$134 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 2/1. 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$352
Santo Domingo
Santo Domingo1 stop$499
Montego Bay
Montego Bay1 stop$439
Oranjestad
Oranjestad1 stop$535
Nassau
Nassau1 stop$377
Kingston
Kingston1 stop$541
Simpson Bay
Simpson Bay1 stop$553
Providenciales
Providenciales1 stop$412
George Town
George Town1 stop$408
Puerto Plata
Puerto Plata1 stop$728
Aguadilla
Aguadilla2 stops$626
Punta Cana
Punta Cana1 stop$352
Santo Domingo
Santo Domingo1 stop$499
Montego Bay
Montego Bay1 stop$439
Oranjestad
Oranjestad1 stop$535
Nassau
Nassau1 stop$377
Kingston
Kingston1 stop$541
Simpson Bay
Simpson Bay1 stop$553
Providenciales
Providenciales1 stop$412
George Town
George Town1 stop$408
Puerto Plata
Puerto Plata1 stop$728
Aguadilla
Aguadilla2 stops$626

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

Tue, Jan 27 - Tue, Feb 3
American Airlines Logo
6:00 am - 8:50 pmSDF-SJU
13h 50m1 stop
American Airlines Logo
7:00 am - 9:16 pmSJU-SDF
15h 16m1 stop
$225American Airlines
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Sat, Feb 21 - Wed, Feb 25
United Airlines Logo
5:54 pm - 6:11 amSDF-SJU
11h 17m2 stops
United Airlines Logo
8:10 am - 2:47 pmSJU-SDF
7h 37m1 stop
$262United Airlines
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Sat, Jan 24 - Sat, Jan 31
Multiple Airlines Logo
6:00 am - 2:50 amSDF-SJU
19h 50m1 stop
Multiple Airlines Logo
3:55 am - 11:45 pmSJU-SDF
20h 50m1 stop
$320Multiple Airlines
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Mon, Jan 5 - Fri, Jan 9
Multiple Airlines Logo
8:53 pm - 11:49 pmSDF-SJU
25h 56m1 stop
Multiple Airlines Logo
5:20 pm - 9:54 amSJU-SDF
17h 34m1 stop
$332Multiple Airlines
Find Deal
Sun, Jan 18 - Sun, Feb 8
Southwest Logo
2:30 pm - 11:10 pmSDF-SJU
7h 40m1 stop
Southwest Logo
6:10 am - 1:35 pmSJU-SDF
8h 25m1 stop
$355Southwest
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Tue, Dec 2 - Sat, Dec 6
Spirit Airlines Logo
6:48 pm - 4:50 pmSDF-PUJ
21h 02m1 stop
Spirit Airlines Logo
6:08 pm - 11:00 amPUJ-SDF
17h 52m1 stop
$367Spirit Airlines
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Fri, Dec 5 - Fri, Dec 12
Delta Logo
10:37 am - 3:43 pmSDF-NAS
5h 06m1 stop
Delta Logo
1:06 pm - 11:59 pmNAS-SDF
10h 53m2 stops
$381Delta
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Sun, Dec 7 - Sun, Dec 14
Spirit Airlines Logo
11:55 am - 4:50 pmSDF-PUJ
27h 55m1 stop
Spirit Airlines Logo
6:08 pm - 11:00 amPUJ-SDF
17h 52m1 stop
$381Spirit Airlines
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Sun, Feb 22 - Thu, Feb 26
Delta Logo
6:36 am - 2:35 pmSDF-PLS
7h 59m1 stop
Delta Logo
2:05 pm - 8:52 pmPLS-SDF
6h 47m1 stop
$412Delta
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Wed, Apr 15 - Wed, Apr 22
Southwest Logo
1:35 pm - 11:40 pmSDF-SJU
10h 05m2 stops
Southwest Logo
5:35 am - 2:45 pmSJU-SDF
9h 10m2 stops
$432Southwest
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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 $565 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 21% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 7 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 4236 reviews
8.1Boarding
8.0Comfort
7.5Entertainment
8.6Crew
7.0Food
Airline reviews

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

10.0 ExcellentStacy, Oct 2025SMF - DEN
Read more Southwest reviews

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.

Flight was delayed due to plane not passing inspection And one of the crew had to time out and we had to wait for another one A 3 hour delay

mandatory demand customer to check their carry on because not enough people check bags.

Connecting flight is on time and boarding was a breeze!

Excellent. Would encourage Southwest to keep current boarding procedures with free style seating. Makes for a fantastic experience

As always, the entire Southwest experience was perfect. Purchasing the tickets on the Southwest web site was effortless, departure and arrival gates were spotless and comfortable, plane was clean and comfortable, crew was excellent and flight was on time. Wheelchair service in Las Vegas at departure was somewhat chaotic and disjointed, but I am not sure if that was Southwest problem, airport problem or combination.

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

They changed planes and the new plane couldn’t carry enough fuel to fly across the country so we had to stop in Kansas City to refuel. Flight was delayed .

Flight was too crowded and seats are too small, especially since passengrs are getting larger. Having a middle seat is ALWAYS tough! Woman on my left was large & kept creeping in to my space. Flight personnel were great! Have more savory rather than sweet snacks please.

