$138 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 4/16. 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, May 14 - Tue, May 19
Delta Logo
1:14 pm - 12:25 am
SJU
-
SDF
11h 11m
1 stop
Delta Logo
6:00 am - 4:33 pm
SDF
-
SJU
10h 33m
1 stop
$242Delta
Fri, Apr 24 - Sun, Apr 26
American Airlines Logo
6:00 am - 10:31 pm
SJU
-
SDF
16h 31m
1 stop
American Airlines Logo
6:06 am - 6:10 pm
SDF
-
SJU
12h 04m
1 stop
$276American Airlines
Thu, May 14 - Tue, May 19
American Airlines Logo
11:59 pm - 10:15 am
SJU
-
SDF
10h 16m
1 stop
American Airlines Logo
7:31 am - 10:05 pm
SDF
-
SJU
14h 34m
1 stop
$299American Airlines
Wed, Aug 5 - Sun, Aug 9
American Airlines Logo
10:32 am - 12:30 am
SJU
-
SDF
13h 58m
1 stop
American Airlines Logo
6:19 am - 10:56 pm
SDF
-
SJU
16h 37m
1 stop
$316American Airlines
Thu, May 14 - Tue, May 19
Southwest Logo
4:25 pm - 11:45 pm
SJU
-
SDF
7h 20m
1 stop
Southwest Logo
1:35 pm - 11:40 pm
SDF
-
SJU
10h 05m
2 stops
$319Southwest
Thu, May 14 - Mon, May 18
Southwest Logo
4:25 pm - 11:45 pm
SJU
-
SDF
7h 20m
1 stop
Southwest Logo
2:40 pm - 11:55 pm
SDF
-
SJU
9h 15m
2 stops
$324Southwest
Thu, Aug 27 - Fri, Sep 4
American Airlines Logo
6:00 am - 10:34 pm
SJU
-
SDF
16h 34m
1 stop
American Airlines Logo
4:49 pm - 11:41 pm
SDF
-
SJU
6h 52m
1 stop
$341American Airlines
Wed, Jul 8 - Sun, Jul 12
Southwest Logo
12:20 pm - 10:30 pm
SJU
-
SDF
10h 10m
1 stop
Southwest Logo
6:35 pm - 12:25 am
SDF
-
SJU
5h 50m
1 stop
$346Southwest
Wed, May 20 - Thu, May 28
United Airlines Logo
6:00 am - 11:56 pm
STI
-
SDF
17h 56m
2 stops
United Airlines Logo
6:30 am - 3:12 pm
SDF
-
STI
8h 42m
1 stop
$651United Airlines
Wed, May 20 - Thu, May 28
United Airlines Logo
2:07 pm - 10:22 pm
STI
-
SDF
8h 15m
1 stop
United Airlines Logo
7:10 am - 3:12 pm
SDF
-
STI
32h 02m
2 stops
$673United Airlines
Useful Info

Good to know

Low seasonFebruary
Cheapest flight$138
Best time to beat the crowds with an average 33% drop in price.
Most popular time to fly with an average 5% 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.
8.0
SouthwestOverall score based on 4324 reviews
8.1Boarding
7.0Food
8.6Crew
8.0Comfort
7.5Entertainment
Airline reviews

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

2.0 MediocreBeth, Mar 2026
MDW - PIT
Read more Southwest reviews

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

Boarding was easy. The seats are small and fairly uncomfortable

I was supposed to be on a later flight. When I showed up at the gate, the woman working there was extremely helpful getting moved up to this earlier flight.

We had a 5 hour delay on the tarmac in Baltimore

Long layover between flights to Long Island from BWI - need better coordination between flights

I elected to pay for the upgrades and found very little difference

The new seating arrangement is so over priced for what you get.

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

No food or entertainment, just a quick 40 minute flight. A little bumpy due to Santa Ana winds but pilot has no control over that. Good flight and landing!

Good but I prefer choose your own seat. With the new assigned seats they should board from the back I see no advantage to this new boarding. Just like every other airline

My recent experience was excellent on Delta! I flew with Delta Comfort and I was really comfortable in my seat. I enjoyed the in-flight service. The flight attendants were so friendly and hospitable. I love the snack on the flight as well. This was my first time flying on Delta and I will definitely consider flying with them again.

My flight was cencaled due with the bad weather on Sunday the crew was poorly mistaken my luggage supposed depart with my flight instead I didn’t have my luggage for almost 3 days the website is poorly respond to my complain until I have someone to do it my connection smooth their not even respon or email me even the have my luggage

Delta needs to step its game up get a more reliable internet service. Internet service was non-existent for this flight.

Mechanical Delay of over an hour with multiple gate changes. Entertainment system down for rejuvenation.

I had a flight cancel and had it rerouted. When the rerouted they put me at a window seat instead of an isle. It was hard sitting by the window because the couple with masks on were making out. I get motion sickness which is why I need to have the isle seat.

NEVER MADE THE FLIGHT BECAUSE DELTA SAID THEY CAN NOT

THEY FAILED ME AND I NEVER GOT ON THE FLIGHT BECAUSE IT WAS SO DELAYED! I ENDED UP HAVING TO PAY OUT OF POCKET FOR A HOTEL AND STAY IN NASHVILLE TO CATCH A FLIGHT FOR THE FOLLOWING DAY. DELTA IS POOR CUSTOMER SERVICE>

8 hours late and the plane smelled like urine, that smell in the morning when your child wet the bed in the night.

My flight was canceled on Sunday. Rebooking took three hours. Had to pay for accommodations another night. New flight was delayed for 5 hours, all that was sent was a 12 dollar food voucher, which doesn’t tell you how to use it. Then when we landed we had to sit on the plane for an hour before we could get off.

Miserable. This entire round trip was miserable. I booked evening flights to and from Detroit on consecutive days that should have had me at my destination by 10:30. Instead I arrived after 3am on my flight to Detroit and after midnight on my return. Multiple unforced errors like awaiting bags to get put on the plane for almost an hour in Detroit and a 20 minute delay to pull up to the gate in Atlanta has me rethinking my assumption that delta is the best and most reliable airline

Rough flight No beverage service due to turbulence Bottom Seat cushion was non existent

Great experience. Good dinner and service. FA's were very nice and attentive.

It was great. Smooth flight, comfortable, left on time and landed on time.

We hoarded. Then we deplaned. Then we waited for 10 hours in the MSP airport due to a wheel misfunction. We understand safety but communication between crew and airport staff was horrible. When we did finally board, we were rushed on and because we were waiting for a “fresh” pilot and crew, we sat in a roasting plane with no A/C for an hour. My question is why was this flight not cancelled right away when they knew this would be a huge issue OR, why did AA not get a substitute plane, considering this was already a full flight? To me, this appears to be a complete breakdown in leadership and utter systems failure. The compensation for completely disrupting travel plans for hundreds, which we paid dearly for, was measly. While we appreciated the lodging for the night, $12 in meal vouchers isn’t going to sustain anyone for over 12 hours. “We apologize; our hands are tied” is no longer an acceptable explanation. We are so completely turned off by this experience and will definitely seek alternative avenues when we need to fly.

Mostly good. The WiFi wasn’t working so that was not great.

I rated the experience "mediocre" because of the 2 hour delay in take off. This is the 4th flight from DFW on AA where there was a delay and in one of the instances (after 13 delays), the flight was cancelled. I understand weather but for the March 18th flight, there was no weather issue in Dallas or Detroit. I called Concierge Key and they were wonderful, booking me on a later flight in case my flight was cancelled. I have flown with American for many years and never has there been this consistent pattern of delays. Very disappointing.

They put me on an earlier and I got home sooner

Crew was rude, almost 6 hour flight after horrific customs re entry line and near flight miss (unable to bug airport food) without food offerings.

Not good. One of my luggage is missing. And until now they can’t find it

Horrible experience upon landing. Probably more due to DCA utter incompetence than AA.

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