Find cheap flights from Kentucky to Grand Cayman

Find cheap flights from Kentucky to Grand Cayman

Search hundreds of travel sites at once for deals on flights to Grand Cayman

Round-trip
Economy
Boston (BOS)
Grand Cayman
Fri 5/7
Fri 5/14
Any month
Compare vs. KAYAK |

Good to know

Low season

NovemberBest time to beat the crowds with an average 4% drop in price.

High season

MarchMost popular time to fly with an average 8% increase in price.

Average price round-trip

$666(avg. price over the last 2 weeks)

Good deal round-trip

$388or less

Good deal one-way

$304or less

FAQs for booking flights from Kentucky to Grand Cayman

How does KAYAK find such low prices on flights from Kentucky to Grand Cayman?

How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Kentucky to Grand Cayman?

What is the Hacker Fare option on flights from Kentucky to Grand Cayman?

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Kentucky to Grand Cayman?

Top airline flying from Kentucky to Grand Cayman

Scores according to KAYAK customer reviews

7.2
American Airlines
Overall score based on 45,481 reviews
7.5
Boarding
7.1
Comfort
7.8
Crew
6.9
Entertainment
6.7
Food
Airline reviews

Cons: "Maintenance problems resulted in original aircraft being unavailable and switching to new aircraft at a different gate. More than 45 min late."

Pros: "I was in first class this time. The seat was comfortable for the flight of roughly 2-1/2 hours. We were served a continental breakfast that was filling and healthy with cereal, fresh fruit, Brie, soft crackers and yogurt. I'd rather have something simple but satisfying than something overcomplicated and possibly not that good. The crew was polite and efficient. I did have to use the lavatory at one point and I was happy that it was clean."
Cons: "The entertainment system was down, but it wasn't American - it was gogoflight or whatever it's called. I ended up listening to my Audible so it turned out alright, but on a 2+ hour flight, it could have been frustrating."

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

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

Pros: "Internet"
Cons: "Turbulence"

Pros: "Crew"
Cons: "Be on time"

Cons: "We had to wait for a flight attendant in Louisville going to Chicago, which made us a little late to OHare. Then we had to wait at OHare for another plane to leave. I ran from the one set of gates to the other, but I missed the boarding, even though the plane was still there. I was extremely disappo"

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

Pros: "Crew was great!"
Cons: "My bag got lost"

Pros: "Would’ve loved if the flight from Louisville to Charlotte weren’t delayed 2 hours for mechanical reasons!"
Cons: "The flight could’ve waited for us instead of leaving on time for Allentown!"

Cons: "Beverages"

Cons: "Unable to connect to the new AA so-fi"

Pros: "Good flight good crew"
Cons: "Hated the connection from terminal 5 to terminal 3 we should not have to go through the departure lounge this added 10 mins or more into a very tight connection."

Pros: "People were friendly"
Cons: "Broke arm off wheelchair"

Cons: "on a 5+ hour flight, that was diverted back to the originating airport due to a passenger who had extreme DTs from excessive drinking the night before, and made the flight return, American offered NO compensation AND the aircraft was so old, there were NO back seat monitors NOR any means to charge our electrical devices!!!"

Pros: "Friendly crew, excellent food options, very clean cabin."
Cons: "I had to pay for water."

Pros: "On time departure and arrival and good flight all around."

Pros: "."
Cons: "Delayed 4 hours there, delayed 5 hours on the way back. Messed up plans a bit"

Cons: "Waited one hour on runway after landing for plane to be towed prior to getting off the plane. This was made worse surrounded by unruly children that no one made an effort to control."

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: "Flight was delayed slightly, but pilot made up most of the time in the air. Everyone was polite and flight was totally uneventful."
Cons: "Seat headrest was weird. Made flight slightly uncomfortable."

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"

Cons: "Made us wait over 2 hours on the tarmac before take off inside the airplane."

Pros: "The crew were friendly and did their job effectively"
Cons: "Lack of seat space Planes seemed old Minimal overhead storage room—carry on fits all other airlines overhead but struggled to get bag in compartment Also, no help from crew with this Seats recline nearly into lap of person behind"

Cons: "Departed late and missed connection due to an overage of fuel. The crew took an additional 45 minutes to defuel the plane of 8000 gallons. Wth?! Have to stay overnight in Chicago now."

Cons: "After being delayed without any explanation, I was told that I would not have my purchased 1st Class seat. To add to that I received no service In economy."

Pros: "Quiet plane."
Cons: "No local temperature control, back of plane too cold, middle too hot. No air vents at seats. 3 hours with no drink service, went to back asked for a diet coke, was told no. Flight attendant who was in the back would not give me one, said they were doing water service now and I should wait."

Cons: "Boarding chaos at Miami airport."

Cons: "I don't like the fact that American Airlines try to get me to put my small carry on bag below both ways in the cargo area it is against FAA to have batteries down there. I have 30,000.00 in cameras and they tried to get me to do this both times saying the bag will not fit. The Flight Attendant each time say that it fits JUST FINE! I'm going to try to avoid American Airlines as much as I can!"

Pros: "My flight wasn't completely full, so I had a row to myself. The pilot was excellent; takeoff and landing were very smooth."
Cons: "I had to gate check my luggage because of the small plane size. Had I had a shorter layover this could have caused an issue for me."

Pros: "The plane"
Cons: "The waiting time due to the storm and the no communication from the crew . 5 hours strand on the tarmac plus 9 flying."

Pros: "Everything was fine except it was inexplicably late!"
Cons: "It was over 30mins late for no reason!"

Pros: "Courteous crew, easy experience smooth "get in and get out" process"
Cons: "Flight was late due to weather but that's beyond anyone's control obviously"

Pros: "I took an aisle seat for more room Glad to be going home"
Cons: "Still not enough leg room"

Pros: "Food was tasty. The attendants left me sleeping but were helpful with bringing me food and drinks after I woke up Great aircraft B777"

Pros: "We made it home."
Cons: "The entertainment system in my seat didn't work. Seat 19D on flight 2580 from MSY to LAX."

Cons: "PAID FOR SEAT WITH EXTRA LEG ROOM AND GOT NONE! DON'T PICK FIRST ROW"

Pros: "i dislike booking with British Airways and ending up flying with American Airlines, who is their partner. This usually happens from US>London, but happened both ways this trip. AA flies outdated aircraft with old entertainment systems. Time for an upgrade! AA crew is okay, but BA crew is better. Might choose a different carrier next time."

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

Pros: "I love that there is a direct flight with no connection to get to Key West. The flight leaves at a reasonable hour, and gets to KW in time to still enjoy the day."
Cons: "They still haven't learned to load from the back forward. I do not like to have to pay extra for certain seats."

Pros: "Chargers in the back of the seat for devices Friendly staff Nice quality airplanes"
Cons: "Paid for WiFi, and it was very choppy and slow. Took over 3-4 min, and several refreshes to send/receive an email."

Pros: "Short duration"
Cons: "Didnt have a seat assignment for me. Told me the flight was overbooked... paid long in advance. Disappointing, finally finally found a seat."

Cons: "On time , pleasant"

Pros: "Music/radio was nice at my seat; got into Sacramento early"
Cons: "No gate # on boarding pass, almost missed flight; kind of had to slouch to look out the window; rough/fast landing"

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."

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

Read more about American Airlines
COVID-19 information

Safety measures for airlines flying from Kentucky to Grand Cayman

Airlines flying from Kentucky to Grand Cayman 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 Kentucky to Grand Cayman

Mandatory masks

Masks required on board, masks provided on flights from Kentucky to Grand Cayman

Social distancing seating

Middle seats unavailable to book on flights from Kentucky to Grand Cayman

Pre-flight testing

Testing for antibodies, testing for symptoms for flights from Kentucky to Grand Cayman

Book cheap flights from Kentucky to Grand Cayman

Recent round-trip flight deals

10/26
Tue
1 stop
American Airlines
6h 36m
SDF - GCM
10/30
Sat
1 stop
American Airlines
7h 23m
GCM - SDF
10/26
Tue
2 stops
American Airlines
18h 56m
SDF - GCM
10/30
Sat
2 stops
American Airlines
16h 30m
GCM - SDF
10/26
Tue
2 stops
American Airlines
8h 35m
SDF - GCM
10/30
Sat
1 stop
American Airlines
7h 48m
GCM - SDF
10/8
Fri
1 stop
American Airlines
9h 12m
LEX - GCM
10/17
Sun
1 stop
American Airlines
7h 54m
GCM - LEX
6/3
Thu
2 stops
American Airlines
17h 37m
LEX - GCM
6/10
Thu
2 stops
American Airlines
19h 44m
GCM - LEX
6/20
Sun
2 stops
American Airlines
8h 24m
LEX - GCM
6/21
Mon
2 stops
American Airlines
19h 44m
GCM - LEX
6/20
Sun
2 stops
American Airlines
8h 24m
LEX - GCM
6/21
Mon
2 stops
American Airlines
19h 44m
GCM - LEX
10/8
Fri
2 stops
American Airlines
7h 01m
LEX - GCM
10/17
Sun
2 stops
American Airlines
9h 22m
GCM - LEX
10/26
Tue
2 stops
Multiple Airlines
10h 50m
SDF - GCM
10/30
Sat
3 stops
Multiple Airlines
26h 08m
GCM - SDF
Show more results
-
1
  • Round-trip
  • One-way
  • Multi-city
  • Trip Builder
  • Economy
  • Premium Economy
  • Business
  • First
  • Multiple
Economy
  • Economy
  • Premium Economy
  • Business
  • First
Economy
  • Economy
  • Premium Economy
  • Business
  • First
Economy
  • Economy
  • Premium Economy
  • Business
  • First
Economy
  • Economy
  • Premium Economy
  • Business
  • First
Economy
  • Economy
  • Premium Economy
  • Business
  • First
Economy
  • Economy
  • Premium Economy
  • Business
  • First