$158 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 8/1. 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$582
Santo Domingo
Santo Domingo2 stops$595
Montego Bay
Montego Bay1 stop$372
Oranjestad
Oranjestad1 stop$463
Nassau
Nassau1 stop$489
Kingston
Kingston2 stops$746
Simpson Bay
Simpson Bay2 stops$575
Providenciales
Providenciales1 stop$503
Bridgetown
Bridgetown2 stops$679
George Town
George Town2 stops$544
Aguadilla
Aguadilla2 stops$787
Puerto Plata
Puerto Plata2 stops$675
Punta Cana
Punta Cana1 stop$582
Santo Domingo
Santo Domingo2 stops$595
Montego Bay
Montego Bay1 stop$372
Oranjestad
Oranjestad1 stop$463
Nassau
Nassau1 stop$489
Kingston
Kingston2 stops$746
Simpson Bay
Simpson Bay2 stops$575
Providenciales
Providenciales1 stop$503
Bridgetown
Bridgetown2 stops$679
George Town
George Town2 stops$544
Aguadilla
Aguadilla2 stops$787
Puerto Plata
Puerto Plata2 stops$675

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

Tue, Jul 21 - Wed, Aug 5
Delta Logo
6:00 am - 11:40 am
SDF
-
SJU
5h 40m
1 stop
Delta Logo
5:49 pm - 12:24 am
SJU
-
SDF
6h 35m
1 stop
$316Delta
Wed, Sep 2 - Sun, Sep 6
American Airlines Logo
6:05 am - 6:34 pm
SDF
-
SJU
12h 29m
2 stops
American Airlines Logo
7:00 am - 10:59 pm
SJU
-
SDF
15h 59m
1 stop
$321American Airlines
Tue, Sep 8 - Wed, Sep 23
American Airlines Logo
6:15 am - 12:48 pm
SDF
-
SJU
6h 33m
1 stop
American Airlines Logo
2:22 pm - 10:55 pm
SJU
-
SDF
8h 33m
1 stop
$341American Airlines
Thu, Aug 13 - Mon, Aug 17
American Airlines Logo
8:12 pm - 12:53 pm
SDF
-
STT
16h 41m
2 stops
American Airlines Logo
4:42 pm - 10:30 am
STT
-
SDF
17h 48m
2 stops
$360American Airlines
Sun, Jul 12 - Wed, Jul 15
Delta Logo
1:02 pm - 10:29 pm
SDF
-
SJU
9h 27m
1 stop
Delta Logo
5:50 pm - 12:26 am
SJU
-
SDF
6h 36m
1 stop
$363Delta
Mon, Jul 20 - Thu, Aug 13
Delta Logo
10:00 am - 8:45 pm
SDF
-
SJU
10h 45m
1 stop
Delta Logo
5:49 pm - 12:34 am
SJU
-
SDF
6h 45m
1 stop
$366Delta
Mon, Jun 29 - Thu, Jul 9
Southwest Logo
5:30 pm - 12:05 am
SDF
-
SJU
6h 35m
1 stop
Southwest Logo
10:20 pm - 10:10 am
SJU
-
SDF
11h 50m
1 stop
$368Southwest
Wed, Jul 8 - Fri, Jul 10
United Airlines Logo
6:00 am - 3:10 pm
SDF
-
MBJ
10h 10m
1 stop
United Airlines Logo
4:12 pm - 10:23 am
MBJ
-
SDF
17h 11m
1 stop
$400United Airlines
Wed, Jun 10 - Wed, Jun 17
United Airlines Logo
7:19 am - 3:35 pm
SDF
-
AUA
8h 16m
1 stop
United Airlines Logo
1:50 pm - 11:56 pm
AUA
-
SDF
10h 06m
1 stop
$463United Airlines
Sun, Oct 4 - Thu, Oct 8
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
$489Breeze 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 January, when tickets cost $113 (return) on average. On the other hand, the most expensive months are May and July, when the average cost of round-trip tickets is $225 and $225 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 2 weeks before departure, which saves you about 19% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 19 weeks before departure.

Good to know

Low seasonAugust
Cheapest flight$158
Best time to beat the crowds with an average 6% drop in price.
Most popular time to fly with an average 11% 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.
7.9
SouthwestOverall score based on 4265 reviews
8.0Comfort
8.1Boarding
7.5Entertainment
8.6Crew
7.0Food
Airline reviews

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.

4.0 OkayAnonymous, May 2026
MDW - LAX
Read more Southwest reviews

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.

I'm glad it wasn't only 75% full because I could get a good seat

if I was good. Not happy that I have to pay extra money to get the seat I need for lake room, but I guess that’s a sign of the times.

Seats were very comfortable. They tilted back. Drinks and snacks were free and served 3 times. Attendants were awesome.

Plane was clean and comfortable. Flight attendants and gate staff were professional, friendly and efficient. Boarding and deplaning were orderly and efficient. All in all, the typical excellent Southwest experience.

Truly terrible. Will never willingly fly southwest again. Seats are worse than before they switched to assigned seating. One flight attendant was the opposite of helpful (rude, unhelpful, dismissive, and as my stranger seatmate said unprompted: a total prick). This caused me, 15 minutes into the flight, to book an alternate return flight home on a competing airline (first class 1.2k purchase instead of my existing planned flight) just so I would not have to ever be on that aircraft, with that terrible service person, with those horrific seats ever again.

Planes were clean, no water or snacks on either flight.

Free & relatively fast Wi-Fi. Would've liked a wider drink selection.

I continue to be satisfied with Delta’s excellent service out of LGA. The digit id works well and gets me through security in no time. Whenever possible, I choose Delta.

Was revoked with Jet Blue due to delay from Kenya Air

The Boarding process was great. Particularly since my wife and I require assistance. The flight attendants were amazing. We travel frequently; they honestly were a cut above. 😀

Enjoyed it very much. Especially liked the free WiFi that Delta offers.

Smooth flight. Left on time, and got in 15 minutes early. Onboard video was great

For some reason, TSA Atlanta didn’t have my bag on the flight on time and they don’t have to provide Delta a reason for that.

WiFi didn’t work on two of four planes. Flight attendants were not overly friendly or welcoming. Planes were extremely slow to board and deplane.

Delta does a great job with entertainment and free wifi. I can still be in touch with my colleagues while in the air.

Seat pitch is horrible especially on the 15 hour flight. Gate crew at SFO was Outstanding. The flight crew was also great.

Easy of boarding, helpfully staff at check in, surprisingly comfortable seating

Check in was chaotic with only one counter for business class and first class. The luggage conveyor belt at JFK airport was broken so the flight departure was delayed which made the flight stressful as I had a tight connection. Although the captain said they could make up the delay, they didn’t do so.

Had a one hour delay due to mechanical issue. I didn’t think I’d be able to make my connecting flight, but they waited for me and greeted me when I arrived to help things run smooth.

Lost of requested seat assignments. Lost my husband's meal choice

6 1/2 hours from Tampa to SFO on a Boeing 737. Cramped. No Service. No real food. One pass for coffee at the beginning and a second pass THREE hours later. And check-in in Tampa was nasty even by United standards. And I am at almost TWO million miles on United. It's a non-stop. But terrible service.

MY FAMILY'S LUGGAGE WAS LOST FROM ROME TO BARI. I WAS THE ONLY ONE THAT RECEIVED MY LUGGAGE FROM ROME TO BARI. AFTER DEPLANING IN BARI, WE WASTED A LOT OF TIME AT BAG CLAIMS LOST AND FOUND REPORTING THE CLAIM AND PLEADING FOR THE BAGS TO BE DELIVERED THE NEXT DAY. WE WERE TOLD THAT IT TAKES 3 DAYS MINIMUM TO DELIVER. MY DAUGHTER AND MY GIRLFRIEND NEEDED THEIR PERSONAL THINGS AND WE WERE STAYING 3 HOURS AWAY FROM THE BARI AIRPORT. WE HAD TO DRIVE 3 HOURS TO THE AIRPORT TO COLLECT OUR LOST LUGGAGE THE NEXT DAY. WE ARE NOT HAPPY WITH THE EXPERIENCE

We had a delay, but thankfully I made it to my connection. Overall it went smooth

The flight had a delay but I made it to my connection. Flight was smooth overall

As I wrote earlier, poor planning and/or communication. At least twice, we were told that we would be boarding in less than ten minutes, only to have the flight again delayed at least another hour.

Ontario airport boarding was very easy to park and access, is clean and TSA took 10 minutes total. Check-in was a breeze and cruise was very nice.

American Airlines II: Delay Boogaloo. Multiple gate changes, delays, boarded and then MORE delays. I hate to say this won’t matter, but posting stuff about major corporations in 2026 is a post-modern “scream into the void.” Was multiple hours late coming home, so there you go.

Awful, tons of delays, I got into Chicago multiple hours late meaning I hit the very traffic I tried so desperately to avoid. Just empty apologies from American Airlines text alerts. Trash behavior from a trash airline.

The flight attendants were very friendly, efficient, and helpful. The plane was ahead of schedule, and it all went very smoothly. Thank you.

They lost my baggage and I am still struggling to the information and update

We got delayed getting out of DFW for broken overhead bins. Once the flight got underway the captain kept the seatbelt sign lit the entire flight despite little perceptible turbulence, preventing use of the rest rooms and any sort of refreshment service in the main cabin.

Flight delays for communication overall not a good experience uncomfortable on the plane. Person in front of me reclined his seat, putting them inches from my lap.

There were flight delays making our flight arrive at our destination after midnight didn’t seem to have enough crew or airplanes for the flights laid over in Dallas should’ve had plenty of time to make it to our next flight only made it because that flight was also delayed because our plane wasn’t even at the airport yet overall have not had a good experience on American

Flight left on time. Captain provided relevant announcements. We had to wait 45 minutes to desembark due to the ramp closed because of lightening.

It's a long flight and that is always difficult. I was comfortable and well. The movies available were great and the crew was good.

My flight today was cancelled because it was Spirit Airlines but have received no refund.

THEY WENT OUT OF BUSINESS AND CANCELED FLIGHT. REPLACEMENT FLIGHTS WERE 300% HIGHER SO MY FAMILY COULD NOT GET TOGETHER. WHY AM I GETTING THIS SURVEY?????

If there WAS a flight it would have been EXCELENT..Maybe?

It would have been better IF IT HAD NOT BEEN CANCELED!!!!

There was no flight. Spirit went bankrupt Right before my departure and kayak did not refund me any money. I would like my refund kayak. How can I get it? Please let me know. Thank you

Flights were canceled due to airline shutting down and haven’t received a reimbursement. Had to book last minute new flights which were expensive

My flight was canceled the morning of the flight. I had to rebook a flight with a different airline that cost me $900 out of my pocket

Are you serious? I know this is an automated message but how can you not update the system?

Had a flight change had to get a credit.will I get my money back.

Shut down without prior notice End up with spending lots of extra $$$

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports