$113 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 1/11. 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 Cana2 stops$454
Santo Domingo
Santo Domingo1 stop$472
Montego Bay
Montego Bay1 stop$439
Oranjestad
Oranjestad1 stop$533
Nassau
Nassau1 stop$377
Kingston
Kingston1 stop$650
Simpson Bay
Simpson Bay1 stop$562
Providenciales
Providenciales1 stop$488
Bridgetown
Bridgetown1 stop$586
George Town
George Town2 stops$459
Puerto Plata
Puerto Plata2 stops$582
Aguadilla
Aguadilla2 stops$432
Punta Cana
Punta Cana2 stops$454
Santo Domingo
Santo Domingo1 stop$472
Montego Bay
Montego Bay1 stop$439
Oranjestad
Oranjestad1 stop$533
Nassau
Nassau1 stop$377
Kingston
Kingston1 stop$650
Simpson Bay
Simpson Bay1 stop$562
Providenciales
Providenciales1 stop$488
Bridgetown
Bridgetown1 stop$586
George Town
George Town2 stops$459
Puerto Plata
Puerto Plata2 stops$582
Aguadilla
Aguadilla2 stops$432

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

dom, fev 1 - qua, fev 4
American Airlines Logo
1:15 pm - 11:59 pmSDF-SJU
9h 44m2 stops
American Airlines Logo
5:51 pm - 11:59 pmSJU-SDF
7h 08m1 stop
$225American Airlines
Find Deal
sáb, fev 21 - qua, fev 25
United Airlines Logo
5:54 pm - 6:11 amSDF-SJU
11h 17m2 stops
United Airlines Logo
8:10 am - 8:14 pmSJU-SDF
13h 04m2 stops
$250United Airlines
Find Deal
sex, dez 5 - sáb, dez 13
Spirit Airlines Logo
11:55 am - 12:45 amSDF-SJU
11h 50m1 stop
Spirit Airlines Logo
5:00 pm - 11:00 amSJU-SDF
19h 00m2 stops
$319Spirit Airlines
Find Deal
sex, dez 5 - dom, dez 7
Spirit Airlines Logo
11:55 am - 12:45 amSDF-SJU
11h 50m1 stop
Spirit Airlines Logo
4:10 am - 11:00 amSJU-SDF
7h 50m1 stop
$342Spirit Airlines
Find Deal
qui, fev 19 - qui, fev 26
Multiple Airlines Logo
6:00 am - 2:50 amSDF-SJU
19h 50m1 stop
Multiple Airlines Logo
11:05 am - 11:45 pmSJU-SDF
13h 40m1 stop
$351Multiple Airlines
Find Deal
qui, abr 30 - dom, mai 3
Delta Logo
10:10 am - 4:15 pmSDF-SJU
6h 05m1 stop
Delta Logo
6:15 am - 12:36 pmSJU-SDF
6h 21m1 stop
$353Delta
Find Deal
ter, nov 18 - sáb, nov 22
Southwest Logo
11:45 am - 10:05 pmSDF-SJU
9h 20m2 stops
Southwest Logo
6:35 am - 2:50 pmSJU-SDF
9h 15m2 stops
$355Southwest
Find Deal
qua, dez 17 - qua, dez 24
Southwest Logo
11:45 am - 10:05 pmSDF-SJU
9h 20m2 stops
Southwest Logo
4:30 pm - 10:50 pmSJU-SDF
7h 20m1 stop
$365Southwest
Find Deal
qua, fev 18 - qua, fev 25
Delta Logo
5:33 am - 3:54 pmSDF-STT
9h 21m1 stop
Delta Logo
2:00 pm - 8:25 pmSTT-SDF
7h 25m1 stop
$371Delta
Find Deal
sex, dez 12 - dom, dez 14
Multiple Airlines Logo
11:21 am - 12:16 amSDF-SJU
11h 55m2 stops
Multiple Airlines Logo
4:10 am - 11:00 amSJU-SDF
7h 50m1 stop
$380Multiple Airlines
Find Deal
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 September, when tickets cost $313 (return) on average. On the other hand, the most expensive months are December and March, when the average cost of round-trip tickets is $566 and $518 respectively.

What’s the cheapest day of the week to fly from Louisville to Caribbean?

The average price of all round-trip flights from Louisville to Caribbean clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Louisville to Caribbean, look for departures on Tuesdays and avoid leaving on a Friday, as it's usually the priciest day. When flying back from Caribbean, Thursday is the cheapest day to fly and Sunday is the most expensive.

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 16% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 14 weeks before departure.

Good to know

Low seasonAugust
Cheapest flight$113
Best time to beat the crowds with an average 8% drop in price.
Most popular time to fly with an average 11% 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.

  • What is the cheapest time of day to fly to Caribbean?

    The cheapest time of day to fly to Caribbean is generally at night, when round-trip flights cost $339 on average. On average, there is no price difference when choosing to fly in the morning or the evening on this flight route. The most expensive time of day to fly to Caribbean is generally in the evening, which is peak travel time and where the average cost of a ticket is $441.

Reviews of the top 5 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 4241 reviews
7.5Entertainment
8.0Comfort
8.1Boarding
7.0Food
8.6Crew
Airline reviews

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

2.0 MediocreAnonymous, Nov 2025ORD - LAS
Read more Southwest reviews

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

Full cans of soda would be nice. A choice between two snacks would be appreciated.

Tried watching free movie and it kept freezing so I couldn’t finish.

All was good. I just had a hard time getting connected to the WiFi/internet during the flight

Sacrament staff are always polite and helpful. Airport is easy to maneuver and boarding is straightforward.

Great flight. Outstanding Service. Southwest was able to put us on a direct flight to Denver when the connection could have been affected by a later arrival to Baltimore. The direct flight was less expensive that the flight with the connection in Baltimore.

