmGCM-SAN
16h 36m2 stops
$557American Airlines
Find Deal
Sat, Dec 6 - Sat, Dec 13
American Airlines Logo
9:54 pm - 12:10 pmSAN-GCM
11h 16m2 stops
American Airlines Logo
8:45 am - 8:57 pmGCM-SAN
15h 12m2 stops
$584American Airlines
Find Deal
Tue, Dec 2 - Mon, Dec 8
United Airlines Logo
5:45 pm - 4:30 pmSAN-GCM
19h 45m3 stops
United Airlines Logo
5:45 pm - 12:50 pmGCM-SAN
22h 05m2 stops
$610United Airlines
Find Deal
Tue, Dec 2 - Mon, Dec 8
United Airlines Logo
5:45 pm - 4:30 pmSAN-GCM
19h 45m3 stops
United Airlines Logo
5:45 pm - 3:02 pmGCM-SAN
24h 17m2 stops
$630United Airlines
Find Deal
Mon, Mar 2 - Fri, Mar 6
 Logo
7:30 pm - 4:25 pmSAN-GCM
17h 55m2 stops
 Logo
10:00 am - 7:31 pmGCM-SAN
12h 31m1 stop
$2,378
Find Deal
Wed, Feb 25 - Wed, Mar 4
 Logo
8:20 am - 1:44 pmSAN-GCM
26h 24m2 stops
 Logo
10:00 am - 7:31 pmGCM-SAN
12h 31m1 stop
$2,380
Find Deal
Fri, Feb 27 - Fri, Mar 6
Delta Logo
10:10 pm - 12:50 pmSAN-GCM
11h 40m1 stop
Delta Logo
2:00 pm - 11:11 pmGCM-SAN
12h 11m1 stop
$3,852Delta
Find Deal
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 February, when tickets cost $548 (return) on average. On the other hand, the most expensive months are March and October, when the average cost of round-trip tickets is $883 and $847 respectively.

What’s the cheapest day of the week to fly from San Diego to Cayman Islands?

The average price of all round-trip flights from San Diego to the Cayman Islands clicked on KAYAK for each day over the last 12 months.

Your flight ticket price will generally be cheaper if you fly to Cayman Islands on a Tuesday and more expensive on a Friday. On your return trip to San Diego, you should consider flying back on a Saturday, and avoid Fridays for better deals.

Good to know

Low seasonFebruary
Cheapest flight$196
Best time to beat the crowds with an average 16% drop in price.
Most popular time to fly and prices are also 1% 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.

  • What is the cheapest time of day to fly to the Cayman Islands?

    The cheapest time of day to fly to the Cayman Islands is generally in the morning, when round-trip flights cost $567 on average. Morning departures are around 8% cheaper than evening flights, on average. The most expensive time of day to fly to the Cayman Islands is generally in the evening, which is peak travel time and where the average cost of a ticket is $617.

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 8939 reviews
7.1Entertainment
7.3Comfort
6.6Food
7.7Boarding
8.1Crew
Airline reviews

From the first moment you interact with United Airlines, you can expect nothing less but extreme frustration. The baggage handler at the bag drop seems completely unbothered by the presence of customers waiting in line. No help was extended to load the baggage whatsoever. And if any of your bags is overweight by 0.01 pound they will make you re-distribute everything in your suitcase just to play power trip. When it was time to board no help was extended to customers to locate their seats. Moreover. It was a chaotic mess at the gate when it was unclear who should board first and everyone just bunched up, trying to get on the plane. I am sure the crew was doing their best to perform their jobs while being paid their wages however it shouldn’t be that hard to smile once or twice when you’re in the business if serving customers. It is a shame for the United States of America to have a flagship carrier of such low caliber. Our flight was also delayed by about an hour and a half due to further delays prior to our inbound flight. Being someone who has travelled for both business and leisure in Asia, Europe, and South America I have never experienced such poor quality of service.

2.0 MediocreMartin, Aug 2025SFO - YVR
Read more United Airlines reviews

From the first moment you interact with United Airlines, you can expect nothing less but extreme frustration. The baggage handler at the bag drop seems completely unbothered by the presence of customers waiting in line. No help was extended to load the baggage whatsoever. And if any of your bags is overweight by 0.01 pound they will make you re-distribute everything in your suitcase just to play power trip. When it was time to board no help was extended to customers to locate their seats. Moreover. It was a chaotic mess at the gate when it was unclear who should board first and everyone just bunched up, trying to get on the plane. I am sure the crew was doing their best to perform their jobs while being paid their wages however it shouldn’t be that hard to smile once or twice when you’re in the business if serving customers. It is a shame for the United States of America to have a flagship carrier of such low caliber. Our flight was also delayed by about an hour and a half due to further delays prior to our inbound flight. Being someone who has travelled for both business and leisure in Asia, Europe, and South America I have never experienced such poor quality of service.

I understand stuff happens, but plane failures are likely due to lack of maintenance. Additionally, air conditioning wasn't working, no snack/drink service, no WiFi. Fortunately, the crew was communicative and light-hearted. United grabbed another plane and we were able to get to our destination.

The pilots were late and it made us 1 hour late. The meat was tough and bok choy was also tough.

Stuck on tarmac for two hours plus a 5.5 hour flight. Rude flight attendant. And no meals, not even for purchase!

I learned that seating towards the end of plane that a line forms for the restroom and people use your chair as a hand railing, bumping your seat consistently. I was seated in the aisle. I think that next time if I am towards the back row I would want to sit in the middle or window seat.

The best airline I have ever travel , really good customer service, attention and service !!

United sent me a mileage plus number last year but that number is invalid so I can’t use it to check into flights or collect mileage. There is human to speak about the problem, only computers who keep asking me if I am using the correct email. It’s so frustrating and I cannot resolve it.

Not a great experience. We paid for the upgrade for premium economy seats and seated ourselves in very comfortable seats. Someone came along with the same seat on their boarding pass. The aircraft had been changed and as a result we were booted out and sent further back to small uncomfortable seats. After complaining we were moved to emergency row seats, which gave us more leg room but the seats don’t recline. For people in our 70’s we found having to sit upright from California to NJ very uncomfortable. Not sure why they chose to move senior citizens instead of the two people that were allowed to take the more comfortable seats. Not happy.

Everything was great. Only thing that could’ve made it better was buy on board options for hot food, but the snacks were decent. The flight attendants were great. I had no complaints. I was able to make it to my destination safely

Boarded plane and then delayed 1.5 hours while on the plane

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.

4 hours late, including over +1 hour waiting in plane to take off. Baggage left behind too.

While waiting to claim my checked luggage, I discovered the airline had lost it. After a long wait and inquiries, I discovered it was on another flight. Fortunately, the airline finally sent my luggage home.

Was not able to watch most shows on the entertainment site. They would not load

Our flight was 1.5 hours delayed. There was no weather for the inbound flight, so I don't understand why. This meant a VERY late arrival and only a quick nap before my morning flight.

Delayed flight, so I switched fights to SFO to Phoenix , Phoenix to DSM. Excellent service through American Airlines

AA re-routed flight from HNL to LAX due to delay. My group of 3 with reserved seats in row 9 was broken up, with one assigned to a middle seat, another in the last row of the plane. Not happy. No explanation to the delay. No apologies. No compensation. Would have been nice to be offered an Admiral Club admission or a voucher for the extra 3 hours of layover in LAX. Could not hear the boarding gate announcements in LAX. Adjacent gate was boarding at the same time. Loud speakers were competing against each other. Barely made my boarding group.

Almost a 6 hour flight and the only food option is a cheese plate… and chips. Also how is it there are no options for texting on American. I’ll be going back to delta and united.

Bad food, small seats that didn’t recline. I thought I was buying a quantas ticket so I feel like I got scammed

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

Information on your arrival and departure airports

Not what you’re looking for? Find thousands of other hotels, flights, car rentals and package deals with KAYAK.