$102 Find Cheap Flights from Puerto Rico to Kentucky - Compare and Save

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Puerto Rico to Kentucky departing on 10/1. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

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Cheap Flights from Puerto Rico to Kentucky

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Puerto Rico to Kentucky that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Puerto Rico to Kentucky

Tue, Sep 29 - Mon, Oct 5
Multiple Airlines Logo
8:45 am - 10:05 am
SJU
-
TYS
25h 20m
1 stop
Multiple Airlines Logo
4:41 pm - 10:13 am
TYS
-
SJU
17h 32m
1 stop
$242Multiple Airlines
Thu, Oct 1 - Mon, Oct 5
Multiple Airlines Logo
7:00 am - 4:37 pm
SJU
-
BNA
10h 37m
1 stop
Multiple Airlines Logo
5:40 pm - 1:52 am
BNA
-
SJU
7h 12m
1 stop
$247Multiple Airlines
Fri, Aug 28 - Fri, Sep 11
Frontier Logo
5:37 pm - 10:05 am
SJU
-
CVG
16h 28m
1 stop
Frontier Logo
12:43 pm - 11:58 pm
CVG
-
SJU
11h 15m
2 stops
$270Frontier
Tue, Oct 20 - Sat, Oct 24
Frontier Logo
4:39 pm - 5:33 pm
SJU
-
CVG
24h 54m
1 stop
Frontier Logo
12:48 pm - 11:41 pm
CVG
-
SJU
10h 53m
2 stops
$274Frontier
Thu, Sep 24 - Mon, Sep 28
Delta Logo
5:59 pm - 11:59 pm
SJU
-
LEX
6h 00m
1 stop
Delta Logo
12:40 pm - 10:19 pm
LEX
-
SJU
9h 39m
1 stop
$296Delta
Thu, Sep 24 - Mon, Sep 28
Delta Logo
5:59 pm - 11:59 pm
SJU
-
LEX
6h 00m
1 stop
Delta Logo
10:08 am - 4:49 pm
LEX
-
SJU
6h 41m
1 stop
$296Delta
Fri, Sep 11 - Sun, Sep 13
American Airlines Logo
3:41 pm - 11:22 pm
SJU
-
SDF
7h 41m
1 stop
American Airlines Logo
6:00 am - 3:29 pm
SDF
-
SJU
9h 29m
1 stop
$336American Airlines
Wed, Oct 21 - Sun, Oct 25
American Airlines Logo
12:13 pm - 12:07 am
SJU
-
SDF
11h 54m
1 stop
American Airlines Logo
5:04 am - 11:20 am
SDF
-
SJU
6h 16m
1 stop
$336American Airlines
Tue, Oct 13 - Sat, Oct 17
Southwest Logo
6:35 am - 5:10 pm
SJU
-
SDF
10h 35m
1 stop
Southwest Logo
5:35 am - 12:25 pm
SDF
-
SJU
6h 50m
1 stop
$336Southwest
Tue, Oct 6 - Sat, Oct 10
Southwest Logo
12:40 pm - 9:35 pm
SJU
-
SDF
8h 55m
1 stop
Southwest Logo
3:35 pm - 10:10 pm
SDF
-
SJU
6h 35m
1 stop
$336Southwest
Booking Insights

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 December, when tickets cost $163 (return) on average. On the other hand, the most expensive months are September and April, when the average cost of round-trip tickets is $560 and $311 respectively.

Good to know

Low season

February

Cheapest flight

$102
Best time to beat the crowds with an average 19% drop in price.
Most popular time to fly and prices are also 12% lower on average.
Flight from San Juan to Nashville

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.

Reviews of the 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 4227 reviews
8.0Comfort
8.6Crew
7.0Food
7.5Entertainment
8.1Boarding
Airline reviews

No wifi, seems to be very common with Southwest currently. Everything else was normal.

8.0 ExcellentSean, Jul 2026
HOU - LGB
Read more Southwest reviews

No wifi, seems to be very common with Southwest currently. Everything else was normal.

Poor customer service, no accommodation for passengers when the flight was delayed over 5 hours.

The flight was fine. Seats were very comfortable. Attendants were very friendly -

Friendly crew kept coming by to make sure all was ok, provide additional refreshments, etc.

It was good. Last flight was delayed but I always say that is in God's plan

Terrible all around. Left prior review detailing massive delay/cancellation to then rebook travel. Topping on the cake was lost luggage even after travel to ultimate destination was secured on a new plane(s).

Never went on board this flight. Kayak uses Underpricer (which is a scam business) as it's "customer service provider". This customer service is a classic bait and switch "service". I Got caught in the UnderPricer Bait and switch scam. 14 hours on the phone with people from India with heavy accents and upselling me to useless products. The original sell was a flight on spirit. Then they contact me later, an say after they have my money that the flight is no good as is is only one seat for a party of two. I am still in dispute to get my money back. Went to Spirit direct and had a beautiful vacation. I should never have used Kayak and their rip off artists UnderPricer.

The seats were a bit cramped and worn, but otherwise okay.

Since the flight wasn’t full, we had some extra room. Crew was great

I like everything about Southwest. From customer service to crew and prices. I travel a lot during the year and Southwest is the best!!

Poor communication, we sat on the plane for an hour before pushing back. They were oversold and with a full plane kept looking for someone to step off for someone else to board. So after an hour wait at the gate we missed our departure window and proceeded to spend an additional hour on the tarmac waiting for a refiled flight plan according to the pilots. Occasional updates, somewhat insensitive crew to passengers needing to use the lavatory (it was 2 hrs beyond what anyone expected). Overall just poor execution...especially when the flight was listed as "arriving early" up until about 30 minutes past our departure time.

No tv. No free wifi. They need to ipgrade these planes - especially on a 2 hour flight.

The seats were really comfortable. Flight crew were friendly with passengers. Overall was a great flight.

Great crew, flight on time, luggage pick up a breeze

Lady Pilot was perfect in every way wheels up to wheels down communication, professionalism, excellent on time departure and on time arrival, excellent communication! Fantastic job with Superb attitude!!

Unfortunately I was stuck next to someone who should have purchased 2 seats instead of taking up their space and mine. I couldn’t move the entire 3+ hour flight. Very uncomfortable flight.

More extra space was awesome. Even though I was on the first groups to board, bin compartments were already occupied by passengers seated on other seat numbers. That is unacceptable.

Crew went over and above to be helpful. Plane had mechanical problems that caused us to depart late.

The flight was excellent, I recommend people to fly with Delta

When we enter the airplane there were many water drops falling from the ceiling all the way long to the seat , and when it departs were even more over us getting the hair wet , and later on was too hot , the A/C not work well.

The gate got changed several times and the flight was delayed over an hour. Awful experience

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

No Snacks or Entertainment. The flight was short, snacks should still be given.

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

My Internet did not work for Outlook email or basically anything. I paid for one hour of in-flight usage and it was terrible. I spent a lot of time on different sites and browsers with no luck and a lot of frustration. Other than that, the flight was on time, crew was nice, service was fine. Seat was OK even though I paid for the extra 6 inches. I cannot imagine how tight the seats in the back must be.

Everything was fine. Flight boarded and departed on time. Seating was spacious enough for my carryon to fit under the seat in front of me. No complaints at all. Flight even arrived early.

Boston ticket agent Cheryl Porter is WONDERFUL. Our Iberia flight to Barcelona was cancelled the morning we were scheduled to leave and Cheryl was our super hero - she found us seats on a flight to London and on to Barcelona. Truly a “can-do” attitude which we appreciated so much after the Iberia ticket agents told us there was “absolutely nothing they could do”. (As did the customer service agents at Iberia’s call center) Ms Porter is truly a wonderful person who genuinely cares about travelers!

I was not given the option to get on a different flight even though I was going to miss my connection due to weather delays (I did). When I called early in the morning, they said it wasn't delayed long enough; though I knew it would be by the time it was time for the flight ... it was and by that time it was too late. I wasn't given the option to pre-board with my toddler, and the food service was less than normal due to delays .... at least that's what the crew said.

American is a steady for me. I always get what I expect from them. Sincere effort to get me from one place to another.

Nothing wrong on this flight but nothing special. It was oversold and they had to bump people which is always bad.

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.