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Find cheap flights from Kentucky to Puerto Rico from $56

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Kentucky to Puerto Rico departing on 9/9. 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
0 bags
Sat 6/22
Sat 6/29

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Good to know

Low season

October

High season

July

Cheapest flight

$56
Best time to beat the crowds with an average 32% drop in price.
Most popular time to fly with an average 7% increase in price.
Flight from Nashville to San Juan

FAQs for booking flights from Kentucky to Puerto Rico

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

    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 Kentucky to Puerto Rico.

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

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Puerto Rico from 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 Kentucky to Puerto Rico?

    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 to Puerto Rico with an airline and back to Kentucky with another airline.

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

    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 to Puerto Rico from Kentucky up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top 3 airlines serving from Kentucky to Puerto Rico

 
Need help choosing which airline to fly with from Kentucky to Puerto Rico? 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.
9.0
Cape AirOverall score based on 54 reviews
9.1Entertainment
8.8Boarding
8.4Comfort
9.4Crew
8.8Food
Airline reviews

It’s less complicated from Culebra to SJU airport. Next time I will prefer to leave from Isla Grande airport to Culebra !!

10.0 ExcellentSonia, Apr 2023CPX - SJU
Read more about Cape Air reviews

It’s less complicated from Culebra to SJU airport. Next time I will prefer to leave from Isla Grande airport to Culebra !!

10 seat Cesna. Equal parts transportation and adventure. 20 minute hop at 10000 feet and 160 mph, sitting 10 feet from the pilot. Panoramic views of the island. Very simple boarding, very low stress. VQS airport tiny, undeveloped. Highly recommended flight, Cape Air doing a great job here.

We traveled in a small Cesna so there was no food or entertainment. The pilot was excellent enjoy being able to see the places we were flying above. It was an OK flight.

Very smooth flight and landing. Pilot delivered his safety instruction in such a monotone that it wasn’t easily understandable. Words were said but he didn't communicate to us. If he was communicating to someone he cared about, he would have used inflection and other nuances of speaking. Virtually all emphasis was removed so it was just blah blah blah (really fast, like the end of a Pharma commercial)

My pilot on Cape Air was AMAZING!!!! I hoping that next time I fly I have him as my pilot. He made me feel safe and secure in his skills.

I so appreciate this service into and out of Glendive. Always a good experience with crew and support team.

It was not what I had expected but it was a great way to see the landscape.

Pros: "ground crew, pilot, flight was smooth and gate connections to Jet Blue in Boston were fantastic!"
Cons: "leg room"
Pros: "The pilot was kind and to the point."
Cons: "The guy who boarded us told me to wait as his computer could not check me in. 10min later he is rushing me to get on the runway. It was 30min before scheduled take off. I had ordered food and had to cancel my order before the café had finished, so he wasted food and did not get paid and I was hurried and boarded the plane hungry. I probably won't use Cape Air again unless it's an emergency situation"
Cons: "Boarded half hour late. No explanation. Pretty standard on Cape Air these days"

Great! I love Jet Blue. My favorite airline! Very efficient, clean and timely.

Run out of snack choices. Why are the seats not padded for your butt? Are we sitting on blocks of wood or metal for $250-300 a pop? This ain’t spirit. Let’s get it together people

We were told that our flight would be delayed for 90+ minutes because of weather, so we went to get something to eat only to have them randomly start boarding 15 minutes after the announcement, with no warning.

Entertainment... No earphones passed out. Many including me couldn't use the TV. Legroom was good. Crew was indifferent and a bit surly. Free wifi was a nice convenience. Check in desk location was unknown. Gate number on the boarding passes was wrong.

Going through JFK’s security is a mess. The TSA security said no shoes on the bins. So, we place our shoes in the belt and they came out all over the belt. Boarding was delayed and Flight as well.

Safe and on time were the positives. The plane wasn't cleaned before boarding, there was garbage and food on the floor and in the seat pocket. The TV screen was small and the picture fuzzy, audio quality was poor. Seatbelt was fraying and seat did not recline properly. No charging ports near the seats,

Confusing. Delay updates were out of whack At one point it said my flight was 25 hours. Three gate changes and two delays only to change back to original departure time. Gate announcer and on board flight attendant (Alejandro) making the announcements was impossible to understand due to accent and speed of speech. After beverage service the rear flight attendants sat back there on their phones. No refills no checking in, one sweep through for trash collection. Very impersonal. Bring back Coke products

Delayed departure. Delayed after landing pulling into gate. Delay due to sky bridge malfunction

Great. Loved that there was WiFi on flight to keep in touch and excellent service of beverages and snacks.

Business class is great. New airplane, very comfortable, better than some of the major airlines I am used to

Delay flight more than 8hours waiting and poor customer service!

Plane was extremely small so mind the size of your carry on

Other than lack of snacks, everything else went very well.

