$116+ Cheap flights from Louisville (SDF) to Caribbean
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/8. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — SJU
Sep 30 — Oct 71
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Louisville to Caribbean with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Louisville to Caribbean
Cheapest
Best
Last-minute
One-way
Cheapest flights from Louisville to CaribbeanExplore the most affordable flight options available from Louisville to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 31, 2026.
Explore the most affordable flight options available from Louisville to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 31, 2026.
This American Airlines deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/187:27 pm -
2 stops15h 33m
Sat 9/263:41 pm -
1 stop7h 41m
Deal found 8/26![American Airlines logo]()
$232
This American Airlines deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/248:39 am -
1 stop6h 22m
Sat 10/317:30 am -
2 stops12h 06m
Deal found 8/26![American Airlines logo]()
$237
This United Airlines deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/1410:37 am -
1 stop9h 23m
Fri 11/208:05 am -
1 stop7h 42m
Deal found 8/27![United Airlines logo]()
$263
This American Airlines deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/177:27 pm -
2 stops15h 33m
Sun 9/206:00 am -
2 stops10h 04m
Deal found 8/26![American Airlines logo]()
$294
This American Airlines deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/85:42 pm -
2 stops16h 02m
Tue 12/158:30 am -
1 stop14h 33m
Deal found 8/26![American Airlines logo]()
$302
This American Airlines deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/96:00 am -
2 stops14h 38m
Tue 12/158:30 am -
1 stop14h 33m
Deal found 8/26![American Airlines logo]()
$307
This United Airlines deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/17:00 am -
2 stops14h 22m
Mon 11/28:25 am -
1 stop9h 37m
Deal found 8/27![United Airlines logo]()
$317
This Kiwi.com deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/159:09 pm -
1 stop26h 48m
Mon 10/197:00 am -
1 stop11h 45m
Deal found 8/29![Multiple Airlines logo]()
$318
This United Airlines deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/88:55 am -
2 stops12h 27m
Mon 12/148:05 am -
2 stops11h 07m
Deal found 8/26![United Airlines logo]()
$322
This American Airlines deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/188:18 pm -
2 stops16h 40m
Sun 10/253:46 pm -
2 stops20h 22m
Deal found 8/26![American Airlines logo]()
$338
This Kiwi.com deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1910:56 am -
2 stops14h 56m
Fri 9/256:42 pm -
1 stop16h 21m
Deal found 8/28![Multiple Airlines logo]()
$341
This Southwest deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/25:10 pm -
1 stop6h 55m
Mon 10/55:35 pm -
1 stop6h 40m
Deal found 8/27![Southwest logo]()
$350
Best flights from Louisville to CaribbeanDiscover carefully curated flight deals from Louisville to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 31, 2026.
Discover carefully curated flight deals from Louisville to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 31, 2026.
This Southwest deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/25:10 pm -
1 stop6h 55m
Mon 10/55:35 pm -
1 stop6h 40m
Deal found 8/27![Southwest logo]()
$350
This United Airlines deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/110:45 am -
1 stop9h 15m
Tue 12/88:05 am -
2 stops11h 07m
Deal found 8/30![United Airlines logo]()
$356
This American Airlines deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/258:18 pm -
1 stop16h 23m
Sat 10/313:58 pm -
2 stops19h 39m
Deal found 8/31![American Airlines logo]()
$398
This Delta deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/256:00 am -
1 stop6h 40m
Sun 11/11:55 pm -
1 stop7h 43m
Deal found 8/27![Delta logo]()
$479
This United deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/216:15 am -
2 stops27h 59m
Sun 10/2512:07 pm -
1 stop7h 23m
Deal found 8/27![Multiple Airlines logo]()
$597
This United Airlines deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/2210:15 am -
1 stop9h 45m
Thu 1/288:25 am -
1 stop9h 07m
Deal found 8/29![United Airlines logo]()
$356
This Southwest deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/273:55 pm -
1 stop7h 15m
Sat 10/315:45 am -
2 stops10h 50m
Deal found 8/28![Southwest logo]()
$356
This American Airlines deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/188:18 pm -
2 stops16h 40m
Sun 10/253:46 pm -
2 stops20h 22m
Deal found 8/29![American Airlines logo]()
$400
This United Airlines deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/159:45 am -
1 stop10h 53m
Tue 9/221:25 pm -
1 stop9h 34m
Deal found 8/26![United Airlines logo]()
$364
This Southwest deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/246:05 pm -
1 stop5h 50m
Sun 11/86:35 am -
1 stop11h 25m
Deal found 8/27![Southwest logo]()
$364
This American Airlines deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/69:48 am -
1 stop10h 25m
Wed 1/1310:32 am -
2 stops12h 17m
Deal found 8/30![American Airlines logo]()
$411
This Southwest deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/198:20 am -
2 stops9h 50m
Fri 9/2511:35 am -
2 stops9h 00m
Deal found 8/28![Southwest logo]()
$421
This Delta deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/65:38 pm -
2 stops18h 52m
Fri 10/234:42 pm -
1 stop6h 17m
Deal found 8/26![Delta logo]()
$523
This American Airlines deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/195:04 am -
1 stop7h 37m
Fri 10/233:46 pm -
2 stops19h 31m
Deal found 8/28![American Airlines logo]()
$440
This United Airlines deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1211:00 am -
2 stops12h 50m
Sun 10/113:56 pm -
1 stop8h 03m
Deal found 8/26![United Airlines logo]()
$454
This Southwest deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/142:00 pm -
1 stop7h 00m
Sat 1/236:55 am -
2 stops9h 05m
Deal found 8/28![Southwest logo]()
$426
This American Airlines deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/278:11 pm -
2 stops16h 40m
Fri 10/21:41 pm -
2 stops21h 02m
Deal found 8/30![American Airlines logo]()
$440
This Delta deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/208:05 am -
1 stop5h 49m
Tue 10/271:15 pm -
1 stop10h 44m
Deal found 8/26![Delta logo]()
$546
This United Airlines deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/126:00 am -
1 stop8h 14m
Thu 11/192:54 pm -
1 stop7h 36m
Deal found 8/29![United Airlines logo]()
$472
This American Airlines deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/158:18 pm -
2 stops19h 44m
Thu 10/222:19 pm -
1 stop7h 48m
Deal found 8/31![American Airlines logo]()
$450
This Delta deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/297:05 am -
1 stop5h 35m
Tue 10/62:05 pm -
1 stop7h 28m
Deal found 8/30![Delta logo]()
$565
This American Airlines deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/196:48 pm -
2 stops18h 45m
Wed 11/255:59 pm -
2 stops16h 29m
Deal found 8/26![American Airlines logo]()
$450
This Southwest deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/263:55 pm -
2 stops21h 30m
Sat 10/32:45 pm -
1 stop6h 10m
Deal found 8/28![Southwest logo]()
$521
This Delta deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/27:05 am -
1 stop6h 48m
Sun 10/43:18 pm -
1 stop8h 41m
Deal found 8/26![Delta logo]()
$606
This United Airlines deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/315:10 am -
2 stops10h 50m
Sat 11/72:55 pm -
1 stop7h 35m
Deal found 8/28![United Airlines logo]()
$579
This American Airlines deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/125:00 am -
2 stops9h 52m
Thu 11/1911:02 am -
2 stops12h 12m
Deal found 8/29![American Airlines logo]()
$482
This Southwest deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/197:50 am -
1 stop6h 10m
Sun 10/252:45 pm -
1 stop9h 30m
Deal found 8/29![Southwest logo]()
$550
This Delta deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/287:05 am -
1 stop6h 35m
Wed 11/44:05 pm -
1 stop7h 42m
Deal found 8/30![Delta logo]()
$613
This American Airlines deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/246:00 am -
2 stops8h 13m
Sat 1/304:16 pm -
2 stops18h 12m
Deal found 8/29![American Airlines logo]()
$483
This United Airlines deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/265:10 am -
1 stop8h 38m
Fri 10/302:20 pm -
1 stop8h 10m
Deal found 8/29![United Airlines logo]()
$592
Last-minute flights from Louisville to CaribbeanDiscover last-minute flight deals from Louisville to Caribbean. Data last updated August 31, 2026 and is based on user searches.
Discover last-minute flight deals from Louisville to Caribbean. Data last updated August 31, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/22:56 pm -
2 stops33h 38m
Sat 9/55:37 pm -
1 stop16h 55m
Deal found 8/26![Multiple Airlines logo]()
$408
This United Airlines deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/159:45 am -
1 stop10h 53m
Tue 9/221:25 pm -
1 stop9h 34m
Deal found 8/26![United Airlines logo]()
$364
This American Airlines deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/177:27 pm -
2 stops15h 33m
Sun 9/206:00 am -
2 stops10h 04m
Deal found 8/26![American Airlines logo]()
$294
This American Airlines deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/177:27 pm -
2 stops15h 33m
Tue 9/226:00 am -
2 stops11h 06m
Deal found 8/30![American Airlines logo]()
$434
This American Airlines deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/187:27 pm -
2 stops15h 33m
Sat 9/263:41 pm -
1 stop7h 41m
Deal found 8/26![American Airlines logo]()
$232
This Kiwi.com deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1910:56 am -
2 stops14h 56m
Fri 9/256:42 pm -
1 stop16h 21m
Deal found 8/28![Multiple Airlines logo]()
$341
This Southwest deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/191:15 pm -
1 stop6h 10m
Fri 9/255:00 am -
1 stop6h 10m
Deal found 8/28![Southwest logo]()
$396
This American Airlines deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/247:27 pm -
2 stops15h 33m
Sat 10/36:00 am -
2 stops12h 50m
Deal found 8/27![American Airlines logo]()
$359
This American Airlines deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/257:27 pm -
2 stops15h 33m
Wed 9/302:58 pm -
2 stops8h 24m
Deal found 8/29![American Airlines logo]()
$356
This Southwest deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/2511:50 am -
1 stop11h 05m
Wed 9/306:00 am -
1 stop6h 40m
Deal found 8/27![Southwest logo]()
$411
This American Airlines deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/267:27 pm -
2 stops17h 24m
Sat 10/31:41 pm -
2 stops21h 02m
Deal found 8/28![American Airlines logo]()
$400
This American Airlines deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/278:11 pm -
2 stops16h 40m
Fri 10/21:41 pm -
2 stops21h 02m
Deal found 8/30![American Airlines logo]()
$440
One-way flights from Louisville to CaribbeanSearch for one-way flight options from Louisville to Caribbean. Find affordable one-way fares based on user searches. Data last updated August 31, 2026.
Search for one-way flight options from Louisville to Caribbean. Find affordable one-way fares based on user searches. Data last updated August 31, 2026.
This American Airlines deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/86:00 am -
1 stop10h 05m
Deal found 8/27![American Airlines logo]()
$116
This American Airlines deal was found by Cheapflights users on 8/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/265:59 pm -
2 stops18h 52m
Deal found 8/26![American Airlines logo]()
$122
This KAYAK deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/206:15 am -
1 stop5h 54m
Deal found 8/27![American Airlines logo]()
$142
This KAYAK deal was found by Cheapflights users on 8/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/217:15 am -
2 stops14h 54m
Deal found 8/27![American Airlines logo]()
$147
This Delta deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/87:00 am -
1 stop8h 15m
Deal found 8/28![Delta logo]()
$178
This Kiwi.com deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2410:55 am -
2 stops22h 30m
Deal found 8/31![Breeze Airways logo]()
$203
This American Airlines deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/276:14 pm -
2 stops16h 03m
Deal found 8/31![American Airlines logo]()
$212
This United Airlines deal was found by Cheapflights users on 8/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/217:00 am -
1 stop6h 45m
Deal found 8/28![United Airlines logo]()
$237
This Kiwi.com deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2410:55 am -
3 stops22h 30m
Deal found 8/31![Multiple Airlines logo]()
$240
This Kiwi.com deal was found by Cheapflights users on 8/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/57:21 pm -
2 stops41h 27m
Deal found 8/29![Multiple Airlines logo]()
$242
This American Airlines deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/248:19 pm -
1 stop15h 01m
Deal found 8/31![American Airlines logo]()
$243
This American Airlines deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/206:00 am -
1 stop7h 23m
Deal found 8/30![American Airlines logo]()
$262
Find flight deals from Louisville to Caribbean
Keep the following information in mind while searching for Louisville to Caribbean flight deals. Data was last updated August 31, 2026.
Round-trip from | $232 (American Airlines) |
|---|---|
One-way from | $116 (American Airlines) |
Popular in | December |
Cheapest in | February |
Average price | $390 |
Cheapflights Fare Finder
Customize your flight search to find flights from Louisville to Caribbean that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated August 31, 2026.
