$158 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 27 - Sun, Aug 30
American Airlines Logo
1:38 pm - 11:11 pm
SJU
-
SDF
9h 33m
2 stops
American Airlines Logo
8:30 am - 2:53 pm
SDF
-
SJU
6h 23m
1 stop
$220American Airlines
Thu, Aug 27 - Sun, Aug 30
American Airlines Logo
1:38 pm - 11:11 pm
SJU
-
SDF
9h 33m
2 stops
American Airlines Logo
7:33 am - 6:34 pm
SDF
-
SJU
11h 01m
2 stops
$268American Airlines
Sun, Aug 16 - Tue, Aug 18
American Airlines Logo
7:30 am - 7:25 pm
SJU
-
SDF
11h 55m
1 stop
American Airlines Logo
2:36 pm - 11:59 pm
SDF
-
SJU
9h 23m
1 stop
$290American Airlines
Wed, Aug 26 - Mon, Aug 31
Multiple Airlines Logo
5:01 pm - 10:32 am
SJU
-
SDF
17h 31m
1 stop
Multiple Airlines Logo
11:19 am - 3:58 pm
SDF
-
SJU
28h 39m
1 stop
$307Multiple Airlines
Wed, Aug 19 - Sat, Aug 22
United Airlines Logo
2:20 pm - 10:15 pm
SJU
-
SDF
7h 55m
1 stop
United Airlines Logo
7:10 am - 8:38 pm
SDF
-
SJU
13h 28m
2 stops
$310United 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
$316Delta
Wed, Sep 9 - Sun, Sep 13
Southwest Logo
11:50 am - 9:30 pm
SJU
-
SDF
9h 40m
2 stops
Southwest Logo
4:05 pm - 12:30 am
SDF
-
SJU
8h 25m
2 stops
$321Southwest
Wed, Dec 2 - Tue, Dec 8
American Airlines Logo
2:05 pm - 7:13 pm
SJU
-
SDF
6h 08m
1 stop
American Airlines Logo
6:50 am - 11:52 pm
SDF
-
SJU
16h 02m
1 stop
$322American Airlines
Thu, Aug 27 - Fri, Sep 4
Delta Logo
5:49 pm - 12:34 am
SJU
-
SDF
6h 45m
1 stop
Delta Logo
3:25 pm - 10:29 pm
SDF
-
SJU
7h 04m
1 stop
$326Delta
Wed, Nov 4 - Sun, Nov 8
United Airlines Logo
6:00 am - 11:15 pm
STI
-
SDF
18h 15m
1 stop
United Airlines Logo
6:30 am - 11:51 pm
SDF
-
STI
16h 21m
1 stop
$755United Airlines
Useful Info

Good to know

Low seasonFebruary
Cheapest flight$158
Best time to beat the crowds with an average 36% drop in price.
Most popular time to fly with an average 1% increase 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 4235 reviews
8.6Crew
7.5Entertainment
7.0Food
8.0Comfort
8.1Boarding
Airline reviews

there were two flight attendants that were up front...that were the best! They get KUDOs for making my trip only fantastic. Tell them Jeff said that!

10.0 ExcellentAnonymous, Jun 2026
OKC - LAS
Read more Southwest reviews

there were two flight attendants that were up front...that were the best! They get KUDOs for making my trip only fantastic. Tell them Jeff said that!

OKay. I sat in the back of the plane and it was really loud between babies and little kids, and adults who.like to talk a lot and loudly most of the flight.

Flight coming out of Buffalo was delayed, so we had to be rescheduled on another flight from Baltimore to Phoenix which means we had a long layover and got home 3.5 hours late. Shuttle to parking stopped at 10pm, so we had to pay for an Uber to the parking lot and got charged an extra day of parking since it was after midnight. Not the best experience. Long day!

Was fine, delayed and feels like southwest is always late

I don't know why flying out of Sarasota requires two plane changes.

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

The flight was smooth. The Southwest experience has degraded overall, but this one was okay.

No gluten free snacks. Seats felt worn or bare bones even though it was a new 737 MAX 8.

One major problem that was very unprofessional and uncalled for. Plane landed and we had to wait 20 minutes to get off the plane since they were waiting for someone to come to the gate to drive the jetway. Southwest couldn't have someone available and waiting for the plane to land? Is there only one person in Hobby airport who knows to drive the jetway? Was he at lunch? In the bar? Uncomfortable and uncalled for!

