Find cheap flights from Cleveland to the Cayman Islands

Find cheap flights from Cleveland to the Cayman Islands

Search hundreds of travel sites at once for deals on flights to the Cayman Islands. Bundle your flight + hotel and save!

Round-trip
Economy
Cleveland (CLE)
Cayman Islands
Mon 1/3
Mon 1/10
Any month
Bundle with KAYAK |
Include hotels

Good to know

Low season

September

High season

February

Average price round-trip

$546

Good deal round-trip

$426
Best time to beat the crowds with an average 3% drop in price.
Most popular time to fly with an average 9% increase in price.
(avg. price over the last 2 weeks)
or less

Top tips for finding cheap flights to the Cayman Islands

  • Book at least 2 weeks before departure in order to get a below-average price.
  • High season is considered to be November and December. The cheapest month to fly to the Cayman Islands is September.

FAQs - booking Cayman Islands flights

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

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Top airlines flying Cleveland Hopkins Intl to Cayman Islands

Scores according to KAYAK customer reviews

8.1
JetBlue
Overall score based on 19,895 reviews
8.3
Boarding
8.2
Comfort
8.6
Crew
7.9
Entertainment
7.8
Food
Airline reviews

Cons: "Nothing. Jet blue continues to impress me. Love the leg room and entertainment options"

Cons: "The power outlets did not work."

Pros: "nothing"
Cons: "the flight was hours late, they didn't offer an answer or apology and when we arrived the bags took way to long to arrive. Never flying jetblue ever again"

Pros: "Seat was comfortable and the food options were good"
Cons: "Service could have been better."

Pros: "I like the free Wi-Fi free movies and the free Beverages and snacks oh and the flight was good too"

Cons: "Flight information"

Pros: "The ability to purchase headphones and a blanket for a fair price."
Cons: "There was a child (guessing) with gas that made the air quality unpleasant several times."

Cons: "Tvs weren’t working. Also was 30 minute dely which in turn made us rush and just make our connecting flight. But apparently our luggage wasn’t as lucky. It did not arrive in Orlando which made us wait another 2 hours for the plane to arrive with them. They arrived ruffled and my zipper was brok"

Pros: "Nice to be offered free chips. The windows seemed cleaner then a lot of other jet planes."
Cons: "One of the washroom floors was sticky only partway into the flight."

Pros: "Seats were great, crew was lovely and helpful, bathrooms were extremely clean and well-maintained."
Cons: "More time in between our connecting flight because we almost missed it with a delay"

Cons: "clearly communicate delays. We had no idea what was happening or what our options were."

Pros: "Noting. I don’t plan to fly Jet Blue again, if I can help it."
Cons: "Everything. Mechanical issues, causing an 8 hour delay which made us to have to rebook to BWI and pay an extra $160 for a taxi home."

Pros: "El personal es muy amable"
Cons: "Que no viajen mas para la ciudad de Santiago de los caballeros en D.R.es una pena de verdad para mi ."

Cons: "My first flight was delayed an hour due to pilot error (we left the gate on time, but sat on the tarmac for an hour). This caused me to miss my connecting flight, which stranded me at JFK because they only had one flight per day to my destination. JetBlue's customer service told me I could not reach my destination until the next day, which was unacceptable (I had a morning interview). In fact, the only thing they said they could do was *PARTIALLY* refund my ticket, even though they stranded me in a completely different city. They also said I would "be able to" book a new flight with a different carrier, which cost roughly $400, using my own money. In the end, I spent about an hour talking with customer service until they were "nice enough" to do a partial refund with an additional credit equaling the remainder of my $400 ticket to fly with them in the future. It was still a very poor interaction with customer service."

Cons: "My only suggestion is to improve the volume and clarity of the announcements."

Pros: "Staff at gate"

Pros: "The staff consistently went above and beyond what I have experienced flying other airlines. The superior service began with the ticketing agent at Cleveland Hopkins airport and extended through to the flight crew. I am a convert. Whenever I can fly Jet Blue I will. I’ll tell all my friends and family that they should too."

Cons: "How can an airline lose a checked bag on a direct flight? They have confirmed it was loaded but can’t find it. How is that possible? It didn’t come out of the baggage carousel so where did it go? Disappointing and maddening conclusion to an otherwise good experience."

Pros: "They unloaded the entire plane and put me on a flight 5 hours later"
Cons: "Avoid Jet Blue the employees have not ever taken curtesy training"

Pros: "Staff was friendly and the pilot smooth ride!!"
Cons: "Flight delay"

Pros: "Flight was pretty seamless, lots of room."
Cons: "Nothing bad to say"

Pros: "Full plane...left on time. Very good experience"

Cons: "My seat did not recline."

Pros: "Unimpressed!! Flight delayed for 2 hours and lost my bags. 2 days later, my bag has not arrived. Apparently it is on the way. Not sure when it will get here."

Pros: "The crew was very helpful with updates."
Cons: "The flight was delayed. Got in very late, but the crew kept us informed of what was going on."

Pros: "crew was polite quiet flight"

Pros: "Everything went smoothly. The plane was small but very nice and well kept and the flight itself couldn’t have been smoother!"

Pros: "Check in team was good with helping us check our bags"
Cons: "Every leg of the flights were delayed causing issues with our other travel (bus, etc.). Plane way extra delayed once everyone got on the plane because they needed to deliver food to the plane...which was only for purchase on a 6+ hour flight. Within reach of my seat 3 of the tvs didn't work. I probably won't fly JetBlue again if I don't have to."

Pros: "Excellent"

Pros: "The snacks and the room on the plane were really nice. Also I enjoyed being able to watch a movie."

Pros: "airplane flew safely. crew was courteous. no significant flight delay."

Pros: "Best service and smooth ride"

Pros: "the older gentleman who scanned our boarding passes was so very nice."
Cons: "the steward on the plane was mediocre - not the norm for jet blue. He was hard to understand, did not greet us, and brought me the wrong drink. I did not say anything, but not what I've come to expect from jet blue"

Pros: "Too much turbulence"

Pros: "Everything went as planned and was on time. Very easy to fly with. Extremely satisfied."

Pros: "So much leg room and free WiFi and DirecTV. United, take a lesson!"
Cons: "Compared to all the others, JetBlue was the best."

Pros: "Everyone was cheerful, efficient and nice"
Cons: "Airplanes are uncomfortable, not just yours"

Pros: "The crew on the flight was fantastic. The flight was delayed and made me worried about my connecting flight from LGB to SFO. They kept me up to date on its status and figured out a contingency plan."
Cons: "The flight was delayed 2.5 hours for mechanical issues, and the inflight entertainment was below average. Could watch live TV which was nice but the entertainment pamphlet in the seat back pocket stated that there were 3 movies available but I could not find them."

Cons: "Delayed two hours"

Cons: "Flight was delayed by over an hour and we never got an explanation as to why. Just an apology from the pilot once we finally took off."

Pros: "Comfort"

Pros: "Always great!"

Cons: "Security line at JFK is awful. They only let expedited boarders through, and didn't process other lines for 30 minutes. Many people missed their flights. Even worse, a free screener was standing there, but didn't want to work. Only after many people complained did he start processing our line. And then the TVs on our airplane were broken."

Cons: "Had a lot of trouble connecting to wifi. I wasn't sure how to do it or it wasn't working properly."

Pros: "Friendly staff at check in, gate and flight. Went smoothly and efficiently"

Pros: "Polite and attentive service Early arrival Thanks"

Pros: "Standard seat comfortable! Prompt checkin and quick baggage pick up."
Cons: "Tbe reading lughts were broken for our seats. Rats!! That meant I coild not avoid the captive audience video screen and that was annoying."

Cons: "My light was out so I could not read and my air was not working so it was too warm."

Pros: "Boarding was easy. I like the Dunkin Donuts coffee"
Cons: "My overhead light and tv we're both not working. The stewardess was rude when I brought it up. Told me to move to the next empty seat dismissively. I bought a window seat on purpose and did not want to move. My concerns were left unaddressed"

"Newer airplane!"

