$110 Find Cheap Flights from Caribbean to Kentucky - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Caribbean to Kentucky departing on 9/26. 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.
1 adult
1 adult, Economy, 0 bags

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Good to know

Low seasonSeptember
Cheapest flight$110
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly with an average 4% increase in price.
Flight from San Juan to Louisville

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.

  • How many airports are there in Kentucky?

    There are 4 airports in Kentucky. The busiest airport is Louisville Airport (SDF), with 64% of all flights arriving there.

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

    The cheapest month for flights from Caribbean to Kentucky is December, when tickets cost $84 (return) on average. On the other hand, the most expensive months are April and May, when the average cost of round-trip tickets is $198 and $198 respectively.

  • How long is the flight to Kentucky?

    An average nonstop flight from Caribbean to Kentucky takes 10h 52m, 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 05m.

  • What are the most popular destinations in Kentucky?

    Based on KAYAK flight searches, the most popular destination is Nashville (37% of total searches to Kentucky). The next most popular destinations are Knoxville (26%) and Louisville (17%). Searches for flights to Cincinnati (14%), to Lexington (6%) 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 4249 reviews
7.5Entertainment
8.1Boarding
8.6Crew
8.0Comfort
7.0Food
Airline reviews

Overall good, just screaming kids in the area the whole flight.

8.0 ExcellentAnonymous, Jul 2026
MDW - MHT
Read more Southwest reviews

Overall good, just screaming kids in the area the whole flight.

My experience will Southwest was good. I wish there was more entertainment and the boarding process was slow at time but other than that my experience was great definitely will be flying with SouthWest again.

Flight was delayed by 2 hours, meaning that a flight to Dwnver which should have arrived at 11pm came into the airport at 1 am. Made for a very long day.

I think Southwest is the number one airline that anyone can fly I have flown for the first time Frontier and what a joke and their customer service United was a very strange experience I'm only sticking to Southwest from here on out for sure

Great job! My family doesnt fly often but we felt safe 100%

Great job Southwest! My family doesn't fly often but we felt safe the whole time.

SW can't get their wifi right. I upgrade to insure wifi service but the last two trips had intermittent service. Not worth the extra costs.

The flight was late. The crew was rude. There was no food. Cramped and uncomfortable. Nothing about this flight was good.

The seats were a bit cramped and worn, but otherwise okay.

Since the flight wasn’t full, we had some extra room. Crew was great

It is usually very pleasant. Good service for the price, international flights are even better

We never made it on this flight because we missed our connection due to o delayed flight from Jackson.

We had a terrible experience. The flight was delayed several hours, so we missed our connection. We were told to wait at the airport. At around 11:00 pm, the flight was cancelled. There were no available seats out of Jackson for the next two days. Fortunately, we had the foresight to rebook on United for the next day. However, we had to spend a long day at the airport and an overnight at a mediocre hotel. It was a miserable way to spend part of our vacation. We also sacrificed our $450 deposit on our California hotel because we could not get there.

delta wifi wouldn’t work boarding was not in sequence flight crew spent most of their time on the phone with the lights off pretending no one wanted or needed anything

Friendly flight attendant Quick checking for baggage drop Quick TSA lines

Crew was absolutely fantastic and we’re so welcoming and friendly ❤️

We got stuck on the tarmac taxiing after landing early so we didn’t get off the plane until an hour later than we thought we would

It was okay. We were delayed for weather reasons, but the pilots and the flight control staff figured a way around the storm and were able to get us to Los Angeles safely. Not all the staff members were polite, but the entertainment on the flight was good.

So terrible. My flight was 4 hours delayed and we weren't notified til last second within an hour of boarding. WE had to sit on the plane for 4 hours. ridiculous.

Lady Pilot was perfect in every way wheels up to wheels down communication, professionalism, excellent on time departure and on time arrival, excellent communication! Fantastic job with Superb attitude!!

The gate got changed several times and the flight was delayed over an hour. Awful experience

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

No Snacks or Entertainment. The flight was short, snacks should still be given.

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

My Internet did not work for Outlook email or basically anything. I paid for one hour of in-flight usage and it was terrible. I spent a lot of time on different sites and browsers with no luck and a lot of frustration. Other than that, the flight was on time, crew was nice, service was fine. Seat was OK even though I paid for the extra 6 inches. I cannot imagine how tight the seats in the back must be.

Everything was fine. Flight boarded and departed on time. Seating was spacious enough for my carryon to fit under the seat in front of me. No complaints at all. Flight even arrived early.

Boston ticket agent Cheryl Porter is WONDERFUL. Our Iberia flight to Barcelona was cancelled the morning we were scheduled to leave and Cheryl was our super hero - she found us seats on a flight to London and on to Barcelona. Truly a “can-do” attitude which we appreciated so much after the Iberia ticket agents told us there was “absolutely nothing they could do”. (As did the customer service agents at Iberia’s call center) Ms Porter is truly a wonderful person who genuinely cares about travelers!

I was not given the option to get on a different flight even though I was going to miss my connection due to weather delays (I did). When I called early in the morning, they said it wasn't delayed long enough; though I knew it would be by the time it was time for the flight ... it was and by that time it was too late. I wasn't given the option to pre-board with my toddler, and the food service was less than normal due to delays .... at least that's what the crew said.

American is a steady for me. I always get what I expect from them. Sincere effort to get me from one place to another.

Nothing wrong on this flight but nothing special. It was oversold and they had to bump people which is always bad.

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.