They don’t keep you updated on the flight status very well. It was late but nothing said

Pros: "Nothing!!! Horrible airline with horrible staff members."
Cons: "Everything. The staff and crew of Intercaribbean airlines are very unprofessional and not helpful at all. On top of the flight delays all the luggage for that particular flight was left in Kingston. Everybody was rather nonchalant and unapologetic about the situation. I was told I would get the the following day. The next day only two of my three bags showed up. I was not compensated for the inconvenience and was told point blank that they will only deliver one of my bags to my address even though they were the reason I had NONE of my luggage in the first place. They are disgusting!!! I would never recommend this airline to anyone."
Pros: "Nice people"
Cons: "A long walk to the D3 gate, but there were no amenities there I.e. snacks (to be fair a new terminal is under construction)"
Cons: "There was no air. I understand when you are on the ground it can be limited but even after getting to altitude there was no air conditioning."
Cons: "The flight was delayed for over three hours, apparently it is a regular occurence."
Pros: "almost nothing"
Cons: "The plane had a problem that forced us to turn around right after take off and as of this writing we still don’t know what’s going on or how long we are stuck here. Planes are old and apparently maintenance could be better."
Cons: "Was a bit difficult understanding the flight attendant, she had a thick Spanish accent"

Book cheap flights from Kentucky to Puerto Rico

Recent round-trip flight deals

8/21Wed
1 stopSpirit Airlines
15h 44mBNA-SJU
8/24Sat
1 stopSpirit Airlines
6h 05mSJU-BNA
$126
8/20Tue
1 stopSpirit Airlines
12h 11mBNA-SJU
8/24Sat
1 stopSpirit Airlines
6h 05mSJU-BNA
$131
6/18Tue
1 stop
25h 35mBNA-SJU
6/22Sat
1 stop
17h 25mSJU-BNA
$196
6/25Tue
1 stop
25h 35mBNA-SJU
6/29Sat
1 stop
17h 25mSJU-BNA
$206
9/6Fri
2 stopsAmerican Airlines
11h 21mCVG-SJU
9/10Tue
2 stopsAmerican Airlines
11h 05mSJU-CVG
$221
9/6Fri
1 stopAmerican Airlines
17h 05mCVG-SJU
9/10Tue
2 stopsAmerican Airlines
11h 05mSJU-CVG
$223
8/13Tue
1 stopDelta
6h 23mCVG-SJU
8/27Tue
1 stopDelta
9h 31mSJU-CVG
$224
8/15Thu
1 stopDelta
5h 49mCVG-SJU
8/22Thu
1 stopDelta
9h 14mSJU-CVG
$244
8/17Sat
2 stopsUnited Airlines
15h 25mCVG-SJU
8/20Tue
1 stopUnited Airlines
9h 53mSJU-CVG
$359
10/16Wed
2 stopsUnited Airlines
14h 35mCVG-SJU
10/24Thu
1 stopUnited Airlines
8h 35mSJU-CVG
$412

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Recent one-way flight deals

9/9Mon
1 stopSpirit Airlines
14h 55mBNA-SJU
$56
9/9Mon
1 stopSpirit Airlines
14h 55mBNA-SJU
$62
6/23Sun
1 stop
14h 18mCVG-SJU
$131
7/9Tue
1 stopFrontier
9h 59mTYS-SJU
$135
6/4Tue
1 stopFrontier
16h 47mCVG-SJU
$140
6/23Sun
2 stops
18h 13mCVG-SJU
$160
5/29Wed
1 stopAmerican Airlines
13h 30mSDF-SJU
$166
5/29Wed
2 stopsAmerican Airlines
19h 55mSDF-SJU
$178
5/30Thu
2 stopsUnited Airlines
16h 42mCVG-SJU
$207
10/27Sun
2 stopsUnited Airlines
24h 33mBNA-SJU
$351

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Last minute flights from Kentucky to Puerto Rico

Last minute flight, train and bus deals

5/25Sat
multi-stop
11h 58mBNA-SJU
5/29Wed
multi-stop
16h 54mSJU-BNA
$355
5/25Sat
multi-stopFrontier
15h 46mCVG-SJU
5/31Fri
multi-stopFrontier
7h 25mSJU-CVG
$365
5/25Sat
multi-stopSpirit Airlines
11h 58mBNA-SJU
5/29Wed
multi-stopSpirit Airlines
18h 28mSJU-BNA
$367
5/25Sat
multi-stopSpirit Airlines
11h 58mBNA-SJU
5/28Tue
multi-stopSpirit Airlines
8h 38mSJU-BNA
$401
5/25Sat
multi-stopAmerican Airlines
9h 05mCVG-SJU
5/31Fri
multi-stopAmerican Airlines
16h 16mSJU-CVG
$499
5/26Sun
multi-stopAmerican Airlines
9h 53mTYS-SJU
5/28Tue
multi-stopAmerican Airlines
5h 56mSJU-TYS
$511
5/25Sat
multi-stopUnited Airlines
11h 33mCVG-SJU
5/30Thu
multi-stopUnited Airlines
9h 56mSJU-CVG
$520
5/25Sat
multi-stopDelta
10h 19mSDF-SJU
6/20Thu
multi-stopDelta
10h 48mSJU-SDF
$543
5/25Sat
multi-stopDelta
10h 19mSDF-SJU
6/21Fri
multi-stopDelta
10h 48mSJU-SDF
$568
5/25Sat
multi-stopUnited Airlines
9h 52mSDF-SJU
5/29Wed
multi-stopUnited Airlines
12h 43mSJU-SDF
$579

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Flights to Puerto Rico

Return flight deals:

Puerto Rico - Kentucky

Cabin classes: