$121 Find Cheap Flights from Louisville to Caribbean

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Louisville to Caribbean departing on 4/11. 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 Louisville to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$419
Santo Domingo
Santo Domingo1 stop$569
Montego Bay
Montego Bay1 stop$352
Oranjestad
Oranjestad1 stop$409
Nassau
Nassau1 stop$438
Kingston
Kingston1 stop$546
Simpson Bay
Simpson Bay2 stops$540
Providenciales
Providenciales1 stop$383
Bridgetown
Bridgetown1 stop$652
George Town
George Town1 stop$379
Puerto Plata
Puerto Plata2 stops$673
Punta Cana
Punta Cana1 stop$419
Santo Domingo
Santo Domingo1 stop$569
Montego Bay
Montego Bay1 stop$352
Oranjestad
Oranjestad1 stop$409
Nassau
Nassau1 stop$438
Kingston
Kingston1 stop$546
Simpson Bay
Simpson Bay2 stops$540
Providenciales
Providenciales1 stop$383
Bridgetown
Bridgetown1 stop$652
George Town
George Town1 stop$379
Puerto Plata
Puerto Plata2 stops$673

Book Cheap Louisville to Caribbean Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Louisville to Caribbean 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 Louisville to Caribbean

Mon, May 11 - Sat, May 16
Southwest Logo
12:15 pm - 11:25 pm
SDF
-
SJU
11h 10m
1 stop
Southwest Logo
2:10 pm - 9:55 pm
SJU
-
SDF
7h 45m
1 stop
$254Southwest
Sun, Apr 26 - Sat, May 2
Delta Logo
7:05 am - 4:23 pm
SDF
-
SJU
9h 18m
1 stop
Delta Logo
6:15 am - 4:49 pm
SJU
-
SDF
10h 34m
1 stop
$266Delta
Mon, Apr 13 - Thu, Apr 16
American Airlines Logo
7:52 pm - 12:03 pm
SDF
-
SJU
16h 11m
1 stop
American Airlines Logo
4:30 pm - 8:38 am
SJU
-
SDF
16h 08m
1 stop
$276American Airlines
Tue, May 19 - Thu, May 28
Delta Logo
7:08 am - 4:33 pm
SDF
-
SJU
9h 25m
1 stop
Delta Logo
5:43 pm - 12:25 am
SJU
-
SDF
6h 42m
1 stop
$279Delta
Sat, Apr 11 - Wed, Apr 15
American Airlines Logo
7:33 am - 8:51 pm
SDF
-
SJU
13h 18m
1 stop
American Airlines Logo
6:00 am - 10:31 pm
SJU
-
SDF
16h 31m
1 stop
$281American Airlines
Thu, Apr 9 - Thu, Apr 16
American Airlines Logo
6:01 am - 9:24 pm
SDF
-
SJU
15h 23m
1 stop
American Airlines Logo
7:25 am - 10:08 pm
SJU
-
SDF
14h 43m
1 stop
$282American Airlines
Sat, May 2 - Sat, May 9
United Airlines Logo
2:30 pm - 9:24 pm
SDF
-
SJU
6h 54m
1 stop
United Airlines Logo
1:00 am - 1:22 pm
SJU
-
SDF
12h 22m
2 stops
$283United Airlines
Mon, May 11 - Wed, May 27
American Airlines Logo
5:41 pm - 4:32 am
SDF
-
SJU
10h 51m
1 stop
American Airlines Logo
6:20 am - 5:42 pm
SJU
-
SDF
11h 22m
1 stop
$296American Airlines
Sun, May 17 - Wed, May 20
United Airlines Logo
5:50 am - 12:20 pm
SDF
-
STT
6h 30m
1 stop
United Airlines Logo
2:10 pm - 10:22 pm
STT
-
SDF
8h 12m
1 stop
$300United Airlines
Thu, Sep 17 - Sun, Sep 20
Breeze Airways Logo
9:09 pm - 8:30 am
SDF
-
NAS
11h 21m
1 stop
Breeze Airways Logo
10:15 am - 8:29 pm
NAS
-
SDF
10h 14m
1 stop
$487Breeze Airways
Booking Insights

KAYAK's insights & trends for Louisville to Caribbean flights

Get data-powered insights and trends into flights from Louisville to Caribbean to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest month to fly from Louisville to Caribbean?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Louisville to Caribbean, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Louisville to Caribbean is October, when tickets cost $310 (return) on average. On the other hand, the most expensive months are December and June, when the average cost of round-trip tickets is $565 and $481 respectively.

How far in advance should I book a flight from Louisville to Caribbean?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights from Louisville to Caribbean, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Louisville to Caribbean, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 12 weeks before departure.

Good to know

Low seasonAugust
Cheapest flight$121
Best time to beat the crowds with an average 5% drop in price.
Most popular time to fly with an average 3% increase in price.
Flight from Louisville to San Juan

FAQs - booking Caribbean flights

  • How does KAYAK find such low prices on flights from Louisville to Caribbean?

    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 Louisville to Caribbean.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Louisville to Caribbean?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Louisville to 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 Louisville to Caribbean?

    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 from Louisville to Caribbean with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Louisville to Caribbean?

    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 from Louisville to Caribbean up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top 5 airlines serving from Louisville to Caribbean

 
Need help choosing which airline to fly with from Louisville to Caribbean? 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 4325 reviews
7.0Food
8.0Comfort
8.6Crew
8.1Boarding
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.

This was a Latam operated flight. Seats seemed a bit narrow in business class. Older aircraft.

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.

Good quick flight on a small but comfortable plane. I'm 6'3 and had plenty of space.

Experience was great - no complaints. Took off on time, landed early. Got to the gate relatively quickly - took a little bit of extra time to deplane but nothing excessive.

Business class seats felt very cramped compared to other airlines.

Economy plus was so cramped I could not use my laptop. It was beyond bad.

OK, we were delayed and had to de plane and reboard.

United is one airline which regardless of how many separate United tickets in existence, if one flight breaks down, the airline will take care of all the flights.

Both our flights were delayed. Almost didn’t get in the second flight. Staff was rude to the bone.

Both my flight where delayed Had 25min to make it to my transfer flight

Everything was on time and service on the flight was great!

Wifi Bluetooth features for watching in flight movie was horrible. Screen kept blacking out no connection of sound although it said connected. Other than that smooth trip .

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.

Perhaps this is an airport issue, but being in a takeoff queue for over an hour in the taxiing lane is unacceptable. We will definitely be seeking alternative avenues for air travel in the future.

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

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.

Smooth flight staff very friendly and we arrived 15 mins earlier

I was in the airport when I'll check the status of my flight and it was canceled and without any reason. The worst of the worst ...

I never had an opportunity to experience them! They cancelled my flight TWICE!!!

Return flight was canceled. Needed to reschedule with another airline the next day. Cost an an additional $84. At another airport 45 miles further away

Spent seven hours in the airport with spirit pushing he flight time back two hours every two hours only to then have it canceled without explanation. The employees said, “They’ve been doing this for the last five days.” Would have been great if they told us to expect that when we arrived.

Seat do not reclined and tight space. Flight changed so many times hard to keep up.

Bad airline to travel with my flight was delayed for more than 3 hours they act like it’s normal

No WiFi, no outlets to charge phones, no complimentary beverages on a 6 hour flight

Length of flight was fine Delay of over 3 hours was very bad!! Flight down was delayed 1.5 hours

Delayed 11 hours with two being on our destinations tarmac, no compensation or refund and was told I would actually get charged a $200 cancellation fee if I decided to switch airlines for my return flight. For their inconvenience they gave a $10 meal voucher to split between two people in a airport.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports