$113 Find Cheap Flights from Caribbean to Louisville - 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 to Louisville departing on 8/25. 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 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

Thu, Aug 6 - Mon, Aug 10
American Airlines Logo
6:00 am - 5:59 pm
SJU
-
SDF
11h 59m
2 stops
American Airlines Logo
11:10 am - 9:55 pm
SDF
-
SJU
10h 45m
2 stops
$226American Airlines
Wed, Sep 16 - Mon, Sep 21
American Airlines Logo
6:27 am - 11:22 pm
SJU
-
SDF
16h 55m
2 stops
American Airlines Logo
7:27 pm - 1:54 pm
SDF
-
SJU
18h 27m
2 stops
$230American Airlines
Wed, Oct 21 - Sun, Oct 25
American Airlines Logo
12:13 pm - 12:07 am
SJU
-
SDF
11h 54m
1 stop
American Airlines Logo
5:04 am - 11:20 am
SDF
-
SJU
6h 16m
1 stop
$261American Airlines
Thu, Aug 27 - Fri, Sep 4
Delta Logo
5:49 pm - 12:34 am
SJU
-
SDF
6h 45m
1 stop
Delta Logo
1:21 pm - 10:29 pm
SDF
-
SJU
9h 08m
1 stop
$271Delta
Thu, Sep 17 - Tue, Sep 29
American Airlines Logo
3:41 pm - 11:22 pm
SJU
-
SDF
7h 41m
1 stop
American Airlines Logo
7:27 pm - 1:54 pm
SDF
-
SJU
18h 27m
2 stops
$276American Airlines
Thu, Aug 13 - Tue, Aug 18
Delta Logo
7:00 am - 2:18 pm
SJU
-
SDF
7h 18m
1 stop
Delta Logo
11:17 am - 10:29 pm
SDF
-
SJU
11h 12m
1 stop
$283Delta
Fri, Oct 30 - Sat, Nov 7
United Airlines Logo
7:05 am - 7:01 pm
SJU
-
SDF
11h 56m
2 stops
United Airlines Logo
10:25 am - 9:00 pm
SDF
-
SJU
9h 35m
1 stop
$296United Airlines
Thu, Sep 17 - Tue, Sep 29
United Airlines Logo
2:20 pm - 10:15 pm
SJU
-
SDF
7h 55m
1 stop
United Airlines Logo
7:00 am - 8:38 pm
SDF
-
SJU
13h 38m
2 stops
$299United Airlines
Fri, Aug 7 - Mon, Aug 10
Multiple Airlines Logo
6:00 am - 8:20 pm
SJU
-
SDF
14h 20m
1 stop
Multiple Airlines Logo
9:10 pm - 4:11 pm
SDF
-
SJU
19h 01m
1 stop
$305Multiple Airlines
Thu, Aug 13 - Fri, Aug 21
Multiple Airlines Logo
3:50 am - 8:20 pm
POS
-
SDF
16h 30m
2 stops
Multiple Airlines Logo
10:39 am - 8:00 pm
SDF
-
POS
9h 21m
1 stop
$848Multiple Airlines
Useful Info

Good to know

Low seasonFebruary
Cheapest flight$113
Best time to beat the crowds with an average 36% drop in price.
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.
7.9
SouthwestOverall score based on 4246 reviews
7.5Entertainment
7.0Food
8.1Boarding
8.6Crew
8.0Comfort
Airline reviews

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.

8.0 ExcellentAnonymous, Jul 2026
PHL - BNA
Read more Southwest reviews

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.

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.

The seats were a bit cramped and worn, but otherwise okay.

