$103 Find Cheap Flights from Louisville to Caribbean Islands

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 Islands departing on 8/26. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Caribbean Islands

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Louisville to Caribbean Islands, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Louisville to Caribbean Islands, as well as popular online travel agencies
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Cheap Flights from Louisville to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$265
Santo Domingo
Santo Domingo1 stop$351
Montego Bay
Montego Bay1 stop$305
Oranjestad
Oranjestad1 stop$431
Nassau
Nassau1 stop$435
Kingston
Kingston1 stop$368
Simpson Bay
Simpson Bay1 stop$422
Providenciales
Providenciales1 stop$528
Bridgetown
Bridgetown2 stops$566
George Town
George Town1 stop$440
Puerto Plata
Puerto Plata2 stops$579
Aguadilla
Aguadilla1 stop$820
Punta Cana
Punta Cana1 stop$265
Santo Domingo
Santo Domingo1 stop$351
Montego Bay
Montego Bay1 stop$305
Oranjestad
Oranjestad1 stop$431
Nassau
Nassau1 stop$435
Kingston
Kingston1 stop$368
Simpson Bay
Simpson Bay1 stop$422
Providenciales
Providenciales1 stop$528
Bridgetown
Bridgetown2 stops$566
George Town
George Town1 stop$440
Puerto Plata
Puerto Plata2 stops$579
Aguadilla
Aguadilla1 stop$820

Book Cheap Louisville to Caribbean Islands 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 Islands 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 Islands

Mon, Oct 13 - Tue, Oct 28
American Airlines Logo
3:35 pm - 11:59 pmSDF-SJU
8h 24m1 stop
American Airlines Logo
7:05 am - 5:54 pmSJU-SDF
10h 49m2 stops
$205American Airlines
Find Deal
Sun, Sep 7 - Thu, Sep 11
Delta Logo
6:00 am - 4:36 pmSDF-SJU
10h 36m1 stop
Delta Logo
5:41 pm - 11:52 pmSJU-SDF
6h 11m1 stop
$215Delta
Find Deal
Sat, Sep 6 - Fri, Sep 12
Spirit Airlines Logo
8:30 am - 11:04 amSDF-SJU
26h 34m1 stop
Spirit Airlines Logo
11:59 am - 10:28 pmSJU-SDF
10h 29m1 stop
$226Spirit Airlines
Find Deal
Sun, Sep 7 - Thu, Sep 11
American Airlines Logo
10:00 am - 11:37 pmSDF-SJU
13h 37m2 stops
American Airlines Logo
3:50 pm - 11:59 pmSJU-SDF
8h 09m1 stop
$235American Airlines
Find Deal
Sat, Sep 20 - Mon, Sep 22
Spirit Airlines Logo
10:14 am - 12:44 amSDF-SJU
14h 30m1 stop
Spirit Airlines Logo
1:59 am - 9:19 amSJU-SDF
7h 20m1 stop
$243Spirit Airlines
Find Deal
Fri, Sep 19 - Sun, Sep 21
Southwest Logo
4:20 pm - 11:30 pmSDF-SJU
7h 10m1 stop
Southwest Logo
5:45 am - 12:25 pmSJU-SDF
6h 40m1 stop
$245Southwest
Find Deal
Sun, Sep 7 - Fri, Sep 12
United Airlines Logo
7:20 am - 2:44 pmSDF-SJU
7h 24m1 stop
United Airlines Logo
1:05 am - 1:17 pmSJU-SDF
12h 12m2 stops
$288United Airlines
Find Deal
Sun, Sep 28 - Fri, Oct 3
Delta Logo
7:33 pm - 12:32 pmSDF-PUJ
16h 59m2 stops
Delta Logo
1:57 pm - 9:27 amPUJ-SDF
19h 30m2 stops
$319Delta
Find Deal
Tue, Aug 26 - Sat, Aug 30
United Airlines Logo
6:15 am - 1:31 pmSDF-NAS
7h 16m1 stop
United Airlines Logo
2:53 pm - 10:02 amNAS-SDF
19h 09m2 stops
$481United Airlines
Find Deal
Fri, Nov 28 - Mon, Dec 8
Southwest Logo
5:30 pm - 1:00 pmSDF-NAS
19h 30m2 stops
Southwest Logo
1:10 pm - 10:10 pmNAS-SDF
9h 00m1 stop
$540Southwest
Find Deal
Booking Insights

KAYAK's insights & trends for Louisville to Caribbean Islands flights

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

Can I save money by flying with a layover from Louisville to Caribbean Islands?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $408, prices are generally cheapest when you fly direct.

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

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Louisville to Caribbean Islands, 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 Islands is October, when tickets cost $371 (return) on average. On the other hand, the most expensive months are March and December, when the average cost of round-trip tickets is $573 and $565 respectively.

What’s the cheapest day of the week to fly from Louisville to Caribbean Islands?

The average price of all round-trip flights from Louisville to Caribbean Islands clicked on KAYAK for each day over the last 12 months.

Your flight ticket price will generally be cheaper if you fly to Caribbean Islands on a Tuesday and more expensive on a Friday. On your return trip to Louisville, you should consider flying back on a Thursday, and avoid Sundays for better deals.

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

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 Islands, 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 Islands, you should book around 2 weeks before departure, which saves you about 26% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 2 weeks before departure.


Good to know

Low seasonAugust
Cheapest flight$103
Best time to beat the crowds with an average 10% drop in price.
Most popular time to fly with an average 5% increase in price.
Flight from Louisville to San Juan

FAQs - booking Caribbean Islands flights

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

    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 Islands.

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

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

    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 Islands 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 Islands?

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

  • What is the cheapest time of day to fly to Caribbean Islands?

    The cheapest time of day to fly to Caribbean Islands is generally at night, when round-trip flights cost $339 on average. On average, there is no price difference when choosing to fly in the morning or the evening on this flight route. The most expensive time of day to fly to Caribbean Islands is generally in the evening, which is peak travel time and where the average cost of a ticket is $441.

Reviews of the top 5 airlines serving from Louisville to Caribbean Islands

 
See real verified KAYAK customer reviews for airlines flying from Louisville to Caribbean Islands. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Louisville to Caribbean Islands? 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 4241 reviews
8.6Crew
7.5Entertainment
8.1Boarding
8.0Comfort
7.0Food
Airline reviews

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

2.0 MediocreAnonymous, Jul 2025AUS - RDU
Read more Southwest reviews

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

The quality of Southwest Airlines continues to degrade each time I fly with them. If it were not for the free luggage, I would probably choose another airline. Their prices are a little bit competitive, but way too high for the quality of the service. Southwest is not unique in this way. Domestic flight in the United States of America has continued to be a lower and lower quality product. Very sad when you compare the quality of domestic airlines to that of many international airlines around the world.

Very smooth checking in our luggage with a super pleasant SW agent. I enjoyed a fun entertaining movie.

WiFi did not work. For as outrageous as these flights cost, when they’re advertised with certain services/ features they should be in working order

Worst experience I had on Southwest. Still better than most, but the seating was barely tolerable.

The Southwest employees (all two of them) were very nice and cheerful despite the fact the line to self-check a bag (simply drop it off) was hundreds of people long. Thank God I arrived early to the airport because I stood in this line for at least an hour. Once on the flight that had been delayed by an hour, we had no Wi-Fi and thus no entertainment. Finally, I hope the investor strong arm tactics against Southwest pay off in a short-term windfall to your C-Suite because the rest of you are screwed. I have been a faithful Southwest customer for 15 years due to everything you just got rid of. I'm flying to Idaho and Washington in October, both places I used to simply book with Southwest without a second thought now with Frontier (Washington) and United (Idaho) because they offer everything the "new" Southwest does but cheaper and at better times, destinations, etc. This really makes me sad...

It was okay. The plane was delayed from earlier in the day, but they kept updating the departure time, sometimes later, sometimes earlier. That was stressful. Once we finally got on and took off, it was fine. I was supposed to have a connection in Chicago to Los Angeles, and the time for so late I was rebooked to arrive in LA 3 hours late. The departure time to Chicago later became early enough to have taken my original connection and arrive earlier but that wasn't an option.

It was one and half hour late... Not sure if any other experience matters.

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

For my birthday trip this was my second time ever flying, this trip was the best.

Delayed and took off even later than the scheduled delay time

For a 69 year old with health problems I had the worse experience, no wheelchair when I entered a lady told me to sit and wait while a gentleman told me I had to walk to the Delta station, which I did. I had a carry on and a bag, and I was traveling with my service dog, which was on his carrier and the lady charged me for my carry on luggage, beside all the waiting cause of the delay, I had to walk to get my luggage cause no wheelchair showed up, I am so disappointed. I will get in touch with the company. I got home at 3:00 am, not good for my health situation.

Only issue was with seating. The economy fare we purchased did say there was no guarantee the three people in our party would be seated together, and we were not. At the gate, the agent told us more specifically, the fare we purchased meant we would be seated in middle seats only. This should just be made more obvious.

Great experience on Delta. Staff from baggage check to flight attendants were very courteous and professional. My only issue was a personal preference for pretzels instead of the chips and cookies that were offered.

There was no problems, just a little uncomfortable with seats that do not lay back a little

Always good but we must do something about people in rows ahead of you that don't put their seats back up when they are suppose to. And It's rough to not be able to even lean over to get something out of my purse.

Flight was delayed, 30+ bags had to be gate checked. Crew were very friendly!

Everything was good until we were boarding our connection flight in Atlanta, we were told to gate check our carry-on, but when we got inside the plane, there was plenty of room in the overhead.

Did not know my son and I had different seating arrangements. He was fine, but it was disappointing.

Flight was canceled, and no effort was made to help with rebooking, no hotel vouchers, no car transportation and minimal food voucher and most places for food were closed by the time the voucher was given. Waited for 3 hours for bags. Simply the worst travel experience I have ever had

Was on time until within 1 hour of flight-how does that happen? Staff very friendly.

the delay for 3 hours was understandable due to weather conditions but the flight should’ve provided some on flight compensations or at least provide more food.

Weather delay in Chicago?. No sense of urgency to make connection in Chicago for our connecting flight that wasn't delayed. Connection was missed.

Our flight was understandably diverted to a small regional airport in Laramie, Wyoming due to weather conditions, which I fully recognize and appreciate. However, the low rating stems from the experience that followed: passengers remained on board for over an hour without the option to deplane and stretch, despite the aircraft being stationary. Although the pilot opened the cabin door, only he was permitted to exit. Meanwhile, passengers grew increasingly uncomfortable as warm summer air entered the cabin through the open door, and being in the second row meant we were impacted immediately. While the flight attendants made efforts to keep everyone at ease, I believe allowing passengers to deplane briefly, given the extended delay, would have significantly improved the overall experience.

I never flew. Flight was canceled. DIA worst airport in the country. Avoid at all costs.

I learned that seating towards the end of plane that a line forms for the restroom and people use your chair as a hand railing, bumping your seat consistently. I was seated in the aisle. I think that next time if I am towards the back row I would want to sit in the middle or window seat.

The best airline I have ever travel , really good customer service, attention and service !!

United could have one single once of customer service. No human United employee would help me with the invalid mileage plus number, they said I had to speak with the computer.

United sent me a mileage plus number last year but that number is invalid so I can’t use it to check into flights or collect mileage. There is human to speak about the problem, only computers who keep asking me if I am using the correct email. It’s so frustrating and I cannot resolve it.

It was delayed instead of departing at 9:20pm, we departed at 11pm… putting us in Columbus after 2am! It was awful. Had I known about the delay, I could have spent some time in the United Lounge… I was starving because I started my journey in Budapest… so I was exhausted and hungry. Plus I had to make new arrangements to be picked up at the airport in Columbus, instead of midnight it was 2:30 am after getting luggage and out of airport. Not feasible. I would have just stayed in Chicago for the night and gotten a morning flight.

Very poor delay in dfw was really bad n long

Our flight was 1.5 hours delayed. There was no weather for the inbound flight, so I don't understand why. This meant a VERY late arrival and only a quick nap before my morning flight.

Because of rescheduling, they had to put me on a flight that didn't go through Dallas

It was very difficult to stretch my knee out and I am very short. I also had a torn tendon in my knee which made it extra uncomfortable anyways. My husband is 6'2" and I can't imagine him flying in that plane.

3 hour weather delay followed by 1 hour (and counting) maintenance delay. UGH!

Couldn’t get the door on the plane to close leading to a nearly 2 hour delay. But, hey at least they didn’t cancel the flight.

Flight was cancelled 3 hrs AFTER etd. Thetefore Missed connection from JFK to New Zealand . No accommodation provided… This cost ne aporox 1000 USD in extra expenses and turned whst should have been a 24 hr trip ftom Boston - New Zealand into a VERY expensive , late 70+ hr nightmare … Complete nonsense!!!

After we'd boarded , they canceled the flight. The crew didn't even know , we just all received text messages. Then after they deplaned us , AA was just like "too bad, go F your self, we sure ain't gonna help you"

The plane was broken so we had to change planes.

The flight got delayed 2.5 hrs due to a maintenance issue that cause a domino effect. American should have spare planes for when something like this happens.

The flight was 3.5 hrs delayed. I was not notified prior to arriving to the airport via spirit app. or via boarding pass that I already had loaded on my phone. The agent that i saw at the counter didn’t mention anything about the delay either. I only saw the update after logging in to my email account.

The flight and boarding process was smooth. Wifi was unavailable and I prepaid for it. Have requested a refund

Had a issue with catching flight due to airline, was unable to board flight

Spirit is a very uncomfortable travel experience. It’s cheap but you are squeezed into the seats like canned meat.

Not great. Seats uncomfortable. Crew a little rude. Amenities like wifi and drinks way too expensive.

Late departure by 1:45min. No explanation why. During boarding inconsistent policing of their baggage rules. Before takeoff and lamdimg strange obsession with window shade and armrest positions. Don't know why they care. 15 min tarmac delay on arrival, they blamed airport congestion but we were the o lh flight waiting, it was clear it was due to poor staff planning (only one ground crew to receive airplanes and multiple arrivals) Got there but was rrally lame the whole trip.

The seat belt was lengthy enough that I did not need an extender. Courteous and helpful flight attendants.

We sat on the tarmac for an hour waiting for a gate to deplane.

Friendly employees, good seat, on time, Great flight. Pilot and attendants greeted passengers as we deplaned. However, I could not ever understand what the flight attendant was saying on the mic. It was too fast, and too loud.

Everything was fine, but there was no food or entertainment, so I didn’t know how to rate that.

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