$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
Fri, Aug 14 - Mon, Aug 17
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
$255Multiple Airlines
Wed, Sep 16 - Mon, Sep 21
Southwest Logo
2:25 pm - 9:30 pm
SJU
-
SDF
7h 05m
1 stop
Southwest Logo
6:00 pm - 11:50 pm
SDF
-
SJU
5h 50m
1 stop
$258Southwest
Thu, Sep 17 - Tue, Sep 29
American Airlines Logo
4:06 pm - 12:04 am
SJU
-
SDF
7h 58m
1 stop
American Airlines Logo
7:27 pm - 1:32 pm
SDF
-
SJU
18h 05m
2 stops
$268American Airlines
Thu, Aug 27 - Fri, Sep 4
Delta Logo
2:59 pm - 10:08 pm
SJU
-
SDF
7h 09m
1 stop
Delta Logo
3:25 pm - 10:29 pm
SDF
-
SJU
7h 04m
1 stop
$271Delta
Wed, Aug 12 - Mon, Aug 17
Multiple Airlines Logo
6:00 am - 10:32 am
SJU
-
SDF
28h 32m
2 stops
Multiple Airlines Logo
9:10 pm - 4:11 pm
SDF
-
SJU
19h 01m
1 stop
$272Multiple Airlines
Wed, Aug 5 - Sun, Aug 9
Delta Logo
5:49 pm - 12:24 am
SJU
-
SDF
6h 35m
1 stop
Delta Logo
7:05 am - 4:38 pm
SDF
-
SJU
9h 33m
1 stop
$283Delta
Sat, Aug 1 - Sun, Aug 23
United Airlines Logo
12:30 am - 9:26 am
POS
-
SDF
32h 56m
2 stops
United Airlines Logo
5:15 am - 12:50 am
SDF
-
POS
43h 35m
2 stops
$714United Airlines
Sat, Aug 1 - Sun, Aug 23
United Airlines Logo
12:30 am - 11:54 am
POS
-
SDF
11h 24m
1 stop
United Airlines Logo
9:45 am - 11:23 pm
SDF
-
POS
13h 38m
1 stop
$744United 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
8.0Comfort
8.6Crew
7.5Entertainment
8.1Boarding
7.0Food
Airline reviews

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.

6.0 GoodAnonymous, Jun 2026
TPA - DAL
Read more Southwest reviews

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.

It was just okay, no frills, basic transportation with no luxury. No screens on the seats, no water or drinks on a short flight. Full flight but at least it was on time.

Flight was constantly delayed with significant changes in time, it was supposed to get to Colorado Springs at 8:30 PM but it got there after midnight.

Over a 3 hour flight. The turbulence was almost imperceptible except for 2 short periods which were not bad and over quickly. The attendants claimed "Safety first" and sat looking at their phones for 3 hours with no drink or snack service. This isn't the first time with Southwest. I thinkit may be there new plan of operation. Oh, and it was June 18, Southwest's Birthday which offered free drinks. NOT.

Flight was delayed, full flight and I had to change gates. Southwest flights are always late later in the day.

Flight was delayed over 3 hours. Planes were dirty. Staff indifferent. And they serve vegan pretzels as snacks.

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

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.

I was in Comfort and we didn’t get any drinks, chips or anything! First Class got full service on the flight and Comfort got nothing. Seat was horrible and uncomfortable

My flight was delayed by 4 hours in 30 minute increments. The gate agents were amazing but the communication was not. We were told that there was a maintenance issue but they didn't know what it was. That didn't inspire confidence. Then they said they found it and it was fixed and the pilot just needed to sign off. Then the pilot needed to talk to the other pilot from the arriving flight and we'd be fine. Then we were waiting for the pilot to call back. Then the maintenance issue wasn't fixed. Then they decided we were getting a new plane (why didn't they decide this earlier??). Fine. But then they announced we were changing gates AND terminals. And we were boarding in 20 minutes. So we all had to run to the new terminal gate. We could have taken off at that time, but we then had to wait for all the people who rebooked on a different flight to book this flight again. That took 30+ minutes because there was only one gate agent. When everyone ditched this flight, I saw it as an opportunity to upgrade to comfort. Delta, the greedy jerks they are, charged me $121. After their delay, their fault, their issues, couldn't even discount an upgrade. They only handed out $12 meal vouchers for the delay. I can't even get a snack from starbucks for that.

The crew was very inconsiderate and rude. My flight was scheduled to depart at 6:00am. I received a call from the crew at 5:40am, asking if I was going to make the flight because I was the only one that hasn't boarded yet and boarding ends at 5:50am. I let them know that I will be at the gate in a few minutes, before the 5:50am cutoff. When I arrived at the gate at 5:45am the gate was closed. Departing early on last minute notice without having all passengers on board is inconsiderate and unprofessional.

The flight was late which i understand happens. But we flew Delta one and the Crew was stiff and not that friendly. They didnt offer beverages after they served the lunch. I dont usually do reviews but i felt i must tell you about this crew. They were american not european. We are platinum members and we are usually treated much better

FA was a bit strange and dodgy not very characteristic of Delta

Not really a “Delta” problem but worth mentioning: Boarding was a difficult process. TSA seemed understaffed and Pre-Check took longer than regular TSA. The supervisor was frazzled and yelled at travelers. Once through TSA, we had to put our carry-ons through another x-ray machine. Then queue up to board with both boarding pass and ID. Then, when we got to the stairs on the tarmac, we had to show our boarding pass again. Maybe this is just normal for Kona since the terminal is outdoors (but still a “secured” area).

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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