$98 Find Cheap Flights from Caribbean to Kentucky

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Low seasonMarch
High seasonJuly
Cheapest flight$98
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 Cincinnati

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 11h 37m, 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 5h 50m.

  • What are the most popular destinations in Kentucky?

    Based on KAYAK flight searches, the most popular destination is Nashville (35% of total searches to Kentucky). The next most popular destinations are Lexington (26%) and Cincinnati (16%). Searches for flights to Knoxville (11%), to Louisville (9%) and to Blountville (2%) 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 4278 reviews
8.6Crew
7.1Food
8.2Boarding
7.6Entertainment
8.0Comfort
Airline reviews

Southwest is Southwest. No frills. If you're luck enough to get a happy crew (we did), then it makes for a nicer flight.

10.0 ExcellentMichael, Jun 2025SMF - SEA
Read more Southwest reviews

Southwest is Southwest. No frills. If you're luck enough to get a happy crew (we did), then it makes for a nicer flight.

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

We sat on the plane on the tarmac for 4 hours.

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

Flight crew and cabin crew were great. I had to rearrange flights because my original flight was 3hrs delayed for weather, the rub is the flight I moved to boarded on time then we sat at the gate for 2 hours because scheduling stole our first officer for another flight, TWICE. Then our actual FO was an hour delayed. To make it worse my original flight went from a 3 hour delay to departing 15min EARLY. Just poor scheduling operations all around.

Bring back peanuts Take our drink orders when were all seated, especially after you switch to assigned seating.

Staff was far less than helpful at all times. Departure and arrival times mean nothing to Southwest. Extremely disappointed, will never fly with them again, and I’ll be sure to share my experience with all.

It is southwest seat was ok. Not the most comfortable seat

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

I like for how they process during check in. It was very smoothly.

The flight was scheduled for 2:30 PM. Early in the morning we got a text message saying the flight was delayed and rescheduled for 3:00 PM. We got to the airport with that in mind. Then we got a message during check-in at the flight was rescheduled again for 2:30 PM. We almost missed our flight. In fact, our bags Were told that they would not make it. At the end, everything worked out. But it is very stressful.

Most aspects were good however if they assign boarding zones they ought to enforce them or why bother? My luggage from SAN-JFK-MAD was lost in NY so I without my main bag for two days upon arrival in Spain. They were helpful in tracking it and eventually delivered it to my hotel. The flub was because of a delay upon arrival in NYC. I had booked 2 1/2 hours between flights but we had to hold on the taxiway for an hour after landing while waiting for a clear gate which likely caused the baggage error.

Excellent check-in. Crew was good. Excellent communication from flight deck.

Great overall. There was a bit of turbulence so they could only serve water because too much turbulence for the carts. Was glad they prioritized safety though

Excellent flight, the planes were newer, they did a nice job with boarding, great service overall.

Great service. Flight was delayed while we sat on the runway for a couple of hours. Weather related. Staff made is very bearable. The steward servicing the first class cabin was exceptional. Thank you! 💗

5 hours of delay that could've been much shorter if Delta had taken the 1 hour delay they imposed on the flight before boarding to run any of the plane checks required for flight to find the hydraulic issue that required nearly 3 hours to fix. $24 of meal credit buys a sandwich and a soft drink. Poor communication within the terminal about what gate we'd be re-boarding from and when we'd be re-boarding.

Amazing flight! I have never noticed the uniforms of the attendants before in twenty years of flying except today when one female had the most amazing dress on. It was beautifully designed and showed she was in charge. I never dreamed I would google who designed Delta uniforms . The ultimate compliment is when another woman admires your outfit. . I hope your designer puts it on the market

It would be nice if was given wires ear buds. Overall was a good experience was able to sleep on the plane

They cancelled my flight and downgraded me to economy and only gave me $250 for the downgrade

Loved the staff, boarding and drink options! Wish the comfort of the seat could have been better nevertheless

The flight crew were friendly and attentive. Food was good and they passed out ice cream and drinks awhile after Lunch was done. The ice cream was a nice treat! I found several movies to watch during the flight. There was many movies and tv shows to choose from. We flew Premium economy and there was enough leg room to be comfortable. The seats were also comfortable. I would fly AA again if the airfare isn’t expensive.

The chair cushions may need an upgrade. I have been noticing they are so worn out, thin so you’d sit in a dip 😄. Other than that, all was an enjoyable trip. Thanks AA!

I’m impressed that we were on time in Sacramento after having a late departure in Newark and our made it. The staff was friendly and warm.

Cramped seats. FAA should make airlines have more legroom, for even short people complain

5.5 hour delay with no explanation on why, along with no proactive effort to reaccomodate me.

It was one of my worst flight ever. First they were changing the gate for at least 4 times, changing from gate D7 to D12 to D44. Considering the size of the Miami Airport, we are talking about long distance and the train at the airport was not working. Then the flight was delayed around one hour. Then finally we boarded into the plane and when everybody was seated, there was an announcement that there is an issue with one of the tire of the plane, so we all had to get out of the plane with our belongings, to replace the tire. So we had around 2.5-hour delay

Most miserable flight ever. We waited almost 2 hours on the runway because the flight was oversold. American offered $1200 credit. Then there was some nonsense about weight distribution. Ridiculous. No food for 8 plus hours on the flight. I will be writing a letter.

Honestly, I haven’t flown American in years, probably due to the pandemic and my being unable to travel for certain periods in the last two years, but it was a good experience to dig out or obtain a new American Airlines account after many years of traveling for business with American in the past.

Book cheap flights from Caribbean to Kentucky

Recent round-trip flight deals

7/10Thu
1 stopSpirit Airlines
10h 57mSJU-BNA
7/14Mon
1 stopSpirit Airlines
10h 53mBNA-SJU
$184
7/7Mon
1 stopFrontier
19h 10mSJU-CVG
7/13Sun
1 stopFrontier
13h 37mCVG-SJU
$196
7/11Fri
2 stops
31h 16mSJU-BNA
7/17Thu
1 stop
11h 06mBNA-SJU
$214
10/2Thu
1 stopAmerican Airlines
8h 39mSJU-CVG
10/7Tue
1 stopAmerican Airlines
6h 27mCVG-SJU
$225
7/11Fri
1 stop
16h 58mSJU-BNA
7/17Thu
1 stop
11h 06mBNA-SJU
$232
9/12Fri
2 stopsSouthwest
11h 40mSJU-BNA
9/15Mon
1 stopSouthwest
12h 25mBNA-SJU
$239
10/3Fri
1 stopSouthwest
6h 35mSJU-CVG
10/6Mon
1 stopSouthwest
6h 30mCVG-SJU
$250
10/3Fri
2 stopsAmerican Airlines
11h 03mSJU-CVG
10/6Mon
1 stopAmerican Airlines
17h 04mCVG-SJU
$256
7/16Wed
1 stopDelta
6h 19mSJU-LEX
7/22Tue
1 stopDelta
10h 34mLEX-SJU
$302
8/29Fri
1 stopDelta
6h 10mSJU-SDF
9/2Tue
1 stopDelta
9h 22mSDF-SJU
$305

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Recent one-way flight deals

6/25Wed
1 stopFrontier
28h 15mSJU-CVG
$98
7/13Sun
1 stopSpirit Airlines
10h 57mSJU-BNA
$98
6/24Tue
1 stopAmerican Airlines
9h 21mSJU-CVG
$113
8/22Fri
1 stopDelta
6h 10mSJU-SDF
$118
8/22Fri
1 stopDelta
6h 04mSJU-LEX
$118
10/7Tue
1 stopUnited Airlines
8h 08mSJU-BNA
$120
10/15Wed
2 stopsAmerican Airlines
9h 07mSJU-CVG
$138
10/13Mon
1 stopUnited Airlines
8h 08mSJU-BNA
$139
9/3Wed
1 stopSouthwest
7h 25mSJU-BNA
$158
8/20Wed
2 stopsSouthwest
10h 25mSJU-BNA
$160

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Last minute flights from Caribbean to Kentucky

Last minute flight, train and bus deals

6/19Thu
multi-stopFrontier
7h 13mSJU-CVG
6/23Mon
multi-stopFrontier
9h 50mCVG-SJU
$212
6/19Thu
multi-stopFrontier
28h 31mSJU-BNA
6/27Fri
multi-stopFrontier
14h 17mBNA-SJU
$230
6/21Sat
multi-stop
23h 25mSJU-BNA
7/22Tue
multi-stop
10h 37mBNA-SJU
$331
6/22Sun
multi-stop
15h 15mSJU-BNA
6/30Mon
multi-stop
5h 44mBNA-SJU
$379
6/19Thu
multi-stopSouthwest
8h 40mSJU-BNA
6/27Fri
multi-stopSouthwest
8h 35mBNA-SJU
$535
6/18Wed
multi-stopAmerican Airlines
9h 46mSJU-BNA
6/24Tue
multi-stopAmerican Airlines
10h 21mBNA-SJU
$541
6/19Thu
multi-stopAmerican Airlines
8h 51mSJU-BNA
6/28Sat
multi-stopAmerican Airlines
5h 46mBNA-SJU
$550
6/18Wed
multi-stopDelta
10h 38mSJU-BNA
6/24Tue
multi-stopDelta
6h 53mBNA-SJU
$580
6/22Sun
nonstopSouthwest
4h 15mSJU-BNA
6/30Mon
multi-stopSouthwest
6h 25mBNA-SJU
$646
6/21Sat
multi-stopDelta
9h 53mSJU-BNA
7/22Tue
multi-stopDelta
12h 34mBNA-SJU
$2,764

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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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