Delays delays delays. Late taking off, late landing, wait for a gate, etc.

Boarded on time but once we were ready for take off, the crew determined that, although every seat was taken, somehow someone was on the wrong flight. Delay, delay delay, announcements and ended up with one person checking EVERY ID against their passenger Manifest only to figure out it was a "clerical error." We departed 54 minutes late causing me to run in the St. Louis Airport to make my connection and lose the priority boarding spot I had paid for. Unnecessary delay.

I was re-booked onto another flight because my original flight was delayed and I would have missed my connector. I ended up in the “C” group after paying extra to be in the “A “ group on the original flight. At least if you’re going to re-book people, re-book them into the same group.

I truly love flying with Delta. They have always treated me with the upmost respect

Our flight attendant in FIRST CLASS was one of the worst I’ve ever had. She was not at all pleasant, nor particularly good at her service.

Everything went well and was good. Nothing exceptional, but no complaints either. Cheap seats are pretty comfortable.

Staff were friendly and happy. Delta could make sure passengers that don't have the app know of changes. Without Kayak I would not have known about the change of gate or the delay. Kayak was faster to notify me.

They ended up paying for the bag twice, but the counter wouldn't take my baggage receipt. Left it to me to resolve. Not sure how to resolve the issue.

The customer service before board was very rude and when I expressed my concerns about making the connecting flight she laughed and told me I bought the wrong ticket. I explained once it showed the flight was delayed it no longer let me change seats or anything. I was trying to upgrade to make sure I would get to the next gate on time.

Non stop on long haul is the way to go. Great experience

The aircraft interior is old and tired on this aircraft. The entertainment system never worked despite the crews attempt to reset the system.

The flight used a B767 with a very old interior from before 2014. The entertainment system did not work at all during the flight despite attempts to reset the system. It was like they flew this route just to be competitive.

Old plane and old configuration/seats but still comfortable for a morning flight

Plane boarded early a quickly, was mostly full. We left close to on time. And landed early.

My experience on this United Airlines flight was highly uncomfortable, primarily due to two issues: Cabin Temperature: The temperature on the Boeing 737 MAX 8 was unacceptably high, feeling consistently around 80 degrees throughout the flight. This made sleeping impossible and significantly detracted from the experience. Seating Arrangement: Being stuck in a middle seat for a six-and-a-half-hour overnight flight compounded the discomfort. Moving forward, I will always purchase a seat assignment to avoid this situation.

Premium Plus is a really good idea for longer flights

7 hours delayed due to operational issues on United’s end. Basically laziness.

Short flight but an "eager to help" crew made the journey more enjoyable!

Flight was delayed only slightly before takeoff due to traffic control. However, the flight arrived early to ORD. Good flight. United has been very reliable for me.

The person I bought the ticket for didn’t make the flight.

Lately I like the planes have been exceptionally filthy. There’s lines of dust and dirt all across the ceiling in the vents, and the cracks in between the seats are literally full of food. It’s definitely not the quality of service that I was used to with United. I’m also very disappointed with the Wi-Fi! All I wanna do is knock out a few work jobs while I’m trapped in my seat And it spools so bad. They did provide me with a refund, but the process of getting that refund is so complicated. It’s unfortunate.

Another delayed flight. When the delays exceed the duration of the flight, it’s a problem.

Excellent flight. Smooth, efficient boarding. Quick flight. Arrived early at STL.

We loved the steward on the plane. He made the night enjoyable

I enjoyed the extra leg room compared to other airlines. The first stewards made my daughter’s birthday special by giving her an extra snack. Then the last one coming home from Chicago to Appleton made our night really enjoyable Thanks for making our trip enjoyable

The flight was smooth, the pilot kept us informed about delays and we arrived more of less on time

Flight delay was communicated before leaving for airport which caused it to be a non-event. Great flight and crew!

Did not get any refreshments. Crew was very nice but limited. Small seats

Wish some foods provided rather than just biscuit/cookie for flight more than 2 hours

Wish a flight with more than 2 hours with some snack rather than just cookie/biscuit.

The flight attendant, a black woman with curly hair who sat near Row 21, was wonderful and kind.

It was good..clean, comfy seat. Friendly warm welcoming crew. Was able to check my cabin luggage at the gate which I was able to pickup in a decent time from baggage claim. The app gave all updates from delays to baggage claim info. Overall smooth flight.

Flight was delayed leaving Dallas. Arrived about 2 hours later than scheduled.

The Hawaiian lady that boarded me was rude and the one help me a the ticket counter was rude

My experience was terrible. They cancelled my flight twice. They kept delaying it and leading me on, acting like the flight was going to go when it never had a chance. I missed out on valuable family time because of spirit and I won’t be flying with them again.

Prices for bags are extremely expensive and if you go higher on weight, the charge is ridiculous.

The flight was cancelled at the last minute. Will never fly Spirit again. Without a doubt the worst airline around.

My flight was delayed several times and eventually cancelled. Then the re-booked flight for 8pm was delayed multiple times over, and eventually it would have forced me to be at the airport for 9 hours. I accepted a rebook for the following day, fortunately I was able to stay with my friend again in New York, but if I didn’t have him as a resource it would have been much more upsetting.

Horrible, delay after delay due to our plane needing fuel.

Rough landings but comfortable and affordable if you can pack light

the plane was not full so the flight attendant had me move to an empty row which made for a good flight. The software for logging on and booking and confirming the flight is much too cumbersome.

Always comes in handy when I want a quick weekend getaway.

For the price I could have taken a “name brand” airline. No drink no snack and constant emails trying to get addition money for EVERYTHING other airlines include in the price. It looks cheaper but it’s Judy bait and switch and emails non stop!

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports