$168 Find Cheap Flights from Louisville to Caribbean - Compare and Save

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 9/15. 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.
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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$457
Santo Domingo
Santo Domingo1 stop$600
Montego Bay
Montego Bay1 stop$462
Oranjestad
Oranjestad1 stop$425
Nassau
Nassau1 stop$421
Kingston
Kingston1 stop$776
Simpson Bay
Simpson Bay1 stop$539
Providenciales
Providenciales1 stop$423
Bridgetown
Bridgetown2 stops$740
George Town
George Town1 stop$424
Aguadilla
Aguadilla1 stop$475
Punta Cana
Punta Cana1 stop$457
Santo Domingo
Santo Domingo1 stop$600
Montego Bay
Montego Bay1 stop$462
Oranjestad
Oranjestad1 stop$425
Nassau
Nassau1 stop$421
Kingston
Kingston1 stop$776
Simpson Bay
Simpson Bay1 stop$539
Providenciales
Providenciales1 stop$423
Bridgetown
Bridgetown2 stops$740
George Town
George Town1 stop$424
Aguadilla
Aguadilla1 stop$475

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

ن, أكتوبر 26 - ر, نوفمبر 4
Multiple Airlines Logo
7:08 pm - 11:38 pm
SDF
-
SJU
28h 30m
1 stop
Multiple Airlines Logo
5:39 pm - 8:29 pm
SJU
-
SDF
27h 50m
1 stop
$235Multiple Airlines
ن, أغسطس 17 - ح, أغسطس 30
Multiple Airlines Logo
9:10 pm - 4:11 pm
SDF
-
SJU
19h 01m
1 stop
Multiple Airlines Logo
6:35 am - 10:29 am
SJU
-
SDF
27h 54m
1 stop
$285Multiple Airlines
س, أغسطس 22 - س, أغسطس 29
American Airlines Logo
6:08 am - 3:52 pm
SDF
-
STT
9h 44m
2 stops
American Airlines Logo
4:42 pm - 11:51 pm
STT
-
SDF
7h 09m
1 stop
$340American Airlines
ح, يناير 17 - ر, يناير 20
American Airlines Logo
7:20 pm - 2:02 pm
SDF
-
STT
17h 42m
2 stops
American Airlines Logo
6:39 pm - 12:11 pm
STT
-
SDF
18h 32m
2 stops
$365American Airlines
خ, سبتمبر 10 - خ, سبتمبر 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
$421Breeze Airways
ث, نوفمبر 3 - ث, نوفمبر 10
United Airlines Logo
7:10 am - 1:48 pm
SDF
-
MBJ
6h 38m
1 stop
United Airlines Logo
3:20 pm - 9:43 am
MBJ
-
SDF
18h 23m
2 stops
$462United Airlines
ح, سبتمبر 6 - ح, سبتمبر 13
Breeze Airways Logo
11:12 am - 8:55 am
SDF
-
NAS
21h 43m
1 stop
Breeze Airways Logo
10:15 am - 8:29 pm
NAS
-
SDF
10h 14m
1 stop
$463Breeze Airways
ر, يناير 6 - ج, يناير 8
Delta Logo
7:00 am - 1:30 pm
SDF
-
NAS
6h 30m
1 stop
Delta Logo
6:10 pm - 9:54 am
NAS
-
SDF
15h 44m
1 stop
$476Delta
ر, يناير 6 - ج, يناير 8
Delta Logo
7:00 am - 1:30 pm
SDF
-
NAS
6h 30m
1 stop
Delta Logo
4:25 pm - 9:54 am
NAS
-
SDF
17h 29m
2 stops
$480Delta
ح, أكتوبر 4 - خ, أكتوبر 8
United Airlines Logo
7:25 am - 1:47 pm
SDF
-
NAS
6h 22m
1 stop
United Airlines Logo
2:35 pm - 11:41 pm
NAS
-
SDF
9h 06m
1 stop
$489United 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 $463 (return) on average. On the other hand, the most expensive months are June and December, when the average cost of round-trip tickets is $677 and $633 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 3 weeks before departure, which saves you about 23% 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

September

Cheapest flight

$168
Best time to beat the crowds with an average 12% 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 4228 reviews
8.6Crew
7.5Entertainment
8.0Comfort
7.0Food
8.1Boarding
Airline reviews

Poor customer service, no accommodation for passengers when the flight was delayed over 5 hours.

2.0 MediocreChristopher, Jul 2026
DEN - SJC
Read more Southwest reviews

Poor customer service, no accommodation for passengers when the flight was delayed over 5 hours.

Friendly crew kept coming by to make sure all was ok, provide additional refreshments, etc.

It was good. Last flight was delayed but I always say that is in God's plan

Red eye from San Diego. Temperature of the cabin was way too warm and the air duct flowed very little air.

Overall good, just screaming kids in the area the whole flight.

My experience will Southwest was good. I wish there was more entertainment and the boarding process was slow at time but other than that my experience was great definitely will be flying with SouthWest again.

Flight was delayed by 2 hours, meaning that a flight to Dwnver which should have arrived at 11pm came into the airport at 1 am. Made for a very long day.

I think Southwest is the number one airline that anyone can fly I have flown for the first time Frontier and what a joke and their customer service United was a very strange experience I'm only sticking to Southwest from here on out for sure

Great job! My family doesnt fly often but we felt safe 100%

Great job Southwest! My family doesn't fly often but we felt safe the whole time.

My son’s suitcase was left behind at SFO and did not make the flight.

Seats were not bad enough and uncomfortable good legroom in the emergency exit row we were in, but we were forbidden to hold my grandson on my lap for a little while, and the stewardess passed us saying it was against regulations which makes little or no sense when you’re 36,000 feet. The food snacks were really bad. Tasteless tasted like wallpaper, but we’re supposed to be protein bars, and the announcements were all completely incoherent because of the noise of the airplane and the lowness and crackly nature of the PA system.. this was disgraceful. No one in our party could understand a word of what the captain or the flight attendant were saying —not a word! The landing was a little hairy in a pretty stiff crosswind -we bounced before the plane stabilized on the runway

Chaotic boarding at these gates, multiple gates squeezed in at the very end of a concourse, behind a restaurant. Agents gave up on boarding by individual zones. Flight itself was uneventful, which is all we hope for any more.

Unprepared to rebook a flight of people. Uncommunicative. When I received updates in the app it was well after the announcement in the hold room. Offered a single $12 meal voucher, not enough for a sandwich at DEN, for a 17 hour delay. No one was able to explain their meal or hotel reimbursement policy for this cancellation, just handed a card to call the Help desk. My previous flight went through several delays and was finally cancelled, without explanation. The customer help desk closed while there was a long line. I then waited in line for a gate agent almost an hour while simultaneously on hold and trying to text with a remote Delta agent. Communicating with the text agent was almost impossible; they could not find any flights that got me back to my original city before the following evening. Kept offering itineraries that did not get me back to my origin airport or involved additional layovers. In 50 minutes on hold, never got through to an agent by phone. Finally spoke to one of the gate agents who was able to rebook on a red eye that had only one stop and got me back in the afternoon the next day, rather than late evening. Later by email, Delta offered 10,000 loyalty points for the inconvenience of the cancellation. The crew on the red eye flight were delightful. I don’t remember any food or entertainment on that flight.

Flight team was great and we even arrived ahead of plan!

It was good delayed again but once on board the flight crew were very good the entertainment and wifi worked on this plane and we were offered snacks and drinks

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.

Wonderful flight! The crew was good, check-in was good and orderly and the flight was uneventful and good.

Gluten free snack options and meals that offer both gluten free and dairy free.

The pilot was late so we didn’t take off til almost 2 hours late.

The SFO lounge closes at 12 midnight. My flight took off at 2AM

Not a bad flight but a long delay boarding and taking off due to the pilot not arriving on time.

The experience with United Airlines was excellent; however, the experience with Houston Intercontinental Airport (IAH) was horrible. Although our flight departed from Terminal B, we had to go through security in Terminal C and then get on a train for travel to Terminal B. Additionally, there was significant walking required to get to the boarding location.

Delayed 2 hours while stuck on the aircraft. If the luggage was properly loaded the first time we probably wouldn’t have been delayed at all

The international portion was good. Food and beverage options were good. The sustainable wooden eatery was less than desirable. Your Star Alliance partner ANA provided real silverware. I'm 6'3" & 198 lbs and felt cramped in the exit row. How can that be? Flight attendant all had a pleasant disposition which is always good.

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.

Patrons with larger bags were asked to check the bags when boarding. Seems like the most effective, and least costly way, way to successfully use the cramped space.

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

Information on your arrival and departure airports