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

Only beverages were offered to first class and I thought the flight attendant could have also served the Delta Comfort as well instead of sitting down and staring at her phone and walking past all of us to the back of the plane to charge her phone more. There was a complete lack of turbulence and was safe enough for flights attendant to walk around in the front of the plane, collect trash and serve a few people water and turn off the seat belt light. Also didn’t enforce people putting their seats into the upright position and allowed two passengers to remain reclined during landing. They seemed out to lunch completely. Usually my experience on Delta is much better.

The seats were really comfortable. Flight crew were friendly with passengers. Overall was a great flight.

Arrived early, comfortable seats (Comfort+). Mediocre food, poor wifi (intermittent).

Long story short, it was one of the better flight experiences I've had in some time when compared with other airlines.

Flight was great! This flight from Atlanta was even better than when I paid for Comfort from SNA to Atlanta.

Great crew, flight on time, luggage pick up a breeze

Was on time, normal boarding. The worst flight attendents and service I ever seen,, can't believe Delta can have such service. Bathroom was dirty and no toilet paper, paper towels and used toilet paper all over the floor, when I tried to tell flight attendant she didn't even let me to finish and turn around. Very rude. Wi fi didn't work.

Connection flights should be spaced out farther because too close I missed my connection.

Definitely a southern flavor. Cordiality was evident even though no drinks or snacks were served.

On time! There were plenty of airport employees who were able to keep us moving in the right direction. The crew on the plane were professional.

The flight attendants were extremely sourly and borderline rude. I did not feel appreciated as an AA customer once.

The flight back to Dallas was delayed, which has happened to me several times with American Airlines. There was no announcement, no update sent out, no compensation offered for the inconvenience.

It wa sort of on time; the cab was left with some trash

Our flight from JFK to Madrid was delayed. We had to go from one side of the Madrid airport (Terminal 4s to the far end of terminal 4 - Gate K98) to our gate in less than 30 minutes. Put passport control and security/baggage check and that’s very hard unless you’re Usain Bolt. I called Iberia Airlines and the telephone customer service told me that I was going to have to pay to re-book. Luckily the help desk in the airport (who was dealing with dozens of people from the same JFK-Madrid flight) did not charge us extra to reschedule to a flight 8 hours later. They also gave us a voucher for breakfast and lunch. Glad the actual person at the airport had some actual sense.

As always, most AA flights that we fly are almost ALWAYS delayed and that too multiple times. Very frustrating

Boarding was smooth and seamless and the flight was without incident.

Very hard to beat a British Airways international flight…the crews are always so amazing! One flight attendant that really stood out was Emma…she was very personable and accommodating with any request we had!!

Our flight was repeatedly delayed for maintenance problems: scheduled for 9.30am, eventually delayed to 7pm! Very very inconvenient! AA should have provided a substitute plane much earlier.. On the other hand, Customer Service crew in Charlotte helped us to reach NY (LGA) by late afternoon. Thank you Patricia!! The actual flight was quick and very comfortable. As always a. excellent, professional crew. [no food on a a short hop).

Take-off delayed an hour because of a missing flight officer, so,arrived in Charlotte lates causing many passengers to miss connections. Otherwise a very good flight, safe and comfortable, with an excellent professional crew.

Little time between flight from Dallas to flight to Gainesville. We chose this one, 43 minutes between, because the price for a connection with at least an hour between, was so much higher. Had to ask passengers on the Dallas flight to please allow us to deplane ahead of them. The economy passengers allowed this. We had to walk very fast to the next gate, 35 gates away. Thankfully all in the same terminal. Getting to the small Gainesville plane was a little confusing as you enter an area that is boarding many small planes at the same time. We stood in the wrong line for about 15 seconds before realizing it was not our Gainesville flight. Since I had boarded at this gate in the past, I knew to check the signs carefully so we weren’t lost. The first class seat experience was wonderful. I really enjoyed the upgrade. We were offered an alcohol drink as soon as we sat down. I got something different but it was a great gesture especially since we really had to hurry to make the flight. We had packed expecting we might miss this connection, but made it. Our luggage didn’t miss the flight. American Airlines delivered our bags to our home the next day. That was very convenient!

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