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Puerto Rico

$110+ Cheap flights from Kentucky to Puerto Rico

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 8/17. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — SJU
Aug 7 — Aug 141
Fri 8/7
Fri 8/14
1 adult, Economy
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Cheap flight deals from Kentucky to Puerto Rico

Cheapest flights from Kentucky to Puerto Rico
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 July 8, 2026.

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 9/257:27 pm
SDF
-
SJU
2 stops15h 33m
American Airlines
Wed 9/306:00 am
SJU
-
SDF
2 stops11h 14m
American Airlines
Deal found 7/7$220
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/68:15 am
TYS
-
SJU
1 stop16h 26m
Multiple Airlines
Thu 8/136:44 am
SJU
-
TYS
1 stop12h 55m
Multiple Airlines
Deal found 7/7$223
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
1 stop7h 34m
United Airlines
Mon 9/142:55 pm
SJU
-
SDF
1 stop8h 04m
United Airlines
Deal found 7/7$236
This Kiwi.com deal was found by Cheapflights users on 7/2. 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 8/1012:50 pm
TYS
-
SJU
1 stop24h 51m
Multiple Airlines
Fri 8/146:26 am
SJU
-
TYS
1 stop15h 58m
Multiple Airlines
Deal found 7/2$244
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/147:15 pm
TYS
-
SJU
1 stop29h 26m
Multiple Airlines
Sun 8/237:00 am
SJU
-
TYS
1 stop9h 25m
Multiple Airlines
Deal found 7/7$245
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/19:05 pm
LEX
-
SJU
1 stop27h 36m
Multiple Airlines
Fri 8/76:00 am
SJU
-
LEX
1 stop28h 30m
Multiple Airlines
Deal found 7/7$262
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/266:00 am
LEX
-
SJU
1 stop7h 42m
Delta
Tue 9/15:49 pm
SJU
-
LEX
1 stop6h 10m
Delta
Deal found 7/4$266
This Kiwi.com deal was found by Cheapflights users on 7/3. 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 8/178:35 am
TYS
-
SJU
1 stop16h 06m
Multiple Airlines
Sat 8/226:35 am
SJU
-
TYS
1 stop27h 29m
Multiple Airlines
Deal found 7/3$266
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$268
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/1012:50 pm
TYS
-
SJU
1 stop24h 51m
Multiple Airlines
Sat 8/156:00 am
SJU
-
TYS
1 stop10h 13m
Multiple Airlines
Deal found 7/7$269
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/312:40 pm
TYS
-
SJU
1 stop25h 20m
Multiple Airlines
Thu 8/66:00 am
SJU
-
TYS
1 stop8h 06m
Multiple Airlines
Deal found 7/7$271
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/147:15 pm
TYS
-
SJU
1 stop29h 26m
Multiple Airlines
Mon 8/246:44 am
SJU
-
TYS
1 stop11h 51m
Multiple Airlines
Deal found 7/7$272

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 July 8, 2026.

Round-trip from

$220
(United Airlines)

One-way from

$110
(American Airlines)

Popular in

December

Cheapest in

October

Average price

$496
From Kentucky to Puerto Rico
Search Deals
One-way flight from Kentucky to Puerto Rico
Search Deals
Highest demand for flights based on searches. 3% potential increase in price ($14 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in July 2026
Search Deals

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 2,558,603 searches. Data last updated July 8, 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

Price

Cheapest round-trip
Quickest round-trip

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

Wed 8/26

6:00 am-1:42 pm

1 stop7h 42m

San Juan Luis Munoz Marin Intl

Tue 9/1

5:49 pm-11:59 pm

1 stop6h 10m

$266

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

Mon 10/26

7:10 am-2:40 pm

1 stop7h 30m

San Juan Luis Munoz Marin Intl

Fri 10/30

1:35 pm-11:28 pm

1 stop9h 53m

$310

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

Fri 8/28

11:50 am-10:50 pm

1 stop11h 00m

San Juan Luis Munoz Marin Intl

Sun 8/30

5:30 am-5:45 pm

1 stop12h 15m

$316

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

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

Sat 8/15

2:39 pm-10:29 pm

1 stop7h 50m

San Juan Luis Munoz Marin Intl

Fri 8/21

1:19 pm-9:06 pm

1 stop7h 47m

$316

NashvilleAguadilla

BNA - BQN

BNABQN

Nashville Intl

Wed 10/14

1:15 pm-11:09 pm

1 stop8h 54m

Aguadilla Borinquen

Tue 10/20

12:15 am-8:26 am

1 stop9h 11m

$322

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

Sat 8/29

11:15 am-11:43 pm

1 stop12h 28m

San Juan Luis Munoz Marin Intl

Sat 9/12

10:16 am-11:51 pm

2 stops13h 35m

$326

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

Fri 10/23

8:03 pm-11:31 am

2 stops15h 28m

San Juan Luis Munoz Marin Intl

Sat 10/31

2:27 pm-11:57 pm

2 stops9h 30m

$326

NashvilleSan Juan

BNA - SJU

BNASJU

Nashville Intl

Wed 9/23

11:15 am-10:00 pm

1 stop9h 45m

San Juan Luis Munoz Marin Intl

Tue 9/29

6:00 am-1:15 pm

2 stops8h 15m

$326

NashvilleSan Juan

BNA - SJU

BNASJU

Nashville Intl

Sun 10/4

6:15 am-3:42 pm

1 stop8h 27m

San Juan Luis Munoz Marin Intl

Fri 10/9

3:56 pm-11:14 pm

1 stop8h 18m

$326

Flights are sorted by cheapest round-trip flights first.

Deals found on 7/5

Showing 1-10 of 60 resultsSorted by cheapest first
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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.
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

What is the cheapest month to book a flight from Kentucky to Puerto Rico?

Currently, January is the cheapest month in which you can book a flight from Kentucky to Puerto Rico (average of $113). Flying from Kentucky to Puerto Rico 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 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 83 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.

  • How long is the flight from Kentucky to Puerto Rico?

    Departing from Kentucky to Puerto Rico will take you 9h 08m. Airlines will cover a distance of 1807 mi. When browsing for deals, the options you’ll see will be for both nonstop flights and flights with stops.

  • What are the cheapest airlines to fly from Kentucky to Puerto Rico one-way?

    For one-way options, check prices for Delta. According to our data, you can fly for as low as $113. Users have also found prices from $123 and $142 on American Airlines and Southwest, respectively.

  • Can I find deals for flights from Kentucky to Puerto Rico that include hotel bookings?

    Yes. In addition to deals on Kentucky to Puerto Rico flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Kentucky to Puerto Rico?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Kentucky to Puerto Rico.

  • Can I find deals for business class flights from Kentucky to Puerto Rico?

    Yes. Cheapflights offers flight deals from Kentucky to Puerto Rico by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Kentucky to Puerto Rico?

    Currently, January is the cheapest month in which you can book a flight from Kentucky to Puerto Rico (average of $113). Flying from Kentucky to Puerto Rico 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.

See more FAQs

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 for Kentucky to Puerto Rico

See prices for flight routes from nearby airports that may be better suited for you.
John F Kennedy Intl to Santiago de los Caballeros flights
Orlando to Luis Munoz Marin Intl flights
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Atlanta to Luis Munoz Marin Intl flights
Hobby to Luis Munoz Marin Intl flights
LaGuardia to Punta Cana flights
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Tampa to Luis Munoz Marin Intl flights
LaGuardia to Santo Domingo flights
George Bush Intcntl to Luis Munoz Marin Intl flights
Dulles Intl to Punta Cana flights
Atlanta to Punta Cana flights
Boston to Oranjestad flights
John F Kennedy Intl to Bridgetown flights
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LaGuardia to Montego Bay flights
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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 2,558,603 searches. Data last updated July 8, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$205Average$488FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$225Average$472FlexibilityNo cancel feeOn-time63%
American AirlinesCheapest$226Average$474FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$259Average$472FlexibilityNo cancel feeOn-time69%

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