What airlines fly to Caribbean?

American Airlines, Delta and Southwest are the top three most popular airlines that fly to Caribbean from Kentucky according to our data. American Airlines is the first choice among our users, with 58% of people opting to fly with this airline when traveling to Caribbean. Keep in mind that there are 5 different airlines that fly to Caribbean on a routine basis, so you have a few additional options to choose from.

What is the cheapest airline that flies from Kentucky to Caribbean?

Spirit Airlines, Southwest, and American Airlines are the most popular carriers operating from Kentucky to Caribbean

How long is the flight from Kentucky to Caribbean?

If you’re flying from a popular airport in Kentucky, such as Lexington or Louisville, and flying into Caribbean, then you can expect flight times to average 17h 01m and 18h 33m, respectively.

When did momondo last update prices for flights from Kentucky to Caribbean?

Prices for flights from Kentucky to Caribbean were last updated today.

How many operators does momondo search for flights from Kentucky to Caribbean?

There are 7 operators available for flights from Kentucky to Caribbean as of July 2025.

How old do you have to be to fly from Kentucky to Caribbean?

Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Kentucky to Caribbean.

What documentation or ID do you need to fly to Caribbean?

The travel and health documents required for your trip to Caribbean can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Caribbean. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

$88 Cheap Flights from Kentucky to Caribbean in 2025

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Find the cheapest flights from Kentucky to Caribbean

Round-trip

One-way

Last minute

Direct

Cheap round-trip flights

8:17 am - 9:48 pmBNA-SJU

12h 31m1 stop

3:19 pm - 11:23 pmSJU-BNA

9h 04m1 stop

$181Spirit Airlines

Find Deal

lun., ago. 18 - mié., sep. 10

10:37 am - 12:44 amBNA-SJU

13h 07m1 stop

6:00 am - 5:04 pmSJU-BNA

13h 04m1 stop

$189Spirit Airlines

Find Deal

jue., oct. 30 - lun., nov. 10

6:55 am - 2:15 pmBNA-SJU

6h 20m1 stop

5:45 am - 10:25 amSJU-BNA

6h 40m1 stop

$195Southwest

Find Deal

vie., oct. 31 - mié., nov. 5

3:35 pm - 11:59 pmSDF-SJU

8h 24m1 stop

7:05 am - 5:54 pmSJU-SDF

10h 49m2 stops

$205American Airlines

Find Deal

lun., oct. 13 - mar., oct. 28

6:49 pm - 11:11 amCVG-SJU

16h 22m2 stops

3:00 pm - 11:59 pmSJU-CVG

8h 59m1 stop

$205American Airlines

Find Deal

mié., oct. 1 - mar., oct. 7

5:15 am - 11:41 amBNA-SJU

5h 26m1 stop

1:51 pm - 10:39 pmSJU-BNA

10h 48m1 stop

$205Delta

Find Deal

sáb., nov. 1 - jue., nov. 6

6:00 am - 4:36 pmSDF-SJU

10h 36m1 stop

5:41 pm - 11:52 pmSJU-SDF

6h 11m1 stop

$215Delta

Find Deal

dom., sep. 7 - jue., sep. 11

8:00 am - 3:54 pmCVG-SJU

7h 54m1 stop

9:30 pm - 10:47 amSJU-CVG

13h 17m1 stop

$233Frontier

Find Deal

sáb., ago. 16 - sáb., ago. 16

9:30 am - 6:02 pmCVG-SJU

8h 32m1 stop

9:30 pm - 10:47 amSJU-CVG

13h 17m1 stop

$238Frontier

Find Deal

mié., ago. 13 - sáb., ago. 16

3:35 pm - 11:00 pmCVG-SJU

6h 25m1 stop

6:15 am - 12:20 pmSJU-CVG

7h 05m1 stop

$242Southwest

Find Deal

sáb., nov. 8 - sáb., nov. 15

American Airlines flights from Kentucky to Caribbean

Our best American Airlines deals on Kentucky to Caribbean flight tickets

American Airlines

Oct 1

CVG6:49 pmCincinnati Cinci./N. Kentucky

16h 22m

2 stops

SJU11:11 amSan Juan Luis Munoz Marin Intl

Oct 7

SJU3:00 pmSan Juan Luis Munoz Marin Intl

8h 59m

1 stop

CVG11:59 pmCincinnati Cinci./N. Kentucky

$205

Find similar

American Airlines

Oct 10

CVG1:05 pmCincinnati Cinci./N. Kentucky

10h 54m

1 stop

SJU11:59 pmSan Juan Luis Munoz Marin Intl

Oct 18

SJU5:30 amSan Juan Luis Munoz Marin Intl

7h 05m

1 stop

CVG12:35 pmCincinnati Cinci./N. Kentucky

$235

Find similar

American Airlines

Oct 10

CVG11:00 amCincinnati Cinci./N. Kentucky

12h 59m

1 stop

SJU11:59 pmSan Juan Luis Munoz Marin Intl

Oct 18

SJU5:30 amSan Juan Luis Munoz Marin Intl

10h 00m

1 stop

CVG3:30 pmCincinnati Cinci./N. Kentucky

$240

Find similar

Spirit Airlines flights from Kentucky to Caribbean

Our best Spirit Airlines deals on Kentucky to Caribbean flight tickets

Spirit Airlines

Aug 18

BNA8:17 amNashville Intl

12h 31m

1 stop

SJU9:48 pmSan Juan Luis Munoz Marin Intl

Sep 10

SJU3:19 pmSan Juan Luis Munoz Marin Intl

9h 04m

1 stop

BNA11:23 pmNashville Intl

$181

Find similar

Spirit Airlines

Oct 30

BNA10:37 amNashville Intl

13h 07m

1 stop

SJU12:44 amSan Juan Luis Munoz Marin Intl

Nov 10

SJU6:00 amSan Juan Luis Munoz Marin Intl

13h 04m

1 stop

BNA5:04 pmNashville Intl

$189

Find similar

Spirit Airlines

Nov 1

BNA8:03 pmNashville Intl

16h 53m

1 stop

STT1:56 pmSaint Thomas Island Cyril E King

Nov 11

STT4:06 pmSaint Thomas Island Cyril E King

7h 06m

1 stop

BNA9:12 pmNashville Intl

$190

Find similar

Fly from

Fly to

Route

Depart

Return

Price

NashvilleSan Juan

BNA - SJU

BNASJU

Nashville Intl

lun. 8/18

8:17 am-9:48 pm

1 stop12h 31m

San Juan Luis Munoz Marin Intl

mié. 9/10

3:19 pm-11:23 pm

1 stop9h 04m

$181

NashvilleSan Juan

BNA - SJU

BNASJU

Nashville Intl

jue. 10/30

10:37 am-12:44 am

1 stop13h 07m

San Juan Luis Munoz Marin Intl

lun. 11/10

6:00 am-5:04 pm

1 stop13h 04m

$189

NashvilleSan Juan

BNA - SJU

BNASJU

Nashville Intl

vie. 10/31

6:55 am-2:15 pm

1 stop6h 20m

San Juan Luis Munoz Marin Intl

mié. 11/5

5:45 am-10:25 am

1 stop6h 40m

$195

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

lun. 10/13

3:35 pm-11:59 pm

1 stop8h 24m

San Juan Luis Munoz Marin Intl

mar. 10/28

7:05 am-5:54 pm

2 stops10h 49m

$205

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

mié. 10/1

6:49 pm-11:11 am

2 stops16h 22m

San Juan Luis Munoz Marin Intl

mar. 10/7

3:00 pm-11:59 pm

1 stop8h 59m

$205

NashvilleSan Juan

BNA - SJU

BNASJU

Nashville Intl

sáb. 11/1

5:15 am-11:41 am

1 stop5h 26m

San Juan Luis Munoz Marin Intl

jue. 11/6

1:51 pm-10:39 pm

1 stop10h 48m

$205

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

dom. 9/7

6:00 am-4:36 pm

1 stop10h 36m

San Juan Luis Munoz Marin Intl

jue. 9/11

5:41 pm-11:52 pm

1 stop6h 11m

$215

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

sáb. 8/16

8:00 am-3:54 pm

1 stop7h 54m

San Juan Luis Munoz Marin Intl

sáb. 8/16

9:30 pm-10:47 am

1 stop13h 17m

$233

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

mié. 8/13

9:30 am-6:02 pm

1 stop8h 32m

San Juan Luis Munoz Marin Intl

sáb. 8/16

9:30 pm-10:47 am

1 stop13h 17m

$238

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

sáb. 11/8

3:35 pm-11:00 pm

1 stop6h 25m

San Juan Luis Munoz Marin Intl

sáb. 11/15

6:15 am-12:20 pm

1 stop7h 05m

$242

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first

How to get the cheapest flight ticket from Kentucky to Caribbean

Look no further. We've gone through all the searches for this route on momondo so you have the important information and insights to find the cheapest flight ticket for your trip

Prices

Airlines

Other information

What is the cheapest month to fly to Caribbean?

In general, October is the cheapest month to fly from Kentucky to Caribbean. Due to it being the ‘off-season’ during this time, you can expect flight prices to be around $371. If you don’t want to visit Caribbean in October, then you should wait until January to fly from Kentucky, when ticket prices are also cheap, with an average price of $374.

What is the cheapest day to depart on your flight to Caribbean?

The cheapest day to depart from Kentucky to Caribbean is on a Tuesday when prices can be found for as low as $372. If your travel schedule is flexible, try to avoid departing on a Friday because tickets tend to average around $459. These prices are subject to change though, so be sure to set up a Price Alert for flights to Caribbean.

What is the cheapest time of day to depart on your flight to Caribbean?

In the evening is the cheapest time of day to fly from Kentucky to Caribbean when you can find flight prices for as low as $339. Flying to Caribbean in the evening is an ideal time because this is during off-peak travel hours. Flights in the afternoon are often more expensive with an average ticket price of $441.

How far in advance should I book a flight to Caribbean?

You are more likely to see cheaper flights to Caribbean from Kentucky when booking weeks ahead of your departure date. In general, you can expect to find flights to Caribbean for around $442 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Caribbean from Kentucky for as low as $379 on momondo.

Can stopping save me money on Kentucky to Caribbean flights?

You could potentially save up to 51% on your flight if you consider stops on a Kentucky to Caribbean flight.

Cheap Kentucky to Caribbean flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Kentucky to Caribbean

Best Price Found	$88
Fastest flight time	3h 55m
Direct flights	Sun
Airports in Caribbean	6 airports

The best one-way flight to Caribbean from Kentucky in the past 72 hours is $88. The best round-trip flight deal from Kentucky to Caribbean found on momondo in the last 72 hours is $181.

The fastest flight from Kentucky to Caribbean takes 3h 55m

Direct flights go from Kentucky to Caribbean on Sunday. Airlines offering direct flights are: Southwest and Frontier.

There are 6 airports near Caribbean: Nassau Intl (NAS), Saint Thomas Island Cyril E King (STT), Punta Cana (PUJ), Montego Bay Sangster Intl (MBJ), Providenciales (PLS), San Juan Luis Munoz Marin Intl (SJU)

Search flight deals

When did momondo last update prices for flights from Kentucky to Caribbean?
Prices for flights from Kentucky to Caribbean were last updated today.
How many operators does momondo search for flights from Kentucky to Caribbean?
There are 7 operators available for flights from Kentucky to Caribbean as of July 2025.
How old do you have to be to fly from Kentucky to Caribbean?
Although the minimum age for a child to fly alone is five, airlines that offer an unaccompanied minor (UMNR) service may have their own age limits, which could be impacted by factors such as flight length, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Kentucky to Caribbean.
What documentation or ID do you need to fly to Caribbean?
The travel and health documents required for your trip to Caribbean can vary based on your itinerary and personal situation. As a rule, consider having multiple documents such as a national ID card or driver’s license, and a passport valid for six-months after you plan to arrive at Caribbean. We always recommend checking with your airline or a trusted third party such as IATA to get advice.

Best airlines flying from Kentucky to Caribbean

Compare and see reviews for airlines that fly from Kentucky to Caribbean with momondo

Airline	Rating	Free Cancellation	Price
Spirit Airlines	PriceFrom $152	Free Cancellation	Rating 6.3 8,048 reviews	Search Spirit Airlines flights
Southwest	PriceFrom $225	Free Cancellation	Rating 8.0 4,246 reviews	Search Southwest flights
Delta	PriceFrom $225	Free Cancellation	Rating 8.0 7,981 reviews	Search Delta flights
United Airlines	PriceFrom $275	Free Cancellation	Rating 7.4 8,900 reviews	Search United Airlines flights
American Airlines	PriceFrom $276	Free Cancellation	Rating 7.2 10,000 reviews	Search American Airlines flights

Why use momondo?

Why should I use momondo to find a flight deal from Kentucky to Caribbean?

To find the flight that best suits your needs, momondo gathers a range of flights from a large pool of different airlines and agents; you can then use our insights and filters to find and book the right flight to Caribbean from Kentucky.

Can I find flights from Kentucky to Caribbean with flexible booking policies on momondo?

Flights from Kentucky to Caribbean with flexible booking policies can be found by using the search form above and then selecting our dedicated flexible booking filter, which will highlight only the flights where this policy is applied.

How can momondo help me find flights from Kentucky to Caribbean?

momondo offers useful filters to help you find the right flight. Choose specific flight times, airports or even what payment method you prefer. We have numerous options to help you book your ideal flight from Kentucky to Caribbean.

I’m not ready to book a flight from Kentucky to Caribbean right now. Can momondo alert me if prices change?

Yes momondo offers price alerts on flights to Caribbean from Kentucky. After performing a search on this page you should be able to see the price alert set up feature. Simply provide a valid email address and momondo will instantly alert you when prices change.