Pros: "Got on the plane. Grateful we got to where we were going. Smooth transition to aircraft."
Cons: "Seating order was not good. Plane should seat from the back to the front. It was reverse order and a little taxing. No one came to check on passengers, offer concessions etc."

Cons: "My eyes were watering and my nose was itchy for the entire flight and I had to hold back sneezes and I think there was something in the air on the plane that was causing this to happen. I was double-masking and I do not have allergies. I wonder if it had to do with the chemicals used to disinfect the plane between flights? I was not very comfortable, to say the least. Everything else was great, though, but I don’t think I will be flying again anytime soon."

Pros: "A crew member saw me struggling to walk and offered a wheelchair, explained to me that I would be met with one throughout my trip. Her name was Donna!! Problem occurred when we got to Dallas."
Cons: "Instead of circling in the sky, they could have had the pilot take the alternate route he eventually took anyway, in the first place. My family and I still don’t know if we’re going to get a flight to El Paso/ stand by. So much 4 seeing my armyson before he deploys, recipient time waisted over bad decisions on to of everything else, entitled woman on the plane insults me on the lane for no reason. The crew was amazing though."

Pros: "I am no longer comfortable with airline seats, bad nerve in back of leg."
Cons: "Poor communication about “Red-tagging” carry on luggage"

Pros: "Special assistance readily available"
Cons: "The weather"

Pros: "Crew members were okay"
Cons: "Wifi could be better"

Pros: "Very friendly and accommodating."
Cons: "tv screens on the back of seats"

Pros: "The friendly service from everyone including desk, wheelchair service, and flight crew"
Cons: "Not much at all. Everyone took very good care of me."

Cons: "The attendants attitude."

Pros: "Crew"
Cons: "6 hour delay"

Pros: "Great airplane. Enjoy the 2 seat rows."

Pros: "The crew was fantastic and very nicely got us into an earlier flight and allowed my wife and I to sit together for our 10th anniversary"
Cons: "The entertainment apps were difficult to use"

Pros: "The friendly informative team when we learned our plane broke. I switched to Charlotte connection earlier as a Miami one made no sense as Miami is south of Atlanta final destination. We had a different outcome than expected yet staff cared for us."
Cons: "Plane better maintained as before take off a hydraulic part broke and we were grounded . We arrived home hours later than planned because of this."

Pros: "WiFi entertainment system."
Cons: "Hard seats, no arm padding. No power to recharge phone and iPad."

Pros: "My bag was lost!!!"
Cons: "To have my bag delivered"

Cons: "On time"

Pros: "I liked the ability to choose my meal before the flight."
Cons: "Customer Service at the Priority Check-in could have been much friendlier, I’ve experienced much better customer service from Delta Airlines. Plus the flight attendants could have been more attentive that sitting up front in the galley and just chatting with each other."

Cons: "Departing on time...30 minutes late."

Pros: "Very professional and timely. My last six flights with American have been without a hitch and right on time. If I were a business traveler, which I am not, American Airlines would be my go to carrier. Quite satisfied with this airline and have been for a long time. Thanks!"

Pros: "The crew"
Cons: "I just don’t understand how a flight can be delayed three hours from weather the day before. And, of course, we arrived and there was no gate for us. They had three hours to have a gate ready for us. AA fail!"

Cons: "See above"

Pros: "Check in"
Cons: "Missed connection"

Cons: "They charge for coffee."

Pros: "Boarding was efficient and fast"
Cons: "Nothing in particular"

Cons: "Supposed to leave saturday, but didnt cause the lady at airlines said i need a visa when i did not need a visa.now its tuesday in austrailia and im stuck in airport because quantos doest know where my bags are. This trip is turning or turned into a total disaster!"

Pros: "Standard AA domestic flight. Once we were boarded and underway, things were fine. Crew was friendly, the aircraft was cleaned on the turn from the prior flight, and we didn't sit on the tarmac too long when arriving at DFW. Normal operations for AA domestic."
Cons: "Unfortunately, normal operations for AA domestic means boarding 20-30 minutes late, which delayed the arrival a bit. In general, AA could provide more accurate updates and boarding information for their flights. For example, if the inbound aircraft arrives at the time my flight should be boarding, I want to see an updated departure time, rather than maintaining the "on time" status right up until five minutes before the new boarding time. Generally it takes 25-30 minutes to turn the plane for the next outbound flight."

Pros: "We got to our destination aver 12 hours late."
Cons: "In addition to being rebooked approximately 12 hours after our original flight, this flight left about 40 minutes late."

Pros: "Crew was nicw"

Cons: "Now pay significant more for carry on bags for another mediocre airline where it is not significantly cheaper."

Pros: "Arrived slightly early. The crew was efficient and friendly. The interior and seats looked new."
Cons: "Nothing was negative."

Cons: "Coach seating is too tight"

Pros: "Like my AA rides > 90% of the time. The usual prob is sketchy gogo service."
Cons: "Nogo gogo"

Cons: "Plane was dirty and crew inattentive."

Pros: "Short flight, nothing much to say."

Pros: "The crew on both flights to Cancun were very nice!! thanks"

Pros: "Speedy boarding, friendly crew."
Cons: "Seats are definitely cramped."

Cons: "Boarding chaos at Miami airport."

Pros: "The gate agent was having a bad night because she did not get a break. I am platinum pro and would not upgrade me because she said I was not on the list but she put 2 people in first who were not even advantage members"

Pros: "In General, as a premium passenger, I usually enjoy the premium cabin experience; however, it was lacking this time."
Cons: "In first class, three/four of us requested headphones/headsets; the flight attendant informed us that there were no headphones/headsets; thus, we could not watch any programming In first class, there were two meal options, but one was almost immediately depleted before the flight attendant arrived at my row."

Pros: "Flight was smooth and ontime"
Cons: "Flight was extremely expensive."

Pros: "We boarded fast and the flight was smooth. The crew was very friendly."
Cons: "The sears were a little uncomfortable. They went terrible but my back started to go out on my 2 hour plans ride."

Cons: "Was not able to check in online in advance. AA wouldn't recognize the booking # that was emailed to me. Sat on the plane for nearly 3 hours while a mechanical issue was looked at; lateness of the flight meant we missed our connection. When we got to the table for people who would miss connections to get our boarding pass for a rescheduled flight, there wasn't one for us. We got there, but this wasn't really a great experience."

Pros: "Nothing"
Cons: "I selected an aisle seat because I have very bad anxiety and when I got there to print off my ticket I was assigned a middle seat. It was very uncomfortable"

Pros: "Good flight! Smooth landing!"
Cons: "N/A"

Cons: "The flight was cancelled without notification."

Pros: "Fabulous crew and service, absolutely fantastic."
Cons: "Having to get off!"

Pros: "The free mivies, the leg room was good also"
Cons: "Flight left late and yge long wait for the baggage. Too long!"

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

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."

Read more about JetBlue
COVID-19 information

Safety measures for airlines flying from Cleveland to the Cayman Islands

Airlines flying from Cleveland 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 Cleveland to the Cayman Islands

Mandatory masks

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

Social distancing seating

Middle seats unavailable to book on flights from Cleveland to the Cayman Islands

Pre-flight testing

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

Book cheap flights from Cleveland to Cayman Islands

Recent round-trip flight deals

2/4
Fri
1 stop
Multiple Airlines
6h 11m
CLE - GCM
2/14
Mon
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Multiple Airlines
14h 36m
GCM - CLE
2/22
Tue
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Multiple Airlines
18h 40m
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2/26
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Multiple Airlines
10h 11m
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5/21
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JetBlue
6h 11m
CLE - GCM
5/28
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JetBlue
10h 44m
GCM - CLE
2/20
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Multiple Airlines
20h 55m
CLE - GCM
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27h 56m
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1/5
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15h 25m
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16h 17m
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