$110 Find Cheap Flights from Louisville to Caribbean Islands

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 Islands 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

KAYAK searches hundreds of travel sites at once for deals on flights to Caribbean Islands

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Louisville to Caribbean Islands, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Louisville to Caribbean Islands, as well as popular online travel agencies
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Cheap Flights from Louisville to Caribbean Islands

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$395
Oranjestad
Oranjestad2 stops$410
Nassau
Nassau1 stop$458
Kingston
Kingston1 stop$733
Simpson Bay
Simpson Bay1 stop$490
Providenciales
Providenciales1 stop$423
Bridgetown
Bridgetown2 stops$711
George Town
George Town2 stops$539
Aguadilla
Aguadilla1 stop$564
Puerto Plata
Puerto Plata2 stops$725
Punta Cana
Punta Cana1 stop$477
Santo Domingo
Santo Domingo1 stop$610
Montego Bay
Montego Bay1 stop$395
Oranjestad
Oranjestad2 stops$410
Nassau
Nassau1 stop$458
Kingston
Kingston1 stop$733
Simpson Bay
Simpson Bay1 stop$490
Providenciales
Providenciales1 stop$423
Bridgetown
Bridgetown2 stops$711
George Town
George Town2 stops$539
Aguadilla
Aguadilla1 stop$564
Puerto Plata
Puerto Plata2 stops$725

Book Cheap Louisville to Caribbean Islands 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 Islands 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 Islands

Fri, Sep 18 - Tue, Sep 22
Southwest Logo
4:10 pm - 11:05 pm
SDF
-
SJU
6h 55m
1 stop
Southwest Logo
5:15 am - 11:10 am
SJU
-
SDF
5h 55m
1 stop
$220Southwest
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
Sun, Aug 23 - Wed, Aug 26
Delta Logo
6:00 am - 11:46 am
SDF
-
SJU
5h 46m
1 stop
Delta Logo
5:49 pm - 12:24 am
SJU
-
SDF
6h 35m
1 stop
$226Delta
Sat, Oct 3 - Fri, Oct 9
United Airlines Logo
7:00 am - 2:44 pm
SDF
-
SJU
7h 44m
1 stop
United Airlines Logo
3:56 pm - 11:59 pm
SJU
-
SDF
8h 03m
1 stop
$248United Airlines
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
Sun, Aug 23 - Wed, Aug 26
American Airlines Logo
5:00 am - 4:57 pm
SDF
-
SJU
11h 57m
2 stops
American Airlines Logo
7:30 am - 11:11 pm
SJU
-
SDF
15h 41m
1 stop
$261American Airlines
Sun, Aug 30 - Wed, Sep 2
Multiple Airlines Logo
11:12 am - 12:34 am
SDF
-
SJU
13h 22m
1 stop
Multiple Airlines Logo
5:37 pm - 10:32 am
SJU
-
SDF
16h 55m
1 stop
$264Multiple Airlines
Fri, Sep 25 - Wed, Sep 30
Delta Logo
6:00 am - 11:45 am
SDF
-
SJU
5h 45m
1 stop
Delta Logo
5:59 pm - 11:59 pm
SJU
-
SDF
6h 00m
1 stop
$271Delta
Tue, Aug 11 - Tue, Aug 18
United Airlines Logo
6:15 am - 1:33 pm
SDF
-
NAS
7h 18m
1 stop
United Airlines Logo
12:35 pm - 10:59 pm
NAS
-
SDF
10h 24m
1 stop
$458United Airlines
Thu, Dec 3 - Thu, Dec 17
Breeze Airways Logo
9:09 pm - 8:30 am
SDF
-
NAS
11h 21m
1 stop
Breeze Airways Logo
10:15 am - 8:29 pm
NAS
-
SDF
10h 14m
1 stop
$491Breeze Airways
Booking Insights

KAYAK's insights & trends for Louisville to Caribbean Islands flights

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

Can I save money by flying with a layover from Louisville to Caribbean Islands?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $344, prices are generally cheapest when you fly direct.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Louisville to Caribbean Islands, 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 Islands is January, when tickets cost $160 (return) on average. On the other hand, the most expensive months are February and November, when the average cost of round-trip tickets is $340 and $335 respectively.

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

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 Islands, 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 Islands, you should book around 2 weeks before departure, which saves you about 23% 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 Islands flights

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

    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 Islands.

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

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

    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 Islands 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 Islands?

    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 Islands 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 Islands

 
See real verified KAYAK customer reviews for airlines flying from Louisville to Caribbean Islands. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Louisville to Caribbean Islands? 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 4246 reviews
8.1Boarding
8.6Crew
7.5Entertainment
8.0Comfort
7.0Food
Airline reviews

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.

6.0 GoodAnonymous, Jun 2026
TPA - DAL
Read more Southwest reviews

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.

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.

The CRJ-900 was clean but the overhead air vents were broken in our First Class row, making the cabin very hot until about 30 mins into the flight. The flight attendants were both extremely apologetic and accommodating though so that is why I rated the flight as very good. They checked on us many times and truly showed they cared. The snacks for an hour and a half flight could be better. Would be nice if there was a small plated meal over convenient store snacks. WiFi also was not working. And it would be nice if Delta had adjustable headrests on these planes.

New high end luggage ruined/zippers broken, items missing. All happened on return flight from msp to mso. Do better! Not store bought luggage but high end personalized ogio custom embroidered luggage. Total slap in the face ontop of an extra luggage fee that took me 3 hrs on chat to resolve.

It was as good as it could be. Flying is not a pleasant experience these days.

The plane was old and thus the seats were not good. No cushion left whatsoever, and it all was a bit worn out.

I was in Comfort and we didn’t get any drinks, chips or anything! First Class got full service on the flight and Comfort got nothing. Seat was horrible and uncomfortable

My flight was delayed by 4 hours in 30 minute increments. The gate agents were amazing but the communication was not. We were told that there was a maintenance issue but they didn't know what it was. That didn't inspire confidence. Then they said they found it and it was fixed and the pilot just needed to sign off. Then the pilot needed to talk to the other pilot from the arriving flight and we'd be fine. Then we were waiting for the pilot to call back. Then the maintenance issue wasn't fixed. Then they decided we were getting a new plane (why didn't they decide this earlier??). Fine. But then they announced we were changing gates AND terminals. And we were boarding in 20 minutes. So we all had to run to the new terminal gate. We could have taken off at that time, but we then had to wait for all the people who rebooked on a different flight to book this flight again. That took 30+ minutes because there was only one gate agent. When everyone ditched this flight, I saw it as an opportunity to upgrade to comfort. Delta, the greedy jerks they are, charged me $121. After their delay, their fault, their issues, couldn't even discount an upgrade. They only handed out $12 meal vouchers for the delay. I can't even get a snack from starbucks for that.

The crew was very inconsiderate and rude. My flight was scheduled to depart at 6:00am. I received a call from the crew at 5:40am, asking if I was going to make the flight because I was the only one that hasn't boarded yet and boarding ends at 5:50am. I let them know that I will be at the gate in a few minutes, before the 5:50am cutoff. When I arrived at the gate at 5:45am the gate was closed. Departing early on last minute notice without having all passengers on board is inconsiderate and unprofessional.

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.

Great staff. Clean plane, but we were delayed for more than an hour due to maintenance issues and had to board another plane.

I was very disappointed with my experience at the United Airlines baggage check. The representative was rude and unhelpful. I was required to remove approximately 1.5 pounds from my two checked bags, even though it was a very small amount over the limit. The interaction was unnecessarily unpleasant, and I expected much better customer service. I hope United will review this incident and provide additional customer service training to its staff.

No extra snacks were available. Meals quality is terrible. Crew was not friendly.

I was exhausted from a long day. The flight was smooth. The first flight during my 3 week travel that took off on time.

Agents at gate were not immediately available to solve problems and once they did they didn’t fix all the fight connections

1 flight cancelled Had to fly out of different city Flight at new departure city was delayed 3 hours causing us to miss connecting flights. By the time we did make it to Prague our luggage did not. Had to wait day and a half for luggage to be delivered. Customer service was not good. Agents did not arrive at gate until 5-10 minutes before boarding

I needed internet for critical matters and it never worked.

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

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.

I cancelled this flight 2 days before departure but I followed your texts and emails and IF you were correct this flight turned into a nightmare.

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.

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 Islands

Information on your arrival and departure airports