$110 Find Cheap Flights from Louisville to Caribbean

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Louisville to Caribbean departing on 8/26. 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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Cheap Flights from Louisville to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$477
Santo Domingo
Santo Domingo1 stop$610
Montego Bay
Montego Bay1 stop$397
Oranjestad
Oranjestad1 stop$450
Nassau
Nassau2 stops$499
Kingston
Kingston2 stops$757
Simpson Bay
Simpson Bay1 stop$515
Providenciales
Providenciales1 stop$463
Bridgetown
Bridgetown2 stops$720
George Town
George Town1 stop$579
Aguadilla
Aguadilla1 stop$582
Punta Cana
Punta Cana1 stop$477
Santo Domingo
Santo Domingo1 stop$610
Montego Bay
Montego Bay1 stop$397
Oranjestad
Oranjestad1 stop$450
Nassau
Nassau2 stops$499
Kingston
Kingston2 stops$757
Simpson Bay
Simpson Bay1 stop$515
Providenciales
Providenciales1 stop$463
Bridgetown
Bridgetown2 stops$720
George Town
George Town1 stop$579
Aguadilla
Aguadilla1 stop$582

Book Cheap Louisville to Caribbean Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Louisville to Caribbean that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Louisville to Caribbean

Sun, Aug 30 - Wed, Sep 2
United Airlines Logo
7:25 am - 3:42 pm
SDF
-
SJU
8h 17m
1 stop
United Airlines Logo
3:56 pm - 11:59 pm
SJU
-
SDF
8h 03m
1 stop
$220United Airlines
Sat, Aug 29 - Mon, Aug 31
United Airlines Logo
7:25 am - 3:42 pm
SDF
-
SJU
8h 17m
1 stop
United Airlines Logo
2:20 pm - 10:15 pm
SJU
-
SDF
7h 55m
1 stop
$223United Airlines
Mon, Oct 19 - Mon, Oct 26
American Airlines Logo
6:13 pm - 2:35 pm
SDF
-
STT
20h 22m
2 stops
American Airlines Logo
5:40 pm - 12:45 pm
STT
-
SDF
19h 05m
2 stops
$224American Airlines
Wed, Aug 12 - Wed, Aug 19
Delta Logo
1:17 pm - 10:29 pm
SDF
-
SJU
9h 12m
1 stop
Delta Logo
12:56 pm - 9:33 pm
SJU
-
SDF
8h 37m
1 stop
$226Delta
Sun, Aug 9 - Fri, Aug 14
Southwest Logo
3:35 pm - 10:45 pm
SDF
-
SJU
7h 10m
1 stop
Southwest Logo
6:00 am - 1:35 pm
SJU
-
SDF
7h 35m
1 stop
$258Southwest
Fri, Sep 25 - Wed, Sep 30
American Airlines Logo
7:27 pm - 11:00 am
SDF
-
SJU
15h 33m
2 stops
American Airlines Logo
2:58 pm - 11:22 pm
SJU
-
SDF
8h 24m
2 stops
$268American Airlines
Sat, Oct 3 - Thu, Oct 8
Southwest Logo
3:40 pm - 11:50 pm
SDF
-
SJU
8h 10m
2 stops
Southwest Logo
5:20 pm - 12:40 am
SJU
-
SDF
7h 20m
1 stop
$273Southwest
Fri, Aug 14 - Thu, Aug 20
Multiple Airlines Logo
9:10 pm - 4:11 pm
SDF
-
SJU
19h 01m
1 stop
Multiple Airlines Logo
6:45 am - 9:49 am
SJU
-
SDF
27h 04m
1 stop
$280Multiple Airlines
Sat, Aug 29 - Mon, Aug 31
Delta Logo
6:00 am - 4:38 pm
SDF
-
SJU
10h 38m
1 stop
Delta Logo
7:00 am - 2:18 pm
SJU
-
SDF
7h 18m
1 stop
$283Delta
Thu, Aug 6 - Wed, Aug 12
Multiple Airlines Logo
9:24 pm - 8:25 pm
SDF
-
PUJ
23h 01m
1 stop
Multiple Airlines Logo
11:52 am - 10:32 am
PUJ
-
SDF
22h 40m
2 stops
$477Multiple Airlines
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?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Louisville to Caribbean, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Louisville to Caribbean is January, when tickets cost $113 (return) on average. On the other hand, the most expensive months are May and July, when the average cost of round-trip tickets is $225 and $225 respectively.

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

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Louisville to Caribbean, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Louisville to Caribbean, you should book around 2 weeks before departure, which saves you about 28% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 16 weeks before departure.

Good to know

Low seasonAugust
Cheapest flight$110
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.
7.9
SouthwestOverall score based on 4242 reviews
8.0Comfort
8.6Crew
8.1Boarding
7.0Food
7.5Entertainment
Airline reviews

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

2.0 MediocreIrene, Jun 2026
DEN - SFO
Read more Southwest reviews

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

Crew was rude, flight was late, wifi didn't work, no food, basically nothing about this flight was good.

