$158+ Cheap flights from Louisville (SDF) to Caribbean Islands
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 7/4. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — SJU
Jun 24 — Jul 11
Round-trip
1 adult, Economy
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Find cheap flights from Louisville to Caribbean Islands 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
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Cheapest flights from Louisville to Caribbean IslandsExplore the most affordable flight options available from Louisville to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 25, 2026.
Explore the most affordable flight options available from Louisville to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 25, 2026.
This Delta deal was found by Cheapflights users on 5/22. 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 7/216:00 am
SDF
- SJU
1 stop5h 46m
Delta
Wed 8/55:49 pm
SJU
- SDF
1 stop6h 35m
Delta
Deal found 5/22![Delta logo]()
$316
This American Airlines deal was found by Cheapflights users on 5/25. 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 9/26:05 am
SDF
- SJU
2 stops12h 29m
American Airlines
Sun 9/67:00 am
SJU
- SDF
1 stop15h 59m
American Airlines
Deal found 5/25![American Airlines logo]()
$321
This American Airlines deal was found by Cheapflights users on 5/25. 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 8/138:12 pm
SDF
- STT
2 stops16h 41m
American Airlines
Mon 8/174:42 pm
STT
- SDF
2 stops17h 48m
American Airlines
Deal found 5/25![American Airlines logo]()
$360
This Delta deal was found by Cheapflights users on 5/21. 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.
Thu 7/3010:00 am
SDF
- SJU
1 stop10h 45m
Delta
Tue 8/42:59 pm
SJU
- SDF
1 stop6h 30m
Delta
Deal found 5/21![Delta logo]()
$363
This United Airlines deal was found by Cheapflights users on 5/22. 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 9/116:00 am
SDF
- SJU
1 stop6h 54m
United Airlines
Fri 9/182:20 pm
SJU
- SDF
1 stop7h 55m
United Airlines
Deal found 5/22![United Airlines logo]()
$366
This Southwest deal was found by Cheapflights users on 5/21. 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 6/293:00 pm
SDF
- SJU
1 stop9h 25m
Southwest
Thu 7/910:20 pm
SJU
- SDF
1 stop11h 50m
Southwest
Deal found 5/21![Southwest logo]()
$368
This Delta deal was found by Cheapflights users on 5/25. 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 9/27:05 am
SDF
- MBJ
1 stop5h 39m
Delta
Sat 9/54:59 pm
MBJ
- SDF
1 stop6h 10m
Delta
Deal found 5/25![Delta logo]()
$372
This United Airlines deal was found by Cheapflights users on 5/21. 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 7/410:05 am
SDF
- MBJ
1 stop6h 05m
United Airlines
Thu 7/92:40 pm
MBJ
- SDF
2 stops17h 47m
United Airlines
Deal found 5/21![United Airlines logo]()
$377
This United Airlines deal was found by Cheapflights users on 5/24. 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 5/286:15 am
SDF
- MBJ
1 stop8h 15m
United Airlines
Sat 5/304:33 pm
MBJ
- SDF
1 stop18h 21m
United Airlines
Deal found 5/24![United Airlines logo]()
$380
This American Airlines deal was found by Cheapflights users on 5/25. 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
SDF
- SJU
2 stops15h 33m
American Airlines
Wed 9/306:27 am
SJU
- SDF
2 stops16h 29m
American Airlines
Deal found 5/25![American Airlines logo]()
$381
This American Airlines deal was found by Cheapflights users on 5/25. 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 9/26:28 am
SDF
- MBJ
1 stop7h 44m
American Airlines
Sat 9/55:08 pm
MBJ
- SDF
2 stops19h 01m
American Airlines
Deal found 5/25![American Airlines logo]()
$382
This American Airlines deal was found by Cheapflights users on 5/25. 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 12/91:02 pm
SDF
- SJU
2 stops9h 51m
American Airlines
Mon 12/142:05 pm
SJU
- SDF
2 stops9h 51m
American Airlines
Deal found 5/25![American Airlines logo]()
$386
Best flights from Louisville to Caribbean IslandsDiscover carefully curated flight deals from Louisville to Caribbean Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 25, 2026.
Discover carefully curated flight deals from Louisville to Caribbean Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 25, 2026.
This United Airlines deal was found by Cheapflights users on 5/22. 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 8/205:15 am
SDF
- SJU
1 stop9h 29m
United Airlines
Wed 8/262:20 pm
SJU
- SDF
1 stop7h 55m
United Airlines
Deal found 5/22![United Airlines logo]()
$316
This Delta deal was found by Cheapflights users on 5/25. 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 9/27:05 am
SDF
- MBJ
1 stop5h 39m
Delta
Sat 9/54:59 pm
MBJ
- SDF
1 stop6h 10m
Delta
Deal found 5/25![Delta logo]()
$372
This American Airlines deal was found by Cheapflights users on 5/25. 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 9/26:28 am
SDF
- MBJ
1 stop7h 44m
American Airlines
Sat 9/55:08 pm
MBJ
- SDF
2 stops19h 01m
American Airlines
Deal found 5/25![American Airlines logo]()
$382
This Southwest deal was found by Cheapflights users on 5/20. 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 7/35:30 pm
SDF
- SJU
1 stop6h 35m
Southwest
Thu 7/910:20 pm
SJU
- SDF
1 stop11h 50m
Southwest
Deal found 5/20![Southwest logo]()
$411
This Breeze Airways deal was found by Cheapflights users on 5/23. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/49:09 pm
SDF
- NAS
1 stop11h 21m
Breeze Airways
Thu 10/810:15 am
NAS
- SDF
1 stop10h 14m
Breeze Airways
Deal found 5/23![Breeze Airways logo]()
$489
This Copa Airlines deal was found by Cheapflights users on 5/20. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2210:05 am
SDF
- PUJ
2 stops16h 07m
Copa Airlines
Thu 8/271:59 pm
PUJ
- SDF
2 stops20h 19m
Copa Airlines
Deal found 5/20![Copa Airlines logo]()
$673
This United Airlines deal was found by Cheapflights users on 5/21. 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 7/410:05 am
SDF
- MBJ
1 stop6h 05m
United Airlines
Thu 7/92:40 pm
MBJ
- SDF
2 stops17h 47m
United Airlines
Deal found 5/21![United Airlines logo]()
$377
This Delta deal was found by Cheapflights users on 5/24. 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.
Thu 6/251:02 pm
SDF
- SJU
1 stop9h 25m
Delta
Sat 7/45:56 pm
SJU
- SDF
1 stop6h 25m
Delta
Deal found 5/24![Delta logo]()
$418
This Southwest deal was found by Cheapflights users on 5/21. 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 6/136:55 pm
SDF
- SJU
1 stop6h 20m
Southwest
Tue 6/166:30 am
SJU
- SDF
1 stop10h 15m
Southwest
Deal found 5/21![Southwest logo]()
$453
This American Airlines deal was found by Cheapflights users on 5/23. 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 8/138:40 am
SDF
- STT
1 stop6h 21m
American Airlines
Mon 8/174:42 pm
STT
- SDF
2 stops19h 25m
American Airlines
Deal found 5/23![American Airlines logo]()
$477
This United Airlines deal was found by Cheapflights users on 5/22. 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.
Wed 7/81:48 pm
SDF
- SJU
1 stop7h 36m
United Airlines
Mon 7/132:05 am
SJU
- SDF
1 stop9h 49m
United Airlines
Deal found 5/22![United Airlines logo]()
$444
This Delta deal was found by Cheapflights users on 5/24. 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.
Thu 6/251:02 pm
SDF
- SJU
1 stop9h 25m
Delta
Fri 7/107:30 am
SJU
- SDF
1 stop10h 19m
Delta
Deal found 5/24![Delta logo]()
$465
This American Airlines deal was found by Cheapflights users on 5/24. 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 6/233:22 pm
SDF
- STT
2 stops19h 50m
American Airlines
Wed 7/14:49 pm
STT
- SDF
2 stops17h 17m
American Airlines
Deal found 5/24![American Airlines logo]()
$477
This Southwest deal was found by Cheapflights users on 5/23. 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 8/132:15 pm
SDF
- SJU
2 stops8h 50m
Southwest
Sun 8/166:00 am
SJU
- SDF
2 stops8h 10m
Southwest
Deal found 5/23![Southwest logo]()
$486
This Delta deal was found by Cheapflights users on 5/23. 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.
Sat 8/16:00 am
SDF
- STT
1 stop8h 23m
Delta
Sat 8/83:33 pm
STT
- SDF
1 stop6h 32m
Delta
Deal found 5/23![Delta logo]()
$486
This Southwest deal was found by Cheapflights users on 5/20. 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 6/1910:45 am
SDF
- SJU
1 stop13h 30m
Southwest
Fri 6/265:15 pm
SJU
- SDF
1 stop7h 10m
Southwest
Deal found 5/20![Southwest logo]()
$496
This American Airlines deal was found by Cheapflights users on 5/21. 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 7/76:00 am
SDF
- AUA
1 stop10h 59m
American Airlines
Mon 7/135:59 pm
AUA
- SDF
2 stops19h 32m
American Airlines
Deal found 5/21![American Airlines logo]()
$498
This United Airlines deal was found by Cheapflights users on 5/25. 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 6/1310:00 am
SDF
- MBJ
1 stop6h 10m
United Airlines
Sat 6/204:33 pm
MBJ
- SDF
1 stop18h 21m
United Airlines
Deal found 5/25![United Airlines logo]()
$501
This Delta deal was found by Cheapflights users on 5/25. 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 9/296:00 am
SDF
- PLS
1 stop6h 45m
Delta
Tue 10/62:05 pm
PLS
- SDF
1 stop9h 57m
Delta
Deal found 5/25![Delta logo]()
$503
This American Airlines deal was found by Cheapflights users on 5/23. 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 10/216:45 am
SDF
- PLS
1 stop7h 05m
American Airlines
Wed 10/281:35 pm
PLS
- SDF
1 stop8h 03m
American Airlines
Deal found 5/23![American Airlines logo]()
$508
This Southwest deal was found by Cheapflights users on 5/25. 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 7/316:05 pm
SDF
- SJU
2 stops7h 20m
Southwest
Mon 8/37:00 am
SJU
- SDF
2 stops9h 25m
Southwest
Deal found 5/25![Southwest logo]()
$511
This United Airlines deal was found by Cheapflights users on 5/23. 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 6/226:15 am
SDF
- MBJ
1 stop8h 15m
United Airlines
Mon 6/292:40 pm
MBJ
- SDF
2 stops17h 42m
United Airlines
Deal found 5/23![United Airlines logo]()
$526
This Delta deal was found by Cheapflights users on 5/25. 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.
Thu 5/288:10 am
SDF
- SJU
1 stop8h 23m
Delta
Tue 6/21:14 pm
SJU
- SDF
1 stop11h 11m
Delta
Deal found 5/25![Delta logo]()
$504
This Southwest deal was found by Cheapflights users on 5/21. 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 7/233:35 pm
SDF
- SJU
2 stops9h 45m
Southwest
Thu 7/3010:20 pm
SJU
- SDF
1 stop11h 50m
Southwest
Deal found 5/21![Southwest logo]()
$511
This American Airlines deal was found by Cheapflights users on 5/25. 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 7/198:19 pm
SDF
- STT
2 stops19h 41m
American Airlines
Sat 8/15:01 pm
STT
- SDF
1 stop7h 33m
American Airlines
Deal found 5/25![American Airlines logo]()
$517
This Copa Airlines deal was found by Cheapflights users on 5/25. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/189:00 am
SDF
- PUJ
2 stops27h 23m
Copa Airlines
Sat 7/2512:51 pm
PUJ
- SDF
2 stops21h 32m
Copa Airlines
Deal found 5/25![Copa Airlines logo]()
$766
This United Airlines deal was found by Cheapflights users on 5/23. 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 11/75:35 am
SDF
- PLS
1 stop8h 20m
United Airlines
Fri 11/132:30 pm
PLS
- SDF
1 stop8h 45m
United Airlines
Deal found 5/23![United Airlines logo]()
$548
This Delta deal was found by Cheapflights users on 5/25. 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 5/297:08 am
SDF
- SJU
1 stop6h 30m
Delta
Tue 6/21:14 pm
SJU
- SDF
1 stop11h 11m
Delta
Deal found 5/25![Delta logo]()
$504
This American Airlines deal was found by Cheapflights users on 5/24. 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 7/36:25 pm
SDF
- AUA
1 stop17h 18m
American Airlines
Sat 7/112:09 pm
AUA
- SDF
1 stop8h 54m
American Airlines
Deal found 5/24![American Airlines logo]()
$523
This United Airlines deal was found by Cheapflights users on 5/21. 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 6/297:55 pm
SDF
- NAS
2 stops15h 33m
United Airlines
Fri 7/33:59 pm
NAS
- SDF
1 stop8h 00m
United Airlines
Deal found 5/21![United Airlines logo]()
$556
Last-minute flights from Louisville to Caribbean IslandsDiscover last-minute flight deals from Louisville to Caribbean Islands. Data last updated May 25, 2026 and is based on user searches.
Discover last-minute flight deals from Louisville to Caribbean Islands. Data last updated May 25, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 5/22. 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 5/238:08 pm
SDF
- MBJ
2 stops16h 37m
American Airlines
Fri 5/295:17 pm
MBJ
- SDF
2 stops17h 32m
American Airlines
Deal found 5/22![American Airlines logo]()
$427
This United Airlines deal was found by Cheapflights users on 5/24. 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 5/286:15 am
SDF
- MBJ
1 stop8h 15m
United Airlines
Sat 5/304:33 pm
MBJ
- SDF
2 stops15h 54m
United Airlines
Deal found 5/24![United Airlines logo]()
$377
This United Airlines deal was found by Cheapflights users on 5/20. 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 5/2810:00 am
SDF
- MBJ
1 stop6h 10m
United Airlines
Sun 5/314:33 pm
MBJ
- SDF
2 stops15h 53m
United Airlines
Deal found 5/20![United Airlines logo]()
$388
This American Airlines deal was found by Cheapflights users on 5/21. 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 5/307:07 pm
SDF
- SJU
1 stop17h 50m
American Airlines
Fri 6/56:21 am
SJU
- SDF
1 stop16h 47m
American Airlines
Deal found 5/21![American Airlines logo]()
$416
This United Airlines deal was found by Cheapflights users on 5/23. 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 6/121:48 pm
SDF
- SJU
1 stop7h 36m
United Airlines
Tue 6/167:20 am
SJU
- SDF
1 stop7h 17m
United Airlines
Deal found 5/23![United Airlines logo]()
$405
This American Airlines deal was found by Cheapflights users on 5/22. 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 6/233:22 pm
SDF
- STT
2 stops19h 50m
American Airlines
Wed 7/14:49 pm
STT
- SDF
2 stops17h 17m
American Airlines
Deal found 5/22![American Airlines logo]()
$431
This Delta deal was found by Cheapflights users on 5/24. 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.
Thu 6/251:02 pm
SDF
- SJU
1 stop9h 25m
Delta
Sat 7/45:56 pm
SJU
- SDF
1 stop6h 25m
Delta
Deal found 5/24![Delta logo]()
$418
This Southwest deal was found by Cheapflights users on 5/22. 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 6/275:15 pm
SDF
- SJU
1 stop6h 25m
Southwest
Wed 7/16:30 am
SJU
- SDF
1 stop10h 15m
Southwest
Deal found 5/22![Southwest logo]()
$363
This American Airlines deal was found by Cheapflights users on 5/22. 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 6/287:43 am
SDF
- SJU
1 stop15h 17m
American Airlines
Wed 7/16:21 am
SJU
- SDF
1 stop16h 42m
American Airlines
Deal found 5/22![American Airlines logo]()
$421
This Southwest deal was found by Cheapflights users on 5/21. 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 6/293:00 pm
SDF
- SJU
1 stop9h 25m
Southwest
Thu 7/910:20 pm
SJU
- SDF
1 stop11h 50m
Southwest
Deal found 5/21![Southwest logo]()
$368
This American Airlines deal was found by Cheapflights users on 5/24. 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 6/2912:00 pm
SDF
- SJU
2 stops11h 59m
American Airlines
Sat 7/117:25 am
SJU
- SDF
2 stops15h 38m
American Airlines
Deal found 5/24![American Airlines logo]()
$406
This American Airlines deal was found by Cheapflights users on 5/24. 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 6/296:51 am
SDF
- SJU
1 stop17h 08m
American Airlines
Fri 7/1010:35 am
SJU
- SDF
2 stops12h 28m
American Airlines
Deal found 5/24![American Airlines logo]()
$413
One-way flights from Louisville to Caribbean IslandsSearch for one-way flight options from Louisville to Caribbean Islands. Find affordable one-way fares based on user searches. Data last updated May 25, 2026.
Search for one-way flight options from Louisville to Caribbean Islands. Find affordable one-way fares based on user searches. Data last updated May 25, 2026.
This United Airlines deal was found by Cheapflights users on 5/21. 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 8/15:50 pm
SDF
- SJU
2 stops11h 39m
United Airlines
Deal found 5/21![United Airlines logo]()
$158
This United Airlines deal was found by Cheapflights users on 5/24. 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 7/47:15 am
SDF
- STT
2 stops9h 45m
United Airlines
Deal found 5/24![United Airlines logo]()
$158
This United Airlines deal was found by Cheapflights users on 5/24. 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 5/306:00 am
SDF
- MBJ
2 stops10h 10m
United Airlines
Deal found 5/24![United Airlines logo]()
$162
This United Airlines deal was found by Cheapflights users on 5/23. 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 6/236:00 am
SDF
- MBJ
1 stop10h 10m
United Airlines
Deal found 5/23![United Airlines logo]()
$181
This United Airlines deal was found by Cheapflights users on 5/25. 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 7/311:48 pm
SDF
- SJU
1 stop7h 36m
United Airlines
Deal found 5/25![United Airlines logo]()
$193
This American Airlines deal was found by Cheapflights users on 5/24. 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 6/166:25 pm
SDF
- STT
2 stops19h 22m
American Airlines
Deal found 5/24![American Airlines logo]()
$204
This Delta deal was found by Cheapflights users on 5/21. 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 7/296:00 am
SDF
- SJU
1 stop10h 45m
Delta
Deal found 5/21![Delta logo]()
$205
This American Airlines deal was found by Cheapflights users on 5/25. 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 6/47:43 am
SDF
- SJU
1 stop15h 17m
American Airlines
Deal found 5/25![American Airlines logo]()
$208
This American Airlines deal was found by Cheapflights users on 5/21. 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 7/3012:00 pm
SDF
- SJU
2 stops26h 12m
American Airlines
Deal found 5/21![American Airlines logo]()
$209
This American Airlines deal was found by Cheapflights users on 5/21. 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 7/3112:00 pm
SDF
- SJU
2 stops21h 45m
American Airlines
Deal found 5/21![American Airlines logo]()
$216
This American Airlines deal was found by Cheapflights users on 5/21. 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 7/2912:00 pm
SDF
- SJU
2 stops21h 45m
American Airlines
Deal found 5/21![American Airlines logo]()
$221
This United Airlines deal was found by Cheapflights users on 5/24. 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 6/166:00 am
SDF
- STT
1 stop6h 20m
United Airlines
Deal found 5/24![United Airlines logo]()
$223
Find flight deals from Louisville to Caribbean Islands
Keep the following information in mind while searching for Louisville to Caribbean Islands flight deals. Data was last updated May 25, 2026.
Round-trip from | $316 (Delta) |
|---|---|
One-way from | $158 (United Airlines) |
Popular in | December |
Cheapest in | October |
Average price | $484 |
Cheapflights Fare Finder
Customize your flight search to find flights from Louisville to Caribbean Islands 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 2,558,603 searches. Data last updated May 25, 2026.
Use the filters below to find and compare flights from Louisville to Caribbean Islands that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
LouisvilleSan Juan
SDF - SJU
SDFSJU
Louisville Intl
Thu 8/20
5:15 am-2:44 pm
1 stop9h 29m
San Juan Luis Munoz Marin Intl
Wed 8/26
2:20 pm-10:15 pm
1 stop7h 55m
$316
Quickest round-trip
LouisvilleMontego Bay
SDF - MBJ
SDFMBJ
Louisville Intl
Wed 9/2
7:05 am-11:44 am
1 stop5h 39m
Montego Bay Sangster Intl
Sat 9/5
4:59 pm-12:09 am
1 stop6h 10m
$372
LouisvilleMontego Bay
SDF - MBJ
SDFMBJ
Louisville Intl
Sat 7/4
10:05 am-3:10 pm
1 stop6h 05m
Montego Bay Sangster Intl
Thu 7/9
2:40 pm-9:27 am
2 stops17h 47m
$377
LouisvilleMontego Bay
SDF - MBJ
SDFMBJ
Louisville Intl
Wed 9/2
6:28 am-1:12 pm
1 stop7h 44m
Montego Bay Sangster Intl
Sat 9/5
5:08 pm-1:09 pm
2 stops19h 01m
$382
LouisvilleSan Juan
SDF - SJU
SDFSJU
Louisville Intl
Fri 7/3
5:30 pm-12:05 am
1 stop6h 35m
San Juan Luis Munoz Marin Intl
Thu 7/9
10:20 pm-10:10 am
1 stop11h 50m
$411
LouisvilleSan Juan
SDF - SJU
SDFSJU
Louisville Intl
Thu 6/25
1:02 pm-10:27 pm
1 stop9h 25m
San Juan Luis Munoz Marin Intl
Sat 7/4
5:56 pm-12:21 am
1 stop6h 25m
$418
LouisvilleSan Juan
SDF - SJU
SDFSJU
Louisville Intl
Wed 7/8
1:48 pm-9:24 pm
1 stop7h 36m
San Juan Luis Munoz Marin Intl
Mon 7/13
2:05 am-11:54 am
1 stop9h 49m
$444
LouisvilleSan Juan
SDF - SJU
SDFSJU
Louisville Intl
Sat 6/13
6:55 pm-1:15 am
1 stop6h 20m
San Juan Luis Munoz Marin Intl
Tue 6/16
6:30 am-4:45 pm
1 stop10h 15m
$453
LouisvilleSan Juan
SDF - SJU
SDFSJU
Louisville Intl
Thu 6/25
1:02 pm-10:27 pm
1 stop9h 25m
San Juan Luis Munoz Marin Intl
Fri 7/10
7:30 am-5:49 pm
1 stop10h 19m
$465
LouisvilleSaint Thomas Island
SDF - STT
SDFSTT
Louisville Intl
Thu 8/13
8:40 am-3:01 pm
1 stop6h 21m
Saint Thomas Island Cyril E King
Mon 8/17
4:42 pm-12:07 pm
2 stops19h 25m
$477
Showing 1-10 of 55 resultsSorted by cheapest first
Best time to book a flight from Louisville to Caribbean Islands
Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands from Louisville with our price prediction graph.
SDF-STT
SDF-AUA
SDF-SJU
SDF-MBJ
SDF-SXM
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 Islands
SDF-zzEPX
SDF-STT
SDF-AUA
SDF-SJU
SDF-MBJ
What is the cheapest month to book a flight from Louisville to Caribbean Islands?
Currently, January is the cheapest month in which you can book a flight from Louisville to Caribbean Islands (average of $160). Flying from Louisville to Caribbean Islands in February is currently the most expensive (average of $340). 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 Islands?
The price you pay for your flight from Louisville to Caribbean Islands may vary depending on when you book. For the best chance of a lower fare, look to book 17 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
Reviews of airlines servicing Caribbean Islands
Get insights into the airlines that provide service to Caribbean Islands. 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 Islands. Reviews last updated May 25, 2026.
Get a feel of what it's like to fly with Southwest,Delta, andUnited Airlines from Louisville to Caribbean Islands by reading reviews from past customers. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.6
Food
7.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Food
7.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Food
7.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Food
7.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Crew
8.6
Food
7.0
Entertainment
7.5
Overall
8.0
Boarding
8.1
Comfort
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Related info for your journey
Find useful and relevant information for your journey from Louisville to Caribbean Islands. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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Alternative routes for Louisville to Caribbean Islands
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Caribbean Islands by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Louisville to Caribbean Islands by cabin class
Find flights from Louisville to Caribbean Islands, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Louisville and Caribbean Islands flights
Browse other Louisville and Caribbean Islands flight options. Last updated on May 25, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Louisville to Caribbean Islands flights
Consider these flights traveling from Louisville to Caribbean Islands.
Top 5 airlines flying from Louisville to Caribbean Islands
Discover the top 5 airlines that operate flights from Louisville to Caribbean Islands. 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 2,558,603 searches. Data last updated May 25, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$160 | Average$585 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$176 | Average$488 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$225 | Average$638 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$238 | Average$575 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$259 | Average$522 | FlexibilityNo cancel fee | On-time69% |