$111 Find Cheap Flights from Caribbean to Louisville

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight to Louisville departing on 1/14. 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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Everything you should know

Cheapest round-trip
$230
Overall average: $423
American Airlines
Wed 3/25Sun 3/29
SJU - SDF • 1 stop
Cheapest one-way
$111
Typical prices: $153-$471
Spirit Airlines
Wed 1/14
SJU - SDF • 1 stop
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Flight Deals
Useful Info
Flight Deals

Cheap Flights from Caribbean to Louisville

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Caribbean to Louisville 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 Caribbean to Louisville

Wed, Mar 25 - Sun, Mar 29
American Airlines Logo
7:40 am - 12:27 am
SJU
-
SDF
16h 47m1 stop
American Airlines Logo
7:57 pm - 10:40 am
SDF
-
SJU
14h 43m1 stop
$230American Airlines
Wed, May 13 - Mon, May 18
American Airlines Logo
6:25 am - 11:41 pm
SJU
-
SDF
17h 16m1 stop
American Airlines Logo
6:31 pm - 4:00 am
SDF
-
SJU
9h 29m1 stop
$265American Airlines
Fri, Feb 20 - Thu, Feb 26
Multiple Airlines Logo
4:31 pm - 11:05 am
SJU
-
SDF
19h 34m1 stop
Multiple Airlines Logo
2:26 pm - 12:41 am
SDF
-
SJU
9h 15m1 stop
$293Multiple Airlines
Fri, Feb 20 - Thu, Feb 26
Spirit Airlines Logo
4:31 pm - 11:05 am
SJU
-
SDF
19h 34m1 stop
Spirit Airlines Logo
3:33 pm - 1:37 am
SDF
-
SJU
33h 04m2 stops
$302Spirit Airlines
Tue, May 19 - Sat, May 30
American Airlines Logo
8:30 am - 12:14 am
SJU
-
SDF
15h 44m1 stop
American Airlines Logo
7:48 am - 10:35 pm
SDF
-
SJU
14h 47m1 stop
$312American Airlines
Wed, Mar 25 - Sun, Mar 29
American Airlines Logo
6:00 am - 3:58 pm
SJU
-
SDF
9h 58m2 stops
American Airlines Logo
7:57 pm - 12:53 pm
SDF
-
SJU
16h 56m1 stop
$342American Airlines
Wed, May 13 - Mon, May 18
Southwest Logo
5:35 am - 2:45 pm
SJU
-
SDF
9h 10m2 stops
Southwest Logo
4:45 pm - 11:40 pm
SDF
-
SJU
6h 55m1 stop
$345Southwest
Wed, May 13 - Mon, May 18
Southwest Logo
5:35 am - 3:05 pm
SJU
-
SDF
9h 30m2 stops
Southwest Logo
11:10 am - 11:25 pm
SDF
-
SJU
12h 15m2 stops
$371Southwest
Thu, Feb 19 - Sun, Feb 22
United Airlines Logo
4:00 pm - 11:59 pm
STI
-
SDF
8h 59m1 stop
United Airlines Logo
6:15 am - 2:53 pm
SDF
-
STI
7h 38m1 stop
$575United Airlines
Thu, Feb 19 - Sun, Feb 22
United Airlines Logo
6:00 am - 8:09 pm
STI
-
SDF
15h 09m2 stops
United Airlines Logo
6:15 am - 2:53 pm
SDF
-
STI
7h 38m1 stop
$580United Airlines
Useful Info

Good to know

Low seasonFebruary
Cheapest flight$111
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly and prices are also 7% lower on average.
Flight from San Juan to Louisville

FAQs for booking flights from Caribbean to Louisville

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

    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 Caribbean to Louisville.

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

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

    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 to Louisville with an airline and back to Caribbean with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Caribbean to Louisville?

    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 to Louisville from Caribbean up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 3 airlines serving from Caribbean to Louisville

 
Need help choosing which airline to fly with from Caribbean to Louisville? 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 4258 reviews
8.1Boarding
7.5Entertainment
7.0Food
8.6Crew
8.0Comfort
Airline reviews

They sent a notice that they were boarding an hour early. We had to leave the club and run to the gate. They said sorry, that came from corporate and was a mistake. They did not have enough seating because the flight before it had not taken off on time. They moved our gate and delayed it for an hour.

2.0 MediocreRobert, Dec 2025
LAS - TPA
Read more Southwest reviews

They sent a notice that they were boarding an hour early. We had to leave the club and run to the gate. They said sorry, that came from corporate and was a mistake. They did not have enough seating because the flight before it had not taken off on time. They moved our gate and delayed it for an hour.

The boarding and seat assignment system no longer works for me, but I know it is being replaced. Otherwise, I am good with the overall experience.

The lead steward kept singing about "San Francisco" and hotel California---more annoying than humorous....needs work. Flight was smooth and on time.

Still a fan of open seating. Flight was on schedule and arrived on time. The 737 MAX is very comfortable.

Airline travel is always too cramped to really be pleasant, but the cabin crew on this flight did a pretty good job of making up for it by putting on some music during boarding and sprinkling a few funny remarks into the safety briefing and announcements, and just generally being friendly and helpful. It definitely reminded me of why I prefer the in-flight experience on Southwest!

No delays and arrived to destination 30 min early. Staff was super friendly.

San Diego airport is brand new, spacious, airy and very smooth checkin at SW baggage drop.

It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.

Crew could have been friendlier, maybe I'm spoiled by SW crews. In flight wifi was good. Would be nice to have more food offerings on a 4 plus hour flight

Had to get off plane from prior flight even though I had to reboard same plane to continue to my final destination.

Flight delays both to Detroits and return flight . The flight to Detroit was associated with mechanical difficulty

Flight was operated by Virgin Atlantic and it was up to their usual high standard. Minor grips about some issues, but they are really first world issues and as a whole, was an excellent flight.

I am extremely disappointed that delta internal pilot manuals now refer to the Gulf of Mexico as the “gulf of America”. You can bow down to the Orange turd on your own. I will never fly delta again

Delta One upgrade it would have been great if my tray extended (it was jammed and wouldn’t pull out), seatbelt had too much slack & my little cabin door didn’t close properly

I paid for a business class ticket on Delta. It was sourced to Virgin Atlantic. They changed out the aircraft which had fewer upper class tickets. Even though I'd checked into the lounge, was receiving alerts via kayak about the delay and changes; no one informed me that the seat would be changed - until I attempted to board and was told that I would have an economy seat or they could search to put me on another airline. Even the flight crew were informed of this change (10 passengers were bumped out of Upper Class) around 2 pm (1400) time. Hours would have helped to consider alternatives instead of making a last minute change. There needs to be compensation from both Delta and Virgin given this change in service/experience.

Wasn't a Delta issue I don't think, but seems there was a Delta flight at each of the 2 Dallas airports at the same exact time, both to Atlanta. I was evidently booked on the one at Love Airport, but the Carey transport shuttle took me to DFW instead and I ended up missing the flight by just a few minutes. Was able to book a Southwest flight from Love Airport, but was a big loss of time and an inconvenience.

Every single flight that we got on was delayed by several hours or more. I honestly didn’t think we would get out of Atlanta because our flight was supposed to leave at 7:59 and it kept getting kicked back further and further. Delta stands for Don’t Ever Leave The Airport!

Great. I had to modify a flight. That was easy and free. Thank You

I noticed that the planes seem to be outdated. There was no entertainment per se. Also, the waiting area did not have any working electrical outlets

Original flight was cancelled and when i was rebooked by the airline, they couldn't seat me in the same type of seat as I had originally booked (went from window/aisle to middle/middle and one was a bulkhead seat, and other wasn't in the same class)

For whatever reason, the flight was not catered -we were told it would be a 45 minute delay waiting for catering - so no food. There were opened candy and peanuts in the seatback pocket. Flight landed early in DFW but due to the assigned gate not being available, we sat on the ground for 30 minutes waiting for the gate to open - making the flight actually arrive at the gate late.

The pilot greased the landing and the crew was fantastic.

I bought wifi and most of the flight could not even use it my apps would just spin. I couldn't even listen to music. super frustrating.

delayed due to weather. Could not communicate with family since the wifi was broken

Experience was good, however I had a delay due to weather happening and had to re purchase a seat on a new plane for a higher price (could be my own issue and misunderstanding) but other than that situation. First time flyer (by myself) was terrific!! The last from ORD to ALO didn't have wifi, but it was only 45 minutes so I'm sure that was part of the reason. Overall my experience was great! Next time I will remember to buy tickets with longer layovers. The delays really saved my overall anxiety. :)

Flight was on time is the only good thing. Person loading the plane called 1-6 to board at the same time, made it chaotic. Plane was too small for even putting backpacks in overhead. Seat for normal sized people were too small. The WIFI didn't work. When we landed had to wait because not enough ground crew.

Did not understand a single word the attendant said on the pa system. I was glad it was not an emergency.

Gate was overcrowded. Gate agents performed very well. Flight crew was top notch! Efficient & professional & courteous. Both meals not thermalized well. Dinner main dish was actually cold in the center. Almost inedible. Breakfast sandwich was lukewarm.

The boarding was as always, the crew tried their best but not enough. The food was a disaster I had dietary restrictions that were half met because the company did not loaded the food for the flight. The entertainment screen was fine but content was not and also they removed the free messaging option from the flight and they charged 30 dollars for that crappy bandwidth. This flight is not worth the cost and the company is going down on quality.

Awful. They won’t help me with anything. I booked on American but they abdicated to Iberia. The ticket was overpriced. Everything negative

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