$106+ 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 5/11. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — SJU
May 10 — May 171
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Louisville to Caribbean 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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Louisville to Caribbean Islands
Cheapest
Best
Last-minute
One-way
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 April 10, 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 April 10, 2026.
This CheapOair deal was found by Cheapflights users on 4/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/16:06 pm
SDF
- SJU
1 stop25h 16m
Spirit Airlines
Thu 5/78:04 pm
SJU
- SDF
1 stop13h 24m
Spirit Airlines
Deal found 4/10![Spirit Airlines logo]()
$208
This CheapOair deal was found by Cheapflights users on 4/7. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/810:33 am
SDF
- SJU
1 stop8h 26m
Spirit Airlines
Sun 5/108:04 pm
SJU
- SDF
1 stop13h 24m
Spirit Airlines
Deal found 4/7![Spirit Airlines logo]()
$233
This CheapOair deal was found by Cheapflights users on 4/9. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/246:06 pm
SDF
- SJU
1 stop25h 16m
Spirit Airlines
Fri 5/112:57 pm
SJU
- SDF
1 stop28h 07m
Spirit Airlines
Deal found 4/9![Spirit Airlines logo]()
$234
This Kiwi.com deal was found by Cheapflights users on 4/9. 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.
Thu 4/236:06 pm
SDF
- SJU
1 stop25h 16m
Spirit Airlines
Thu 4/3012:57 pm
SJU
- SDF
1 stop28h 07m
Spirit Airlines
Deal found 4/9![Spirit Airlines logo]()
$238
This Kiwi.com deal was found by Cheapflights users on 4/8. 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.
Fri 5/16:06 pm
SDF
- SJU
2 stops30h 48m
Multiple Airlines
Thu 5/78:04 pm
SJU
- SDF
1 stop13h 24m
Multiple Airlines
Deal found 4/8![Multiple Airlines logo]()
$260
This Kiwi.com deal was found by Cheapflights users on 4/6. 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.
Fri 4/246:06 pm
SDF
- SJU
1 stop25h 16m
Multiple Airlines
Fri 5/16:00 am
SJU
- SDF
1 stop11h 04m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$261
This United Airlines deal was found by Cheapflights users on 4/6. 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.
Sun 5/105:50 am
SDF
- STT
1 stop6h 30m
United Airlines
Fri 5/151:22 pm
STT
- SDF
1 stop8h 37m
United Airlines
Deal found 4/6![United Airlines logo]()
$300
This Kiwi.com deal was found by Cheapflights users on 4/6. 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.
Fri 4/246:06 pm
SDF
- AUA
1 stop20h 30m
Spirit Airlines
Fri 5/13:41 pm
AUA
- SDF
1 stop25h 23m
Spirit Airlines
Deal found 4/6![Spirit Airlines logo]()
$309
This Kiwi.com deal was found by Cheapflights users on 4/9. 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.
Fri 5/87:48 pm
SDF
- SXM
1 stop17h 42m
Multiple Airlines
Sun 5/102:35 pm
SXM
- SDF
1 stop18h 53m
Multiple Airlines
Deal found 4/9![Multiple Airlines logo]()
$314
This United Airlines deal was found by Cheapflights users on 4/8. 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 4/259:07 am
SDF
- STT
1 stop7h 53m
United Airlines
Fri 5/14:45 pm
STT
- SDF
1 stop7h 14m
United Airlines
Deal found 4/8![United Airlines logo]()
$320
This Kiwi.com deal was found by Cheapflights users on 4/9. 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.
Sat 5/910:33 am
SDF
- SXM
1 stop26h 57m
Spirit Airlines
Thu 5/142:35 pm
SXM
- SDF
1 stop18h 53m
Spirit Airlines
Deal found 4/9![Spirit Airlines logo]()
$324
This American Airlines deal was found by Cheapflights users on 4/7. 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.
Wed 5/65:38 pm
SDF
- STT
2 stops17h 57m
American Airlines
Wed 5/1312:25 pm
STT
- SDF
1 stop11h 34m
American Airlines
Deal found 4/7![American Airlines logo]()
$325
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 April 10, 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 April 10, 2026.
This United Airlines deal was found by Cheapflights users on 4/5. 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.
Sun 5/105:50 am
SDF
- STT
1 stop6h 30m
United Airlines
Fri 5/151:22 pm
STT
- SDF
1 stop8h 37m
United Airlines
Deal found 4/5![United Airlines logo]()
$300
This Delta deal was found by Cheapflights users on 4/5. 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.
Tue 6/237:05 am
SDF
- SJU
1 stop6h 26m
Delta
Tue 6/305:56 pm
SJU
- SDF
1 stop6h 36m
Delta
Deal found 4/5![Delta logo]()
$316
This American Airlines deal was found by Cheapflights users on 4/5. 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 5/167:52 pm
SDF
- STT
2 stops15h 43m
American Airlines
Tue 5/195:05 pm
STT
- SDF
1 stop6h 54m
American Airlines
Deal found 4/5![American Airlines logo]()
$320
This Southwest deal was found by Cheapflights users on 4/5. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/252:15 pm
SDF
- SJU
2 stops8h 50m
Southwest
Wed 9/302:25 pm
SJU
- SDF
1 stop7h 05m
Southwest
Deal found 4/5![Southwest logo]()
$391
This Kiwi.com deal was found by Cheapflights users on 4/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/229:10 pm
SDF
- NAS
1 stop16h 40m
Multiple Airlines
Wed 5/274:00 pm
NAS
- SDF
1 stop17h 28m
Multiple Airlines
Deal found 4/7![Multiple Airlines logo]()
$463
This Breeze Airways deal was found by Cheapflights users on 4/9. 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 Breeze Airways is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/279:09 pm
SDF
- NAS
1 stop11h 21m
Breeze Airways
Thu 10/110:15 am
NAS
- SDF
1 stop10h 14m
Breeze Airways
Deal found 4/9![Breeze Airways logo]()
$469
This Kiwi.com deal was found by Cheapflights users on 4/8. 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.
Sat 5/2310:33 am
SDF
- SXM
1 stop26h 57m
Spirit Airlines
Sat 5/302:35 pm
SXM
- SDF
1 stop18h 53m
Spirit Airlines
Deal found 4/8![Spirit Airlines logo]()
$533
This United Airlines deal was found by Cheapflights users on 4/5. 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.
Tue 5/55:54 am
SDF
- STT
1 stop6h 26m
United Airlines
Fri 5/82:10 pm
STT
- SDF
1 stop8h 12m
United Airlines
Deal found 4/5![United Airlines logo]()
$300
This Delta deal was found by Cheapflights users on 4/9. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/176:00 am
SDF
- SJU
1 stop10h 35m
Delta
Fri 8/211:06 pm
SJU
- SDF
1 stop5h 55m
Delta
Deal found 4/9![Delta logo]()
$316
This American Airlines deal was found by Cheapflights users on 4/10. Clicking the “Pick Dates” 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 4/277:01 pm
SDF
- STT
2 stops17h 06m
American Airlines
Fri 5/15:05 pm
STT
- SDF
1 stop6h 54m
American Airlines
Deal found 4/10![American Airlines logo]()
$320
This United Airlines deal was found by Cheapflights users on 4/5. 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.
Mon 4/206:00 am
SDF
- STT
1 stop7h 08m
United Airlines
Fri 4/242:10 pm
STT
- SDF
1 stop9h 49m
United Airlines
Deal found 4/5![United Airlines logo]()
$300
This United Airlines deal was found by Cheapflights users on 4/8. 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 4/259:07 am
SDF
- STT
1 stop7h 53m
United Airlines
Fri 5/14:45 pm
STT
- SDF
1 stop7h 14m
United Airlines
Deal found 4/8![United Airlines logo]()
$320
This Delta deal was found by Cheapflights users on 4/10. Clicking the “Pick Dates” 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 5/97:05 am
SDF
- MBJ
1 stop9h 29m
Delta
Fri 5/151:18 pm
MBJ
- SDF
1 stop10h 07m
Delta
Deal found 4/10![Delta logo]()
$352
This American Airlines deal was found by Cheapflights users on 4/7. 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.
Wed 9/26:19 am
SDF
- MBJ
1 stop7h 01m
American Airlines
Sat 9/53:20 pm
MBJ
- SDF
2 stops17h 45m
American Airlines
Deal found 4/7![American Airlines logo]()
$362
This Delta deal was found by Cheapflights users on 4/5. 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.
Tue 5/511:12 am
SDF
- MBJ
1 stop5h 05m
Delta
Tue 5/124:59 pm
MBJ
- SDF
1 stop6h 26m
Delta
Deal found 4/5![Delta logo]()
$352
This Southwest deal was found by Cheapflights users on 4/5. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/183:05 pm
SDF
- SJU
1 stop7h 45m
Southwest
Sat 9/265:05 am
SJU
- SDF
1 stop6h 05m
Southwest
Deal found 4/5![Southwest logo]()
$431
This American Airlines deal was found by Cheapflights users on 4/5. 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 6/278:08 pm
SDF
- MBJ
2 stops18h 00m
American Airlines
Sat 7/45:17 pm
MBJ
- SDF
2 stops17h 25m
American Airlines
Deal found 4/5![American Airlines logo]()
$391
This Southwest deal was found by Cheapflights users on 4/6. 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.
Wed 4/227:00 am
SDF
- SJU
2 stops11h 10m
Southwest
Fri 4/245:05 am
SJU
- SDF
2 stops9h 55m
Southwest
Deal found 4/6![Southwest logo]()
$436
This United Airlines deal was found by Cheapflights users on 4/5. 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.
Sun 5/106:00 am
SDF
- STT
1 stop9h 43m
United Airlines
Thu 5/144:45 pm
STT
- SDF
1 stop7h 14m
United Airlines
Deal found 4/5![United Airlines logo]()
$390
This Delta deal was found by Cheapflights users on 4/8. 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.
Sun 4/266:00 am
SDF
- STT
1 stop7h 51m
Delta
Fri 5/13:05 pm
STT
- SDF
1 stop8h 54m
Delta
Deal found 4/8![Delta logo]()
$391
This American Airlines deal was found by Cheapflights users on 4/5. 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.
Mon 7/67:11 pm
SDF
- MBJ
1 stop19h 12m
American Airlines
Mon 7/135:17 pm
MBJ
- SDF
2 stops17h 07m
American Airlines
Deal found 4/5![American Airlines logo]()
$397
This Kiwi.com deal was found by Cheapflights users on 4/6. 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 5/212:27 pm
SDF
- SXM
2 stops47h 03m
Multiple Airlines
Thu 5/282:35 pm
SXM
- SDF
1 stop18h 53m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$538
This Delta deal was found by Cheapflights users on 4/7. 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 5/86:00 am
SDF
- SJU
1 stop6h 01m
Delta
Mon 5/115:43 pm
SJU
- SDF
1 stop6h 42m
Delta
Deal found 4/7![Delta logo]()
$396
This American Airlines deal was found by Cheapflights users on 4/7. 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.
Wed 9/28:06 pm
SDF
- MBJ
2 stops16h 57m
American Airlines
Sun 9/63:20 pm
MBJ
- SDF
2 stops17h 45m
American Airlines
Deal found 4/7![American Airlines logo]()
$401
This Southwest deal was found by Cheapflights users on 4/5. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/36:05 pm
SDF
- SJU
2 stops7h 15m
Southwest
Fri 7/101:15 pm
SJU
- SDF
2 stops9h 10m
Southwest
Deal found 4/5![Southwest logo]()
$491
This United Airlines deal was found by Cheapflights users on 4/7. 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 5/167:15 am
SDF
- STT
1 stop9h 45m
United Airlines
Tue 5/194:45 pm
STT
- SDF
1 stop7h 14m
United Airlines
Deal found 4/7![United Airlines logo]()
$410
This Southwest deal was found by Cheapflights users on 4/9. 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.
Sun 7/52:30 pm
SDF
- SJU
2 stops9h 55m
Southwest
Thu 7/95:00 am
SJU
- SDF
2 stops9h 55m
Southwest
Deal found 4/9![Southwest logo]()
$491
This American Airlines deal was found by Cheapflights users on 4/7. 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 5/298:08 pm
SDF
- MBJ
2 stops16h 37m
American Airlines
Wed 6/32:08 pm
MBJ
- SDF
1 stop8h 38m
American Airlines
Deal found 4/7![American Airlines logo]()
$410
This United Airlines deal was found by Cheapflights users on 4/7. 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 5/296:00 am
SDF
- MBJ
1 stop10h 10m
United Airlines
Wed 6/312:52 pm
MBJ
- SDF
1 stop8h 58m
United Airlines
Deal found 4/7![United Airlines logo]()
$421
This Southwest deal was found by Cheapflights users on 4/6. 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.
Sun 10/45:25 am
SDF
- SJU
1 stop8h 20m
Southwest
Mon 10/125:30 am
SJU
- SDF
2 stops9h 30m
Southwest
Deal found 4/6![Southwest logo]()
$501
Last-minute flights from Louisville to Caribbean IslandsDiscover last-minute flight deals from Louisville to Caribbean Islands. Data last updated April 10, 2026 and is based on user searches.
Discover last-minute flight deals from Louisville to Caribbean Islands. Data last updated April 10, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 4/9. 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.
Thu 4/236:06 pm
SDF
- SJU
1 stop25h 16m
Spirit Airlines
Thu 4/3012:57 pm
SJU
- SDF
1 stop28h 07m
Spirit Airlines
Deal found 4/9![Spirit Airlines logo]()
$238
This CheapOair deal was found by Cheapflights users on 4/9. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/246:06 pm
SDF
- SJU
1 stop25h 16m
Spirit Airlines
Fri 5/112:57 pm
SJU
- SDF
1 stop28h 07m
Spirit Airlines
Deal found 4/9![Spirit Airlines logo]()
$234
This Kiwi.com deal was found by Cheapflights users on 4/6. 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.
Fri 4/246:06 pm
SDF
- SJU
1 stop25h 16m
Multiple Airlines
Fri 5/16:00 am
SJU
- SDF
1 stop11h 04m
Multiple Airlines
Deal found 4/6![Multiple Airlines logo]()
$261
This Kiwi.com deal was found by Cheapflights users on 4/6. 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.
Fri 4/246:06 pm
SDF
- AUA
1 stop20h 30m
Spirit Airlines
Fri 5/13:41 pm
AUA
- SDF
1 stop25h 23m
Spirit Airlines
Deal found 4/6![Spirit Airlines logo]()
$309
This United Airlines deal was found by Cheapflights users on 4/8. 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 4/259:07 am
SDF
- STT
1 stop7h 53m
United Airlines
Fri 5/14:45 pm
STT
- SDF
1 stop7h 14m
United Airlines
Deal found 4/8![United Airlines logo]()
$320
This CheapOair deal was found by Cheapflights users on 4/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/16:06 pm
SDF
- SJU
1 stop25h 16m
Spirit Airlines
Thu 5/78:04 pm
SJU
- SDF
1 stop13h 24m
Spirit Airlines
Deal found 4/10![Spirit Airlines logo]()
$208
This Kiwi.com deal was found by Cheapflights users on 4/8. 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.
Fri 5/16:06 pm
SDF
- SJU
2 stops30h 48m
Multiple Airlines
Thu 5/78:04 pm
SJU
- SDF
1 stop13h 24m
Multiple Airlines
Deal found 4/8![Multiple Airlines logo]()
$260
This American Airlines deal was found by Cheapflights users on 4/7. 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.
Wed 5/65:38 pm
SDF
- STT
2 stops17h 57m
American Airlines
Wed 5/1312:25 pm
STT
- SDF
1 stop11h 34m
American Airlines
Deal found 4/7![American Airlines logo]()
$325
This CheapOair deal was found by Cheapflights users on 4/7. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/810:33 am
SDF
- SJU
1 stop8h 26m
Spirit Airlines
Sun 5/108:04 pm
SJU
- SDF
1 stop13h 24m
Spirit Airlines
Deal found 4/7![Spirit Airlines logo]()
$233
This Kiwi.com deal was found by Cheapflights users on 4/9. 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.
Fri 5/87:48 pm
SDF
- SXM
1 stop17h 42m
Multiple Airlines
Thu 5/142:35 pm
SXM
- SDF
1 stop18h 53m
Multiple Airlines
Deal found 4/9![Multiple Airlines logo]()
$314
This Kiwi.com deal was found by Cheapflights users on 4/9. 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.
Sat 5/910:33 am
SDF
- SXM
1 stop26h 57m
Spirit Airlines
Thu 5/142:35 pm
SXM
- SDF
1 stop18h 53m
Spirit Airlines
Deal found 4/9![Spirit Airlines logo]()
$324
This United Airlines deal was found by Cheapflights users on 4/6. 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.
Sun 5/105:50 am
SDF
- STT
1 stop6h 30m
United Airlines
Fri 5/151:22 pm
STT
- SDF
1 stop8h 37m
United Airlines
Deal found 4/6![United Airlines logo]()
$300
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 April 10, 2026.
Search for one-way flight options from Louisville to Caribbean Islands. Find affordable one-way fares based on user searches. Data last updated April 10, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 4/5. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/1110:33 am
SDF
- SJU
1 stop8h 26m
Spirit Airlines
Deal found 4/5![Spirit Airlines logo]()
$106
This Cheapflightsfares deal was found by Cheapflights users on 4/8. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/1010:33 am
SDF
- SJU
1 stop8h 26m
Spirit Airlines
Deal found 4/8![Spirit Airlines logo]()
$125
This Kiwi.com deal was found by Cheapflights users on 4/8. 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.
Fri 5/87:48 pm
SDF
- SJU
1 stop23h 11m
Multiple Airlines
Deal found 4/8![Multiple Airlines logo]()
$140
This Kiwi.com deal was found by Cheapflights users on 4/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/236:06 pm
SDF
- SJU
1 stop18h 17m
Multiple Airlines
Deal found 4/7![Multiple Airlines logo]()
$155
This Delta deal was found by Cheapflights users on 4/8. 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.
Mon 5/186:00 am
SDF
- SJU
1 stop10h 33m
Delta
Deal found 4/8![Delta logo]()
$158
This CheapOair deal was found by Cheapflights users on 4/9. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/810:33 am
SDF
- SJU
1 stop8h 26m
Spirit Airlines
Deal found 4/9![Spirit Airlines logo]()
$163
This Kiwi.com deal was found by Cheapflights users on 4/8. 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.
Mon 5/187:48 pm
SDF
- SJU
3 stops21h 38m
Multiple Airlines
Deal found 4/8![Multiple Airlines logo]()
$164
This Kiwi.com deal was found by Cheapflights users on 4/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/229:10 pm
SDF
- NAS
1 stop22h 05m
Multiple Airlines
Deal found 4/7![Multiple Airlines logo]()
$164
This CheapOair deal was found by Cheapflights users on 4/7. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/256:06 pm
SDF
- SJU
1 stop25h 16m
Spirit Airlines
Deal found 4/7![Spirit Airlines logo]()
$171
This Mytrip deal was found by Cheapflights users on 4/8. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/1810:33 am
SDF
- SJU
2 stops23h 45m
Spirit Airlines
Deal found 4/8![Spirit Airlines logo]()
$172
This Kiwi.com deal was found by Cheapflights users on 4/5. 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.
Mon 5/1110:33 am
SDF
- SJU
3 stops30h 53m
Multiple Airlines
Deal found 4/5![Multiple Airlines logo]()
$174
This Kiwi.com deal was found by Cheapflights users on 4/9. 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 6/89:10 pm
SDF
- SJU
2 stops27h 34m
Multiple Airlines
Deal found 4/9![Multiple Airlines logo]()
$176
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 April 10, 2026.
Round-trip from | $208 (CheapOair) |
|---|---|
One-way from | $106 (Cheapflightsfares) |
Popular in | December |
Cheapest in | October |
Average price | $383 |
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 April 10, 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
LouisvilleSaint Thomas Island
SDF - STT
SDFSTT
Louisville Intl
Sun 5/10
5:50 am-12:20 pm
1 stop6h 30m
Saint Thomas Island Cyril E King
Fri 5/15
1:22 pm-9:59 pm
1 stop8h 37m
$300
LouisvilleSaint Thomas Island
SDF - STT
SDFSTT
Louisville Intl
Tue 5/5
5:54 am-12:20 pm
1 stop6h 26m
Saint Thomas Island Cyril E King
Fri 5/8
2:10 pm-10:22 pm
1 stop8h 12m
$300
LouisvilleSaint Thomas Island
SDF - STT
SDFSTT
Louisville Intl
Mon 4/20
6:00 am-1:08 pm
1 stop7h 08m
Saint Thomas Island Cyril E King
Fri 4/24
2:10 pm-11:59 pm
1 stop9h 49m
$300
LouisvilleSan Juan
SDF - SJU
SDFSJU
Louisville Intl
Tue 6/23
7:05 am-1:31 pm
1 stop6h 26m
San Juan Luis Munoz Marin Intl
Tue 6/30
5:56 pm-12:32 am
1 stop6h 36m
$316
LouisvilleSan Juan
SDF - SJU
SDFSJU
Louisville Intl
Mon 8/17
6:00 am-4:35 pm
1 stop10h 35m
San Juan Luis Munoz Marin Intl
Fri 8/21
1:06 pm-7:01 pm
1 stop5h 55m
$316
LouisvilleSaint Thomas Island
SDF - STT
SDFSTT
Louisville Intl
Sat 5/16
7:52 pm-11:35 am
2 stops15h 43m
Saint Thomas Island Cyril E King
Tue 5/19
5:05 pm-11:59 pm
1 stop6h 54m
$320
LouisvilleSaint Thomas Island
SDF - STT
SDFSTT
Louisville Intl
Mon 4/27
7:01 pm-12:07 pm
2 stops17h 06m
Saint Thomas Island Cyril E King
Fri 5/1
5:05 pm-11:59 pm
1 stop6h 54m
$320
LouisvilleSaint Thomas Island
SDF - STT
SDFSTT
Louisville Intl
Sat 4/25
9:07 am-5:00 pm
1 stop7h 53m
Saint Thomas Island Cyril E King
Fri 5/1
4:45 pm-11:59 pm
1 stop7h 14m
$320
LouisvilleMontego Bay
SDF - MBJ
SDFMBJ
Louisville Intl
Sat 5/9
7:05 am-3:34 pm
1 stop9h 29m
Montego Bay Sangster Intl
Fri 5/15
1:18 pm-12:25 am
1 stop10h 07m
$352
Quickest round-trip
LouisvilleMontego Bay
SDF - MBJ
SDFMBJ
Louisville Intl
Tue 5/5
11:12 am-3:17 pm
1 stop5h 05m
Montego Bay Sangster Intl
Tue 5/12
4:59 pm-12:25 am
1 stop6h 26m
$352
Showing 1-10 of 51 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-SJU
SDF-STT
SDF-AUA
SDF-SXM
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 Islands
SDF-zzEPX
SDF-SJU
SDF-STT
SDF-AUA
SDF-SXM
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 $165). Flying from Louisville to Caribbean Islands in June is currently the most expensive (average of $255). 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.
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 April 10, 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.
Boarding
8.1
Entertainment
7.5
Crew
8.6
Comfort
8.0
Food
7.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Entertainment
7.5
Crew
8.6
Comfort
8.0
Food
7.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Entertainment
7.5
Crew
8.6
Comfort
8.0
Food
7.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Entertainment
7.5
Crew
8.6
Comfort
8.0
Food
7.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Entertainment
7.5
Crew
8.6
Comfort
8.0
Food
7.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Boarding
8.1
Entertainment
7.5
Crew
8.6
Comfort
8.0
Food
7.0
Overall
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.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Top destinations
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 April 10, 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 April 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$176 | Average$380 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$198 | Average$531 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$225 | Average$637 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$240 | Average$596 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$246 | Average$532 | FlexibilityNo cancel fee | On-time69% |