$106 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 5/11. 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$349
Santo Domingo
Santo Domingo1 stop$590
Montego Bay
Montego Bay1 stop$352
Oranjestad
Oranjestad1 stop$303
Nassau
Nassau1 stop$448
Kingston
Kingston2 stops$704
Simpson Bay
Simpson Bay1 stop$457
Providenciales
Providenciales1 stop$465
Bridgetown
Bridgetown1 stop$652
George Town
George Town1 stop$481
Puerto Plata
Puerto Plata2 stops$675
Aguadilla
Aguadilla2 stops$744
Punta Cana
Punta Cana1 stop$349
Santo Domingo
Santo Domingo1 stop$590
Montego Bay
Montego Bay1 stop$352
Oranjestad
Oranjestad1 stop$303
Nassau
Nassau1 stop$448
Kingston
Kingston2 stops$704
Simpson Bay
Simpson Bay1 stop$457
Providenciales
Providenciales1 stop$465
Bridgetown
Bridgetown1 stop$652
George Town
George Town1 stop$481
Puerto Plata
Puerto Plata2 stops$675
Aguadilla
Aguadilla2 stops$744

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

Fri, Apr 24 - Fri, May 1
Multiple Airlines Logo
7:48 pm - 7:22 pm
SDF
-
SJU
23h 34m
1 stop
Multiple Airlines Logo
6:00 am - 6:58 pm
SJU
-
SDF
12h 58m
1 stop
$226Multiple Airlines
Fri, May 1 - Thu, May 7
Spirit Airlines Logo
6:06 pm - 7:22 pm
SDF
-
SJU
25h 16m
1 stop
Spirit Airlines Logo
8:04 pm - 9:28 am
SJU
-
SDF
13h 24m
1 stop
$232Spirit Airlines
Fri, Apr 24 - Fri, May 1
Multiple Airlines Logo
6:06 pm - 7:22 pm
SDF
-
SJU
25h 16m
1 stop
Multiple Airlines Logo
6:00 am - 5:04 pm
SJU
-
SDF
11h 04m
1 stop
$261Multiple Airlines
Fri, Apr 24 - Fri, May 1
Multiple Airlines Logo
7:48 pm - 12:29 am
SDF
-
SJU
28h 41m
2 stops
Multiple Airlines Logo
6:00 am - 6:58 pm
SJU
-
SDF
12h 58m
1 stop
$262Multiple Airlines
Sun, May 10 - Fri, May 15
United Airlines Logo
5:50 am - 12:20 pm
SDF
-
STT
6h 30m
1 stop
United Airlines Logo
1:22 pm - 9:59 pm
STT
-
SDF
8h 37m
1 stop
$300United Airlines
Sun, May 10 - Fri, May 15
American Airlines Logo
7:52 pm - 11:35 am
SDF
-
STT
15h 43m
2 stops
American Airlines Logo
5:05 pm - 8:38 am
STT
-
SDF
15h 33m
2 stops
$320American Airlines
Wed, May 6 - Wed, May 13
American Airlines Logo
5:38 pm - 11:35 am
SDF
-
STT
17h 57m
2 stops
American Airlines Logo
12:25 pm - 11:59 pm
STT
-
SDF
11h 34m
1 stop
$325American Airlines
Mon, Apr 20 - Thu, Apr 23
United Airlines Logo
5:00 am - 3:31 pm
SDF
-
STT
10h 31m
1 stop
United Airlines Logo
2:10 pm - 11:59 pm
STT
-
SDF
9h 49m
1 stop
$390United Airlines
Thu, Apr 30 - Wed, May 6
Delta Logo
7:05 am - 1:51 pm
SDF
-
STT
6h 46m
1 stop
Delta Logo
1:22 pm - 11:59 pm
STT
-
SDF
10h 37m
1 stop
$466Delta
Fri, Aug 14 - Mon, Aug 17
Delta Logo
6:00 am - 11:41 am
SDF
-
GCM
6h 41m
1 stop
Delta Logo
12:56 pm - 10:36 pm
GCM
-
SDF
8h 40m
1 stop
$517Delta
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 $306 (return) on average. On the other hand, the most expensive months are December and June, when the average cost of round-trip tickets is $570 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 4 weeks before departure.

Good to know

Low seasonAugust
Cheapest flight$106
Best time to beat the crowds with an average 4% drop in price.
Most popular time to fly with an average 5% 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 4338 reviews
8.1Boarding
8.6Crew
7.5Entertainment
7.0Food
8.0Comfort
Airline reviews

Terrible. Even though there’s assigned seating now, they are still the slowest boarding airline of anyone.

2.0 MediocreJames, Apr 2026
LAX - MCO
Read more Southwest reviews

Terrible. Even though there’s assigned seating now, they are still the slowest boarding airline of anyone.

The Air hostess were very rude on my flight from Houston to Austin . Their regular communication itself felt a they are shouting at people.

Communication about the delayed flight was poor. We were told to move gates three times but that was bad information. We went from gate 128 to gate 126 and then to gate 123 and back to gate 126. Communication about the delay was bad. Ended up being 1 1/2 hour late getting home.

Plane was late. Zero service for 2+ hour flight and it was not that bumpy.

It was good from LAX to Phoenix, But the connection in Phoenix to Tulsa was not that great. The staff on both flights were great. The choice of free entertainment was ok nothing to brag about. The 45 min delay because of some electrical issue wasn't great from Phoenix to Tulsa. We sat there with hardly any air, The seat I had was between windows so the side of the plane pushed in on you. My being a bigger man it then made the seating area uncomfortable. The seats on the plane had no power to connect to recharge your phone or anything. I would recommend that they should look into a slot or clamp to hold your phone to enjoy while watching the entertainment choices hands-free. Also make it possible to raise the inner seat by the window be able to raise the arm rest up to make more room for larger people to set more comfortably. I would also say other then that stop price gouging the airfare or nickel and diming everything. Not fair for people having to fly for emergencies and be paying for higher prices due to the season or holidays. Your making your money either way and the cost of flying is still going to be the same regardless if there's 100 people or 200 people.

Had a great flight. Delayed takeoff, but comfortable. Snacks were good.

Love them will get a Southwest card to track my points and keep flying with them. My family and I were pleased with the services.

I have roller bag with food and medication told me I couldn't bring on my 2nd flight today. 15 years flying with SW never an issue with that bag.

Southwest continues to do less for more money. Flight attendants used to be fun and friendly. But now it’s like they don’t even see you. Such a shame.

Great flight. Good snacks and drinks. Grateful it was free. The flight from Nashville to louisville, i think her name was Tracy (not sure that's right) super awesome, nice and cheerful. She really enjoyed being at work today! She was the person who scanned the boarding pass on flight wn941. She should be recommended for a raise !

We departed and landed early which was a nice surprise. The boarding process was slow.

N Everything was perfect from boarding to assistance to baggage in Tampa

Subpar. The seating on the plane is almost unbearable. We are literally touching and/or sitting on each other which is totally unacceptable and shameful. Pilots and crew was very accommodating and friendly.

The boarding was organized and informative but the plane was tight meaning that you were sitting on one another and extremely uncomfortable. It’s disappointing that can’t have common seating comfort on the plane.

Loved the crew! Sucks that we went from 1 hour and 8 minute layover to a 3 hour layover. But weather sucks like that.

I was told that they needed to check my bag at the gate and to pick it up at the gate in Richmond. No big deal. I know they can't control the weather, but we flew around RIC for 45 minutes to avoid the storm and were 25 minutes late leaving as well. Once we landed, we were told to go to baggage claim to pick up our luggage. I went to bathroom, paid for parking, and went to the assigned baggage claim location. United flight people came down with us as well. They got their luggage immediately. Next, South West people came down about 10 minutes later. They got their luggage next. We finally got our luggage around 30 minutes in waiting. Was not a wonderful experience. No reflection on Delta, but the ground crew was lousy at best.

Everything could have benn better. Short fly, no food, no entertainment and no wifi.

Flight delayed. Air broken. Cabin was hot enough to pass out. Delta shuttle’s becoming worse and worse.

my mom urmila patel needed a wheelchair which was not available on the curbside. she needed to walk almost 50 meters inside (at the risk of falling) and then had to wait in line to get a wheelchair (this is not ok). Once obtained she had to seat in it for 30-45 minutes for someone to take her in thru the checkin process (which was fairly smooth and easy). the lady who helped her with her checkin process was very courteous and helpful

On the return flight, flight attendant Britt went out of her way to inform passengers that several of us had tight connections.

Flight left on time, arrived early, pleasant staff provided water, coffee, etc. access to bathrooms was reasonable and were well maintained. blankets were available, lots of entertainment options. LUGGAGE SERVICE WAS GREAT. I got my one checked bag quickly and was able to make a bus connection for a 2 hour bus ride saving me from waiting another 1.5 hours.

The boarding process was straightforward. One pertinent observation regarding all boarding procedures is that if an individual requires assistance or possesses a special status and is part of preboarding, it is advisable to limit the number of passengers who can preboard with them, rather than the entire, sometimes large, companion groups. The seats are uncomfortable, and the entertainment options are significantly inferior compared to other airlines. During the snack service, I requested an additional bag of snacks, but my request was denied. Initially, the flight attendant agreed to my request.becoming a strange accurate moment. The flight duration was four hours.

The flight was officially delayed 3 times, and was actually later than that. Combined, it was a 3 hour delay, but there was no recognition (miles, voucher, etc). The crew seemed stressed. The captain sounded nervous in his announcements. The flight itself was smooth and uneventful.

United didn’t even try to hold the flight for me. They knew I had a tight connection and when I arrived at the gate less than 10 mins after final boarding the flight had already gone. The gate agent wasn’t even notified that I was on my way. She was told I wasn’t at the airport

Great until we got to FRA. The next trip leg we were put in Business Class where seats had minimal padding!!!! They were awful and United Airlines needs to have their Lufthansa partner up their game or I won’t fly with them again!!

I had a good time. However, I paid for the wifi and it was in and out the whole flight.

one staffer was frustrated (it happen); the flight was late and the pilot mentioned they'll make amend but the snacks were the same, other than that the aircraft was clean and everything went smooth, no complaints

The wheelchair service is useless. They live you in different spots, not tell you anything just wait. I waited 30 minutes in Frankfurt when decided to walk the 25 minutes distance. In Budapest nobody came.

It was perfect! I've never flown with United before, but I definitely will in the future

I had a cancelled flight because of technical issues going to my destination, and a delayed flight coming home. All told it wasn’t a total bust.

Delays experienced in boarding/take off due to incoming plane delayed. However, the boarding time/depart time in the app was significantly delayed in providing these updates. Usually not updated until an hour after we should have already boarded. Poorly managed.

Bag drop was very disorganized in Miami. All main cabin passengers were shunted to just a few lanes and they had an equal number of lanes for first class passengers but there was nobody on those lines. They did nothing to bring the main cab and passengers over to the open lines and they just had employees standing there and doing nothing

there are no options s for snack besides cookies would ve nice to have a salty option n

We did not have enough time to make our connecting flight. As a result, we were put onto a different airline for our second leg. The different airline was NOT comparable to British Airlines, and our arrival was significantly delayed. The actual flight on BA was amazing.

We left at 1030 am pacific from LA and supposed to land at 7 pm Eastern in NY. They made a detour, stopped in Philadelphia and didn’t land till 1130 PM Eastern!!! Worst flight experience with no pilot communication with no explanation as to what was going on. Everyone was very frustrated to say the least.

Going non stop to lax like I paid for. Not stopping in MCI for gas. Too long of delays

Human interaction. Thought there would be more service-even a smile would have been nice.

It was canceled at the last minute. While I was literally at the airport. Messed my entire trip up.

Seat was VERY uncomfortable. Flight was delayed and then boarded slowly. The crew was super helpful with boarding and supporting maximizing the luggage in the overhead.

Crew at the gate was very crabby and not at all polite. The plane was very hot the entire flight. And the seat cushion was very worn out.

Long long delay, no AC while delayed, gate changes, just for the most uncomfortable flight of your life.

Everything was smooth sailing. Great crew, easy flight and was surprised with an upgraded seat. Thank you all!

My first time experience with Spirit Air was not good at all.The reason i did not know to cancel 24Hrs before flight depature you do charge cancellation fee. It's ridiculous policy.Actually you should provide full voucher instead of charging cancellation fee. Confirmation Code# ZNVPHG Thanks Much , Rita S

I truly admired that the last minute flight attendants were willing to come to serve flight # 1465 and think they should be extra compensated. Doesn't have to beonetary a star a permanent position with Spirit as long as she flies etc. They were o so pleasant and accommodating. 😊😊. Please also serve water. Plain unadulterated water 💧! Invest in a filter of your own the cost of bottles are a penny on the dollar and you could have a plug on advertising with labeling. This could be hilarious "WATER TO REFREST THE SPIRIT FROM SPIRIT ITSELF!" - Free idea!😄😄😄. Anyway overall, though a tad late the flight met expectations. Thanks you Spirit, for everything.

We were delayed and the bag charge fees are very expensive.

The worst. My flight was canceled :-- by email! -- at 10pm, just 8 hours prior to departure. Normally, given the early departure time, I would've been asleep. I was lucky to be awake and to be able to take action. Even worse, it turns out that the flight wasn't canceled (confirmed because I was at the airport and saw it loading), Spirit just canceled my reservation, probably because I got such a good rate! Utterly appalling. Notably, Spirit did not inform you (Kayak) of the change, so I kept getting alerts from you.

It was my first time flying with spirit. It was amazing. I loved it.

Horrible airline .. my flight was cancel , the only offer to flight next day was no good for me , representative from spirit advise everybody to buy the new ticket from southwest airline and spirit will pay back the money we spend on new ticket but after we did this they don’t want to pay us back , .. customer service is not help anybody Chat text messages it is horrible also , robots can’t answer and help u with anything … I send the complains to head quarter in Miami and department of transportation

Attention to detail. Luggage was lost in flight, after I confirmed it was connecting. Never made it to the destination airport.

The ticket price are reasonable, however, they can do better with the price on the luggage. Overall, I will continue using spirit.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports