$116 Find Cheap Flights from Louisville to Caribbean - Compare and Save

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Cheap Flights from Louisville to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 5 days
Punta Cana
Punta Cana1 stop$502
Santo Domingo
Santo Domingo1 stop$600
Montego Bay
Montego Bay1 stop$442
Nassau
Nassau1 stop$477
Providenciales
Providenciales1 stop$598
Bridgetown
Bridgetown1 stop$662
George Town
George Town1 stop$417
Aguadilla
Aguadilla1 stop$629
Puerto Plata
Puerto Plata2 stops$705
Punta Cana
Punta Cana1 stop$502
Santo Domingo
Santo Domingo1 stop$600
Montego Bay
Montego Bay1 stop$442
Nassau
Nassau1 stop$477
Providenciales
Providenciales1 stop$598
Bridgetown
Bridgetown1 stop$662
George Town
George Town1 stop$417
Aguadilla
Aguadilla1 stop$629
Puerto Plata
Puerto Plata2 stops$705
Booking Insights

KAYAK's insights & trends for Louisville to Caribbean flights

Get data-powered insights and trends into flights from Louisville to Caribbean to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest month to fly from Louisville to Caribbean?

The cheapest month for flights from Louisville to Caribbean is January, when tickets cost $470 (return) on average. On the other hand, the most expensive months are June and December, when the average cost of round-trip tickets is $674 and $639 respectively.

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

To get a below average price on the flight from Louisville to Caribbean, you should book around 3 weeks before departure, which saves you about 21% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 24 weeks before departure.

Good to know

Low season

August

Cheapest flight

$116
Best time to beat the crowds with an average 7% drop in price.
Most popular time to fly with an average 14% increase in price.
Flight from Louisville to San Juan

FAQs - booking Caribbean flights

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

    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 Louisville to Caribbean.

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

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

    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 Louisville to Caribbean 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 Louisville to Caribbean?

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

Reviews of the top 4 airlines serving from Louisville to Caribbean

 
Need help choosing which airline to fly with from Louisville to Caribbean? 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 4205 reviews
7.5Entertainment
8.1Boarding
8.6Crew
7.0Food
8.0Comfort
Airline reviews

Seated at front bulkhead for a smidge extra leg room away from home and on flight back home. Away crew was very proactive about assuring our carryons had space close behind us (because no seat in front of us our personal items had to be in a small bin overhead). They actively required passengers place overhead luggage on its side so more items could fit in bins. Home crew made no such efforts. I had to struggle back rows to get overhead bags upon landing, no crew help then either, and some disgruntled passengers as I and others retrieved our bags. There was a system that worked pretty well. The home bound crew just didn't feel like working.

4.0 OkayMather, Aug 2026
Read more Southwest reviews

Seated at front bulkhead for a smidge extra leg room away from home and on flight back home. Away crew was very proactive about assuring our carryons had space close behind us (because no seat in front of us our personal items had to be in a small bin overhead). They actively required passengers place overhead luggage on its side so more items could fit in bins. Home crew made no such efforts. I had to struggle back rows to get overhead bags upon landing, no crew help then either, and some disgruntled passengers as I and others retrieved our bags. There was a system that worked pretty well. The home bound crew just didn't feel like working.

Southwest has inacted unfriendly customer policies like other airlines. Watch the fine print very carefully if you are having to alter flight arrangements. Rules are now complicated and very stilted to travelers sacrificing travel funds (unlike before where the simple, straight forward flight change policy was worth the extra premium for ticket price.) On the positive side, SW Flight crews are still wonderfully helpful.

Flight left on time and was early landing. Seats not comfortable and not enough space…

Flight left on time. Seat spacing is way too small…

It would have been better if the flight was on time

Fairly good - the seats seemed more comfortable on this flight. The staff out of Detroit were quite friendly. But they directed us to the wrong carousel for luggage. :(

Just crazy with times being pushed and pushed and pushed and gate crew at Philly super rude and unprofessional with many under stress with delays.

I liked the new boarding process. I thought the buyup options (legroom, early boarding) to be easy to request and reasonably priced. All the Southwest team from gate to in-flight were so nice.

