$122 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 3/17. 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$412
Santo Domingo
Santo Domingo1 stop$361
Montego Bay
Montego Bay1 stop$435
Oranjestad
Oranjestad1 stop$343
Nassau
Nassau1 stop$448
Kingston
Kingston1 stop$544
Simpson Bay
Simpson Bay1 stop$552
Providenciales
Providenciales1 stop$413
Bridgetown
Bridgetown1 stop$582
George Town
George Town1 stop$409
Puerto Plata
Puerto Plata1 stop$599
Aguadilla
Aguadilla2 stops$972
Punta Cana
Punta Cana1 stop$412
Santo Domingo
Santo Domingo1 stop$361
Montego Bay
Montego Bay1 stop$435
Oranjestad
Oranjestad1 stop$343
Nassau
Nassau1 stop$448
Kingston
Kingston1 stop$544
Simpson Bay
Simpson Bay1 stop$552
Providenciales
Providenciales1 stop$413
Bridgetown
Bridgetown1 stop$582
George Town
George Town1 stop$409
Puerto Plata
Puerto Plata1 stop$599
Aguadilla
Aguadilla2 stops$972

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, Feb 24 - Wed, Mar 4
Delta Logo
3:33 pm - 11:58 pm
SDF
-
SJU
7h 25m
1 stop
Delta Logo
6:15 am - 2:34 pm
SJU
-
SDF
9h 19m
1 stop
$246Delta
Mon, May 4 - Fri, May 8
Multiple Airlines Logo
7:48 pm - 2:31 pm
SDF
-
SJU
18h 43m
1 stop
Multiple Airlines Logo
6:00 am - 6:58 pm
SJU
-
SDF
12h 58m
1 stop
$258Multiple Airlines
Tue, Apr 21 - Mon, Apr 27
Spirit Airlines Logo
3:33 pm - 2:31 pm
SDF
-
SJU
22h 58m
1 stop
Spirit Airlines Logo
9:49 pm - 2:38 pm
SJU
-
SDF
16h 49m
1 stop
$259Spirit Airlines
Sat, Mar 7 - Wed, Mar 18
Multiple Airlines Logo
12:00 pm - 11:13 pm
SDF
-
SJU
10h 13m
1 stop
Multiple Airlines Logo
7:54 pm - 2:33 pm
SJU
-
SDF
18h 39m
1 stop
$272Multiple Airlines
Wed, May 6 - Wed, May 13
Spirit Airlines Logo
12:33 pm - 10:09 pm
SDF
-
SJU
9h 36m
1 stop
Spirit Airlines Logo
3:36 pm - 2:38 pm
SJU
-
SDF
23h 02m
1 stop
$283Spirit Airlines
Tue, Mar 3 - Tue, Mar 10
American Airlines Logo
7:35 am - 6:09 pm
SDF
-
SJU
9h 34m
2 stops
American Airlines Logo
7:11 am - 11:59 pm
SJU
-
SDF
16h 48m
1 stop
$286American Airlines
Mon, Mar 2 - Mon, Mar 9
United Airlines Logo
5:35 am - 4:02 pm
SDF
-
PUJ
9h 27m
1 stop
United Airlines Logo
1:55 pm - 10:13 pm
PUJ
-
SDF
8h 18m
1 stop
$429United Airlines
Sun, Feb 15 - Thu, Feb 19
American Airlines Logo
6:06 am - 1:33 pm
SDF
-
MBJ
7h 27m
1 stop
American Airlines Logo
3:53 pm - 10:04 am
MBJ
-
SDF
18h 11m
1 stop
$435American Airlines
Wed, Mar 18 - Wed, Mar 25
United Airlines Logo
7:05 am - 4:25 pm
SDF
-
PUJ
9h 20m
2 stops
United Airlines Logo
11:56 am - 7:42 pm
PUJ
-
SDF
7h 46m
1 stop
$437United Airlines
Tue, Jun 9 - Wed, Jun 17
Southwest Logo
7:25 am - 6:30 pm
SDF
-
NAS
11h 05m
2 stops
Southwest Logo
8:45 am - 4:45 pm
NAS
-
SDF
8h 00m
2 stops
$494Southwest
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 September, when tickets cost $313 (return) on average. On the other hand, the most expensive months are December and March, when the average cost of round-trip tickets is $565 and $508 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 9% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 16 weeks before departure.

