Find cheap flights from San Diego to the Cayman Islands

Find cheap flights from San Diego to the Cayman Islands

Round-trip
Economy
San Diego (SAN)
Cayman Islands
Fri 12/4
Fri 12/11
Any month
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Good to know

Low season

October Best time to beat the crowds with an average 5% drop in price.

High season

December Most popular time to fly with an average 12% increase in price.

Average price round-trip

$691 (avg. price over the last 2 weeks)

Good deal round-trip

$376 or less

Good deal one-way

$220 or less

Top tips for finding cheap flights to the Cayman Islands

  • Book at least 4 weeks before departure in order to get a below-average price.
  • High season is considered to be January, November and December. The cheapest month to fly to the Cayman Islands is January.

FAQs - booking Cayman Islands flights

How long is the flight to the Cayman Islands from San Diego?

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How does KAYAK find such low prices on flights to the Cayman Islands?

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Top airlines flying San Diego to Cayman Islands

Scores according to KAYAK customer reviews

7.2
American Airlines
Overall score based on 44,911 reviews
7.5
Boarding
7.1
Comfort
7.8
Crew
6.8
Entertainment
6.7
Food
Airline reviews

Pros: "By luck, I had a seat between myself and the other person in my row. It would have been tight, otherwise. Crew was friendly and polite."
Cons: "The seats on the flight were placed very close together - felt very constricting. Takeoff and landing were a bit rough."

Pros: "Really disappointed as my bags was not check thru.It was rechecked at London and British airway charged me for my baggage. I want to make sure that my way back to Oslo London London San Diego has no charge . It is an international flight and I am allowed 23kg one checked bag ."

Cons: "Damaged one baggage, and delayed arrival of other baggage for 2 days that forced me to cancel a following trip."

Cons: "delayed/not on time"

Cons: "3 boarding doors less than 50 feet apart with departures leaving within 15 min of each other created a difficult to penetrate gaggle."

Pros: "The flights didn't have any delays"
Cons: "Seat wasn't comfortable."

Pros: "The flight was great--good food, good service, good entertainment, on time."
Cons: "They lost our luggage. Four people traveling together arrived in Phnom Penh, but our luggage didn't. It took almost 2 days to be reunited with our luggage."

Cons: "The crew looked very bored."

Pros: "Staff at SAN was good helpful. Check in was seemless."
Cons: "Wishing that they would serve something to drink — even if I would have to pay for it. Flight attendant gave me wrong directions and I left for another terminal while my carry on luggage (which had to be checked) was still at the gate. I had to wait until it arrived at baggage claim."

Cons: "Coach seating is too tight"

Pros: "Take-off and landing were smooth."
Cons: "Was not able to track the progress of the flight on the monitors No entertainment Seats do not provide comfortable leg room"

Pros: "The friendly and attentive flight staff."

Pros: "The entertainment system is awesome made the flight go by so fast seats were comfortable"
Cons: "While using the entertainment system the airplane announcement system was way too loud I believe you are going to have lawsuits eventually for loss of hearing everybody around me was jerking to take the earphones out of their ears because the announcement system was way too loud across the entertainment system"

Cons: "Poor customer service"

Pros: "AA put us in a hotel and gave $12 (per person) food voucher for missed connection due to delay for maintenance."
Cons: "Our luggage was lost for 2.5 hrs in PHX airport, due to mix-up by service rep at customer service. AA attendant at gate at CLT was extremely rude and unprofessional when I accuse Left my boarding passes in seat pocket. Would not summon someone to retrieve it. Made me wait until entire plane was disembarked and cleaned, and made me wait some more after. She was super snarky, made rude comments, and almost made my family miss our connection to EWN. I will never, ever, fly AA again. Worst customer service and tons of issues with maintenance, luggage handling, and delays."

Pros: "On time departures and arrivals. This domestic first leg of the flight had fairly good leg room and seat width."

Pros: "I initially booked my flight via Kayak for a cheap no hassle price"
Cons: "My initial booking was with Iberia Airlines and a few days prior to my Flight was switched over to American Airlines. Had i known I would be flying with AA, I would have opted for a more expensive option as I've a great disdain for AA. My flight from JFK was not the model aircraft I was promised and thus did not have ac chargers or Wifi in the plane. In my opinion, I was bait and switched via Kayak"

Cons: "Taking 2 shuttle buses to transfer from AA to PAL."

Pros: "we had all the necessary conditions for work, rest, sleep and eating. The level of service has increased"
Cons: "Nothing"

Pros: "Polite, friendly helpful staff. Plane left on time."
Cons: "There were no window or aisle seats available for free, so I had to pay for the extra cost seats."

Pros: "The flight schedule"
Cons: "The hardens of the seats. Rather seat on the floor"

Pros: "Nothing"
Cons: "Had to cancel my flight and call the company. Was talking to a computer for 30 min before I finally talked to someone. It cost me in fees to basically cancel my flight which ended up being just as much as my entire flight ticket. Got refunded a total of $12 to use towards my next flight. Never flying or booking a flight with American Airlines at all. Kayak couldn't even help with accommodations. Southwest is the only company that will actually hold those credits for you. Everywhere else is just trying to scam you."

Pros: "Seats are the most uncomfortable seats ever"

Pros: "Nothing"
Cons: "The customer service and the lack of assistance from the airline ground staff was horrible ."

Pros: "Seats reclined, beverage service."
Cons: "Wish movie would have been a better movie, not animated."

Pros: "Overall, I'm pleased with BA."
Cons: "This flight didn't have the individual TV screens."

Pros: "Flight was pretty much what you'd expect, pretty basic"
Cons: "For a 5 hour flight I woulda been nice to have more than just two cookies for a snack. Luckily I brought me own. Also there's no entertainment except for 1 magazine, so again, if you're flying American you better supply yourself with whatever you'll want before boarding"

Pros: "At 6' 2" I was surprised that, with the seat in front of me not reclined (and fortunately no one ever did), my knees actually had a bit of room and were not pressed into the seat back in front of me. That and the flight schedule went smoothly - everything was on time."
Cons: "Maybe a couple of other sandwich options might have gotten me to pay for one."

Cons: "Fat ads sitting next to me should have purchased 2 seats"

Pros: "Entertainment was free."
Cons: "Had to wait for mechanical issues so we were delayed."

Pros: "Kayak did not refund or have an option to exchange my ticket for a later time in the year."
Cons: "My tickets were 415.00 and I wanted to change the dates and couldn't since I bought from a third party I had to pay an extra 400."

Pros: "The staff was friendly and helpful"
Cons: "There was a ton of turbulence"

Pros: "Boarding was smooth. Flight was on time. Some weather en route but pilot was able to avoid the turbulence. Overall a good flight."
Cons: "Unrelated to the flight- but immigration and customs in Grand Cayman was slow. 200+ people arrived on this plane and there ware 4 immigration agents although they had more stations. We spent about a half hour in line in each- immigration and then customs. Rental cars is another situation to be aware of regarding insurance."

Pros: "The flight was great. There was free in seat entertainment with tons of movies! The flight attendant gave me free fruit & cheese plate to go with my wine. Great service, easy fast boarding & the flight was early!"

Cons: "You need to add a not applicable choice to your list. I did not eat the snacks offered on the flight nor was there any entertainment that I could find."

Cons: "Flight was extremely cold and no blankets. Flight attendant was extremely rude when politely asked for one."

Pros: "every flight was on time and left promptly. hostesses were courteous and helpful"

Pros: "friendly crew members/ great intertainment"

Pros: "On time"
Cons: "Food. Cold breakfast sandwich. Really? Cold bacon and egg."

Cons: "Horrible disorganization at boarding. Board from back to front for goodness sake...its common sense."

Cons: "This flight was good, but when I fly in July I pay extra for protection and extra for better seat. Flight was canceled and they put me on different plane, which make my day in San Diego very difficult, because I miss my meeting, I didn't get better seat ither,instead I got seat in front of toilet and for 3 hours have to listen door bunging and terrible smell. I never been compensate for canceling flight or extra seat price.Nobody care even apologize. I hope that was just unforchened incident and I still like your company and still flying with AA, but I was really disappointed. Sincerely Vera Vasiley."

Pros: "I arrived at Dusseldorf"
Cons: "First flight was delayed 5:30 hours, so I was moved to different flights because I would not have made my connections but those flights were uncomfortable and had bad service and the people working didnt even so much as offer me complimentary peanuts"

Pros: "Nothing"
Cons: "Uncomfortable. No entertainment."

Cons: "Waiting for copilot while sitting in a small warm plane for over 45 minutes...."

Pros: "The flight was on time and boarding went smoothly."
Cons: "Didn't eat or watch the movie. There needs to be an n/a rating available for this review."

Pros: "Middle seat on a five hour flight + no Tv on the plane made for quite the uncomfortable experience."

Cons: "Flight was inexplicably late crew was lazy and mumbled directions seats were uncomfortable and cramped"

Cons: "Seats are so crowed that you can not move without touching the people next to you. My body was so cramped by the time I got to Chicago I could hardly move. Plus we were stranded on the runway which prevented us from leaving the plane for another hour. It was so hot and stuffy in there. This made for an even longer day because I had a 3 hour drive after getting to Chicago to my home"

Pros: "Always. Always. Always"
Cons: "The fact that going to and from New Orleans takes as much time as flying around the planet twice."

Cons: "Free food was lacking for a 5 hr flight. Pretzels and a pack of cookies."

Pros: "It was quite average, nothing special.They severed some drinks and you get a bag of pretzels. The staff was very friendly and nice. It was only a 1 1/2 flight, so the only entertainment is magazines."
Cons: "The legroom was fine for me, but if you are about 6ft tall or over, you will feel a little cramped. Try to get an exit row seat if can."

Pros: "plane is new/crew was friendly"
Cons: "no legroom/food was horrible; worst ever on any flight I have taken to and from korea. Worst"

Cons: "Made me take off sweater out of my bag cause my bag was 0.5 lbs over weight."

Pros: "Flight was on time and luggage was not lost. In flight meal service was better than average."
Cons: "in the last row battling for share if the armrest."

Cons: "United and SAS are really separate and hard to manage reservation. Seats changed from what I purchased and it was uncomfortable. I don't think I will do a mixed airline flight again even though they quote them as a Star Aliance. Also, flying through Chicago ORD is not great. The international terminal is completely separate so you have to take a train, pour out water, enter security (and they don't have a TSA Pre). All around uggh."

Pros: "This reflects first leg flight from San Fran to Chicago."
Cons: "Cramped and uncomfortable"

Cons: "they canceled the flight and put us on american airlines wich was terrible"

Cons: "Flight was delayed until the next morning because of weather"

Pros: "Bad weather caused my flights to be re-routed, but United did wonderful in arranging for an similar arrival time to my final destination. I am very grateful for that. I can't judge the airline on something they have no control over."
Cons: "The bad weather that caused my flights to be re-routed!"

Pros: "The Stroopwaffle"
Cons: "The hour delay"

Pros: "We arrived safely on time."
Cons: "Bathroom is too small. Announcements were anxiety inducing. Sick people on the airplane spreading germs."

Cons: "Don't like being squeezed in, but it is what it is"

Pros: "Crew were nice and flight was on time."
Cons: "I didn't know i needed an app before i will be able to enjoy entertainment on board, so i had to pay for internet to be able to download the app to be able to watch movie. PA system wasn't gud."

Pros: "Both flights were great! They left on time, the one from San Diego left earlier than scheduled. Kayak was most informative with flight info and upon arrival, indicating the bagage claim number via email!"
Cons: "N.A. Everything was great."

Cons: "There is nothing more disappointing than having your flight delayed after a long week when all you want to do is get home to be with family."

Pros: "Seats were comfy, and the snack (caramel-filled waffle cookie) was a nice little treat."
Cons: "I didn't know to download the United entertainment app in advance. Once I found out at boarding, it was too late."

Pros: "Soda"
Cons: "The fact that they lost my luggage for the second time."

Pros: "Smooth and plenty of juice and soda."
Cons: "I've never really felt cramped on a plane before this trip but maybe I'm fatter?"

Pros: "Entertainment is pretty slick."
Cons: "Boarding process, crew was not pleasant, late getting the jet bridge to the plane. You know there are multiple 40-50 minute connections, but you take 15 minutes to get the jet bridge. Flight was "on time" I'm sure according to your stats."

Pros: "Nothing"
Cons: "Everything was awfuli it was a terrible experience.Nobody could tell me what was going on. I was to arrive in Seattle at around 6.15 pm "but " I did not arrive till 10.30 pm. I got home at 1.45 am wed morning"

Pros: "The seats"
Cons: "No entertainment without buying!!!"

Pros: "Flight Attendants were fantastic!"

Cons: "Flight was cancelled... First it was delayed, then mechanical error, then the pilots passed their flying ability. The way it was all handled was horrible. I travel a lot and this was the worst experience I've ever had."

Pros: "The flight was on time good flying no issues! !!!!! Landed in time to catch my connecting flight."

Pros: "Great seat"

Pros: "Window seats on both flights saved me on my overnight flight. Thanks Kayak!"
Cons: "The second flight had a pretty old plane with smaller seats."

Pros: "That United got me to where I wanted to go."
Cons: "That airline companies are so strict about making changes & the cost involved. I couldn't believe the price to change a date on a return flight. I went to Alaska airlines & bought a one way ticket for $30 less than the price of the change. Better times & schedules too. I was at one time a premier flyer almost a 1K status flyer with United. Now, I don't even bother. United Airlines Suck!!!!!"

Pros: "This leg of the trip was fine, on time and they provided blankets! Satisfied, but the mobile version of this rating site does not allow me to change the rating to higher."

Pros: "Kyak Notified me every step of the way basically dummy proofed my flight don't know if other sites do this as well but got gate change notifications and all changes!!"

Cons: "Seat was very uncomfortable. The video screen could not be turned off and kept waking me up, bad on an overnight flight."

Cons: "The flight seemed very unorganized. Once we had to make a random refuel in Canada I knew something was up besides the bad weather excuse they gave. The crew didn't seem to be able to pass any information along and gave either misleading info if any at all. There was no food or snacks given with it being a 5 hour flight to a 7 hr flight with the mishap to get more fuel."

Pros: "That I got bumped to first class on my flight the next day."
Cons: "I had a 47 minute layover scheduled. I had an hour delay on my first flight and they didn't hold anyone's connecting flight, which ended up being the last flights out for the night. By the time we got hotel vouchers, our bags and a shuttle to the hotel there was less than 4 hours to actually sleep. If I had known how slow the process was I would have opted to sleep in the airport so I got more than 3 hours of sleep."

Pros: "I arrived alive."
Cons: "United Airlines has one job, to move people from one location to the next. I'm concerned that United thinks it's in the data transfer business or the package hauling business or some kind of "gotcha' Internet business. There were never enough people at United to help me with my problem. Those real human employees that I found were mostly overworked, over regimented and procedure focused."

Pros: "That being said, I liked that they has Moscow Mules for purchase. The gate agent was very kind & helped check my husbands bag as the overhead bin space was full. The crew was fine."
Cons: "My first beef with United is that I needed to change my flight 36 hours after purchasing it & wanted a 200.00 change fee for a 79.00 flight, it was more cost effective to purchase a new ticket to with another airline than change my ticket. Silly really."

Pros: "Smaller plane! Easy board, quick flight"
Cons: "Seats are packed in, no wifi, arrived way early sat on tar mat no fresh air my chest was hurting from the smell of jet fumes until we finally pulled into a gate!"

Pros: "Nice crew ,on time , no extra fee for carry on and drinks. Over all comfortable. I will fly United again !!!!!"

Pros: "Morning flights are always rough but this was a joy....only 29 passengers....peace and quiet!"
Cons: "Nothing"

Cons: "Waiting for 3 hrs past boarding time for crew to arrive. Waiting on plane for 11/2 for plane to b de iced. Waiting for crew to get permission to fly because they went past hrs to fly"

Cons: "Seats are are thin and uncomfortable. Flight delayed from Chicago to Allentown because of an empty chair that could not unrecline. Ended up landing 35 minutes late."

Pros: "Nothing"
Cons: "I was charged 25.00 for luggage both ways which I wasn't told in advance.Also sat in airport a long time before being told my flight was cancelled and it was last flight.My daughter was by her self and didn't have money.She ask them could they put her in hotel and they told her no only discount.My daughter then told them she had no money and the clerk was very rude and told her well that's all they were going to do.At that point my daughter called me upset and crying because they didn't tell her prior and was rude about it.She do not fly and I had just had surgery and I could not go to her grand mother funeral with her.I had to call around to see if anyone knew someone in New Orleans to go get her for the night.My sister friend ended up picking her up 2hr later and she didn't know her but we had no choice cause her aunt had already left to go back home.It was a very upsetting situation and very stressful.I travel alot and I flew with this airlines before years ago and it was fine.Very disappointed about this whole trip."

Cons: "The fact that they kept delaying it by 30 minute intervals for four hours until eventually it was cancelled. Oh and now the new flight is delayed 30 minutes."

Pros: "On time, good flight from travel time prospective"
Cons: "Tight seating, mix up on seating, no overhead lighting during the flight"

Pros: "Morning flights were cancelled on a different airline, so I hopped onto Kayak and got us flights out so we could start our Thanksgiving vacation. United was great."

Cons: "No inflight movie. Couldn't get wifi without paying. Food wa awful and priced to high. Had to pay for my check in bag."

Pros: "I actually give this flight an overall a 5. The setting won't let me edit the stars for some reason. It was on time and everything went smoothly"
Cons: "None"

Pros: "I liked everything feel comfortable flying by air plane"

Pros: "Timely boarding and service."

Pros: "Everything was great."
Cons: "Except the entertaiment."

Pros: "The seats from San Diego to Dullas airport were fine and not too tight"
Cons: "The fact that there was no entertainment system on our way back when there was one on my way to San Diego (even though it cost 7.99$) And the wifi was 15.99$ !!?? Seriously??! It's 2015 .. There should be no flight that lasts that long and not have an entertainment system !"

Read more about American Airlines
COVID-19 information

Safety measures for airlines flying from San Diego to the Cayman Islands

Airlines flying from San Diego to the Cayman Islands have enacted additional safety measures and adjusted policies to better accommodate travelers. Policies vary by airline.

Heightened sanitation

Daily cleaning, installation of cabin HEPA filters on flights from San Diego to the Cayman Islands

Mandatory masks

Masks required on board, masks provided on flights from San Diego to the Cayman Islands

Social distancing seating

Middle seats unavailable to book on flights from San Diego to the Cayman Islands

Pre-flight testing

Testing for antibodies, testing for symptoms for flights from San Diego to the Cayman Islands

Book cheap flights from San Diego to Cayman Islands

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