Since the flight wasn’t full, we had some extra room. Crew was great

Everything about this flight was good except for the very end when I reached my destination. Everyone from the tune to the wheelchair escorts were great with the case were great but I miss you with people at the check in this at the very end. I need help from the chicken desk because I forgot my pillow on the plane The female worker at the chicken desk said that they found my pillow and she was going to retrieve it for me. She left a 30 minutes without any update and her so she saw me walking back and forth waiting for her and they didn't even bother calling her or radioing her for any updates. They were busy because they were behind schedule and they were overwhelmed but thanks because at least glanced me and try to give me an update just a quick radio check or phone call. I don't care about the pillow but if you tell me to wait, I waited for at least half an hour before I said something and I just left because they wouldn't bother talking to me so I could, so everything's going in the review. I took pictures of the two men that were left working at the check-in counter. The totally ignored me despite the signals I've been giving them. I don't see any offers in the kayak review to add pictures or screenshots so I'm going to post another review I don't know their name but I'm pretty sure Delta will find other names when they see the review. Google with pictures. There was another guy at the chicken counter bring an orange workers vest who finally left after telling me that the girl that was retrieving my pillow is working the gates now. That would have been if they just told me that's what happened. But I had no update. Make me wait for nothing. Thank you Delta airlines!

We had a great experience with Delta. They helped us from the start at the kiosk all the way to our final destination, including help reassigning and upgrading our seats free of charge at the gates, escorts with the wheelchair for my brother and even getting our luggage at baggage claim for us. I also had special help because I forgot my pillow on the plane. The wheelchair escort contacted for associates at the check-in desk all the way back to the plane and retrieved my pillow for me.

I am a Diamond Medallion Delta traveller and this was a disappointing flight. They allowed half the flight to preboard before Delta One and Diamond Medallion. Once on the plane in my Delta Premium Select seat we were not given any welcome or greeting. Throughout the flight the flight attendant also did not make us feel any sort of special service or attention and even rushed us when she did bring us a snack to pick in the dark not even offering a light to look at what it was -- she was overall not helpful and not accommodating. for the extra cost of the seat it was honestly not a special experience this flight. heads up that even the warm cookies are now packaged. I ate nothing. There really was nothing that was special, stood out or exceptional. Luckily I mostly slept. But I was disappointed and question if I may try a different flight next time I go to Tokyo. The last few Delta flights have been less than great. which makes me very sad.

Crew was real good, flight was smooth and came in early.

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.

The internet that was free was terrible, the turbulence was pretty bad - uncontrollable I know.

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.

Lady Pilot was perfect in every way wheels up to wheels down communication, professionalism, excellent on time departure and on time arrival, excellent communication! Fantastic job with Superb attitude!!

The gate got changed several times and the flight was delayed over an hour. Awful experience

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

No Snacks or Entertainment. The flight was short, snacks should still be given.

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

My Internet did not work for Outlook email or basically anything. I paid for one hour of in-flight usage and it was terrible. I spent a lot of time on different sites and browsers with no luck and a lot of frustration. Other than that, the flight was on time, crew was nice, service was fine. Seat was OK even though I paid for the extra 6 inches. I cannot imagine how tight the seats in the back must be.

Everything was fine. Flight boarded and departed on time. Seating was spacious enough for my carryon to fit under the seat in front of me. No complaints at all. Flight even arrived early.

Boston ticket agent Cheryl Porter is WONDERFUL. Our Iberia flight to Barcelona was cancelled the morning we were scheduled to leave and Cheryl was our super hero - she found us seats on a flight to London and on to Barcelona. Truly a “can-do” attitude which we appreciated so much after the Iberia ticket agents told us there was “absolutely nothing they could do”. (As did the customer service agents at Iberia’s call center) Ms Porter is truly a wonderful person who genuinely cares about travelers!

I was not given the option to get on a different flight even though I was going to miss my connection due to weather delays (I did). When I called early in the morning, they said it wasn't delayed long enough; though I knew it would be by the time it was time for the flight ... it was and by that time it was too late. I wasn't given the option to pre-board with my toddler, and the food service was less than normal due to delays .... at least that's what the crew said.

American is a steady for me. I always get what I expect from them. Sincere effort to get me from one place to another.

Nothing wrong on this flight but nothing special. It was oversold and they had to bump people which is always bad.

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