Find cheap flights from Kentucky to Caribbean from $79
This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight departing on 1/13. 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.
Round-trip
1 adult
Economy
Sat 1/6
Sat 1/13
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FAQs for booking flights from Kentucky to Caribbean
Top 5 airlines serving from Kentucky to Caribbean
8.0
Cape AirOverall score based on 266 reviews
71food
78comfort
84boarding
87crew
84overall
74entertainment
Airline reviews
It’s less complicated from Culebra to SJU airport. Next time I will prefer to leave from Isla Grande airport to Culebra !!
It’s less complicated from Culebra to SJU airport. Next time I will prefer to leave from Isla Grande airport to Culebra !!
10 seat Cesna. Equal parts transportation and adventure. 20 minute hop at 10000 feet and 160 mph, sitting 10 feet from the pilot. Panoramic views of the island. Very simple boarding, very low stress. VQS airport tiny, undeveloped. Highly recommended flight, Cape Air doing a great job here.
My pilot on Cape Air was AMAZING!!!! I hoping that next time I fly I have him as my pilot. He made me feel safe and secure in his skills.
Pros: "The pilot was kind and to the point."
Cons: "The guy who boarded us told me to wait as his computer could not check me in. 10min later he is rushing me to get on the runway. It was 30min before scheduled take off. I had ordered food and had to cancel my order before the café had finished, so he wasted food and did not get paid and I was hurried and boarded the plane hungry. I probably won't use Cape Air again unless it's an emergency situation"
Pros: "Amazing view"
Cons: "Warning about what to take from carry-on, since it wasn't available during flight"
Pros: "I had the opportunity to sit in the co-pilots seat! What an amazing experience.. Flight departed on time too."
Cons: "Nothing at all.."
Pros: "Pilot did a great job, flight was as smooth as glass for the 7 of us passengers!"
Pros: "Staff were great - courteous, professional and friendly. Plane was a fun experience as always."
Cons: "Not Cape Air’s fault, but the smoky haze (from fires in CA, OR, NV) diminished some of the long views - vistas were not quite as beautiful as on past flights."
Pros: "Got a shuttle from the plane to my terminal at STL. Very convenient."
Cons: "Rather loud, but I don’t think there was much the airline could do about that. Maybe earplugs."
Pros: "Crew was pilot and helpful in explaining the situation to me."
Cons: "Got bumped from a flight to make way for a pilot in training. The fact that this happened on christmas eve made it even worse. Had to wait until boarding to find out that was being bumped and was told I shouldn't have been allowed to check in."
No comments, the complete handling and flying was excellent,keep up the good works.
Pros: "Friendly crew"
Cons: "Too much noise in the cabin. Ear protection should be recommended by airline."
Pros: "They are very organized small air line . Our flight was on time"
Pros: "***Our luggage did arrive as promised. ***Our flight from Tortola was cancelled, almost ensuring we would miss our connecting flight from St Martin. Thankfully some employees at the airport (Don't know to what airline they belonged, I don't recall seeing a single WinAir employee the entire time) hired a charter TurboProp for all of us (about 15 people). I think the kudos go to the airport rather than WinAir."
Cons: "*** If you are travelling to the BVI's and travel on WinAir, be aware that if your checked luggage weighs the limit that it will most likely come the next day. This happened to my girlfriend and I on separate occasions. While we did both receive our luggage the next day, there was no communication from WinAir. I had to call them repeatedly and stress the urgency with getting the baggage (I was on a chartered boat. I didn't want to hold the boat up for my bag). My theory is that the luggage gets sent on a boat from St Martin to Tortola as heavy bags can't be brought onto the island hopper airplanes they use to shuttle between the islands. *** After waiting at the Tortola Airport in the departures area for about an hour (about 10 minutes before our plane was to take off) I hadn't seen a single WinAir employee. I finally asked an employee of another airline if they could tell us what was going on. About 15 minutes later someone (Airport rep??) came out and told us our flight was cancelled and that they had booked us a charter turboprop to ensure we get there on time. After about 3 minutes we were ushered out to a plane that was loaded with our luggage and ready to go."
Pros: "I love flying Winair between SXM and EUX. The flights are short, safe, and provide a beautiful view of the beautiful islands."
Pros: "There is a magnificent view of the island on the way in. Make sure you have a camera ready!"
Cons: "The flight was delayed 2 hrs. They don't offer connecting the bags with other airlines. I wish it could be a better option"
Cons: "Terrible flight, over an hour late and no one knew how late was the flight...will never fly again with this company, will use Air St Barth..."
Cons: "Flight was delayed up to 45 minutes due to lack of grounds staff to load luggage on plane"
Pros: "Quick, smooth flight (a bit of turbulence). Great pilots and counter personnel were friendly"
Cons: "Left late, no update to passengers to say it was delayed."
Pros: "After booking through kayak, they lost my reservation and I was put on standby. I was treated very rudely at check in and I almost missed the flight."
Delay flight more than 8hours waiting and poor customer service!
Plane was extremely small so mind the size of your carry on
Other than lack of snacks, everything else went very well.
They don’t keep you updated on the flight status very well. It was late but nothing said
Pros: "Nothing!!! Horrible airline with horrible staff members."
Cons: "Everything. The staff and crew of Intercaribbean airlines are very unprofessional and not helpful at all. On top of the flight delays all the luggage for that particular flight was left in Kingston. Everybody was rather nonchalant and unapologetic about the situation. I was told I would get the the following day. The next day only two of my three bags showed up. I was not compensated for the inconvenience and was told point blank that they will only deliver one of my bags to my address even though they were the reason I had NONE of my luggage in the first place. They are disgusting!!! I would never recommend this airline to anyone."
Pros: "Nice people"
Cons: "A long walk to the D3 gate, but there were no amenities there I.e. snacks (to be fair a new terminal is under construction)"
Cons: "There was no air. I understand when you are on the ground it can be limited but even after getting to altitude there was no air conditioning."
Pros: "almost nothing"
Cons: "The plane had a problem that forced us to turn around right after take off and as of this writing we still don’t know what’s going on or how long we are stuck here. Planes are old and apparently maintenance could be better."
Cons: "Was a bit difficult understanding the flight attendant, she had a thick Spanish accent"
Pros: "Crew was good. Got there safely!"
Cons: "Maintenance issue caused us to have to get back off the plane, causing delay. Better safe than sorry, though!"
This has been, by far, my worst experience with an airline company. I had a reservation for a Tuesday at 8:30 pm departure from Gainesville, FL (1.5 hours - direct flight) I received an email on Monday that my flight had been changed to Monday at night to depart from Jacksonville, FL (and it was an 11 .5 hours flight ). There was no way I would have had the time to gather my things, drive 1.5 hours to the Jacksonville airport, and make it on time to board the plane. Besides, I had a full day of work on Tuesday. The only good thing I xan say about Silver airlines is that they did give me a refund, but I had to wait about 4 hours for a call back
Avoid this airline. They are unreliable and will cancel your flight for no reason.
Flight was canceled about 14 hours before takeoff with no explanation and no contingency. Had to purchase an $860.00 ticket on another Airline. Have not received an email about a refund.
Jetblue cannot manage connecting flights. Had to haul checked luggage between terminals 1 and 3 at FLL twice
Cons: "Boarding inside instead of walking outside and In flight WiFi or entertainment needed"
Cons: "2+ hours late, over 15 alerts regarding delaus beginning night prior to flight!"
Pros: "Nothing"
Cons: "The plane had technical difficulties and they have delayed us 5 times when the airline should have gotten a new plane for all of us."
Pros: "Nothing"
Cons: "The airline canceled the flight so had to stay over night in FL... now I am paying for a room and having to pay for a boat I am not even on. This is a very bad airline"
Pros: "Crew was pleasant and friendly"
Cons: "The plane was smaller than I expected and rickety. It was loud and vibrated the entire flight. The seat was uncomfortable. Crew was friendly; however, I asked to move to an empty window seat and was told the seat was “unavailable.” Do not recommend. Not worth the money you save."
Cons: "Multiple delays before and AFTER boarding, too. Frustrating and my experience on this same flight with this same airline several months ago was similarly delayed and disorganized."
Book cheap flights from Kentucky to Caribbean
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1/13Sat
1 stopSpirit Airlines
15h 22mSDF-SJU
$79
2/4Sun
1 stopSpirit Airlines
12h 50mSDF-SJU
$89
2/4Sun
2 stopsSpirit Airlines
13h 56mSDF-SJU
$104
1/13Sat
2 stopsSpirit Airlines
16h 10mSDF-SJU
$126
2/21Wed
1 stopDelta
6h 27mSDF-NAS
$136
2/21Wed
2 stopsAmerican Airlines
8h 36mSDF-NAS
$145
12/12Tue
1 stop
18h 05mSDF-SJU
$162
12/12Tue
2 stops
16h 47mSDF-SJU
$194
1/19Fri
2 stopsAmerican Airlines
17h 09mLEX-SJU
$253
12/29Fri
1 stopDelta
5h 36mSDF-SJU
$316
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15h 22mSDF-SJU
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13h 49mSJU-SDF
$155
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14h 02mSDF-SJU
1/27Sat
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7h 55mSJU-SDF
$156
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6h 52mSDF-SJU
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8h 22mSJU-SDF
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15h 18mSDF-STT
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16h 42mSDF-SJU
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2 stopsUnited Airlines
15h 47mSJU-SDF
$331
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2 stopsAmerican Airlines
13h 44mSDF-SJU
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2 stopsAmerican Airlines
8h 34mSJU-SDF
$348
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29h 31mSDF-AUA
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2 stopsCopa Airlines
21h 44mAUA-SDF
$649
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26h 40mSDF-AUA
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2 stopsCopa Airlines
21h 26mAUA-SDF
$702
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12/11Mon
multi-stopSpirit Airlines
18h 58mSDF-SJU
12/18Mon
multi-stopSpirit Airlines
18h 00mSJU-SDF
$302
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18h 05mSDF-SJU
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8h 30mSJU-SDF
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8h 18mSDF-MBJ
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8h 37mMBJ-SDF
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15h 08mSDF-SJU
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multi-stopSpirit Airlines
14h 39mSJU-SDF
$332
12/12Tue
multi-stopDelta
7h 18mSDF-STT
12/17Sun
multi-stopDelta
9h 25mSTT-SDF
$731
12/9Sat
multi-stopAmerican Airlines
16h 47mLEX-SJU
12/11Mon
multi-stopAmerican Airlines
6h 47mSJU-LEX
$789
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multi-stopUnited Airlines
8h 35mLEX-SJU
12/16Sat
multi-stopUnited Airlines
21h 23mSJU-LEX
$807
12/10Sun
multi-stopDelta
15h 44mSDF-PUJ
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multi-stopDelta
7h 48mPUJ-SDF
$819
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10h 36mSDF-MBJ
12/11Mon
multi-stopAmerican Airlines
8h 37mMBJ-SDF
$822
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18h 10mSDF-STT
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multi-stopUnited Airlines
7h 57mSTT-SDF
$822
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