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Find cheap flights from Caribbean Islands to Kentucky from $77

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 Islands to Kentucky departing on 6/5. 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
0 bags
Thu 6/6
Thu 6/13

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Good to know

Low season

February

High season

July

Cheapest flight

$77
Best time to beat the crowds with an average 23% drop in price.
Most popular time to fly with an average 14% increase in price.
Flight from San Juan to Louisville

FAQs for booking flights from Caribbean Islands to Kentucky

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

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Kentucky from Caribbean Islands 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 Islands 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 to Kentucky with an airline and back to Caribbean Islands with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Caribbean Islands 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 to Kentucky from Caribbean Islands up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top 4 airlines serving from Caribbean Islands to Kentucky

 
Need help choosing which airline to fly with from Caribbean Islands 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.
7.9
Caribbean AirlinesOverall score based on 188 reviews
8.4Crew
6.7Entertainment
7.6Comfort
6.7Food
8.2Boarding
Airline reviews

There was no music on the flights unless you came with your headset.

10.0 Excellentsusan, Apr 2024MIA - POS
Read more about Caribbean Airlines reviews

There was no music on the flights unless you came with your headset.

Their bar selection could be greatly improved; they only had one spirit option

Music would have been great and information about the flight. Meaning how high and the weather conditions.

It was good but the food was small for the duration of the flight.

I wrote to the entertainment and food OK because it was non-applicable All excellent

Checking in online still requires going on the physical check in line

I enjoyed the smooth flow and well coordinated boarding and the very courteous attitude from the cabin crew We look forward to flying with ya’ll again

Pleasant experience checking in. Seating is way too tight, especially for persons who are not petite. I thought the pilot was excellent in terms of his commentary and information. Wrong gate information on boarding passes. If I was not alert I could have lined up to board the wrong plane.

The crew was excellent, check in was easy ,the food wasn't good, movies should be recent and more selections

The captain was great he made jokes and make thebflight very comfortable. Alerted us about the islands we flew over and Yolandra and her team took great care of us, very personable.

Great. Loved that there was WiFi on flight to keep in touch and excellent service of beverages and snacks.

Flew business class. Everything was excellent. No issues at all. Not very many “good” movies to choose from. But lots of mediocre ones

Business class is great. New airplane, very comfortable, better than some of the major airlines I am used to

Terrible. Flight was cancelled due to the weather in the east and sout east(florida). Did not get any compesation of any kind. According to them, it was not under their control so I lost all the money paid for the 2 fairs from Raleigh, NC to Orlando, Fl.

great flight. Pilot was communicative, flight attendants were excellent. Really nice experience except my tv didn’t work.

The best experience that I have had traveling with JetBlue!

Overall, the flight was better than the flight I took to go to Florida, which had a bunch of problems. The crew is really nice and the plane was new so it had a small problem when we were on the runway, but the flight itself was great. They even made some time back up, which is always a good thing.

Crew was just ok. Flight was packed. On a 3/4 hour flight I would hope they would come around more than once to see if you needed anything further. Not very attentive.

There were multiple delays but JetBlue tried to make the boarding and departure process as quick and efficient as possible. The crew was as detached from reality as could be, meaning: not very friendly and just doing things by the numbers.

Nothing. Jet Blue is a great choice for me And I’m going to miss flying with them Since I travel to Lima Peru very often 😞😞😞

Not good 😐 Over priced baggage fees Small hard seats No wifi or entertainment options 😕

Didn't like anything!! Horrible flight. Small seating area and hard seats. Butt was sore after 2 hour flight to Seattle No entertainment or free refreshments No wifi or USB charging receptacles to charge phone entoute like other airliners Luggage rates were 3 times as much as competitors. Difficult to navigate online luggue process to pre pay before flight Overall bad experience WILL NEVER RIDE OR RECOMMEND FRONTIER TO FRIENDS OR FAMILY MEMBERS!!! THIS IS A SHAME!! MOST MESERIBLE FLIGHT OF MY LIFE!! AND I THOUGHT SPIRIT WAS 👎 YOU GOT THEM BEAD HANDS DOWN!!

Flight was a little late taking off. Seats are too upright, no ports to charge devices, no wifi, no entertainment

Six hour delay. Poor customer service. No voucher. Bad communication. Missed important appointments.

Our flight was delayed an hour, then when we got to board our flight finally, we were waiting in our seats for take off for 45 minutes before it was communicated that there was a maintenance issue therefore we waited on the plane for over an hour while that was resolved. We did not get to Phoenix until almost 3 hours after we were originally supposed to. This was the first and last time I will be flying Frontier.

Flight was canceled with little warning. Flight was rebooked through Ontario, California and connecting flight was delayed by over three hours. Frontier is living up to their Greyhound of the skies reputation for sure.

I purchased a carry on bag online…was supposed to cost $72 but after a whole slew of bs charges, the total was over $175.00. Because of these hidden charges, I will not even consider flying Frontier ever again. It’s just not worth the hassle. I’m scratching this company off my list forever.

Flight was OK. Seats were good no cell phone charges on the plane no TVs or entertainment.

There were 3 leg for the trip and each leg was delayed by 90 minutes or more. The boarding process takes forever with people waiting on the jetway even though most folks do not have carry-on. The whole process is poorly managed.

Flight cancelled and was told by a rude gate agent that they don’t accommodate on other airlines. Had to wait 5 hours for a connecting flight that had a 7 hour layover. Would not allow bags to be checked early so we couldn’t go through security .Had to rent a car for the afternoon to store bags and get a meal. Also incurred a hotel fee. No apology or reason given for the cancellation- just rudeness.

If you take this airline, they WILL change the flight time, and make you miss your connection. It has happened every time I used it. It's so unreliable that I think it shouldn't be offered on Kayak. You will regret it!

In addition to the fact that Silver changed the flight time several days before the trip without offering any choices , I was sick with Covid and unable to go on the trip. I tried to ask Silver for a credit for a flight when I’d recooperated but they don’t do credits, even for illness. I will Never fly on Silver again

I canceled due to a 7 hour delay. Was forced to book another airline last minute , very expensive. Silver Aorways sucks

I spent hours with orbitz to get my tsa # on my ticket. They didn’t have a place to enter. I will never use orbitz again. No customer service. A number in which u press offered options and the message replays instead of getting customer to that area. Silver did not make the promised call back. Finally someone responded to my email and took care of it after I lost hours of my vacation arranging this. Staff on flight barked orders.

Our pilot and flight attendant, Desiree, were great. I always fly this route and this crew was better than most.

The worst flight ever; 1st and last flying to this airlines

Easy boarding and deplaning. Short flight. Water was given but that was it.

Flight was delayed a bit since booking but otherwise everything was very good.

While this is a VERY SMALL plane; take-off to landing was fine. It's the constant departure time changes that wore me out and I'll try to never use this inconsistent airway again. Four delays in one day. Done!!!!!!

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

Book cheap flights from Caribbean Islands to Kentucky

Recent round-trip flight deals

9/17Tue
1 stopAmerican Airlines
6h 12mSJU-SDF
9/24Tue
1 stopAmerican Airlines
9h 45mSDF-SJU
$254
9/9Mon
1 stopSpirit Airlines
14h 41mSTI-SDF
9/25Wed
1 stopSpirit Airlines
7h 27mSDF-STI
$288
6/15Sat
1 stopAmerican Airlines
9h 25mSJU-SDF
6/19Wed
1 stopAmerican Airlines
16h 10mSDF-SJU
$296
9/17Tue
2 stopsAmerican Airlines
7h 44mSJU-SDF
9/24Tue
2 stopsAmerican Airlines
9h 55mSDF-SJU
$297
9/3Tue
1 stopSpirit Airlines
14h 41mSTI-SDF
9/25Wed
1 stopSpirit Airlines
7h 27mSDF-STI
$340
6/27Thu
1 stopAmerican Airlines
10h 32mMBJ-SDF
8/8Thu
1 stopAmerican Airlines
20h 45mSDF-MBJ
$360
9/9Mon
1 stopDelta
10h 57mSJU-LEX
9/11Wed
1 stopDelta
8h 34mLEX-SJU
$394
9/9Mon
1 stopDelta
9h 26mSJU-LEX
9/11Wed
1 stopDelta
6h 28mLEX-SJU
$404
9/16Mon
2 stopsUnited Airlines
13h 42mSJU-SDF
9/24Tue
1 stopUnited Airlines
8h 05mSDF-SJU
$486
7/18Thu
2 stopsUnited Airlines
22h 41mGCM-SDF
7/21Sun
1 stopUnited Airlines
6h 55mSDF-GCM
$501

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Recent one-way flight deals

6/5Wed
1 stopSpirit Airlines
22h 44mSJU-SDF
$77
6/13Thu
1 stopSpirit Airlines
13h 56mSJU-SDF
$109
6/5Wed
2 stopsSpirit Airlines
11h 30mSJU-SDF
$119
8/1Thu
1 stopDelta
7h 45mSJU-SDF
$150
7/18Thu
1 stopDelta
8h 04mSJU-SDF
$177
8/6Tue
2 stopsAmerican Airlines
18h 27mSJU-SDF
$179
7/30Tue
2 stopsAmerican Airlines
16h 15mSJU-SDF
$181
9/9Mon
2 stopsUnited Airlines
10h 37mSJU-LEX
$297
7/25Thu
3 stops
31h 51mSJU-SDF
$309
6/4Tue
2 stopsUnited Airlines
12h 11mSJU-LEX
$387

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Last minute flights from Caribbean Islands to Kentucky

Last minute flight, train and bus deals

5/10Fri
multi-stopSpirit Airlines
9h 09mMBJ-SDF
5/20Mon
multi-stopSpirit Airlines
26h 12mSDF-MBJ
$368
5/10Fri
multi-stopAmerican Airlines
19h 02mMBJ-SDF
5/20Mon
multi-stopAmerican Airlines
16h 38mSDF-MBJ
$383
5/9Thu
multi-stopUnited Airlines
28h 06mMBJ-SDF
5/12Sun
multi-stopUnited Airlines
7h 50mSDF-MBJ
$386
5/9Thu
multi-stopUnited Airlines
29h 01mMBJ-SDF
5/12Sun
multi-stopUnited Airlines
6h 30mSDF-MBJ
$403
5/10Fri
multi-stopAmerican Airlines
10h 46mMBJ-SDF
5/20Mon
multi-stopAmerican Airlines
16h 38mSDF-MBJ
$438
5/9Thu
multi-stopUnited Airlines
28h 06mMBJ-SDF
5/12Sun
multi-stopUnited Airlines
7h 50mSDF-MBJ
$487
5/9Thu
multi-stopUnited Airlines
29h 01mMBJ-SDF
5/12Sun
multi-stopUnited Airlines
7h 50mSDF-MBJ
$564
5/12Sun
multi-stopUnited Airlines
19h 11mPOS-SDF
5/15Wed
multi-stopUnited Airlines
16h 11mSDF-POS
$613
5/12Sun
multi-stopUnited Airlines
19h 11mPOS-SDF
5/15Wed
multi-stopUnited Airlines
17h 28mSDF-POS
$617
5/10Fri
multi-stopAmerican Airlines
9h 18mSJU-LEX
5/12Sun
multi-stopAmerican Airlines
10h 00mLEX-SJU
$791

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Flights to Kentucky

Return flight deals:

Kentucky - Caribbean Islands

Cabin classes:

$337
$358
$341
$50