Flight was crowded and the woman sitting on my left was large & kept crouching in to my space. You need bigger seats or smaller passengers to fit into the seats you DO have! Snack were OK. Would appreciate if airlines had more savory rather than sweet snacks, thank you!

Delayed flight (1hour) plus a long layover after an overnight flight with no backup plane available.

We were delayed, which I think had to do with air traffic control. Otherwise, everything was great.

The boarding process needs to be refined. Sometimes the gate crew calls out the zones and then flip to showing the.zones boarding on the gate monitor display. So, unless you are huddled around the gate lanes watching the monitor, you could miss your boarding zone. Suggest the zones be announced each time a new zone is allowed to board.

The boarding process needs to be refined. Sometimes the gate crew call out the boarding zone, and then flip to the monitor to show which zones are boarding. So unless everyone is gathered around to see the monitor there is usually confusion as wi which zones are boarding.

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.

After boarding the plane in Chicago, the passengers were told that there was a technical problem with the plane. Passengers remained on the plane as they tried to fix the problem. After what was probably an hour passengers were told that there was a need to change planes as the problem was not solved. Passengers disembarked and boarded another plane. After taxing to the runway and waiting for takeoff, passengers were told that owing to the thunderstorm the flight was unable to take off but would try and reroute. After some time passengers were told there wasn't enough fuel for the new route and the plane had to return to the gate for additional fuel. after another log delay the flight got underway. On the plane there was food, drinks, ice or entertainment. We were a glass of water, which appeared rationed. Flight arrived about 5 hours late. The pilot was fantastic and communicated with the passengers throughout the ordeal.

Same as last comment. Food sucks. Quality. Not surprising most people have no clue about nourishment Clearly

Not the fault of United—weather, reroute around weather, time sitting on tarmac, arrived couple hours late, too late for train into city necessitating a much pricier cab but weather…can’t be helped.

Friendly and professional flight crew. Aside from departure delay after boarding, easy flight and smooth landing.

Great smooth flight. Had a seating change, but that was an improvement. Thanks United Airways Crew.

The flight attendants were great, I joked with one I can’t remember her name, a blond, really sweet. I thought it was run well very professional. This was great i survived Spirit, I know for which I speak.

My husband and I recently had an unfortunate experience with Lufthansa. At the Philadelphia International airport, the ground staff refused to board us because we didn’t have a current visa stamped on our passports for Frankfurt. We completely understand that this was our mistake. we should have double-checked the visa requirements before our trip. However, the issue that upset us most was how the situation was handled by the staff. They told us they would mark it as “boarding denied due to visa issue”, but instead they recorded it as “no show”. Because of that incorrect entry, our return flight was automatically cancelled as well, which caused additional stress and expense. Mistakes can happen, but we expected more transparency and accuracy from a reputed airline like Lufthansa. It would have made a big difference if the staff had been more careful and considerate in documenting the situation correctly.

Flight was good but there are way to many announcements for credit cards etc.

The only thing to like was that we eventually got to our destination

Delayed delayed delayed and no offer for food or vouchers

Disliked having to wait a little longer to disembark from the plan when we landed in London

Typically flights with AA are good. The staff are pleasant, welcoming, and efficient.

A couple ladies from the crew were so rude and nasty. Thought they were mad at having to be there especially if you asked a question. This will make me think twice next time if I book a flight with you.

Delays to take off and to leave the plane after landing added a lot of time to this flight.

Poor seat in rear of aircraft Food at Admiral’s Club Terminal D at DFW inedible

Always seated jammed in rear of aircraft Admirals Club food at DFW terminal D was absolute worst food experience and I pay $600/year to eat this dried out junk

Flight was delayed because of a bird strike. They had another plane available within 45 minutes.

Mostly good. Flight was crowded but Airline personnel were very friendly & accommodating. It would be good to have savory snacks rather than just sweet Biscoff cookies.

Excellent experience when I am looking for a budget airline where the main expectation is getting me from point A to point B with no frills.

Great! I intend to use Spirit for future flights. No complaints .

Seats are not very comfortable, maybe a little more padding for a 2hr plus flight

Very sad about what Spirit has become, because the flights I had with them were delayed between an hour and a half and two, terrible service

Vegas is such a quick flight that amenities aren’t the important part, in my opinion. Just get me there efficiently and safely, and that’s exactly what they did!

The flight was severely delayed due to the missing flight attendants.

Absolutely horrible. Usually pay $40-$50 to check luggage in. I tried to check my suitcase in and the price is raised to $70. That's ridiculously greedy c'mon. I had to leave my suitcase with all my clothes and hygiene products and repurchase once i landed in Atlanta. You guys make it really stressful to travel. Don't even want to travel anymore.

They cancelled the flight 3 hours prior departure. Had to spend $400 for a ne way flight with Delta Airlines! Spirit Airlines are not serios!

My luggage didn’t arrive at LAX, so that wasn’t a good experience.

Terrible seat, no in flight entertainment. No complimentary food or drinks. Seats really hurt my back after flying spirit for the day.

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