Use the filters below to find and compare flights from Louisville to Caribbean that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
LouisvilleSan Juan
SDF Louisville Intl - SJU San Juan Luis Munoz Marin Intl
SDFSJU
Louisville Intl
Fri 10/2
5:10 pm-12:05 am
1 stop6h 55m
San Juan Luis Munoz Marin Intl
Mon 10/5
5:35 pm-12:15 am
1 stop6h 40m
$350
LouisvilleSan Juan
SDF Louisville Intl - SJU San Juan Luis Munoz Marin Intl
SDFSJU
Louisville Intl
Tue 12/1
10:45 am-9:00 pm
1 stop9h 15m
San Juan Luis Munoz Marin Intl
Tue 12/8
8:05 am-6:12 pm
2 stops11h 07m
$356
LouisvilleSan Juan
SDF Louisville Intl - SJU San Juan Luis Munoz Marin Intl
SDFSJU
Louisville Intl
Fri 1/22
10:15 am-9:00 pm
1 stop9h 45m
San Juan Luis Munoz Marin Intl
Thu 1/28
8:25 am-4:32 pm
1 stop9h 07m
$356
LouisvilleSan Juan
SDF Louisville Intl - SJU San Juan Luis Munoz Marin Intl
SDFSJU
Louisville Intl
Tue 10/27
3:55 pm-11:10 pm
1 stop7h 15m
San Juan Luis Munoz Marin Intl
Sat 10/31
5:45 am-4:35 pm
2 stops10h 50m
$356
LouisvilleSan Juan
SDF Louisville Intl - SJU San Juan Luis Munoz Marin Intl
SDFSJU
Louisville Intl
Tue 9/15
9:45 am-8:38 pm
1 stop10h 53m
San Juan Luis Munoz Marin Intl
Tue 9/22
1:25 pm-10:59 pm
1 stop9h 34m
$364
LouisvilleSan Juan
SDF Louisville Intl - SJU San Juan Luis Munoz Marin Intl
SDFSJU
Louisville Intl
Sat 10/24
6:05 pm-11:55 pm
1 stop5h 50m
San Juan Luis Munoz Marin Intl
Sun 11/8
6:35 am-5:00 pm
1 stop11h 25m
$364
LouisvilleSaint Thomas Island
SDF Louisville Intl - STT Saint Thomas Island Cyril E King
SDFSTT
Louisville Intl
Sun 10/25
8:18 pm-12:41 pm
1 stop16h 23m
Saint Thomas Island Cyril E King
Sat 10/31
3:58 pm-11:37 am
2 stops19h 39m
$398
LouisvilleSaint Thomas Island
SDF Louisville Intl - STT Saint Thomas Island Cyril E King
SDFSTT
Louisville Intl
Sun 10/18
8:18 pm-12:58 pm
2 stops16h 40m
Saint Thomas Island Cyril E King
Sun 10/25
3:46 pm-12:08 pm
2 stops20h 22m
$400
LouisvilleSan Juan
SDF Louisville Intl - SJU San Juan Luis Munoz Marin Intl
SDFSJU
Louisville Intl
Wed 1/6
9:48 am-9:13 pm
1 stop10h 25m
San Juan Luis Munoz Marin Intl
Wed 1/13
10:32 am-9:49 pm
2 stops12h 17m
$411
LouisvilleSan Juan
SDF Louisville Intl - SJU San Juan Luis Munoz Marin Intl
SDFSJU
Louisville Intl
Sat 9/19
8:20 am-6:10 pm
2 stops9h 50m
San Juan Luis Munoz Marin Intl
Fri 9/25
11:35 am-8:35 pm
2 stops9h 00m
$421
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Louisville to Caribbean
Have a flexible travel schedule? Discover the best time to fly to Caribbean from Louisville with our price prediction graph.
SDF-SJU
SDF-STT
SDF-NAS
SDF-MBJ
SDF-GCM
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Louisville to Caribbean
SDF-0CB
SDF-SJU
SDF-STT
SDF-NAS
SDF-MBJ
What is the cheapest month to book a flight from Louisville to Caribbean?
Currently, January is the cheapest month in which you can book a flight from Louisville to Caribbean (average of $469). Flying from Louisville to Caribbean in June is currently the most expensive (average of $677). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
How far ahead should I book a flight from Louisville to Caribbean?
Booking 71 days in advance of your planned departure date is, on average, the best time to get cheap flights from Louisville to Caribbean. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
Reviews of airlines servicing Caribbean
Get insights into the airlines that provide service to Caribbean. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean. Reviews last updated August 31, 2026.
Get a feel of what it's like to fly with Southwest,Delta, andUnited Airlines from Louisville to Caribbean by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Entertainment
7.5
Overall
8.0
Comfort
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Crew
8.6
Entertainment
7.5
Overall
8.0
Comfort
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Crew
8.6
Entertainment
7.5
Overall
8.0
Comfort
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Crew
8.6
Entertainment
7.5
Overall
8.0
Comfort
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Crew
8.6
Entertainment
7.5
Overall
8.0
Comfort
8.0
Boarding
8.1
Food
7.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Related info for your journey
Find useful and relevant information for your journey from Louisville to Caribbean. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Top countries
Top destinations
Alternative routes for Louisville to Caribbean
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Caribbean by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Louisville to Caribbean by cabin class
Find flights from Louisville to Caribbean, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Louisville and Caribbean flights
Browse other Louisville and Caribbean flight options. Last updated on August 31, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Fly to Caribbean countries
Consider these flights traveling to countries located in Caribbean.
Louisville to Caribbean flights
Consider these flights traveling from Louisville to Caribbean.
Top 4 airlines flying from Louisville to Caribbean
Discover the top 4 airlines that operate flights from Louisville to Caribbean. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated August 31, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$205 | Average$660 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$226 | Average$623 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$259 | Average$566 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$299 | Average$665 | FlexibilityNo cancel fee | On-time63% |