Flight time kept changing and so did the gate. It was very frustrating

Exceptional. The gate crew responded quickly and got me onto this earlier flight as the final passenger, saving me more than four hours of wait time for my reserved flight.

Noting this only because it’s so unusual for delta: this was just an uncomfortable flight. The jet ridge was too hot and the plane wasn’t any better. By the time we got off the ground the AC was on but for such a short flight it was almost too late.

1) It was extremely hot in the cabin. All the passengers were sweating and it almost became suffocating 2) It was a 50 min flight but there was no service. How can a 50 minute flight not have any drink/snack service?

Very bad multiple confusion and miscommunication which i ended up missing my flight.

There was no food, so :( to that one. The flight was delayed by 3 hours. Not Delta's fault. Not the crew's fault. Considering how tired all us passengers were, everything went surprisingly well. The flight crew were very helpful, friendly, and professional. I always fly Delta.

Delta is a perfect partner, offering the gold standard across the board.

Our flight from Detroit to LaGuardia on Thursday 8/20 was delayed from 555 to 910 due to storms and a ground stop at LGA. It’s never fun to be stuck at the airport but I thought the desk crew and captain handled it well and kept us informed. I especially liked how they referred to us as their “LaGuardia family.” I am a loyal delta customer and this is one of the reasons why.

The boarding agent guy in Lexington on 7/23 that boarded the flights to Atlanta is very rude for working in customer service. I know there were delays but he was dismissive rude and arrogant. Most native Kentucky residents are nice and very cordial he needs to eat a big ole piece of humble pie. I watched him be rude to several people and as much as he could of filled up a delayed flight to save you money and he was so rude to people it was ridiculous. Next no water or snacks on short flights is awful 1st you delay a flight then do not even offer water on the flight.. No thanks I like delta better but I travel ever week and to be treated like this might as well fly American at least they offer water and have better rewards.

The staff was fine. The plane was extremely tight, and I paid for the wifi and it did not work at all. I was actually going to ask for a refund.

Left on time and arrived early this extending our 31 minute transfer. Bags made it also!

The crew was very polite as I have a few handicaps and everything was made pleasant. Check-in was easy as I was brought on board by the wheelchair assistant. One flight attendant did make sure my personal item was carefully stored under the seat in front of me. I was made to feel welcome as a customer as I made my first trip with a few disabilities. Entertainment and wifi worked quite well. The only food service were snacks and drinks. Those were okay. Overall it was a very smooth flight and encouraged me to use Delta again.

Not a United thing, but late afternoon departures from Denver with thunderstorms is always prone to delays.

Kayak booked this flight with only 1h 20min layover in Chicago. This made it impossible for me and several other passengers to reach this flight. Moreover, the gate closed boarding in spite of several passengers still on their way without waiting even one more minute. However, the plane departed with 20min (!) delay, i.e., there would have been at least 15 min time to let the delayed passengers board without causing any delays. I complained and as a "thank you" the attendent booked us on the last (!) flight to Indianapolis ~7h later! Thankfully, I caught the spitefulness and the United customer line rebooked the flight to an earlier flight. Although I can't grade this particular flight since I never had a chance to take it, Kayak made the mistake of a too short layover and the crew at the gate was awful.

With discover in general was very good but from Munich yo Palermo was poor

Sitting in coach even in the larger leg space is extremely uncomfortable and the staff pay no attention.

Really delayed, no effort to support customers other than “sometimes we run late.”

It was serviceable, nothing special but nothing awful on this leg.

On boarding crew at the airport called in the boarding numbers too early meaning before the previous line was completed resulting in later numbers getting to board ahead. Also she asked those who boarded from number 3 to have the tags in their carry-on bags and leave it in the jet bridge. Most of the overhead bins were empty though. This is more work for the ground staff in addition to more inconvenience for passengers waiting to get their carry-ons from the jet bridge.

Polaris seat is plush and conducive to sleep. Cabin crew was experienced, highly attentive and helpful when any need arose, such as finding a lost phone in the seat mechanism. Food was a disappointment, especially the Japanese items coming out of Newark all seemed a bit overcooked, though the empanada snacks served midway were a hit.

The male air hostess was rude and didn’t provide good customer service. Didn’t even offer me a drink

This trip was a Christmas gift to our family. We were flying from Lexington to Palm Springs. When we were checking in the ticket agent said one bags was over weight by 4 LBS. We were flying first class which has baggage weight of 70 LBS per bag, one bag was 54LBS. We then had to take items from one bag to another. The agent also saw we had a dog with us. Once on the plane we were seated with the dog in the carrier. The United ticket agent came in the plane with two other people, I believe one was TSA and the other some security officer. The United agent said we had not paid for the dog ticket. We had paid for the ticket when we purchased our tickets. She did not give me time to find the email receipt. She then threatened all three of us with either I come with her or she would have all three of physically removed from the plane. I left the plane to pay for another ticket. She had to take my credit back to where we checked in. She acted as if it needed to be done immediately. She said we had 3 minutes. We then sat at the gate for approximately another 45 minutes. This was so embarrassing…to be threatened to be removed from a plane that we paid for all tickets including the dog. The flight attendance on the next leg of our trip were not very attentive to the passengers. On the plus side all the flights were on time. All in all, this was a miserable way to start a holiday vacation. United Airlines showed no compassion towards the whole incident. I feel we were purposely neglected.

Flight was good, little delayed because of busy plane traffic

I had ridiculously long body search because I have knee and hip replacements

Better perks for corporate employees whom travel often and spend a lot of money with the airlines. Snacks were terrible chips crackers are ideas. Flight and crew were great comfort was fine entertainment not so great so so called status members means nothing

Flight had mechanical issues and it was delayed 30 mins - some of us boarded and then had to deplane.

Delayed flight. Missed connection, AA put us on a later connecting flight. The connection flight was delayed 4 times and we had to deplane. Didnt get home until 3am, when I was supposed to be home at 8:30p. Zero compensation offered from American. I would not fly them again.

Better snacks but flight and crew were amazing on this flight

The AA app really sucks ... Every flight & connecting flights were delayed over 30 mins. One connecting flight on American Eagle said it was delayed in its arrival ... when it was actually parked across from the gate for over 1 hr before they pulled it to the gate. Seats in the economy/ main cabin are packed together like sardines ... no leg room.

To start, I’d like to say that every American Airline personnel I interacted with on the ground, especially flight crew, was very friendly and did their best to help me out. Despite this, however, my experience with the airline was an entire mess. The 7:19 PM flight was heavily delayed due to weather, and pushed to 10:30 AM the next morning. Because of this, I had to spend the night inside of the airport. At some point later in the night, I got an email saying that the flight had been canceled. I called the support number, and the representative on the other line told me that the flight was still on and that I didn’t need to rebook. The next morning, no one came to the gate to open the door for the crew until almost 11 AM. By this time the flight crew had been waiting for over an hour, and they had called management to get someone to open the door for them multiple times. Around 11:30, the gate screen had changed to a different flight. I ended up buying a last minute ticket with Southwest airline just to get to Chicago, because the next flight with American wasn’t until 7:19 pm that day. Now, earlier that morning my suitcase had been sent ahead of me to ORD. I went to baggage claim to ask them if I could have my suitcase forwarded to where I was staying. The representative at SDF baggage claim said they could and put the claim in for me. As I was going back through TSA, I got an email that the airline had found my suitcase, but the next step was to send it BACK to SDF. I called the airline support number again, and I made it clear that my suitcase needed to stay in Chicago and to not come back to SDF. The representative told me that they would hold my suitcase at ORD and that it wasn’t going to be forwarded anywhere. Once I got there, I found that they had loaded my suitcase onto a plane to send it back to SDF. Thankfully, I had gotten to the baggage claim counter in time for them to put in a request to bring my suitcase back up. My refund with the airline is processing already, but because of this entire experience and miscommunication at every turn of the way, I will not book with American Airlines in the future.

Cabin was roomy enough to easily slide my carry on under the seat in front of me!

They needed to de-ice the plane. Apparently airlines have a problem keeping their de-icing vehicles in good repair. After we backed away from the gate we sat and didn't move for nearly an hour. Nearly an HOUR with minimal communication from the flight crew. Eventually the sun took care of what American Airlines could not and melted the minimal ice. We finally took of a hour late which, in turn, jacked up our connection in Chicago.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports