$137+ Cheap flights from Kentucky to Puerto Rico
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/19. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — SJU
Nov 3 — Nov 101
Round-trip
1 adult, Economy
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Find cheap flights from Kentucky to Puerto Rico 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 Kentucky to Puerto Rico
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Cheapest flights from Kentucky to Puerto RicoExplore the most affordable flight options available from Kentucky to Puerto Rico. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 4, 2026.
Explore the most affordable flight options available from Kentucky to Puerto Rico. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 4, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/96:53 pm -
1 stop19h 26m
Tue 12/86:25 am -
2 stops35h 07m
Deal found 9/30![Multiple Airlines logo]()
$242
This Kiwi.com deal was found by Cheapflights users on 10/2. Clicking the “Pick Dates” 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 12/65:25 pm -
1 stop26h 12m
Thu 12/106:25 am -
1 stop10h 40m
Deal found 10/2![Multiple Airlines logo]()
$282
This Kiwi.com deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/267:08 pm -
1 stop20h 09m
Thu 10/296:15 am -
2 stops14h 14m
Deal found 9/29![Multiple Airlines logo]()
$294
This Kiwi.com deal was found by Cheapflights users on 10/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/197:35 pm -
1 stop19h 43m
Fri 10/235:11 pm -
2 stops17h 00m
Deal found 10/2![Multiple Airlines logo]()
$302
This Kiwi.com deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/267:08 pm -
1 stop20h 09m
Fri 10/303:59 pm -
2 stops18h 12m
Deal found 9/29![Multiple Airlines logo]()
$305
This Kiwi.com deal was found by Cheapflights users on 9/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/88:37 pm -
1 stop12h 38m
Thu 11/127:00 am -
2 stops14h 29m
Deal found 9/30![Multiple Airlines logo]()
$310
This Kiwi.com deal was found by Cheapflights users on 9/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/166:53 pm -
1 stop19h 26m
Sat 11/2110:54 pm -
2 stops37h 05m
Deal found 9/30![Multiple Airlines logo]()
$327
This Kiwi.com deal was found by Cheapflights users on 9/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/229:43 pm -
1 stop28h 10m
Wed 10/286:25 pm -
1 stop26h 28m
Deal found 9/30![Multiple Airlines logo]()
$328
This Kiwi.com deal was found by Cheapflights users on 10/3. Clicking the “Pick Dates” 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 11/27:08 pm -
1 stop19h 11m
Mon 11/97:00 am -
1 stop12h 03m
Deal found 10/3![Multiple Airlines logo]()
$343
This Kiwi.com deal was found by Cheapflights users on 10/2. Clicking the “Pick Dates” 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 10/188:59 pm -
1 stop16h 32m
Thu 10/227:00 am -
1 stop13h 23m
Deal found 10/2![Multiple Airlines logo]()
$343
This Kiwi.com deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/267:08 pm -
1 stop20h 09m
Sat 10/316:11 pm -
1 stop27h 18m
Deal found 9/29![Multiple Airlines logo]()
$347
This Kiwi.com deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/238:10 pm -
1 stop25h 45m
Thu 10/296:15 am -
2 stops14h 14m
Deal found 9/29![Multiple Airlines logo]()
$348
Best flights from Kentucky to Puerto RicoDiscover carefully curated flight deals from Kentucky to Puerto Rico that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 4, 2026.
Discover carefully curated flight deals from Kentucky to Puerto Rico that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 4, 2026.
This United Airlines deal was found by Cheapflights users on 10/2. Clicking the “Pick Dates” 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 12/78:45 am -
2 stops14h 51m
Thu 12/104:55 pm -
1 stop8h 01m
Deal found 10/2![United Airlines logo]()
$356
This Southwest deal was found by Cheapflights users on 10/2. Clicking the “Pick Dates” 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 12/612:05 pm -
1 stop12h 00m
Wed 12/912:30 pm -
1 stop10h 20m
Deal found 10/2![Southwest logo]()
$376
This American Airlines deal was found by Cheapflights users on 9/29. 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 10/249:17 am -
2 stops13h 40m
Mon 10/2610:36 am -
2 stops13h 33m
Deal found 9/29![American Airlines logo]()
$566
This United Airlines deal was found by Cheapflights users on 10/2. Clicking the “Pick Dates” 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 10/3011:05 am -
2 stops10h 17m
Tue 11/38:25 am -
1 stop10h 05m
Deal found 10/2![United Airlines logo]()
$371
This United Airlines deal was found by Cheapflights users on 9/29. 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.
Wed 12/27:00 am -
2 stops14h 22m
Thu 12/34:55 pm -
1 stop8h 01m
Deal found 9/29![United Airlines logo]()
$374
This Southwest deal was found by Cheapflights users on 10/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/1611:50 am -
2 stops10h 05m
Thu 11/55:35 am -
2 stops10h 30m
Deal found 10/2![Southwest logo]()
$446
This United Airlines deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/19:02 am -
2 stops13h 55m
Fri 11/61:09 am -
2 stops13h 28m
Deal found 10/1![United Airlines logo]()
$376
This Southwest deal was found by Cheapflights users on 10/3. Clicking the “Pick Dates” 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 12/13:10 pm -
2 stops8h 40m
Wed 12/95:40 am -
2 stops10h 35m
Deal found 10/3![Southwest logo]()
$446
This United Airlines deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/229:32 am -
1 stop10h 52m
Thu 1/288:05 am -
2 stops11h 12m
Deal found 9/29![United Airlines logo]()
$397
This Southwest deal was found by Cheapflights users on 10/3. Clicking the “Pick Dates” 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 11/267:15 am -
2 stops10h 20m
Thu 12/105:40 am -
2 stops10h 35m
Deal found 10/3![Southwest logo]()
$466
This American Airlines deal was found by Cheapflights users on 10/3. Clicking the “Pick Dates” 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 1/308:59 am -
1 stop11h 12m
Sun 2/77:03 am -
1 stop17h 53m
Deal found 10/3![American Airlines logo]()
$571
This Southwest deal was found by Cheapflights users on 10/3. Clicking the “Pick Dates” 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 11/252:10 pm -
2 stops10h 15m
Wed 12/912:30 pm -
2 stops10h 40m
Deal found 10/3![Southwest logo]()
$481
This United Airlines deal was found by Cheapflights users on 10/2. Clicking the “Pick Dates” 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 10/169:40 am -
1 stop10h 58m
Thu 11/52:52 pm -
1 stop9h 38m
Deal found 10/2![United Airlines logo]()
$446
This United Airlines deal was found by Cheapflights users on 9/29. 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 1/1610:15 am -
1 stop9h 45m
Sat 1/232:05 am -
2 stops12h 15m
Deal found 9/29![United Airlines logo]()
$447
This Southwest deal was found by Cheapflights users on 9/29. 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 1/1612:05 pm -
2 stops8h 00m
Sun 1/245:45 am -
2 stops7h 50m
Deal found 9/29![Southwest logo]()
$511
This United Airlines deal was found by Cheapflights users on 10/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/3110:27 am -
2 stops13h 09m
Wed 11/48:05 am -
1 stop7h 42m
Deal found 10/2![United Airlines logo]()
$476
This United Airlines deal was found by Cheapflights users on 9/29. 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 1/2311:00 am -
2 stops12h 36m
Fri 1/292:05 am -
2 stops12h 05m
Deal found 9/29![United Airlines logo]()
$486
This United Airlines deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” 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 10/305:10 am -
2 stops15h 14m
Sat 11/77:40 am -
2 stops14h 12m
Deal found 10/1![United Airlines logo]()
$513
This United Airlines deal was found by Cheapflights users on 10/3. Clicking the “Pick Dates” 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 12/99:00 am -
2 stops14h 36m
Sun 12/132:05 am -
2 stops15h 34m
Deal found 10/3![United Airlines logo]()
$516
This United Airlines deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” 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 10/305:30 am -
2 stops14h 54m
Sat 11/77:40 am -
2 stops12h 30m
Deal found 10/1![United Airlines logo]()
$546
This United Airlines deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/246:00 am -
2 stops14h 38m
Wed 10/2812:00 pm -
2 stops11h 54m
Deal found 10/1![United Airlines logo]()
$605
This United Airlines deal was found by Cheapflights users on 10/4. 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.
Sun 10/185:00 am -
2 stops31h 45m
Tue 10/201:00 am -
2 stops13h 32m
Deal found 10/4![United Airlines logo]()
$714
This United Airlines deal was found by Cheapflights users on 10/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/178:45 am -
2 stops14h 05m
Wed 10/211:25 pm -
2 stops10h 50m
Deal found 10/2![United Airlines logo]()
$831
This United Airlines deal was found by Cheapflights users on 9/29. 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 3/62:25 pm -
1 stop28h 35m
Sun 3/147:10 am -
1 stop7h 30m
Deal found 9/29![United Airlines logo]()
$932
This United Airlines deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/226:24 am -
1 stop16h 33m
Tue 12/291:09 am -
2 stops17h 11m
Deal found 9/30![United Airlines logo]()
$968
Last-minute flights from Kentucky to Puerto RicoDiscover last-minute flight deals from Kentucky to Puerto Rico. Data last updated October 4, 2026 and is based on user searches.
Discover last-minute flight deals from Kentucky to Puerto Rico. Data last updated October 4, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 10/2. Clicking the “Pick Dates” 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 10/188:59 pm -
1 stop16h 32m
Thu 10/227:00 am -
1 stop13h 23m
Deal found 10/2![Multiple Airlines logo]()
$343
This Kiwi.com deal was found by Cheapflights users on 10/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/197:35 pm -
1 stop19h 43m
Fri 10/235:11 pm -
2 stops17h 00m
Deal found 10/2![Multiple Airlines logo]()
$302
This Kiwi.com deal was found by Cheapflights users on 9/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/229:43 pm -
1 stop28h 10m
Wed 10/286:25 pm -
1 stop26h 28m
Deal found 9/30![Multiple Airlines logo]()
$328
This Kiwi.com deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/238:10 pm -
1 stop25h 45m
Thu 10/296:15 am -
2 stops14h 14m
Deal found 9/29![Multiple Airlines logo]()
$348
This Kiwi.com deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/267:08 pm -
1 stop20h 09m
Thu 10/296:15 am -
2 stops14h 14m
Deal found 9/29![Multiple Airlines logo]()
$294
This Kiwi.com deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/267:08 pm -
1 stop20h 09m
Fri 10/303:59 pm -
2 stops18h 12m
Deal found 9/29![Multiple Airlines logo]()
$305
This Kiwi.com deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/267:08 pm -
1 stop20h 09m
Sat 10/316:11 pm -
1 stop27h 18m
Deal found 9/29![Multiple Airlines logo]()
$347
This United Airlines deal was found by Cheapflights users on 10/2. Clicking the “Pick Dates” 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 10/3011:05 am -
2 stops10h 17m
Tue 11/38:25 am -
1 stop10h 05m
Deal found 10/2![United Airlines logo]()
$371
This Kiwi.com deal was found by Cheapflights users on 10/3. Clicking the “Pick Dates” 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 11/27:08 pm -
1 stop19h 11m
Mon 11/97:00 am -
1 stop12h 03m
Deal found 10/3![Multiple Airlines logo]()
$343
This Kiwi.com deal was found by Cheapflights users on 9/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/88:37 pm -
1 stop12h 38m
Thu 11/127:00 am -
2 stops14h 29m
Deal found 9/30![Multiple Airlines logo]()
$310
This Kiwi.com deal was found by Cheapflights users on 9/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/96:53 pm -
1 stop19h 26m
Tue 12/86:25 am -
2 stops35h 07m
Deal found 9/30![Multiple Airlines logo]()
$242
This Kiwi.com deal was found by Cheapflights users on 9/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/166:53 pm -
1 stop19h 26m
Sat 11/2110:54 pm -
2 stops37h 05m
Deal found 9/30![Multiple Airlines logo]()
$327
One-way flights from Kentucky to Puerto RicoSearch for one-way flight options from Kentucky to Puerto Rico. Find affordable one-way fares based on user searches. Data last updated October 4, 2026.
Search for one-way flight options from Kentucky to Puerto Rico. Find affordable one-way fares based on user searches. Data last updated October 4, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/197:35 pm -
1 stop19h 43m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/1![Multiple Airlines logo]()
$137
This Kiwi.com deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/267:08 pm -
1 stop20h 09m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![Multiple Airlines logo]()
$141
This Kiwi.com deal was found by Cheapflights users on 10/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/299:43 pm -
1 stop11h 32m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/2![Multiple Airlines logo]()
$146
This Kiwi.com deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2110:55 am -
2 stops38h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![Multiple Airlines logo]()
$147
This Kiwi.com deal was found by Cheapflights users on 9/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/229:43 pm -
1 stop25h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/29![Multiple Airlines logo]()
$152
This Kiwi.com deal was found by Cheapflights users on 9/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/2810:55 am -
2 stops22h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Multiple Airlines logo]()
$155
This Kiwi.com deal was found by Cheapflights users on 10/3. Clicking the “Pick Dates” 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 11/27:08 pm -
1 stop19h 11m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/3![Multiple Airlines logo]()
$158
This Delta deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/286:00 am -
1 stop10h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![Delta logo]()
$178
This American Airlines deal was found by Cheapflights users on 9/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/299:17 am -
2 stops13h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![American Airlines logo]()
$193
This American Airlines deal was found by Cheapflights users on 9/30. 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 10/289:17 am -
2 stops12h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/30![American Airlines logo]()
$198
This Kiwi.com deal was found by Cheapflights users on 10/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/267:59 pm -
2 stops38h 18m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/2![Multiple Airlines logo]()
$217
This United Airlines deal was found by Cheapflights users on 10/2. Clicking the “Pick Dates” 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 1/316:00 am -
2 stops14h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/2![United Airlines logo]()
$228
Find flight deals from Kentucky to Puerto Rico
Keep the following information in mind while searching for Kentucky to Puerto Rico flight deals. Data was last updated October 4, 2026.
Round-trip from | $242 (Kiwi.com) |
|---|---|
One-way from | $137 (Kiwi.com) |
Popular in | March |
Cheapest in | February |
Average price | $436 |
Cheapflights Fare Finder
Customize your flight search to find flights from Kentucky to Puerto Rico that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated October 4, 2026.
Use the filters below to find and compare flights from Kentucky to Puerto Rico that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
LouisvilleSan Juan
SDF Louisville Intl - SJU San Juan Luis Munoz Marin Intl
SDFSJU
Louisville Intl
Mon 10/26
7:08 pm-12:59 am
2 stops29h 51m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$178
LexingtonSan Juan
LEX Lexington Blue Grass - SJU San Juan Luis Munoz Marin Intl
LEXSJU
Lexington Blue Grass
Wed 10/28
6:00 am-4:49 pm
1 stop10h 49m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$178
LexingtonSan Juan
LEX Lexington Blue Grass - SJU San Juan Luis Munoz Marin Intl
LEXSJU
Lexington Blue Grass
Tue 11/3
7:10 am-10:22 pm
2 stops14h 12m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$178
LouisvilleSan Juan
SDF Louisville Intl - SJU San Juan Luis Munoz Marin Intl
SDFSJU
Louisville Intl
Sun 11/1
9:11 pm-12:59 am
2 stops26h 48m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$184
Quickest round-trip
LouisvilleSan Juan
SDF Louisville Intl - SJU San Juan Luis Munoz Marin Intl
SDFSJU
Louisville Intl
Sun 11/1
6:10 pm-12:55 am
1 stop5h 45m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$188
LouisvilleSan Juan
SDF Louisville Intl - SJU San Juan Luis Munoz Marin Intl
SDFSJU
Louisville Intl
Sat 10/31
10:27 am-11:36 pm
2 stops13h 09m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$188
LouisvilleSan Juan
SDF Louisville Intl - SJU San Juan Luis Munoz Marin Intl
SDFSJU
Louisville Intl
Sat 10/24
6:05 am-12:10 pm
1 stop6h 05m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$188
LouisvilleSan Juan
SDF Louisville Intl - SJU San Juan Luis Munoz Marin Intl
SDFSJU
Louisville Intl
Fri 10/30
10:27 am-9:22 pm
2 stops10h 55m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$188
LouisvilleSan Juan
SDF Louisville Intl - SJU San Juan Luis Munoz Marin Intl
SDFSJU
Louisville Intl
Tue 10/27
5:50 pm-11:50 pm
1 stop6h 00m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$188
LouisvilleSan Juan
SDF Louisville Intl - SJU San Juan Luis Munoz Marin Intl
SDFSJU
Louisville Intl
Sun 10/25
10:37 am-8:00 pm
1 stop9h 23m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$188
Showing 1-10 of 50 resultsSorted by cheapest first
Best time to book a flight from Kentucky to Puerto Rico
Have a flexible travel schedule? Discover the best time to fly to Puerto Rico from Kentucky with our price prediction graph.
LEX-SJU
SDF-SJU
SDF-BQN
PAH-SJU
OWB-SJU
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 Kentucky to Puerto Rico
USKY-PR0
LEX-SJU
SDF-SJU
SDF-BQN
PAH-SJU
What is the cheapest month to book a flight from Kentucky to Puerto Rico?
Currently, August is the cheapest month in which you can book a flight from Kentucky to Puerto Rico (average of $386). Flying from Kentucky to Puerto Rico in December is currently the most expensive (average of $562). 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 Kentucky to Puerto Rico?
To ensure you get the cheapest price possible for a flight from Kentucky to Puerto Rico, you should look to book at least 69 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
Related info for your journey
Find useful and relevant information for your journey from Kentucky to Puerto Rico. 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 Kentucky to Puerto Rico
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Puerto Rico by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Kentucky to Puerto Rico by cabin class
Find flights from Kentucky to Puerto Rico, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Kentucky and Puerto Rico flights
Browse other Kentucky and Puerto Rico flight options. Last updated on October 4, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Find a return flight route from Puerto Rico
Find the right flight back to Kentucky after your stay in Puerto Rico
Kentucky to Puerto Rico flights
Consider these flights traveling from Kentucky to Puerto Rico.
Top 4 airlines flying from Kentucky to Puerto Rico
Discover the top 4 airlines that operate flights from Kentucky to Puerto Rico. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated October 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$225 | Average$476 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$232 | Average$497 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$270 | Average$472 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$316 | Average$502 | FlexibilityNo cancel fee | On-time63% |