Good to know

Low seasonAugust
Cheapest flight$122
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly with an average 4% 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 4274 reviews
8.1Boarding
7.5Entertainment
7.0Food
8.6Crew
8.0Comfort
Airline reviews

I appreciate the staff who allowed me to board though I arrived a little late! Regarding the assigned seating, I had booked my flight before this change and wasn't aware of the change at the time, and so I didn't select a seat at booking as I didn't realize it was relevant. Better communication about the change would have been helpful for preparing.

10.0 ExcellentMeghan, Feb 2026
MCO - DEN
Read more Southwest reviews

I appreciate the staff who allowed me to board though I arrived a little late! Regarding the assigned seating, I had booked my flight before this change and wasn't aware of the change at the time, and so I didn't select a seat at booking as I didn't realize it was relevant. Better communication about the change would have been helpful for preparing.

Flight attendants very hospitable and friendly. Pilot flew a smooth take off and landing.

Paid for premium extra leg room but the bin space for rows 1-3 had to go in rows 4-6 and 4-6 had to go to 7-9 because flight attendants have snacks and their luggage upfront. So we pay extra to have to fight thru traffic to get our bags. Only 2nd day of new seating so hope they fix this.

WIFI was great. My selection for seating is an aisle, but during my trip, I never had an aisle seat. If we can get that corrected, I will be thrilled. No snack or drink on this flight.

WIFI was great. My selection for seating is an aisle, but during my trip, I never had an aisle seat. If we can get that corrected, I will be thrilled.

The wifi on the plane is great. The only issue that I have is that I prefer an aisle seat and on my trips this week, I was either in the middle or window. If we can work to secure aisle seating, I will be thrilled. Nice trip.

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

Everything went smoothly and we even arrived a little bit early.

Great vacation. Can't wait till next year for another one.

Great flight but super high price. Glad it was a business trip and not personal

I was given middle seat on this flight and prior Boston to Seoul flight That is a problem for long flights, Kayak system did not give me a change to select my seats and assigned me middle seats regardless of my elevated status in Delta. This needs immediate attention.

I didn't take this flight. I changed the flight. Why am I getting surveys and notifications on flights that I change. Seems like a defect with Kayak.

Delta One is extraordinary. I fly business when somebody hires me. I just wonder why there is such a chasm between business class and the insanely inhumane and nonsensical coach. The seats are not large enough to fit even my tiny wife. We fly 10% of what we did because we don’t want to pay 5-10 k but for $400 it’s unbearable. It seems like the accountants took over and made stupid decisions. Screw in 20 extra seats and make it so unbearable that people fly 90% less. Just put the damn price up and put some proper chairs in. But business, yay.

Timing, quality of service, promptness and courtesy of the staff

It was last minute due to weather - considering - it was amazing! Good smiles, friendly staff and they were making sure we knew what was going on when and where.

delta last minute gave me a boarding pass for a different flight with no confirmation that they were changing it

The flight was comfortable and uneventful, which is what I desire

The service from the flight attendants were of supreme quality. They greeted and treated everyone with a wide smile. This is totally absent nowadays. Kudos to them!!!!

Excellent flight and got us around tough weather. Only issue was seat TV did not work and crew tried to reboot.

Very large passenger too space from my own seat. Arm board couldn’t be lowered because of his size. It wads very uncomfortable trip, as the flight was full couldn’t move anywhere having back pain because of the position in which I was the entire flight.

Not being stranded in Chicago for her airport to 11:30 tomorrow morning the 3rd

the whole trip was smooth, and as comfortable as flying is these days. flight crew was friendly and very courteous and helpful.

