$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 5/29. 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, Aug 26 - Tue, Sep 8
Delta Logo
5:49 pm - 12:24 am
SJU
-
SDF
6h 35m
1 stop
Delta Logo
3:24 pm - 10:23 pm
SDF
-
SJU
6h 59m
1 stop
$316Delta
Thu, May 14 - Sat, May 23
Multiple Airlines Logo
8:04 pm - 6:58 pm
SJU
-
SDF
22h 54m
1 stop
Multiple Airlines Logo
8:06 pm - 4:01 am
SDF
-
SJU
31h 55m
2 stops
$320Multiple Airlines
Wed, Aug 26 - Tue, Sep 8
American Airlines Logo
1:38 pm - 11:17 pm
SJU
-
SDF
9h 39m
2 stops
American Airlines Logo
8:16 am - 11:59 pm
SDF
-
SJU
15h 43m
1 stop
$322American Airlines
Sat, Aug 15 - Mon, Aug 17
American Airlines Logo
6:51 am - 5:47 pm
SJU
-
SDF
10h 56m
1 stop
American Airlines Logo
8:16 am - 11:59 pm
SDF
-
SJU
15h 43m
1 stop
$326American Airlines
Thu, Aug 27 - Fri, Sep 4
American Airlines Logo
1:38 pm - 12:16 am
SJU
-
SDF
10h 38m
2 stops
American Airlines Logo
7:31 am - 10:24 pm
SDF
-
SJU
14h 53m
1 stop
$341American Airlines
Fri, May 22 - Tue, May 26
American Airlines Logo
5:17 pm - 10:17 am
MBJ
-
SDF
16h 00m
2 stops
American Airlines Logo
8:05 pm - 11:45 am
SDF
-
MBJ
16h 40m
2 stops
$341American Airlines
Thu, Aug 27 - Fri, Sep 4
American Airlines Logo
4:53 pm - 11:44 pm
SJU
-
SDF
6h 51m
1 stop
American Airlines Logo
7:31 am - 10:24 pm
SDF
-
SJU
14h 53m
1 stop
$348American Airlines
Fri, May 22 - Tue, May 26
United Airlines Logo
4:12 pm - 7:18 pm
MBJ
-
SDF
26h 06m
1 stop
United Airlines Logo
6:00 am - 3:10 pm
SDF
-
MBJ
10h 10m
1 stop
$350United Airlines
Thu, Jul 16 - Mon, Jul 20
Southwest Logo
10:20 pm - 10:10 am
SJU
-
SDF
11h 50m
1 stop
Southwest Logo
5:05 pm - 12:15 am
SDF
-
SJU
7h 10m
1 stop
$355Southwest
Mon, Jun 22 - Thu, Jul 30
United Airlines Logo
1:35 pm - 9:26 am
GCM
-
SDF
18h 51m
2 stops
United Airlines Logo
7:19 am - 12:30 pm
SDF
-
GCM
30h 11m
2 stops
$448United Airlines
Useful Info

Good to know

Low seasonFebruary
Cheapest flight$158
Best time to beat the crowds with an average 35% drop in price.
Most popular time to fly with an average 2% 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 4307 reviews
8.1Boarding
8.6Crew
7.0Food
8.0Comfort
7.5Entertainment
Airline reviews

Not having a five hour delay with little notice! The crew was very kind, though, and just as tired as we passengers were. The flight didn't depart until nearly 1 am...and no reason was ever given.

2.0 MediocreAnonymous, May 2026
SEA - SMF
Read more Southwest reviews

Not having a five hour delay with little notice! The crew was very kind, though, and just as tired as we passengers were. The flight didn't depart until nearly 1 am...and no reason was ever given.

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

First time I've had to use the disabled accommodations. And I could not have had a better experience with Southwest, i was having trouble getting from one terminal to another due to my heart failure. And the next thing I know a Southwest agent had made sure. I had a wheelchair at all my flights. Can't thank them enough.

Delayed flight, lack of information, boarding process is a mess as is the carryon luggage causing issues when leaving the plane….just a poor experience.

Comfortable. Easy. No problems. Just wish they had gf options for snacks.

The crew was very kind and made going to Hawaii relaxing and fun to look forward to! Thank you Southwest for a pleasant flight!

This leg was much better, but we did have to have a 3 hour lay o er after coming from a very exhausting hiccup with our flight from BNA to Den

We waited in the airplane for over 45 min for a southwest employee to make the flight. This cause over half the plane to miss their connecting flight in Denver. When we confronted the desk upon arrival, they told us the only flight they had was the next day leaving at 8:50 pm!!! Or they offered to get us to Burbank or LA, but after that we were on our own to get back to Santa Barbara. I paid for a flight from sba to bna bna to sba. My re entry into mom mode has been 💯 rough because of southwest mistake with my flight. And now I’m leaving to Reno tomorrow for a vballl tournament and just discovered that my leg in Vegas has me and my 3 kids on a stand by flight even though I had booked these ticket last year November!! Do better southwest!

Southwest is kind of a slum airline. It’s gotten more expensive over the years for less and less service. I am a Southwest Chase Visa card holder and was forced to choose a seat in the 26th row in the middle seat. However my wife who is a rewards member but doesn’t hold a card or anything else, gets randomly assigned a normally paid seat in row 6! How does that work?

Boarding in Amsterdam is always chaotic. More complicated than needs to be ( boarding pass checked twice, once for general security, then by the airline). The bathrooms on this flight are dirty, and smelly. The food was mediocre at best The crew was decent

Seats in Delta Main are unbelievably close to the seat in front of. Hard to get a backpack under the seat.

Round trip flight to Canada and back to the US was smooth and efficient.

The agent at check in and at the gate were less than thrilled to be at work. I'm not a fan of Kayak's placement on the plane. I got put in the middle seat and none of my preferences were used.

Spanish speaker flight attendants were incredibly rude. A male flight attendant named Allen, grabbed my bag out of the overhead bin and moved it without my permission. When I asked what he was doing, he informed me that the overhead bins were public space? It would be easy to ignore this comment, as you don’t know the whole story, but the flight attendants were militant and rude. Delta, you can do better!

In ATL they have two sets of departure screens. Follow what is on your airline's departure board - the ATL Airport Authority departure board had completely incorrect details about the gate assignment for my flight, which would have made me miss boarding.

Flight was delayed it was hot while sitting on the plane, one engine was working on the plane until they had to do some jimmy rigging down the runway in order for the other engine to charge up. It was ridiculous

The flight was very good and the staff was very friendly and helpful!

The only thing I would say is we tried to get on a standby earlier flight, but with our fair we couldn’t. That seems senseless to leave with open seats..

Very easy to use and convenient, you can perform any action within the same portal

not sure why you ask about food, I n3ver get food on flights except maybe cookies or pretzels. wifi was slow and in and out most of the flight not good.

Everything was fine except the end of the flight. We spent more than an hour circling around Miami due to weather conditions. That was not good.

They lost my bag. ... And I asked them 3 times to 3 different people if my checked bag will maKe it all the way - they all confirmed and at the end it was left at the connection... Bravo

Cancelled BOYH legs of our flight home 30 min before initial boarding

Cancelled the flight half hour before boarding. Then cancelled the connecting flight too.

Delayed due to weather in Dallas (arriving flight arrived late), then boarded the plane only to deboard immediately afterwards, tire needed to be replaced. Flight supposed to depart at 6:15pm but departed at 9:35pm.

Left early arrived early..right amount of talking from pilots..of course had to love the biscuit and water!

I would like a refund for the extra cost the seat I paid for. An oversized person sat next to me and I couldn’t fit on my seat and had to move to another seat.

Boarding gate at LAX was too crowded—two gates next to one another

The flight was delayed about an hour for a maintenance specialist to approve the maintenance repair

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