$158 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 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

Wed, Oct 21 - Sun, Oct 25
American Airlines Logo
3:25 pm - 10:55 pm
SJU
-
SDF
7h 30m
1 stop
American Airlines Logo
4:54 pm - 12:05 am
SDF
-
SJU
7h 11m
1 stop
$316American Airlines
Wed, Sep 9 - Sun, Sep 13
Southwest Logo
5:15 am - 11:10 am
SJU
-
SDF
5h 55m
1 stop
Southwest Logo
5:50 pm - 12:30 am
SDF
-
SJU
6h 40m
1 stop
$321Southwest
Tue, Dec 1 - Mon, Dec 7
American Airlines Logo
7:40 am - 6:38 pm
SJU
-
SDF
11h 58m
2 stops
American Airlines Logo
8:30 am - 8:56 pm
SDF
-
SJU
11h 26m
1 stop
$322American 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
$326Delta
Wed, Sep 9 - Sun, Sep 13
Southwest Logo
11:50 am - 8:35 pm
SJU
-
SDF
8h 45m
2 stops
Southwest Logo
4:05 pm - 12:30 am
SDF
-
SJU
8h 25m
2 stops
$331Southwest
Wed, Sep 16 - Fri, Sep 18
Southwest Logo
11:50 am - 9:30 pm
SJU
-
SDF
9h 40m
2 stops
Southwest Logo
11:50 am - 10:50 pm
SDF
-
SJU
11h 00m
1 stop
$353Southwest
Thu, Jun 25 - Tue, Jun 30
American Airlines Logo
6:21 am - 11:08 pm
SJU
-
SDF
16h 47m
1 stop
American Airlines Logo
11:28 am - 9:58 pm
SDF
-
SJU
10h 30m
2 stops
$378American Airlines
Fri, Jul 10 - Tue, Jul 14
United Airlines Logo
1:35 pm - 9:26 am
GCM
-
SDF
18h 51m
2 stops
United Airlines Logo
6:15 am - 12:30 pm
SDF
-
GCM
7h 15m
1 stop
$570United Airlines
Wed, Jul 8 - Tue, Jul 14
United Airlines Logo
1:35 pm - 11:59 pm
GCM
-
SDF
33h 24m
2 stops
United Airlines Logo
7:55 pm - 12:30 pm
SDF
-
GCM
17h 35m
2 stops
$594United Airlines
Thu, Jul 2 - Sun, Jul 5
Delta Logo
12:59 pm - 12:32 am
GCM
-
SDF
10h 33m
1 stop
Delta Logo
7:05 am - 11:34 am
SDF
-
GCM
5h 29m
1 stop
$614Delta
Useful Info

Good to know

Low seasonFebruary
Cheapest flight$158
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.
8.0
SouthwestOverall score based on 4257 reviews
8.0Comfort
7.5Entertainment
7.0Food
8.1Boarding
8.6Crew
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.

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.

Left /arrived on time. Decent seat space. Like the wifi/plugs and entertainment. Windows and tray table were kinda gross. Attendants didn't start snack service til 40mins before landing. Two rows before us, captain came on to say there's turbulence and recalled staff to seats. So, no drink/snack. Later, attendants didn't stop to see if we had trash nor even look our way. Felt invisible! Almost all pilot announcements were not only unintelligible, but so quiet. We had no idea what she said.

Average seat comfort, a drink and chips were provided, early boarding because we checked a carryon at the gate was nice. Ticket pricing shenanigans, including fees to pick a seat, check a bag, and get food onboard - evidence the industry is reinvigorating last century’s strategies- destroys the experience before one ever arrives at the airport. It’s difficult to recognize any value or sustain loyalty in the end-to-end process making air travel more drudgery than pleasure.

Gate agent was unhelpful for handicapped boarding. Flight attendant seemed untrained.

Great flight with a terrific crew. Uneventful and early arrival. Thank you.

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!

The plane was large, not full, but one with 3 seats near each window and 4 in a row in the middle of the plane. There were screens on the backs of the seats for entertainment and information. To use the entertainment one needs ear plugs that physically plug into the screen. My husband had some he let me use as I only had blue tooth type. The stewards gave out some headphones to some, but when my neighbor asked for some, the steward said no. So maybe they ran out? Idk. Bring the old kind of headphones or earbuds if you want entertainment in case this is the type of entertainment offered. We had a very tight connection in Miami. 43 minutes. The other economy passengers allowed us to get ahead of them because I asked if we could since we were near boarding time for our next flight and 35 gates away. They were extremely kind. First class wasn’t going to allow us to pass through. We did make the next flight. Our baggage didn’t, but they were delivered to us the next day and we were prepared with essentials in our carry on packs.

Food is what you expect on a plane. Nothing gluten free. But that is expected. Drinks, apple juice, was fine. Seat, what I expected. Fine.

This was my first flight on Aer Lingus and it was great. The plane wasn't full so I could move to a seat with extra room. The food was pretty good for airline food and the staff was nice and attentive. I enjoyed the media provided during my 10 hour flight. We arrived home early and it's always good to be home!

Everything went as planned. The only issue I had was with the gate C31 attendant. The person could barely speak English and was very difficult to understand.

The flight took off an hour late which made the connection concerning

We departed early and arrived early The plane was clean and the crew was incredibly efficient another positive experience with American airlines for me.

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