The attendant on board was amazing. She should be doing business/first international long haul.

Although our flight was delayed the overall boarding process was very smooth and the crew was accommodating.

I was fully checked in the prior night and i was unchecked and then didn’t have a seat when I boarded. Instead of an aisle seat, I was out in the middle seat of the very last row of the plane.

In overall it was a good experience, the only down point was that the entertainment screen was working properly.

HORRIBLE, my initial flight was cancelled, they made me pay $200 extra dollars and that got cancelled as well! After 6 cancellations I decided to get a refund because I needed to get home to my babies. Out of $1000+ dollars they offered me only $40 in refund! Totally unacceptable! The flight that they cancelled I was able to fly it on another airline. I had to spend $400 on one way tickets just to get home! I’m still getting the runaround.

First class ticket gets you a choice of chips or nuts. . Just like economy Southwest. Also no screen in the seats. This is first class???!

Seated dude next to me even though lots of empty rows. But main thing was we sat on the tarmac after landing for 30 minutes because of, in the words of the dude who sat next to me, “operational incompetence”. We got changing directions about where to pick up gate checked bags. Pilot and flight attendant were awesome though.

The food was terrible this time. Otherwise pleasant, quiet, on-time.

The screens were inoperable for movies and such, but everything else was just fine

For a 5 1/2 hour flite i considered the "business class" to be subpar. The seats were just ok, no amenities, really nothing more than a long domestic flight. Frankly disappointed.

Delayed an hour due to operational issues. Minimal apologies or care for the significant inconvenience caused. Landed at nearly 1am and they still couldn’t find ground staff to get us off the plane promptly.

This was one of the most frustrating travel experiences I've had to date. I had changed my flight day of to this one as it was slated to depart on time. It ended up being so delayed that my original flight took off before this one did. The boarding process began but eventually stopped and everyone had to get off the plane as a problem was identified. The person at the front desk just tried to laugh it off as if this wasn't already a huge inconvenience. From there, we eventually got to board only to sit at the gate for an additional hour because of some additional issue. This was extremely frustrating and caused a lot of stress.

Update to handle the delay was very bad, crews no smiles or welcome or thanks. Don’t care attitude

It would be nice to have some low carb options in the snacks.

I was trying to take 2 one and a half hour one way trips and I experienced almost 20 delays over the course of those two trips. Only a few of them were due to weather the rest was disorganization

No gates avail at DFW so our incoming had to wait 30 mins for a plane to push back because they Had mechanical. We boarded 90 mins delayed and then we had a mechanical. Come on American…do better. Also at my seat the tray table had not been cleaned. Floor had not been cleaned. But captain and flight Att were very picture and apologetic.

Crew was helpful and cheerful especially when they had no refreshments to work with. The plane was never serviced and had nothing but limited water and coffee onboard. For the price point, a concern of services.

Flight was smooth, quick and felt safe. The 2 delays not happening would have been better but I guess that happens in the airline industry

All of our flights were canceled, though every other airline was flying out and in

We were on the tarmac waiting for a gate at Logan for 40, minutes. The crew handled it well. Can't blame the airline.

That gate is like a ducking shelter at Newark No where to sit Outlets that don’t work Bathrooms that are dirty

Everything was good. On time, boarding fast, flight attendants friendly.

Great, but seats are terrible. Way too cramped for any human.

Spirit has always and will always stink. Absolute worst airline around.

It was smooth sailing snags we had a really smooth landing and a great flight!

I know it's a low-cost airline. However, the seats are very basic, so after two hours of travel, they feel very uncomfortable and cannot be reclined. The two flights from Bogota to Orlando and the return flight were very punctual. The check-in process on the app works very well. I really liked the self-check-in process for luggage at the Orlando airport; it was quick, easy, and very convenient.

The entire experience was so surprisingly pleasant. And the blocked extra seat between us was such an amazing and nice bonus. Great experience all around and I can’t wait to fly with spirit again!

Everything was OK, the deicing took a long time, our connections were almost missed.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports