$113 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 1/22. 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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Everything you should know

Cheapest round-trip
$225
Typical prices: $372-$519
American Airlines
Wed 3/4Mon 3/9
SJU - SDF • 2 stops
Cheapest one-way
$113
Typical prices: $153-$385
Southwest
Thu 1/22
SJU - SDF • 1 stop
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Flight Deals
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Flight Deals

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, Mar 4 - Mon, Mar 9
American Airlines Logo
8:30 am - 4:41 pm
SJU
-
SDF
9h 11m2 stops
American Airlines Logo
7:57 pm - 11:55 am
SDF
-
SJU
15h 58m1 stop
$225American Airlines
Wed, Mar 25 - Sun, Mar 29
American Airlines Logo
7:40 am - 12:27 am
SJU
-
SDF
16h 47m1 stop
American Airlines Logo
7:57 pm - 10:40 am
SDF
-
SJU
14h 43m1 stop
$230American Airlines
Thu, Dec 25 - Thu, Jan 1
Spirit Airlines Logo
6:28 pm - 11:59 pm
SJU
-
SDF
6h 31m1 stop
Spirit Airlines Logo
5:05 am - 10:05 pm
SDF
-
SJU
16h 00m1 stop
$264Spirit Airlines
Wed, Mar 25 - Sun, Mar 29
American Airlines Logo
11:32 am - 9:27 pm
SJU
-
SDF
9h 55m2 stops
American Airlines Logo
7:57 pm - 10:40 am
SDF
-
SJU
14h 43m1 stop
$270American Airlines
Wed, Dec 31 - Mon, Jan 5
Spirit Airlines Logo
6:28 pm - 11:59 pm
SJU
-
SDF
6h 31m1 stop
Spirit Airlines Logo
5:05 am - 11:58 am
SDF
-
SJU
5h 53m1 stop
$306Spirit Airlines
Tue, Dec 30 - Sun, Jan 4
Multiple Airlines Logo
3:14 pm - 11:59 pm
SJU
-
SDF
33h 45m2 stops
Multiple Airlines Logo
5:05 am - 10:05 pm
SDF
-
SJU
16h 00m1 stop
$325Multiple Airlines
Tue, Dec 30 - Mon, Jan 5
Multiple Airlines Logo
2:59 am - 11:59 pm
SJU
-
SDF
22h 00m2 stops
Multiple Airlines Logo
8:53 pm - 11:44 pm
SDF
-
SJU
25h 51m1 stop
$345Multiple Airlines
Thu, Jan 22 - Mon, Jan 26
United Airlines Logo
3:20 pm - 11:23 pm
MBJ
-
SDF
8h 03m1 stop
United Airlines Logo
6:28 am - 2:00 pm
SDF
-
MBJ
7h 32m1 stop
$357United Airlines
Thu, Jan 22 - Mon, Jan 26
United Airlines Logo
3:20 pm - 1:24 pm
MBJ
-
SDF
22h 04m2 stops
United Airlines Logo
6:28 am - 2:00 pm
SDF
-
MBJ
7h 32m1 stop
$361United Airlines
Thu, Jan 29 - Sun, Feb 1
Air Canada Logo
1:30 pm - 7:31 pm
GCM
-
SDF
30h 01m2 stops
Air Canada Logo
2:05 pm - 12:25 pm
SDF
-
GCM
22h 20m2 stops
$968Air Canada
Useful Info

Good to know

Low seasonFebruary
Cheapest flight$113
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly and prices are also 7% lower on average.
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 4253 reviews
7.0Food
8.0Comfort
8.6Crew
7.5Entertainment
8.1Boarding
Airline reviews

The boarding and seat assignment system no longer works for me, but I know it is being replaced. Otherwise, I am good with the overall experience.

8.0 ExcellentRussell, Dec 2025
SAN - OAK
Read more Southwest reviews

The boarding and seat assignment system no longer works for me, but I know it is being replaced. Otherwise, I am good with the overall experience.

The lead steward kept singing about "San Francisco" and hotel California---more annoying than humorous....needs work. Flight was smooth and on time.

Still a fan of open seating. Flight was on schedule and arrived on time. The 737 MAX is very comfortable.

Airline travel is always too cramped to really be pleasant, but the cabin crew on this flight did a pretty good job of making up for it by putting on some music during boarding and sprinkling a few funny remarks into the safety briefing and announcements, and just generally being friendly and helpful. It definitely reminded me of why I prefer the in-flight experience on Southwest!

No delays and arrived to destination 30 min early. Staff was super friendly.

San Diego airport is brand new, spacious, airy and very smooth checkin at SW baggage drop.

It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.

Crew could have been friendlier, maybe I'm spoiled by SW crews. In flight wifi was good. Would be nice to have more food offerings on a 4 plus hour flight

Had to get off plane from prior flight even though I had to reboard same plane to continue to my final destination.

Everything a cheap airline should be at normal airline rates.

Original flight was cancelled and when i was rebooked by the airline, they couldn't seat me in the same type of seat as I had originally booked (went from window/aisle to middle/middle and one was a bulkhead seat, and other wasn't in the same class)

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 food is terrible. The staff is wonderful. Comfort is good.

For some reason, I couldn't choose my seat. The airline gave me a seat when I got there. Not happy about that. Otherwise, everything else was great!

Left on time, a bit delayed due to headwinds most of the trip.

I fly Delta all the time, have Platinum Medallion status. But this route seems to have major problems with delays and seems to never leave on time! Have only taken it twice in the last two weeks, and each time it had delays of more than 1 hour... very disappointed!!!!

Good seats in Main cabin, excellent service and excellent landing

My flight was cancelled with no explanation after I had already cleared security. I was given 4 options to rebook, only one being non-stop like I had paid for. I grabbed it. It was 4 plus hours later and then took off even later. Biggest complaint is that I booked early and had an aisle seat. They gave me a "window" seat in front of the exit row, so the seat did not decline. I weigh all of 103 #s and it was tight for me! For what I paid, I feel I was kind of ripped off. I think they should have given me the empty comfort seat for the inconvenience. There was no apology nor any explanation as to why the flight was cancelled. My guess is it benefitted Delta in some way.

Very smooth, on-time, and pleasantly uneventful flight. The team at the gate and on board were professional and genuinely courteous. The pilot kept us well updated throughout, and both takeoff and landing were steady and enjoyable without any drama. Just a good, solid flight. Thank you! 💗

Staff was exceptional! Everyone was kind, professional and friendly making the trip very pleasant. Thank you!

it was fine, decent flight... dont get food besides cookies or pretzels so not sure why you ask about food. same for entertainment..

I got sick nothing contagious but distressing and the care I received by Kayla? Keighly the flight attendant will be memorable for ever. Thank You

I got sick nothing contagious but distressing enough and the care I received on the flight was astounding.

Waaay too small plane. They also need to up the size of the overhead bins. I would love to keep me 3k with of camera equipment in my hard case baggahe instead of it being thrown into the belly of the plane

Attendants were pleasant and the flight was smooth and relaxed.

A little late at the start but all worked out well.

It was fine. No drinks nor snacks offered though. I thought that was unusual.

I liked the humor of the captain and crew on the flight from Flagstaff to Dallas. They were humorous.

AA delayed the flight for 3 hours and 50 minutes, but delayed the last 2 hours, 30 minutes at a time, so if we knew before, could have stayed at home and worked instead of being at the airport wasting time... The plane's crew was excellent, not their fault.

After arriving in Dallas, the aircraft taxied for an unusually long time and was unable to park at the gate, which caused a significant delay and made me miss my connecting flight. I then had to wait in a very long line to be rebooked, and I was told that no hotel or meal accommodations would be provided. What is even more unacceptable is that my luggage was mishandled and has still not been located. My suitcase contains important medications that I urgently need, and I have been unable to access them due to the airline’s mishandling. This situation has caused me considerable stress and inconvenience, and I need this issue to be resolved immediately.

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