It was just okay, no frills, basic transportation with no luxury. No screens on the seats, no water or drinks on a short flight. Full flight but at least it was on time.

Flight was constantly delayed with significant changes in time, it was supposed to get to Colorado Springs at 8:30 PM but it got there after midnight.

Over a 3 hour flight. The turbulence was almost imperceptible except for 2 short periods which were not bad and over quickly. The attendants claimed "Safety first" and sat looking at their phones for 3 hours with no drink or snack service. This isn't the first time with Southwest. I thinkit may be there new plan of operation. Oh, and it was June 18, Southwest's Birthday which offered free drinks. NOT.

Flight was delayed, full flight and I had to change gates. Southwest flights are always late later in the day.

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

It was great. The gate staff were very helpful in Portland when my son forgot his rolling bag and had to go back to get it just in time to make it on the plane. We really appreciate that. Great job!

Airline is not very senior friendly. Flights are late, forcing us to run to the connecting flight. Food is awful. Wish they would go back to pretzels and peanuts. During flight, pressurization isn’t quite right and all of our ears get plugged. Everything is nickel and dime, charging for boarding, seat selection and legroom. While a screen at the desk in the gate area says check your roll on bag now for free due to space limitation, the employee at the desk will not check the bag without a $100 fee. Insane.

Kayak could’ve posted the correct gate number. Almost missed my flight.

FA was a bit strange and dodgy not very characteristic of Delta

Not really a “Delta” problem but worth mentioning: Boarding was a difficult process. TSA seemed understaffed and Pre-Check took longer than regular TSA. The supervisor was frazzled and yelled at travelers. Once through TSA, we had to put our carry-ons through another x-ray machine. Then queue up to board with both boarding pass and ID. Then, when we got to the stairs on the tarmac, we had to show our boarding pass again. Maybe this is just normal for Kona since the terminal is outdoors (but still a “secured” area).

flight was delayed 4+ hours. there was really no understanding of why? weather? the last hour of delay was post boarding. pilot seat was broken. was that the real reason? nonetheless, long day of inconveniences.

Love me some Delta. One of the few airlines to recognize and support veterans. Easy boarding, flight was on time and arrived early and the flight attendants were excellent on this flight.

I thought the service was very nice and pleasant. There were no hiccups and no issues so overall a good experience.

Very good flight. Crew was great. No issues and we even arrived early.

The flights are constantly late anymore, and they won't even give you a glass of water on the plane. For years, they were able to do a service on this flight from Atlanta to Knoxville and Knoxville Atlanta now they say it's too short of a flight. You can't even get a quick drink of water.

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.

Awful. Delayed flights, missed connection to Toronto. Hotel vouchers were for already booked hotels x3. Giant waste of my time

Horrible I am at almost 2,000,000 miles on United. This was probably the worst flight ever. An hour and a half before takeoff I get a message that they’re changing the plane and I no longer have a seat in Polaris business Supposedly, there was a problem with the plane, but then there was no other plane Finally, they decided to bring a plane from Newark to Washington Dulles Of course the original flight was at 10:45 PM so by the time the plane got there it was 12:30 AM. It had not been cleaned. It had not been catered. They don’t really have people available to do those things when it’s not pre-programmed at 1 o’clock in the morning. The crew had to be changed And the new plane held 28 fewer people than the scheduled plane There is no way you can hate United Airlines enough The people at the gate were actually just fine, but it was management who was completely useless And did they send extra help to the people at the gate? Did they send supervisors? Of course not. Just don’t take United find somebody else or buy a boat

Great experience. Boarding was fast, staff were very nice and funny, everything at the seat worked well.

Boarding was great, and the crew were very friendly. The seats must have been a bit on the older side and you could feel some of the seat components through the padding. Also, the plugs did not work on the row's entertainment screen or charging ports. Checked bag was transferred for connecting flight, and we appreciated how early we had the connecting gate information.

Lost one piece of luggage even though I checked in 2.5 hours before the flight

It was Swiss. Our kosher meals were literally frozen solid and therefore inedible, and the crew didnt care.

For the expense of first class, the seats could have been nicer and higher tier snacks would have been nice.

The boarding process on the departure from LA was rather slow even though I was in Group 1. For first class, I was not expecting to have to pay for Wi-fi but I did and then the wi-fi was spotty. The entree was surprisingly good and so that was a pleasant surprise. However, once I got to Houston, it was terrible. Unfortunately there was bad weather but the constant gate changes for my connecting flight was difficult to manage due to having to navigate back and forth between different terminals.

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.

My experience with American Airlines was great. Unfortunately my stroller was not located and has not been given to me and or reached out in return for in regard to information.

Pilots were fantastic - super smooth. First Class flight attendant was very attentive. Main Cabin flight attendant should try to smooth the rough edges of her voice - very shrill / punitive. Hurt my ears just to listen to her. Recognize they have a (tough) job to do - but tone over speakers needs to be less like scolding a 5 year old.

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.

We were delayed in Charlotte for almost 2 hours because American Airlines didn't have flight attendants for our flight.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports