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Puerto Rico

$103+ 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 11/15. Fares are subject to change and may not be available on all flights or dates of travel.
SDF — SJU
oct. 15 — oct. 221
mié. 10/15
mié. 10/22
1 adult, Economy
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Cheap 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 septiembre 15, 2025.

Round-trip from

$206
(Southwest)

One-way from

$103
(Southwest)

Popular in

December

Cheapest in

October

Average price

$368
From Kentucky to Puerto Rico
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One-way flight from Kentucky to Puerto Rico
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Highest demand for flights based on searches. 1% potential increase in price ($7 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($12 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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Find 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 septiembre 15, 2025.

This Southwest deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” 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.
sáb. 11/155:20 pmBNA - SJU
Nonstop3h 55mSouthwest
sáb. 12/611:20 amSJU - BNA
Nonstop4h 35mSouthwest
Deal found 9/12$206
This Southwest deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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.
sáb. 11/155:20 pmBNA - SJU
Nonstop3h 55mSouthwest
mar. 11/189:40 amSJU - BNA
1 stop8h 50mSouthwest
Deal found 9/15$211
This Kiwi.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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.
lun. 10/137:59 pmCVG - SJU
1 stop19h 25mFrontier
mié. 10/299:00 amSJU - CVG
1 stop15h 59mFrontier
Deal found 9/13$216
This American Airlines deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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.
lun. 12/86:50 amSDF - SJU
1 stop16h 02mAmerican Airlines
jue. 12/112:50 pmSJU - SDF
2 stops7h 58mAmerican Airlines
Deal found 9/14$225
This American Airlines deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” 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.
mar. 10/141:05 pmCVG - SJU
1 stop10h 54mAmerican Airlines
sáb. 10/255:25 amSJU - CVG
1 stop10h 04mAmerican Airlines
Deal found 9/14$225
This American Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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.
jue. 10/308:18 amSDF - SJU
1 stop13h 52mAmerican Airlines
jue. 11/64:56 pmSJU - SDF
1 stop7h 47mAmerican Airlines
Deal found 9/15$226
This Kiwi.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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.
vie. 10/175:25 pmBNA - SJU
1 stop8h 05mMultiple Airlines
sáb. 10/189:48 amSJU - BNA
1 stop29h 29mMultiple Airlines
Deal found 9/13$234
This American Airlines deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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.
mié. 10/16:49 pmCVG - SJU
2 stops16h 22mAmerican Airlines
mar. 10/75:30 amSJU - CVG
1 stop12h 10mAmerican Airlines
Deal found 9/13$235
This American Airlines deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” 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.
sáb. 10/255:30 amEVV - SJU
1 stop17h 24mAmerican Airlines
mié. 10/295:30 amSJU - EVV
2 stops16h 29mAmerican Airlines
Deal found 9/15$235
This Kiwi.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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.
sáb. 10/114:06 pmBNA - SJU
1 stop8h 56mMultiple Airlines
sáb. 10/189:48 amSJU - BNA
1 stop29h 29mMultiple Airlines
Deal found 9/13$236
This Kiwi.com deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” 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.
vie. 10/248:23 amBNA - SJU
1 stop10h 33mMultiple Airlines
dom. 10/265:30 amSJU - BNA
1 stop15h 09mMultiple Airlines
Deal found 9/13$240
This United Airlines deal was found by Cheapflights users on 9/12. Clicking the “Pick Dates” 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.
sáb. 11/152:25 pmBNA - SJU
1 stop8h 11mUnited Airlines
vie. 12/52:05 amSJU - BNA
1 stop8h 57mUnited Airlines
Deal found 9/12$243

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 septiembre 15, 2025.
Use the filters below to find and compare flights from Kentucky to Puerto Rico that are best for you.

Fly from

Kentucky

Fly to

Puerto Rico

Route

Depart

Return

Price

NashvilleSan Juan

BNA - SJU

BNASJU

Nashville Intl

sáb. 11/15

5:20 pm-11:15 pm

Nonstop3h 55m

San Juan Luis Munoz Marin Intl

sáb. 12/6

11:20 am-1:55 pm

Nonstop4h 35m

$206

NashvilleSan Juan

BNA - SJU

BNASJU

Nashville Intl

sáb. 11/15

5:20 pm-11:15 pm

Nonstop3h 55m

San Juan Luis Munoz Marin Intl

mar. 11/18

9:40 am-4:30 pm

1 stop8h 50m

$211

NashvilleSan Juan

BNA - SJU

BNASJU

Nashville Intl

lun. 11/10

2:52 pm-11:13 pm

1 stop6h 21m

San Juan Luis Munoz Marin Intl

jue. 11/13

1:57 pm-11:04 pm

1 stop11h 07m

$215

NashvilleSan Juan

BNA - SJU

BNASJU

Nashville Intl

mar. 11/4

11:19 am-9:00 pm

1 stop7h 41m

San Juan Luis Munoz Marin Intl

jue. 11/20

8:10 am-2:28 pm

1 stop8h 18m

$215

NashvilleSan Juan

BNA - SJU

BNASJU

Nashville Intl

dom. 2/15

7:25 pm-9:55 am

1 stop12h 30m

San Juan Luis Munoz Marin Intl

jue. 2/19

2:20 pm-8:05 pm

1 stop7h 45m

$215

NashvilleSan Juan

BNA - SJU

BNASJU

Nashville Intl

sáb. 10/25

3:30 pm-11:45 pm

1 stop7h 15m

San Juan Luis Munoz Marin Intl

mar. 10/28

6:10 am-2:20 pm

2 stops9h 10m

$215

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

dom. 11/9

5:00 am-8:58 pm

1 stop14h 58m

San Juan Luis Munoz Marin Intl

mié. 11/12

4:43 pm-11:09 pm

1 stop7h 26m

$225

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

jue. 10/30

8:18 am-10:10 pm

1 stop13h 52m

San Juan Luis Munoz Marin Intl

jue. 11/6

4:56 pm-11:43 pm

1 stop7h 47m

$226

EvansvilleSan Juan

EVV - SJU

EVVSJU

Evansville Dress Regional

sáb. 10/25

5:30 am-11:54 pm

1 stop17h 24m

San Juan Luis Munoz Marin Intl

mié. 10/29

5:30 am-8:59 pm

2 stops16h 29m

$235

NashvilleSan Juan

BNA - SJU

BNASJU

Nashville Intl

sáb. 11/15

2:25 pm-12:36 am

1 stop8h 11m

San Juan Luis Munoz Marin Intl

vie. 12/5

2:05 am-9:02 am

1 stop8h 57m

$243

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/15

Showing 1-10 of 60 results
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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, September is the cheapest month in which you can book a flight from Kentucky to Puerto Rico (average of $254). Flying from Kentucky to Puerto Rico in June is currently the most expensive (average of $339). 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.

What is the cheapest time of day to fly from KY to PR?

Find hourly flight availability from Kentucky to Puerto Rico. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated septiembre 15, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Kentucky to Puerto Rico as you normally would.

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 3h 55m. Airlines will cover a distance of 1753 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 Southwest. According to our data, you can fly for as low as $103. Users have also found prices from $108 and $113 on Delta and American Airlines, 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, September is the cheapest month in which you can book a flight from Kentucky to Puerto Rico (average of $254). Flying from Kentucky to Puerto Rico in June is currently the most expensive (average of $339). 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.
Newark to Luis Munoz Marin Intl flights
John F Kennedy Intl to Luis Munoz Marin Intl flights
John F Kennedy Intl to Santo Domingo flights
John F Kennedy Intl to Santiago de los Caballeros flights
Newark to Santiago de los Caballeros flights
LaGuardia to Luis Munoz Marin Intl flights
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Dallas/Fort Worth to Luis Munoz Marin Intl flights
LaGuardia to Punta Cana flights
John F Kennedy Intl to Port of Spain flights
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John F Kennedy Intl to Kingston flights
Hartford to Luis Munoz Marin Intl flights
Atlanta to Montego Bay flights
Hobby to Luis Munoz Marin Intl flights
Fort Lauderdale to Luis Munoz Marin Intl flights
Boston to Punta Cana flights
LaGuardia to Montego Bay flights
Tampa to Luis Munoz Marin Intl flights
LaGuardia to Santo Domingo flights
John F Kennedy Intl to Simpson Bay flights
LaGuardia to Oranjestad flights
Newark to Saint Thomas Island flights
Raleigh to Luis Munoz Marin Intl flights
Dulles Intl to Punta Cana flights
George Bush Intcntl to Luis Munoz Marin Intl flights
Newark to Nassau flights
John F Kennedy Intl to Nassau flights
John F Kennedy Intl to Saint Thomas Island flights
Minneapolis to Luis Munoz Marin Intl flights
LaGuardia to Santiago de los Caballeros flights
O'Hare Intl to Montego Bay flights
Miami to Luis Munoz Marin Intl flights
O'Hare Intl to Punta Cana flights
Atlanta to Punta Cana flights

Top 5 airlines flying from Kentucky to Puerto Rico

Discover the top 5 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 septiembre 15, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$152Average$290FlexibilityNo cancel feeOn-time65%
SouthwestCheapest$225Average$461FlexibilityNo cancel feeOn-time63%
DeltaCheapest$225Average$404FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$263Average$518FlexibilityNo cancel feeOn-time71%
United AirlinesCheapest$275Average$509FlexibilityNo cancel feeOn-time69%

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