$158+ 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 7/28. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — SJU
Jun 29 — Jul 61
Round-trip
1 adult, Economy
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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
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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 May 30, 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 May 30, 2026.
This Delta deal was found by Cheapflights users on 5/26. 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.
Sun 8/237:05 am
SDF
- SJU
1 stop6h 37m
Delta
Sat 8/295:49 pm
SJU
- SDF
1 stop6h 20m
Delta
Deal found 5/26![Delta logo]()
$316
This Southwest deal was found by Cheapflights users on 5/29. 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.
Sun 8/304:05 pm
SDF
- SJU
2 stops8h 25m
Southwest
Thu 9/36:00 am
SJU
- SDF
2 stops9h 30m
Southwest
Deal found 5/29![Southwest logo]()
$321
This American Airlines deal was found by Cheapflights users on 5/27. 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.
Wed 9/26:05 am
SDF
- SJU
2 stops12h 29m
American Airlines
Sun 9/62:33 pm
SJU
- SDF
1 stop8h 26m
American Airlines
Deal found 5/27![American Airlines logo]()
$326
This American Airlines deal was found by Cheapflights users on 5/29. 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.
Tue 9/86:28 am
SDF
- SJU
1 stop16h 47m
American Airlines
Wed 9/232:22 pm
SJU
- SDF
1 stop8h 33m
American Airlines
Deal found 5/29![American Airlines logo]()
$341
This United Airlines deal was found by Cheapflights users on 5/28. 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 7/41:48 pm
SDF
- SJU
1 stop7h 36m
United Airlines
Sat 7/117:20 am
SJU
- SDF
1 stop7h 17m
United Airlines
Deal found 5/28![United Airlines logo]()
$346
This United Airlines deal was found by Cheapflights users on 5/29. 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 7/311:48 pm
SDF
- SJU
1 stop7h 36m
United Airlines
Sun 8/22:05 am
SJU
- SDF
1 stop9h 49m
United Airlines
Deal found 5/29![United Airlines logo]()
$347
This Southwest deal was found by Cheapflights users on 5/29. 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.
Sat 10/311:20 am
SDF
- SJU
2 stops10h 10m
Southwest
Thu 10/85:20 pm
SJU
- SDF
1 stop7h 20m
Southwest
Deal found 5/29![Southwest logo]()
$353
This United Airlines deal was found by Cheapflights users on 5/28. 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 9/35:15 am
SDF
- SJU
1 stop9h 29m
United Airlines
Fri 9/41:00 am
SJU
- SDF
2 stops12h 11m
United Airlines
Deal found 5/28![United Airlines logo]()
$354
This Southwest deal was found by Cheapflights users on 5/29. 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.
Sat 10/36:30 am
SDF
- SJU
1 stop12h 30m
Southwest
Sat 10/105:30 am
SJU
- SDF
1 stop11h 40m
Southwest
Deal found 5/29![Southwest logo]()
$358
This American Airlines deal was found by Cheapflights users on 5/29. 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 8/136:00 am
SDF
- STT
1 stop9h 52m
American Airlines
Mon 8/174:42 pm
STT
- SDF
2 stops17h 48m
American Airlines
Deal found 5/29![American Airlines logo]()
$360
This Delta deal was found by Cheapflights users on 5/27. 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.
Tue 7/216:00 am
SDF
- SJU
1 stop5h 40m
Delta
Wed 8/55:49 pm
SJU
- SDF
1 stop6h 35m
Delta
Deal found 5/27![Delta logo]()
$363
This Delta deal was found by Cheapflights users on 5/27. 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 7/1211:17 am
SDF
- SJU
1 stop11h 12m
Delta
Fri 7/176:00 am
SJU
- SDF
1 stop9h 42m
Delta
Deal found 5/27![Delta logo]()
$366
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 May 30, 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 May 30, 2026.
This Southwest deal was found by Cheapflights users on 5/30. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/304:05 pm
SDF
- SJU
2 stops8h 25m
Southwest
Thu 9/35:30 am
SJU
- SDF
1 stop10h 00m
Southwest
Deal found 5/30![Southwest logo]()
$321
This American Airlines deal was found by Cheapflights users on 5/29. 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.
Sat 11/77:31 pm
SDF
- STT
2 stops15h 36m
American Airlines
Sat 11/146:17 pm
STT
- SDF
2 stops17h 31m
American Airlines
Deal found 5/29![American Airlines logo]()
$360
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.
Sun 7/121:02 pm
SDF
- SJU
1 stop9h 27m
Delta
Fri 7/176:00 am
SJU
- SDF
1 stop9h 42m
Delta
Deal found 5/25![Delta logo]()
$363
This United Airlines deal was found by Cheapflights users on 5/26. 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 7/1410:05 am
SDF
- MBJ
1 stop6h 05m
United Airlines
Tue 7/214:12 pm
MBJ
- SDF
2 stops16h 14m
United Airlines
Deal found 5/26![United Airlines logo]()
$470
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 8/19:00 am
SDF
- PUJ
2 stops26h 04m
Copa Airlines
Sat 8/811:46 am
PUJ
- SDF
2 stops22h 37m
Copa Airlines
Deal found 5/25![Copa Airlines logo]()
$708
This Delta deal was found by Cheapflights users on 5/28. 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.
Wed 9/26:00 am
SDF
- MBJ
1 stop6h 44m
Delta
Sat 9/51:09 pm
MBJ
- SDF
1 stop7h 59m
Delta
Deal found 5/28![Delta logo]()
$372
This Southwest deal was found by Cheapflights users on 5/29. 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 9/73:20 pm
SDF
- SJU
2 stops8h 30m
Southwest
Thu 9/106:00 am
SJU
- SDF
2 stops9h 30m
Southwest
Deal found 5/29![Southwest logo]()
$381
This Southwest deal was found by Cheapflights users on 5/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/33:20 pm
SDF
- SJU
2 stops8h 30m
Southwest
Mon 9/75:30 am
SJU
- SDF
1 stop10h 00m
Southwest
Deal found 5/26![Southwest logo]()
$381
This American Airlines deal was found by Cheapflights users on 5/29. 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.
Tue 9/86:15 am
SDF
- STT
1 stop6h 38m
American Airlines
Tue 9/151:41 pm
STT
- SDF
2 stops20h 02m
American Airlines
Deal found 5/29![American Airlines logo]()
$425
This Delta deal was found by Cheapflights users on 5/30. 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 9/27:05 am
SDF
- MBJ
1 stop5h 39m
Delta
Sun 9/64:59 pm
MBJ
- SDF
1 stop6h 10m
Delta
Deal found 5/30![Delta logo]()
$425
This American Airlines deal was found by Cheapflights users on 5/30. 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 9/27:03 am
SDF
- MBJ
1 stop10h 05m
American Airlines
Sun 9/65:08 pm
MBJ
- SDF
2 stops17h 59m
American Airlines
Deal found 5/30![American Airlines logo]()
$427
This Southwest deal was found by Cheapflights users on 5/29. 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.
Sat 10/33:40 pm
SDF
- SJU
2 stops8h 10m
Southwest
Thu 10/83:20 pm
SJU
- SDF
2 stops9h 20m
Southwest
Deal found 5/29![Southwest logo]()
$390
This United Airlines deal was found by Cheapflights users on 5/26. 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 6/135:51 pm
SDF
- MBJ
2 stops22h 19m
United Airlines
Sat 6/204:33 pm
MBJ
- SDF
1 stop18h 21m
United Airlines
Deal found 5/26![United Airlines logo]()
$506
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.
Mon 7/68:19 pm
SDF
- MBJ
2 stops17h 50m
American Airlines
Mon 7/135:14 pm
MBJ
- SDF
2 stops17h 33m
American Airlines
Deal found 5/25![American Airlines logo]()
$457
This United Airlines deal was found by Cheapflights users on 5/29. 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.
Tue 8/259:45 am
SDF
- SJU
1 stop10h 53m
United Airlines
Thu 8/273:56 pm
SJU
- SDF
1 stop8h 03m
United Airlines
Deal found 5/29![United 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.
Sun 10/45:50 am
SDF
- SJU
1 stop6h 25m
Southwest
Mon 10/125:20 pm
SJU
- SDF
1 stop7h 20m
Southwest
Deal found 5/25![Southwest logo]()
$428
This Southwest deal was found by Cheapflights users on 5/28. 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 7/235:30 pm
SDF
- SJU
1 stop7h 55m
Southwest
Sat 8/16:30 am
SJU
- SDF
1 stop11h 40m
Southwest
Deal found 5/28![Southwest logo]()
$443
This Delta deal was found by Cheapflights users on 5/28. 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.
Fri 8/146:00 am
SDF
- STT
1 stop7h 34m
Delta
Wed 8/192:49 pm
STT
- SDF
1 stop6h 44m
Delta
Deal found 5/28![Delta logo]()
$540
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.
Tue 7/78:15 am
SDF
- AUA
1 stop7h 05m
American Airlines
Mon 7/133:02 pm
AUA
- SDF
1 stop9h 32m
American Airlines
Deal found 5/25![American Airlines logo]()
$493
This United Airlines deal was found by Cheapflights users on 5/27. 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.
Wed 7/86:15 am
SDF
- NAS
1 stop7h 32m
United Airlines
Mon 7/133:59 pm
NAS
- SDF
1 stop8h 00m
United Airlines
Deal found 5/27![United Airlines logo]()
$556
This Delta deal was found by Cheapflights users on 5/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/87:00 am
SDF
- STT
1 stop6h 52m
Delta
Tue 9/152:54 pm
STT
- SDF
1 stop6h 45m
Delta
Deal found 5/29![Delta logo]()
$540
This United Airlines deal was found by Cheapflights users on 5/28. 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 7/27:55 pm
SDF
- NAS
2 stops15h 33m
United Airlines
Mon 7/63:59 pm
NAS
- SDF
1 stop8h 00m
United Airlines
Deal found 5/28![United Airlines logo]()
$556
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 Southwest deal was found by Cheapflights users on 5/28. 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.
Sun 10/412:50 pm
SDF
- SJU
2 stops10h 45m
Southwest
Sun 10/116:00 am
SJU
- SDF
2 stops9h 35m
Southwest
Deal found 5/28![Southwest logo]()
$471
This Delta deal was found by Cheapflights users on 5/29. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/76:00 am
SDF
- STT
1 stop7h 34m
Delta
Sun 9/132:54 pm
STT
- SDF
1 stop5h 58m
Delta
Deal found 5/29![Delta logo]()
$550
This United Airlines deal was found by Cheapflights users on 5/27. 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.
Thu 6/259:00 am
SDF
- NAS
1 stop5h 57m
United Airlines
Wed 7/12:53 pm
NAS
- SDF
2 stops18h 33m
United Airlines
Deal found 5/27![United Airlines logo]()
$560
This American Airlines deal was found by Cheapflights users on 5/26. 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 7/36:25 pm
SDF
- AUA
1 stop17h 18m
American Airlines
Sat 7/115:03 pm
AUA
- SDF
1 stop24h 33m
American Airlines
Deal found 5/26![American Airlines logo]()
$532
This Southwest deal was found by Cheapflights users on 5/27. 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.
Thu 7/2310:45 am
SDF
- SJU
1 stop13h 35m
Southwest
Mon 7/2710:20 pm
SJU
- SDF
1 stop11h 50m
Southwest
Deal found 5/27![Southwest logo]()
$496
This Delta deal was found by Cheapflights users on 5/30. 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.
Mon 7/207:05 am
SDF
- NAS
1 stop6h 56m
Delta
Fri 7/241:16 pm
NAS
- SDF
1 stop6h 06m
Delta
Deal found 5/30![Delta logo]()
$556
This United Airlines deal was found by Cheapflights users on 5/26. 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.
Mon 6/227:47 pm
SDF
- AUA
1 stop19h 48m
United Airlines
Mon 6/295:50 pm
AUA
- SDF
1 stop29h 05m
United Airlines
Deal found 5/26![United Airlines logo]()
$574
Last-minute flights from Louisville to CaribbeanDiscover last-minute flight deals from Louisville to Caribbean. Data last updated May 30, 2026 and is based on user searches.
Discover last-minute flight deals from Louisville to Caribbean. Data last updated May 30, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 5/29. 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.
Sat 6/610:02 am
SDF
- SJU
1 stop10h 32m
United Airlines
Fri 6/192:05 am
SJU
- SDF
1 stop9h 49m
United Airlines
Deal found 5/29![United Airlines logo]()
$447
This Southwest deal was found by Cheapflights users on 5/29. 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.
Sat 6/64:10 pm
SDF
- SJU
1 stop7h 55m
Southwest
Sat 6/2011:20 am
SJU
- SDF
2 stops10h 20m
Southwest
Deal found 5/29![Southwest logo]()
$456
This American Airlines deal was found by Cheapflights users on 5/29. 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.
Mon 6/87:43 am
SDF
- SJU
1 stop15h 17m
American Airlines
Thu 6/111:47 pm
SJU
- SDF
2 stops10h 41m
American Airlines
Deal found 5/29![American Airlines logo]()
$416
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.
Mon 6/158:15 am
SDF
- SJU
1 stop14h 30m
American Airlines
Thu 6/186:21 am
SJU
- SDF
1 stop11h 24m
American Airlines
Deal found 5/25![American Airlines logo]()
$446
This American Airlines deal was found by Cheapflights users on 5/30. 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 6/167:43 am
SDF
- SJU
1 stop15h 17m
American Airlines
Tue 6/236:21 am
SJU
- SDF
1 stop11h 24m
American Airlines
Deal found 5/30![American Airlines logo]()
$431
This American Airlines deal was found by Cheapflights users on 5/26. 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 6/233:22 pm
SDF
- STT
2 stops19h 50m
American Airlines
Wed 7/224:50 pm
STT
- SDF
2 stops18h 57m
American Airlines
Deal found 5/26![American Airlines logo]()
$360
This American Airlines deal was found by Cheapflights users on 5/29. 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.
Tue 6/236:51 am
SDF
- SJU
2 stops11h 34m
American Airlines
Tue 6/307:00 am
SJU
- SDF
2 stops10h 45m
American Airlines
Deal found 5/29![American Airlines logo]()
$436
This Southwest deal was found by Cheapflights users on 5/26. 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 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 5/26![Southwest logo]()
$381
This Southwest deal was found by Cheapflights users on 5/28. 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 6/275:15 pm
SDF
- SJU
1 stop6h 25m
Southwest
Sat 7/45:30 am
SJU
- SDF
1 stop6h 55m
Southwest
Deal found 5/28![Southwest logo]()
$406
This Southwest deal was found by Cheapflights users on 5/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/295:30 pm
SDF
- SJU
1 stop6h 35m
Southwest
Thu 7/910:20 pm
SJU
- SDF
1 stop11h 50m
Southwest
Deal found 5/26![Southwest logo]()
$368
This American Airlines deal was found by Cheapflights users on 5/30. 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.
Mon 6/297:43 am
SDF
- SJU
1 stop15h 17m
American Airlines
Thu 7/910:35 am
SJU
- SDF
2 stops12h 28m
American Airlines
Deal found 5/30![American Airlines logo]()
$413
This Delta deal was found by Cheapflights users on 5/28. 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 6/296:00 am
SDF
- AUA
1 stop6h 20m
Delta
Wed 7/81:55 pm
AUA
- SDF
2 stops21h 56m
Delta
Deal found 5/28![Delta logo]()
$455
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 May 30, 2026.
Search for one-way flight options from Louisville to Caribbean. Find affordable one-way fares based on user searches. Data last updated May 30, 2026.
This Southwest deal was found by Cheapflights users on 5/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/284:15 pm
SDF
- SJU
1 stop6h 35m
Southwest
Deal found 5/26![Southwest logo]()
$158
This Delta deal was found by Cheapflights users on 5/29. 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 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 stop10h 37m
Delta
Deal found 5/29![Delta logo]()
$158
This Southwest deal was found by Cheapflights users on 5/28. 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 7/186:55 pm
SDF
- SJU
1 stop6h 25m
Southwest
Deal found 5/28![Southwest logo]()
$163
This Kiwi.com deal was found by Cheapflights users on 5/28. 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.
Mon 6/229:05 pm
SDF
- SJU
2 stops30h 52m
Multiple Airlines
Deal found 5/28![Multiple Airlines logo]()
$196
This American Airlines deal was found by Cheapflights users on 5/27. 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 6/47:43 am
SDF
- SJU
1 stop15h 17m
American Airlines
Deal found 5/27![American Airlines logo]()
$208
This American Airlines deal was found by Cheapflights users on 5/28. 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.
Fri 6/1911:28 am
SDF
- SJU
2 stops23h 34m
American Airlines
Deal found 5/28![American Airlines logo]()
$209
This Kiwi.com deal was found by Cheapflights users on 5/26. 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 9/1610:56 am
SDF
- NAS
2 stops22h 29m
Breeze Airways
Deal found 5/26![Breeze Airways logo]()
$210
This American Airlines deal was found by Cheapflights users on 5/26. 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 6/37:38 am
SDF
- SJU
1 stop15h 23m
American Airlines
Deal found 5/26![American Airlines logo]()
$213
This Kiwi.com deal was found by Cheapflights users on 5/28. 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.
Mon 6/159:05 pm
SDF
- SJU
2 stops30h 52m
Multiple Airlines
Deal found 5/28![Multiple Airlines logo]()
$216
This Kiwi.com deal was found by Cheapflights users on 5/28. 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.
Fri 7/38:48 pm
SDF
- SJU
1 stop19h 10m
Multiple Airlines
Deal found 5/28![Multiple Airlines logo]()
$217
This Southwest deal was found by Cheapflights users on 5/26. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/166:00 am
SDF
- NAS
1 stop6h 15m
Southwest
Deal found 5/26![Southwest logo]()
$221
This Kiwi.com deal was found by Cheapflights users on 5/28. 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.
Sun 6/218:49 pm
SDF
- SJU
1 stop27h 48m
Multiple Airlines
Deal found 5/28![Multiple Airlines logo]()
$225
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 May 30, 2026.
Round-trip from | $316 (American Airlines) |
|---|---|
One-way from | $158 (Southwest) |
Popular in | December |
Cheapest in | October |
Average price | $484 |
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 2,558,603 searches. Data last updated May 30, 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 - SJU
SDFSJU
Louisville Intl
Sun 8/30
4:05 pm-12:30 am
2 stops8h 25m
San Juan Luis Munoz Marin Intl
Thu 9/3
5:30 am-3:30 pm
1 stop10h 00m
$321
LouisvilleSaint Thomas Island
SDF - STT
SDFSTT
Louisville Intl
Sat 11/7
7:31 pm-12:07 pm
2 stops15h 36m
Saint Thomas Island Cyril E King
Sat 11/14
6:17 pm-10:48 am
2 stops17h 31m
$360
LouisvilleSan Juan
SDF - SJU
SDFSJU
Louisville Intl
Sun 7/12
1:02 pm-10:29 pm
1 stop9h 27m
San Juan Luis Munoz Marin Intl
Fri 7/17
6:00 am-3:42 pm
1 stop9h 42m
$363
LouisvilleMontego Bay
SDF - MBJ
SDFMBJ
Louisville Intl
Wed 9/2
6:00 am-11:44 am
1 stop6h 44m
Montego Bay Sangster Intl
Sat 9/5
1:09 pm-10:08 pm
1 stop7h 59m
$372
LouisvilleSan Juan
SDF - SJU
SDFSJU
Louisville Intl
Mon 9/7
3:20 pm-11:50 pm
2 stops8h 30m
San Juan Luis Munoz Marin Intl
Thu 9/10
6:00 am-3:30 pm
2 stops9h 30m
$381
LouisvilleSan Juan
SDF - SJU
SDFSJU
Louisville Intl
Thu 9/3
3:20 pm-11:50 pm
2 stops8h 30m
San Juan Luis Munoz Marin Intl
Mon 9/7
5:30 am-3:30 pm
1 stop10h 00m
$381
LouisvilleSan Juan
SDF - SJU
SDFSJU
Louisville Intl
Sat 10/3
3:40 pm-11:50 pm
2 stops8h 10m
San Juan Luis Munoz Marin Intl
Thu 10/8
3:20 pm-12:40 am
2 stops9h 20m
$390
LouisvilleSaint Thomas Island
SDF - STT
SDFSTT
Louisville Intl
Tue 9/8
6:15 am-12:53 pm
1 stop6h 38m
Saint Thomas Island Cyril E King
Tue 9/15
1:41 pm-9:43 am
2 stops20h 02m
$425
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
Sun 9/6
4:59 pm-12:09 am
1 stop6h 10m
$425
LouisvilleMontego Bay
SDF - MBJ
SDFMBJ
Louisville Intl
Wed 9/2
7:03 am-4:08 pm
1 stop10h 05m
Montego Bay Sangster Intl
Sun 9/6
5:08 pm-12:07 pm
2 stops17h 59m
$427
Showing 1-10 of 58 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-AUA
SDF-MBJ
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-AUA
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 $113). Flying from Louisville to Caribbean in May is currently the most expensive (average of $225). 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 77 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 May 30, 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.
Entertainment
7.5
Food
7.0
Comfort
8.0
Crew
8.6
Overall
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
Entertainment
7.5
Food
7.0
Comfort
8.0
Crew
8.6
Overall
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
Entertainment
7.5
Food
7.0
Comfort
8.0
Crew
8.6
Overall
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
Entertainment
7.5
Food
7.0
Comfort
8.0
Crew
8.6
Overall
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
Entertainment
7.5
Food
7.0
Comfort
8.0
Crew
8.6
Overall
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
Spirit Airlines
Entertainment
7.5
Food
7.0
Comfort
8.0
Crew
8.6
Overall
8.0
Boarding
8.1
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
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.
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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 May 30, 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 5 airlines flying from Louisville to Caribbean
Discover the top 5 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 2,558,603 searches. Data last updated May 30, 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$608 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$259 | Average$522 | FlexibilityNo cancel fee | On-time69% |