$68 Find Cheap Flights from Caribbean to Kentucky

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Low seasonMarch
High seasonJuly
Cheapest flight$68
Best time to beat the crowds with an average 5% drop in price.
Most popular time to fly with an average 6% increase in price.
Flight from San Juan to Nashville

FAQs for booking flights from Caribbean to Kentucky

  • How does KAYAK find such low prices on flights from Caribbean to Kentucky?

    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 Caribbean to Kentucky.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Caribbean to Kentucky 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 Caribbean to Kentucky?

    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 Caribbean to Kentucky 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 Caribbean to Kentucky?

    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 Caribbean to Kentucky up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest day to fly to Kentucky?

    Based on KAYAK data, the cheapest day to fly to Kentucky is Thursday where round-trip tickets can be as cheap as $353. On the other hand, the most expensive day to fly is Sunday, where round-trip prices are $500 on average.

  • What is the cheapest time of day to fly to Kentucky?

    The cheapest time of day to fly to Kentucky is generally at night, when round-trip flights cost $227 on average. Morning departures are around 5% more expensive than evening flights, on average. The most expensive time of day to fly to Kentucky is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $491.

  • What is the cheapest month to fly from Caribbean to Kentucky?

    The cheapest month for flights from Caribbean to Kentucky is January, when tickets cost $284 (return) on average. On the other hand, the most expensive months are May and November, when the average cost of round-trip tickets is $475 and $459 respectively.

  • How far in advance should I book a flight from Caribbean to Kentucky?

    To get a below average price on the flight from Caribbean to Kentucky, you should book around 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 23 weeks before departure.

  • How long is the flight to Kentucky?

    An average nonstop flight from Caribbean to Kentucky takes 13h 35m, covering a distance of 1597 miles. The shortest route is San Juan Luis Munoz Marin Intl Airport (SJU) to Nashville (BNA) with an average flight time of 4h 15m.

  • What are the most popular destinations in Kentucky?

    Based on KAYAK flight searches, the most popular destination is Nashville (43% of total searches to Kentucky). The next most popular destinations are Cincinnati (16%) and Knoxville (16%). Searches for flights to Louisville (12%), to Lexington (11%) and to Blountville (1%) are also popular.

Reviews of the top 3 airlines serving from Caribbean to Kentucky

 
Need help choosing which airline to fly with from Caribbean to Kentucky? 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.
8.0
SouthwestOverall score based on 4275 reviews
8.0Comfort
7.6Entertainment
7.0Food
8.2Boarding
8.6Crew
Airline reviews

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

4.0 OkayTraci, Jun 2025OAK - SEA
Read more Southwest reviews

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

For my birthday trip this was my second time ever flying, this trip was the best.

after landing, we stay 2 hours on the taxi way before reaching the gate The airline and the crew were good though

No trays in our seats, we sat in first row, purchased a business class fare. Had to hold our drinks and snack in our hands. No plugs for our cell phones. Had to pay for it a drink cocktail each. Seats so uncomfortable.

Flight wasn’t even full, but too many carry-ons caused us to run out of bin space. New bag fee has folks who would usually check their bags carrying on. Watching Southwest morph into Spirit/Frontier is so sad to watch

Sat on tarmac for 2 hours and then missed my connecting flight

First time traveling on Southwest since bag fees were implemented. Usual good service. Just more expensive now.

Everything was on time. I was disappointed by the front section female, African American flight attendant. I did not see her name tag or would have identified by name not race. As passengers moved to the bathroom early in flight, she would say with a disdainful tone “I have to say the seat belt light is on” then go back to her book. Better trained flight attendants say something like be careful the seat belt light is on.

Cluster mess boarding. Can't wait for SWA reserved seating. Internet didn't seem to work on the plane.

Flights delayed by 4-6 hours. Boarding was a mess and unclear. Bags were not at arrival airport and had never even been put on the plane. No idea when I’ll get them. Don’t fly into Denver!

From Atlanta to Savannah - flight connection was way to short (we weren't even late landing ) and flight was already boarding when we landed - we were told we were the last on board and so we had to gate check our bags. Once we got on the plane, there were at least seven open bag spots so that was unnecessary delay. There should be better communication between the gate agent and the crew.

Crew was excellent. Comfort seats not as nice as other kinds of planes.

Not a "Delta" issue, but a JFK issue: We booked a connecting flight with 3 1/2 hours between to clearn immigration and customs. Our inbound flight (BCN to JFK) was on the taxiway 45 minutes which ate into our layover time. Immigtration was insanely quick with the CBP MPC app; however, clearing TSA (again, after we were ALREADY cleared in Spain on the inbound international flight) took over 95 minutes. This left us with 10 minutes before boarding the connecting flight (JFK to SAN) to walk to the far end of Terminal 4 and try to find food. We didn't find any food that could promise to serve us in under 10 minutes so we boarded the Delta flight after coming off a plance and an 8-hour flight knowing that we wouldn't be served any food on the next 5 1/2 hour flight. I feel like Delta needs to put pressure on the JFK TSA to open more screening stations (by our count, we saw only 5 scanners open and a line of - as we said - over 90 minutes. The insult is that we WERE ALREADY SCREENED through TSA, but as you come off one flight into the USA, you have to go through the whole process again. It seems like if you have a connecting flight, there should be a way to pass through immigration and customs without needing to return through TSA.

The way BCN airport handled boarding was a huge improvement over our trip to Spain from JFK. Instead of gate-mosquitos edging in before their zone was called, in BCN they had clearly marked lines for Zones 1-8 and people just lined up correctly. The flight itself was uneventful. The meal (curried chicken and rice) was one of the better meals we've had on Delta. Entertainment options were plentiful, power chargers were available in Main Cabin, and seats were decent. Flight staff were very friendly and positive throughout the 8 hour flight.

It was a great flight and the stewards and stewardess were all kind and accommodating!! The seats were comfortable and entertainment screen excellent!

The checkpoint hornets are always looking fhrough Americans' luggage keeping what they deem impassible! Grrrrr!

There are 4 flights in consecutive gates with about the same departure time. Two flights were boarding at the same time. One was delayed or boarding would be happening at the same time. I am not sure what Delta and LAX need to do to have a better layout at the end of Terminal 2

Flight was an hour late, who knows why. It was OK, nothing outstanding.

Only not having an assigned seat was an issue. Rest was great

There was a security issue at the airport and we were unable to land. We circled endlessly and then landed at another airfield for fuel. We then circled the airport again, almost landed but didn’t fully touch down before circling again. I am thankful to the crew for keeping us safe- the issue was the airline and staff at the airport getting us seats on our connecting flights. That part was hours of searching for someone and getting in double my steps.

I flew Business Class. Rory, one of the Cabin stewards, was attentive, explained the menu, provided appropriate drinks. was

The flight delay in Dallas created a domino effect that impacted all connecting flights, leading to an increase in the number of connections. As a result, I missed my flight from Casablanca to Marrakech due to the tight turnaround when landing in Casablanca. CMN Airport was understaffed; only one employee was available to assist passengers while others just stood by and watched. It was an extremely frustrating situation. Many passengers were crying and banging their hands on the counter while talking to customer service representative Allabough. Unfortunately, Allabough couldn’t change my flight in the system. At the same time, I was on the phone with an American Airlines customer service representative named Solomon, who said he couldn’t make the change either. So, I decided to take an ONYA Voyages train from Casablanca to Marrakech to reach my destination on Friday, June 26. It turned out to be an unpredictable trip.

The flight was fine and the crew awesome. The problem is ORD and AA. Computers went down, ORD fell apart and a 40 min flight turned into a 3 hour trip. Guess the answer is to not try and fly to ORD after noon. But, as I said, crew was awesome and did everything they could to lesson the flight time.

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.

This flight never occurred because AA couldn’t get their act together.

Terrible. Cancelled my original flight. It made getting a boarding pass difficult. The AA employee (in a loud voice, so everyone around could hear) griped at me for not getting a boarding pass 24 hours before. I asked how I was supposed to do that when I had no idea what flight I was going to be on. She said (loudly), “Talk to AA customer service, not me!” I could certainly tell serving customers was not important to her. Our new flight was set to a completely different city. We had to change our rental car, and the price went way up. It took 2-1/2 hours to get checked in. By then our new flight had left. We ended up on stand by and had to split up the family to get to our destination. It cost us the whole first day of the trip. AA needs to employ people who actually care about doing a good job. I suppose those people are getting harder to find, but atleast try.

A cookie and a soda, packed like sardines, will never be a positive experience. Also, boarded a 5:30 flight at 7:45pm

Am still mad at American airlines. You should know it's us travel nurses who are your customers and you treat us like nonsense it's not ok. American airlines took my money, no refund for whatsoever. A trip that was of 466 and I paid 466 and 833 then they chose for me where to sit and refund my seat choices and gave me expensive seats for 79 USD. Kayak doesn't help at all after booking you are on your own. Skyscanner is better

Flight was good & early meaning the gate was changed. With gate change there were no wheelchairs & the gate attendant left without making sure wheelchairs were coming to the changed gate. I had to go to another attendant at another desk to get this done.

This was a horrible experience. For a first class experience, my chair was held together by 3M tape - and I have a photo. The crew weren’t very attentive, somewhat dismissive and forgot my drink and snack, the chair reclined about 3 inches on a 6-hour cross country flight. I was also not informed that there was no lounge available in Newark airport because of renovations, so all around this was one of the worst experiences and I would actively avoid both American and Alaska Air going forward.

Book cheap flights from Caribbean to Kentucky

Recent round-trip flight deals

7/17Thu
1 stopSpirit Airlines
10h 57mSJU-BNA
7/25Fri
2 stopsSpirit Airlines
30h 36mBNA-SJU
$204
8/1Fri
1 stopSpirit Airlines
10h 57mSJU-BNA
8/11Mon
1 stopSpirit Airlines
10h 53mBNA-SJU
$218
10/2Thu
1 stopAmerican Airlines
8h 54mSJU-CVG
10/7Tue
1 stopAmerican Airlines
9h 55mCVG-SJU
$225
8/28Thu
1 stopDelta
5h 50mSJU-SDF
9/1Mon
1 stopDelta
8h 26mSDF-SJU
$225
7/23Wed
1 stopFrontier
28h 20mSJU-CVG
7/28Mon
1 stopFrontier
12h 10mCVG-SJU
$227
7/30Wed
1 stopFrontier
24h 51mSJU-BNA
8/4Mon
1 stopFrontier
26h 01mBNA-SJU
$234
9/13Sat
1 stopDelta
6h 16mSJU-BNA
9/16Tue
1 stopDelta
9h 02mBNA-SJU
$239
9/27Sat
1 stopAmerican Airlines
16h 36mSJU-BNA
10/4Sat
1 stopAmerican Airlines
6h 17mBNA-SJU
$244
8/22Fri
2 stopsSouthwest
9h 50mSJU-BNA
8/26Tue
1 stopSouthwest
9h 25mBNA-SJU
$277
7/17Thu
1 stopSouthwest
13h 25mSJU-SDF
7/22Tue
1 stopSouthwest
9h 10mSDF-SJU
$280

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Recent one-way flight deals

7/17Thu
1 stopSpirit Airlines
10h 57mSJU-BNA
$68
7/20Sun
1 stopSpirit Airlines
10h 57mSJU-BNA
$70
7/9Wed
1 stopFrontier
28h 20mSJU-CVG
$100
10/15Wed
2 stopsAmerican Airlines
11h 21mSJU-CVG
$113
8/21Thu
1 stopDelta
6h 10mSJU-SDF
$113
8/22Fri
1 stopDelta
8h 51mSJU-LEX
$113
7/22Tue
1 stopAmerican Airlines
18h 31mSJU-LEX
$115
10/2Thu
1 stopFrontier
7h 17mSJU-CVG
$132
8/21Thu
1 stopSouthwest
6h 05mSJU-SDF
$138
8/15Fri
1 stopSouthwest
12h 10mSJU-BNA
$158

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Last minute flights from Caribbean to Kentucky

Last minute flight, train and bus deals

7/3Thu
multi-stopFrontier
9h 44mSJU-CVG
7/6Sun
multi-stopFrontier
6h 34mCVG-SJU
$270
7/3Thu
multi-stopFrontier
28h 31mSJU-BNA
7/7Mon
multi-stopFrontier
26h 01mBNA-SJU
$274
7/3Thu
multi-stopFrontier
7h 13mSJU-CVG
7/17Thu
multi-stopFrontier
6h 34mCVG-SJU
$275
7/6Sun
multi-stopSpirit Airlines
22h 09mSJU-BNA
7/14Mon
multi-stopSpirit Airlines
28h 26mBNA-SJU
$375
7/6Sun
multi-stopSpirit Airlines
17h 14mSJU-BNA
7/14Mon
multi-stopSpirit Airlines
28h 26mBNA-SJU
$390
7/2Wed
multi-stopAmerican Airlines
9h 59mSJU-CVG
7/16Wed
multi-stopAmerican Airlines
11h 05mCVG-SJU
$400
7/4Fri
multi-stopAmerican Airlines
10h 42mSJU-CVG
7/17Thu
multi-stopAmerican Airlines
5h 45mCVG-SJU
$434
7/3Thu
multi-stopSouthwest
10h 40mSJU-CVG
7/6Sun
multi-stopSouthwest
9h 30mCVG-SJU
$643
7/2Wed
multi-stopDelta
13h 08mSJU-TYS
7/8Tue
multi-stopDelta
10h 25mTYS-SJU
$2,921
7/3Thu
multi-stopDelta
13h 08mSJU-TYS
7/6Sun
multi-stopDelta
10h 28mTYS-SJU
$2,985

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Everything you need to know for your flight to Kentucky

Cabin class types available on flights to Caribbean

Cabin classes available on flights to Caribbean. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

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