$95 Find Cheap Flights from Puerto Rico to Kentucky

1 adult
1 adult, Economy

KAYAK searches hundreds of travel sites at once for deals on flights to Kentucky

 
These are the airlines KAYAK users have selected most often from within our search results for flights to Kentucky, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results for flights to Kentucky, as well as popular online travel agencies
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KAYAK's insights & trends for flights to Kentucky

Get data-powered insights and trends for flights to Kentucky to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest month to fly from Puerto Rico to Kentucky?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for flights from Puerto Rico to Kentucky, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Puerto Rico to Kentucky is January, when tickets cost $284 (return) on average. On the other hand, the most expensive months are May and November, when the average cost of round-trip tickets is $475 and $459 respectively.

How far in advance should I book a flight from Puerto Rico to Kentucky?

To calculate weekly average prices, KAYAK takes all prices for each week before departure over the last year for round-trip flights to Kentucky, removes the top 0.1% to account for outliers, and then takes the average of all the values for each week.

To get a below average price on the flight from Puerto Rico to Kentucky, you should book around 2 weeks before departure. For the absolute cheapest price, our data suggests you should book 23 weeks before departure.


Good to know

Low seasonMarch
High seasonDecember
Cheapest flight$95
Best time to beat the crowds with an average 1% drop in price.
Most popular time to fly with an average 10% increase in price.
Flight from San Juan to Cincinnati

FAQs for booking flights from Puerto Rico to Kentucky

  • How does KAYAK find such low prices on flights from Puerto Rico to Kentucky?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Puerto Rico to Kentucky.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Puerto Rico to Kentucky?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Puerto Rico to Kentucky is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Puerto Rico to Kentucky?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Puerto Rico to Kentucky with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Puerto Rico to Kentucky?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Puerto Rico to Kentucky up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

  • What is the cheapest day to fly to Kentucky?

    Based on KAYAK data, the cheapest day to fly to Kentucky is Tuesday where round-trip tickets can be as cheap as $369. On the other hand, the most expensive day to fly is Saturday, where round-trip prices are $510 on average.

  • What is the cheapest time of day to fly to Kentucky?

    The cheapest time of day to fly to Kentucky is generally at night, when round-trip flights cost $227 on average. Morning departures are around 5% more expensive than evening flights, on average. The most expensive time of day to fly to Kentucky is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $491.

Top 3 airlines serving from Puerto Rico to Kentucky

 
See real verified KAYAK customer reviews for airlines flying to Kentucky. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline from Puerto Rico to Kentucky. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Puerto Rico to Kentucky? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
8.0
SouthwestOverall score based on 4287 reviews
7.6Entertainment
8.6Crew
8.0Comfort
8.2Boarding
7.1Food
Airline reviews

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

6.0 GoodDavid, Jun 2025BWI - COS
Read more Southwest reviews

Southwest is typically delayed, and it gets wearisome. It is no longer a discount airline and you get way less than you pay for when it comes to comfort and Ce.

We sat on the plane on the tarmac for 4 hours.

I'm not a fan of Southwest's model. I don't like the herding style of boarding.

Flight crew and cabin crew were great. I had to rearrange flights because my original flight was 3hrs delayed for weather, the rub is the flight I moved to boarded on time then we sat at the gate for 2 hours because scheduling stole our first officer for another flight, TWICE. Then our actual FO was an hour delayed. To make it worse my original flight went from a 3 hour delay to departing 15min EARLY. Just poor scheduling operations all around.

Bring back peanuts Take our drink orders when were all seated, especially after you switch to assigned seating.

Staff was far less than helpful at all times. Departure and arrival times mean nothing to Southwest. Extremely disappointed, will never fly with them again, and I’ll be sure to share my experience with all.

It is southwest seat was ok. Not the most comfortable seat

I’ve always loved Southwest. No issues at all. I was flying standby and the gate agent was extremely friendly and helpful. Boarding was smooth and I was able to get a window seat in the emergency exit row. Crew was fantastic! They were very professional and accommodating. We had to divert from our destination due to weather but the flight crew kept everyone at ease and informed us of all pertinent information. Excellent flight

The price of the tickets isn't matching the flight experience. No matter how long the flight is, you're only getting pretzels. The flight attendants looked unkept and over it.

Plz don't take away free bags and free seating

Great service. Flight was delayed while we sat on the runway for a couple of hours. Weather related. Staff made is very bearable. The steward servicing the first class cabin was exceptional. Thank you! 💗

5 hours of delay that could've been much shorter if Delta had taken the 1 hour delay they imposed on the flight before boarding to run any of the plane checks required for flight to find the hydraulic issue that required nearly 3 hours to fix. $24 of meal credit buys a sandwich and a soft drink. Poor communication within the terminal about what gate we'd be re-boarding from and when we'd be re-boarding.

Amazing flight! I have never noticed the uniforms of the attendants before in twenty years of flying except today when one female had the most amazing dress on. It was beautifully designed and showed she was in charge. I never dreamed I would google who designed Delta uniforms . The ultimate compliment is when another woman admires your outfit. . I hope your designer puts it on the market

It would be nice if was given wires ear buds. Overall was a good experience was able to sleep on the plane

My flight was 6 pm 6/6. Every hour they delayed it again - air condition issues then no pilot then the crew had worked too many hours and cancelled the flight at 11 pm. Sent customers to NJ a 45 minutes uber ride to a hotel. Had to be back by 5 am for a 7 am flight and again no pilot etc with another three hours of delays.

The entertainment and wifi mostly didn't work on this flight.

Boarding was tough as we had to take a bus out to the plane and walk up a lot of stairs. Difficult with heavy carry-ons that said I got an entire empty row of seats, which was excellent for an international flight. Food was very mediocre but happy with the comfort so not complaining.

Terrible entertainment system - kept freezing and audio kept cutting out. Snacks were mediocre at best for a 5 hour flight.

The check in and bag drop off for Sky Priority members is slow. The Clear security was also slow - a TSA issue.

Delta is better for short flights and very low need for customer service. Avoid for longer flights

It was one of my worst flight ever. First they were changing the gate for at least 4 times, changing from gate D7 to D12 to D44. Considering the size of the Miami Airport, we are talking about long distance and the train at the airport was not working. Then the flight was delayed around one hour. Then finally we boarded into the plane and when everybody was seated, there was an announcement that there is an issue with one of the tire of the plane, so we all had to get out of the plane with our belongings, to replace the tire. So we had around 2.5-hour delay

Most miserable flight ever. We waited almost 2 hours on the runway because the flight was oversold. American offered $1200 credit. Then there was some nonsense about weight distribution. Ridiculous. No food for 8 plus hours on the flight. I will be writing a letter.

Honestly, I haven’t flown American in years, probably due to the pandemic and my being unable to travel for certain periods in the last two years, but it was a good experience to dig out or obtain a new American Airlines account after many years of traveling for business with American in the past.

The plane was probably full boarding was easy. We were able to check our carry-on luggage for free. It was a return flight through Philly to LA. Never saw a stewardess do a demonstration of emergency Procedures. I think my flight was pretty full

Plane, flight, crew, captain were all great. The first flight had a Chipotle box lunch...delicious.

Plane, flight, crew, captain were all great. The first flight had a Chipotle box lunch...delicious. this return flight not as tasty, but filling.

The flight was 2 hour delayed, otherwise everything was excellent. The delay was due to the hourly limit requirement so given that as a reason, I'm happy with the flight!

Weather delay for 2.5 hours followed by half hour crew delay, did not have ginger ale, uncomfortable seats

The pilots are always hauling in the sky. No issues with boarding only problem was layover was shortened too much by weather but luckily the next flight was still boarding and did not missit

So awful Unreliable Unfriendly Bad Mad Mean Smelly Hot Late Overbooked Understaffed Expensive Cramped Narcs If they were a fruit they’d be rotten durian

Book cheap flights from Puerto Rico to Kentucky

Recent round-trip flight deals

 
These are the cheapest round-trip flights to Kentucky found on KAYAK in the last 72 hours.
8/20Wed
1 stopFrontier
7h 12mSJU-CVG
8/24Sun
1 stopFrontier
13h 23mCVG-SJU
$189
9/11Thu
1 stopFrontier
19h 58mSJU-BNA
9/15Mon
1 stopFrontier
6h 06mBNA-SJU
$189
8/22Fri
1 stopSpirit Airlines
6h 09mSJU-BNA
8/25Mon
1 stopSpirit Airlines
8h 41mBNA-SJU
$214
7/11Fri
1 stopSpirit Airlines
10h 57mSJU-BNA
7/14Mon
1 stopSpirit Airlines
10h 53mBNA-SJU
$216
8/15Fri
1 stopDelta
6h 09mSJU-CVG
8/17Sun
1 stopDelta
5h 40mCVG-SJU
$225
8/21Thu
1 stopDelta
8h 24mSJU-SDF
8/25Mon
1 stopDelta
5h 51mSDF-SJU
$225
9/13Sat
1 stopSouthwest
5h 50mSJU-BNA
9/16Tue
1 stopSouthwest
6h 10mBNA-SJU
$239
10/2Thu
1 stopAmerican Airlines
8h 54mSJU-CVG
10/7Tue
1 stopAmerican Airlines
8h 13mCVG-SJU
$250
8/9Sat
2 stopsAmerican Airlines
18h 27mSJU-CVG
8/20Wed
2 stopsAmerican Airlines
17h 55mCVG-SJU
$265
7/11Fri
1 stopSouthwest
8h 25mSJU-SDF
7/18Fri
1 stopSouthwest
6h 50mSDF-SJU
$275

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Recent one-way flight deals

 
Only flying one-way? Below are some of the best deals for one-way flights to Kentucky found on KAYAK in the last 72 hours.
8/20Wed
1 stopFrontier
7h 12mSJU-CVG
$95
8/22Fri
1 stopFrontier
14h 31mSJU-BNA
$95
7/10Thu
1 stopSpirit Airlines
10h 57mSJU-BNA
$103
7/15Tue
1 stopSpirit Airlines
24h 49mSJU-BNA
$104
10/15Wed
2 stopsAmerican Airlines
10h 37mSJU-CVG
$113
8/21Thu
1 stopDelta
8h 24mSJU-SDF
$113
8/22Fri
1 stopDelta
6h 04mSJU-LEX
$113
6/18Wed
1 stopAmerican Airlines
9h 23mSJU-CVG
$133
6/28Sat
1 stopSouthwest
8h 20mSJU-SDF
$143
6/27Fri
1 stopSouthwest
11h 40mSJU-SDF
$168

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Last minute flights to Kentucky

Last minute flight, train and bus deals

 
These last-minute flight deals are the cheapest flights found on KAYAK in the last 72 hours for flights to Kentucky that are departing in the next 10 days.
6/15Sun
multi-stop
15h 15mSJU-BNA
6/20Fri
multi-stop
12h 19mBNA-SJU
$340
6/14Sat
multi-stop
17h 15mSJU-BNA
6/20Fri
multi-stop
12h 19mBNA-SJU
$358
6/15Sun
multi-stopSouthwest
8h 55mSJU-SDF
6/20Fri
multi-stopSouthwest
10h 05mSDF-SJU
$373
6/17Tue
multi-stopSpirit Airlines
5h 50mSJU-BNA
6/25Wed
multi-stopSpirit Airlines
28h 29mBNA-SJU
$396
6/17Tue
multi-stopSouthwest
9h 05mSJU-SDF
6/19Thu
multi-stopSouthwest
10h 05mSDF-SJU
$398
6/13Fri
multi-stopAmerican Airlines
14h 17mSJU-SDF
6/16Mon
multi-stopAmerican Airlines
9h 34mSDF-SJU
$413
6/16Mon
multi-stopSpirit Airlines
5h 50mSJU-BNA
6/28Sat
multi-stopSpirit Airlines
14h 31mBNA-SJU
$421
6/13Fri
multi-stopAmerican Airlines
10h 11mSJU-SDF
6/16Mon
multi-stopAmerican Airlines
9h 34mSDF-SJU
$448
6/13Fri
multi-stopDelta
6h 43mSJU-SDF
6/16Mon
multi-stopDelta
7h 24mSDF-SJU
$461
6/13Fri
multi-stopDelta
9h 24mSJU-BNA
6/17Tue
multi-stopDelta
5h 44mBNA-SJU
$610

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Everything you need to know for your flight to Kentucky

Cabin class types available on flights to Kentucky

Cabin classes available on flights to Kentucky. Prices are the lowest found on KAYAK over the last 7 days. Price and availability is not guaranteed.

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