$113+ 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 8/18. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — SJU
Aug 8 — Aug 151
Round-trip
1 adult, Economy
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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 July 9, 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 July 9, 2026.
This American Airlines deal was found by Cheapflights users on 7/8. 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 9/306:00 am
SJU
- SDF
2 stops17h 22m
American Airlines
Deal found 7/8![American Airlines logo]()
$220
This United Airlines deal was found by Cheapflights users on 7/8. 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 8/106:00 am
SDF
- SJU
1 stop6h 34m
United Airlines
Thu 8/207:00 am
SJU
- SDF
2 stops13h 36m
United Airlines
Deal found 7/8![United Airlines logo]()
$236
This United Airlines deal was found by Cheapflights users on 7/7. 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 9/117:10 am
SDF
- SJU
2 stops13h 28m
United Airlines
Mon 9/142:55 pm
SJU
- SDF
1 stop8h 04m
United Airlines
Deal found 7/7![United Airlines logo]()
$252
This Kiwi.com deal was found by Cheapflights users on 7/9. 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 8/108:30 pm
SDF
- SJU
1 stop28h 11m
Multiple Airlines
Fri 8/146:00 am
SJU
- SDF
1 stop14h 20m
Multiple Airlines
Deal found 7/9![Multiple Airlines logo]()
$257
This American Airlines deal was found by Cheapflights users on 7/7. 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 9/18:16 am
SDF
- SJU
2 stops10h 17m
American Airlines
Sun 9/67:03 am
SJU
- SDF
1 stop10h 45m
American Airlines
Deal found 7/7![American Airlines logo]()
$268
This American Airlines deal was found by Cheapflights users on 7/9. 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 9/196:20 am
SDF
- SJU
1 stop8h 30m
American Airlines
Wed 9/233:41 pm
SJU
- SDF
1 stop7h 41m
American Airlines
Deal found 7/9![American Airlines logo]()
$273
This American Airlines deal was found by Cheapflights users on 7/8. 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 10/236:29 am
SDF
- SJU
1 stop7h 34m
American Airlines
Tue 10/272:18 pm
SJU
- SDF
2 stops8h 57m
American Airlines
Deal found 7/8![American Airlines logo]()
$274
This Kiwi.com deal was found by Cheapflights users on 7/5. 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 9/279:09 pm
SDF
- SJU
1 stop26h 48m
Multiple Airlines
Fri 10/25:12 pm
SJU
- SDF
1 stop17h 49m
Multiple Airlines
Deal found 7/5![Multiple Airlines logo]()
$276
This Kiwi.com deal was found by Cheapflights users on 7/8. 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 8/2011:12 am
SDF
- SJU
1 stop13h 22m
Multiple Airlines
Sun 8/236:35 am
SJU
- SDF
1 stop27h 14m
Multiple Airlines
Deal found 7/8![Multiple Airlines logo]()
$279
This Kiwi.com deal was found by Cheapflights users on 7/6. 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 8/109:10 pm
SDF
- SJU
1 stop19h 01m
Multiple Airlines
Thu 8/206:35 am
SJU
- SDF
1 stop27h 14m
Multiple Airlines
Deal found 7/6![Multiple Airlines logo]()
$286
This American Airlines deal was found by Cheapflights users on 7/8. 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 10/17:27 pm
SDF
- SJU
2 stops15h 33m
American Airlines
Sun 10/44:06 pm
SJU
- SDF
1 stop7h 58m
American Airlines
Deal found 7/8![American Airlines logo]()
$289
This Delta deal was found by Cheapflights users on 7/7. 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 9/117:05 am
SDF
- STT
1 stop6h 37m
Delta
Fri 9/182:52 pm
STT
- SDF
1 stop7h 07m
Delta
Deal found 7/7![Delta logo]()
$313
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 July 9, 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 July 9, 2026.
This United Airlines deal was found by Cheapflights users on 7/8. 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 9/191:55 pm
SDF
- SJU
1 stop9h 55m
United Airlines
Fri 9/251:00 am
SJU
- SDF
2 stops12h 15m
United Airlines
Deal found 7/8![United Airlines logo]()
$220
This Delta deal was found by Cheapflights users on 7/6. 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 8/221:21 pm
SDF
- SJU
1 stop9h 08m
Delta
Sat 8/297:00 am
SJU
- SDF
1 stop7h 18m
Delta
Deal found 7/6![Delta logo]()
$316
This Southwest deal was found by Cheapflights users on 7/6. 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 10/310:55 am
SDF
- SJU
1 stop11h 15m
Southwest
Thu 10/85:35 pm
SJU
- SDF
1 stop6h 35m
Southwest
Deal found 7/6![Southwest logo]()
$321
This American Airlines deal was found by Cheapflights users on 7/9. 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 11/33:38 pm
SDF
- STT
2 stops19h 29m
American Airlines
Tue 11/106:17 pm
STT
- SDF
2 stops16h 54m
American Airlines
Deal found 7/9![American Airlines logo]()
$328
This United Airlines deal was found by Cheapflights users on 7/7. 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 10/265:50 am
SDF
- SJU
1 stop6h 25m
United Airlines
Fri 10/307:05 am
SJU
- SDF
2 stops13h 36m
United Airlines
Deal found 7/7![United Airlines logo]()
$310
This United Airlines deal was found by Cheapflights users on 7/4. 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 8/189:00 am
SDF
- SJU
2 stops11h 38m
United Airlines
Fri 8/212:20 pm
SJU
- SDF
1 stop7h 55m
United Airlines
Deal found 7/4![United Airlines logo]()
$316
This Delta deal was found by Cheapflights users on 7/8. 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 9/247:05 am
SDF
- SJU
1 stop6h 42m
Delta
Sat 10/35:59 pm
SJU
- SDF
1 stop6h 00m
Delta
Deal found 7/8![Delta logo]()
$348
This Southwest deal was found by Cheapflights users on 7/7. 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 8/81:15 pm
SDF
- SJU
1 stop6h 05m
Southwest
Wed 8/126:00 am
SJU
- SDF
1 stop6h 40m
Southwest
Deal found 7/7![Southwest logo]()
$368
This American Airlines deal was found by Cheapflights users on 7/6. 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 8/206:30 pm
SDF
- MBJ
2 stops18h 12m
American Airlines
Thu 8/2712:47 pm
MBJ
- SDF
1 stop9h 30m
American Airlines
Deal found 7/6![American Airlines logo]()
$407
This Southwest deal was found by Cheapflights users on 7/7. 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 8/214:10 pm
SDF
- SJU
1 stop6h 55m
Southwest
Sun 8/235:00 am
SJU
- SDF
2 stops9h 10m
Southwest
Deal found 7/7![Southwest logo]()
$386
This Delta deal was found by Cheapflights users on 7/7. 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 8/157:05 am
SDF
- MBJ
1 stop5h 39m
Delta
Sat 8/221:09 pm
MBJ
- SDF
1 stop7h 56m
Delta
Deal found 7/7![Delta logo]()
$402
This American Airlines deal was found by Cheapflights users on 7/6. 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 9/27:12 pm
SDF
- MBJ
2 stops17h 30m
American Airlines
Sat 9/512:47 pm
MBJ
- SDF
1 stop8h 30m
American Airlines
Deal found 7/6![American Airlines logo]()
$412
This Southwest deal was found by Cheapflights users on 7/9. 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 10/811:50 am
SDF
- SJU
2 stops10h 05m
Southwest
Tue 10/136:35 am
SJU
- SDF
2 stops9h 55m
Southwest
Deal found 7/9![Southwest logo]()
$388
This United Airlines deal was found by Cheapflights users on 7/5. 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 8/1510:05 am
SDF
- MBJ
1 stop6h 05m
United Airlines
Sat 8/222:40 pm
MBJ
- SDF
2 stops21h 31m
United Airlines
Deal found 7/5![United Airlines logo]()
$407
This American Airlines deal was found by Cheapflights users on 7/8. 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 8/256:05 am
SDF
- AUA
1 stop7h 54m
American Airlines
Sat 8/294:50 pm
AUA
- SDF
1 stop7h 01m
American Airlines
Deal found 7/8![American Airlines logo]()
$413
This Delta deal was found by Cheapflights users on 7/7. 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 9/117:05 am
SDF
- STT
1 stop6h 37m
Delta
Wed 9/232:52 pm
STT
- SDF
1 stop6h 38m
Delta
Deal found 7/7![Delta logo]()
$458
This American Airlines deal was found by Cheapflights users on 7/4. 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 9/27:12 pm
SDF
- MBJ
2 stops19h 37m
American Airlines
Sun 9/62:52 pm
MBJ
- SDF
2 stops18h 26m
American Airlines
Deal found 7/4![American Airlines logo]()
$417
This American Airlines deal was found by Cheapflights users on 7/7. 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 8/216:18 pm
SDF
- AUA
1 stop17h 25m
American Airlines
Wed 8/264:50 pm
AUA
- SDF
2 stops17h 28m
American Airlines
Deal found 7/7![American Airlines logo]()
$418
This Southwest deal was found by Cheapflights users on 7/7. 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 9/147:20 am
SDF
- STT
1 stop6h 30m
Southwest
Sun 9/202:10 pm
STT
- SDF
2 stops9h 00m
Southwest
Deal found 7/7![Southwest logo]()
$472
This Delta deal was found by Cheapflights users on 7/5. 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 8/228:05 am
SDF
- STT
1 stop6h 57m
Delta
Sat 8/294:13 pm
STT
- SDF
1 stop7h 56m
Delta
Deal found 7/5![Delta logo]()
$491
This American Airlines deal was found by Cheapflights users on 7/7. 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 7/318:15 am
SDF
- AUA
1 stop7h 54m
American Airlines
Wed 8/52:32 pm
AUA
- SDF
2 stops20h 03m
American Airlines
Deal found 7/7![American Airlines logo]()
$450
This Delta deal was found by Cheapflights users on 7/7. 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 9/157:05 am
SDF
- STT
1 stop6h 37m
Delta
Wed 9/232:52 pm
STT
- SDF
1 stop6h 38m
Delta
Deal found 7/7![Delta logo]()
$515
This American Airlines deal was found by Cheapflights users on 7/4. 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 9/127:27 pm
SDF
- AUA
2 stops19h 43m
American Airlines
Thu 9/174:10 pm
AUA
- SDF
1 stop7h 12m
American Airlines
Deal found 7/4![American Airlines logo]()
$450
This United Airlines deal was found by Cheapflights users on 7/6. 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 8/195:45 pm
SDF
- NAS
2 stops19h 48m
United Airlines
Wed 8/2612:35 pm
NAS
- SDF
2 stops11h 24m
United Airlines
Deal found 7/6![United Airlines logo]()
$600
This Delta deal was found by Cheapflights users on 7/7. 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 9/187:55 pm
SDF
- PUJ
1 stop15h 47m
Delta
Thu 9/244:00 pm
PUJ
- SDF
1 stop7h 59m
Delta
Deal found 7/7![Delta logo]()
$530
This Southwest deal was found by Cheapflights users on 7/7. 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 1/57:50 am
SDF
- NAS
1 stop4h 25m
Southwest
Sun 1/101:55 pm
NAS
- SDF
1 stop8h 30m
Southwest
Deal found 7/7![Southwest logo]()
$591
This United Airlines deal was found by Cheapflights users on 7/8. 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 9/267:00 am
SDF
- PLS
2 stops9h 05m
United Airlines
Sat 10/312:45 pm
PLS
- SDF
1 stop11h 10m
United Airlines
Deal found 7/8![United Airlines logo]()
$611
This American Airlines deal was found by Cheapflights users on 7/5. 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 9/127:27 pm
SDF
- AUA
2 stops18h 03m
American Airlines
Wed 9/162:31 pm
AUA
- SDF
2 stops20h 45m
American Airlines
Deal found 7/5![American Airlines logo]()
$478
This Delta deal was found by Cheapflights users on 7/8. 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 9/43:25 pm
SDF
- PUJ
2 stops21h 34m
Delta
Wed 9/164:00 pm
PUJ
- SDF
1 stop16h 51m
Delta
Deal found 7/8![Delta logo]()
$535
This Southwest deal was found by Cheapflights users on 7/4. 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 10/315:35 pm
SDF
- NAS
2 stops19h 40m
Southwest
Thu 11/51:10 pm
NAS
- SDF
2 stops7h 50m
Southwest
Deal found 7/4![Southwest logo]()
$595
Last-minute flights from Louisville to CaribbeanDiscover last-minute flight deals from Louisville to Caribbean. Data last updated July 9, 2026 and is based on user searches.
Discover last-minute flight deals from Louisville to Caribbean. Data last updated July 9, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 7/6. 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 8/611:12 am
SDF
- SJU
1 stop13h 29m
Multiple Airlines
Thu 8/206:35 am
SJU
- SDF
1 stop27h 14m
Multiple Airlines
Deal found 7/6![Multiple Airlines logo]()
$301
This Kiwi.com deal was found by Cheapflights users on 7/4. 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 8/79:10 pm
SDF
- SJU
1 stop19h 01m
Multiple Airlines
Mon 8/106:00 am
SJU
- SDF
1 stop14h 20m
Multiple Airlines
Deal found 7/4![Multiple Airlines logo]()
$325
This Southwest deal was found by Cheapflights users on 7/8. 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 8/104:10 pm
SDF
- SJU
1 stop6h 55m
Southwest
Thu 8/206:00 am
SJU
- SDF
1 stop7h 35m
Southwest
Deal found 7/8![Southwest logo]()
$220
This United Airlines deal was found by Cheapflights users on 7/8. 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 8/106:00 am
SDF
- SJU
1 stop6h 34m
United Airlines
Thu 8/207:00 am
SJU
- SDF
2 stops13h 36m
United Airlines
Deal found 7/8![United Airlines logo]()
$236
This Kiwi.com deal was found by Cheapflights users on 7/9. 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 8/108:30 pm
SDF
- SJU
1 stop28h 11m
Multiple Airlines
Fri 8/146:00 am
SJU
- SDF
1 stop14h 20m
Multiple Airlines
Deal found 7/9![Multiple Airlines logo]()
$257
This Kiwi.com deal was found by Cheapflights users on 7/6. 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 8/109:10 pm
SDF
- SJU
1 stop19h 01m
Multiple Airlines
Thu 8/206:35 am
SJU
- SDF
1 stop27h 14m
Multiple Airlines
Deal found 7/6![Multiple Airlines logo]()
$286
This Delta deal was found by Cheapflights users on 7/7. 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 8/157:05 am
SDF
- MBJ
1 stop5h 39m
Delta
Sat 8/221:09 pm
MBJ
- SDF
1 stop7h 56m
Delta
Deal found 7/7![Delta logo]()
$402
This United Airlines deal was found by Cheapflights users on 7/7. 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 8/157:10 am
SDF
- MBJ
2 stops9h 00m
United Airlines
Sat 8/222:40 pm
MBJ
- SDF
2 stops17h 58m
United Airlines
Deal found 7/7![United Airlines logo]()
$407
This Kiwi.com deal was found by Cheapflights users on 7/8. 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 8/2011:12 am
SDF
- SJU
1 stop13h 22m
Multiple Airlines
Sun 8/236:35 am
SJU
- SDF
1 stop27h 14m
Multiple Airlines
Deal found 7/8![Multiple Airlines logo]()
$279
This American Airlines deal was found by Cheapflights users on 7/9. 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 8/228:16 am
SDF
- SJU
1 stop15h 27m
American Airlines
Fri 8/2812:55 am
SJU
- SDF
1 stop8h 50m
American Airlines
Deal found 7/9![American Airlines logo]()
$273
This Delta deal was found by Cheapflights users on 7/6. 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 8/2211:17 am
SDF
- SJU
1 stop11h 12m
Delta
Sat 8/295:49 pm
SJU
- SDF
1 stop6h 20m
Delta
Deal found 7/6![Delta logo]()
$316
This American Airlines deal was found by Cheapflights users on 7/8. 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 8/256:05 am
SDF
- AUA
1 stop7h 54m
American Airlines
Sat 8/294:50 pm
AUA
- SDF
1 stop7h 01m
American Airlines
Deal found 7/8![American Airlines logo]()
$413
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 July 9, 2026.
Search for one-way flight options from Louisville to Caribbean. Find affordable one-way fares based on user searches. Data last updated July 9, 2026.
This American Airlines deal was found by Cheapflights users on 7/8. 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 8/186:05 am
SDF
- SJU
2 stops10h 06m
American Airlines
Deal found 7/8![American Airlines logo]()
$113
This Southwest deal was found by Cheapflights users on 7/4. 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 7/2710:45 am
SDF
- SJU
1 stop10h 30m
Southwest
Deal found 7/4![Southwest logo]()
$158
This American Airlines deal was found by Cheapflights users on 7/6. 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 8/1211:05 am
SDF
- SJU
1 stop12h 10m
American Airlines
Deal found 7/6![American Airlines logo]()
$163
This Kiwi.com deal was found by Cheapflights users on 7/6. 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 8/122:56 pm
SDF
- SJU
2 stops33h 45m
Multiple Airlines
Deal found 7/6![Multiple Airlines logo]()
$175
This American Airlines deal was found by Cheapflights users on 7/7. 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 7/216:48 am
SDF
- MBJ
1 stop7h 48m
American Airlines
Deal found 7/7![American Airlines logo]()
$177
This Southwest deal was found by Cheapflights users on 7/6. 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
Deal found 7/6![Southwest logo]()
$193
This Kiwi.com deal was found by Cheapflights users on 7/5. 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 8/151:11 pm
SDF
- NAS
2 stops19h 44m
Multiple Airlines
Deal found 7/5![Multiple Airlines logo]()
$193
This American Airlines deal was found by Cheapflights users on 7/8. 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 10/206:15 am
SDF
- SXM
2 stops9h 24m
American Airlines
Deal found 7/8![American Airlines logo]()
$194
This Kiwi.com deal was found by Cheapflights users on 7/4. 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 7/266:55 pm
SDF
- SJU
2 stops19h 05m
Multiple Airlines
Deal found 7/4![Multiple Airlines logo]()
$196
This Kiwi.com deal was found by Cheapflights users on 7/4. 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 7/3011:12 am
SDF
- SJU
1 stop13h 29m
Multiple Airlines
Deal found 7/4![Multiple Airlines logo]()
$197
This United Airlines deal was found by Cheapflights users on 7/8. 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 9/296:15 am
SDF
- AUA
1 stop9h 05m
United Airlines
Deal found 7/8![United Airlines logo]()
$198
This United Airlines deal was found by Cheapflights users on 7/7. 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 7/217:15 am
SDF
- MBJ
2 stops8h 55m
United Airlines
Deal found 7/7![United Airlines logo]()
$200
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 July 9, 2026.
Round-trip from | $220 (American Airlines) |
|---|---|
One-way from | $113 (American Airlines) |
Popular in | December |
Cheapest in | October |
Average price | $496 |
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 July 9, 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
Sat 9/19
1:55 pm-11:50 pm
1 stop9h 55m
San Juan Luis Munoz Marin Intl
Fri 9/25
1:00 am-1:15 pm
2 stops12h 15m
$220
LouisvilleSan Juan
SDF - SJU
SDFSJU
Louisville Intl
Mon 10/26
5:50 am-12:15 pm
1 stop6h 25m
San Juan Luis Munoz Marin Intl
Fri 10/30
7:05 am-8:41 pm
2 stops13h 36m
$310
LouisvilleSan Juan
SDF - SJU
SDFSJU
Louisville Intl
Sat 8/22
1:21 pm-10:29 pm
1 stop9h 08m
San Juan Luis Munoz Marin Intl
Sat 8/29
7:00 am-2:18 pm
1 stop7h 18m
$316
LouisvilleSan Juan
SDF - SJU
SDFSJU
Louisville Intl
Tue 8/18
9:00 am-8:38 pm
2 stops11h 38m
San Juan Luis Munoz Marin Intl
Fri 8/21
2:20 pm-10:15 pm
1 stop7h 55m
$316
LouisvilleSan Juan
SDF - SJU
SDFSJU
Louisville Intl
Sat 10/3
10:55 am-10:10 pm
1 stop11h 15m
San Juan Luis Munoz Marin Intl
Thu 10/8
5:35 pm-12:10 am
1 stop6h 35m
$321
LouisvilleSaint Thomas Island
SDF - STT
SDFSTT
Louisville Intl
Tue 11/3
3:38 pm-12:07 pm
2 stops19h 29m
Saint Thomas Island Cyril E King
Tue 11/10
6:17 pm-10:11 am
2 stops16h 54m
$328
Quickest round-trip
LouisvilleSan Juan
SDF - SJU
SDFSJU
Louisville Intl
Thu 9/24
7:05 am-1:47 pm
1 stop6h 42m
San Juan Luis Munoz Marin Intl
Sat 10/3
5:59 pm-11:59 pm
1 stop6h 00m
$348
LouisvilleSan Juan
SDF - SJU
SDFSJU
Louisville Intl
Sat 8/8
1:15 pm-7:20 pm
1 stop6h 05m
San Juan Luis Munoz Marin Intl
Wed 8/12
6:00 am-12:40 pm
1 stop6h 40m
$368
LouisvilleSan Juan
SDF - SJU
SDFSJU
Louisville Intl
Fri 8/21
4:10 pm-11:05 pm
1 stop6h 55m
San Juan Luis Munoz Marin Intl
Sun 8/23
5:00 am-2:10 pm
2 stops9h 10m
$386
LouisvilleSan Juan
SDF - SJU
SDFSJU
Louisville Intl
Thu 10/8
11:50 am-9:55 pm
2 stops10h 05m
San Juan Luis Munoz Marin Intl
Tue 10/13
6:35 am-4:30 pm
2 stops9h 55m
$388
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-MBJ
SDF-AUA
SDF-NAS
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-MBJ
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 August is currently the most expensive (average of $226). 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 July 9, 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.
Overall
7.9
Crew
8.6
Boarding
8.1
Entertainment
7.5
Food
7.0
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Overall
7.9
Crew
8.6
Boarding
8.1
Entertainment
7.5
Food
7.0
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Overall
7.9
Crew
8.6
Boarding
8.1
Entertainment
7.5
Food
7.0
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Overall
7.9
Crew
8.6
Boarding
8.1
Entertainment
7.5
Food
7.0
Comfort
8.0
Reviews
1 / 20
8.0
ExcellentLibby,Jun 2026
TUS - LAS
Overall
7.9
Crew
8.6
Boarding
8.1
Entertainment
7.5
Food
7.0
Comfort
8.0
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.
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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 July 9, 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 2,558,603 searches. Data last updated July 9, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$160 | Average$558 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$225 | Average$655 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$226 | Average$620 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$259 | Average$518 | FlexibilityNo cancel fee | On-time69% |