Latest deals
Insights
FAQs
Reviews
Price Alerts

Cheap flights from Kentucky to Caribbean Islands from $98

This is the cheapest one-way flight price found by a momondo user in the last 72 hours by searching for a flight from Kentucky to Caribbean Islands departing on 10/30. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
1 adult
0 bags

Discover deals from 900+ travel sites with momondo.

Save money when you book flights with momondo

Big names and deals

Big names and deals

Search 100s of travel sites to compare prices.

Filter for what you want

Filter for what you want

Free Wi-Fi? Stopover? Instantly customize your results.

Trusted and free

Trusted and free

We’re completely free to use - no hidden charges or fees.

Price Alerts

Price Alerts

Not ready to book? to track prices.
Search flight deals

Find the cheapest flights from Kentucky to Caribbean Islands

Cheap round-trip flights

Southwest Logo
5:35 am - 2:45 pmBNA-SJU
8h 10m1 stop
Southwest Logo
7:40 am - 5:15 pmSJU-BNA
11h 35m1 stop
$215Southwest
Find Deal
Wed, Oct 15 - Fri, Nov 14
Delta Logo
12:40 pm - 8:30 pmSDF-SJU
6h 50m1 stop
Delta Logo
6:15 am - 11:37 amSJU-SDF
6h 22m1 stop
$225Delta
Find Deal
Tue, Feb 24 - Thu, Mar 5
American Airlines Logo
4:11 pm - 11:52 pmCVG-SJU
6h 41m1 stop
American Airlines Logo
4:44 pm - 11:58 pmSJU-CVG
8h 14m1 stop
$225American Airlines
Find Deal
Sat, Nov 8 - Thu, Nov 13
Multiple Airlines Logo
9:50 pm - 12:29 pmBNA-SJU
12h 39m1 stop
Multiple Airlines Logo
6:00 am - 7:49 pmSJU-BNA
15h 49m1 stop
$226Multiple Airlines
Find Deal
Thu, Dec 4 - Sun, Dec 7
Multiple Airlines Logo
2:06 pm - 12:37 amBNA-SJU
8h 31m1 stop
Multiple Airlines Logo
3:55 am - 12:31 pmSJU-BNA
10h 36m1 stop
$229Multiple Airlines
Find Deal
Thu, Dec 11 - Sun, Dec 14
American Airlines Logo
2:09 pm - 4:55 amCVG-SJU
13h 46m1 stop
American Airlines Logo
6:40 am - 3:37 pmSJU-CVG
9h 57m1 stop
$235American Airlines
Find Deal
Tue, Feb 17 - Wed, Feb 25
United Airlines Logo
6:07 am - 2:40 pmBNA-SJU
7h 33m1 stop
United Airlines Logo
1:05 am - 9:05 amSJU-BNA
9h 00m1 stop
$239United Airlines
Find Deal
Mon, Oct 27 - Tue, Oct 28
United Airlines Logo
10:47 am - 8:38 pmBNA-SJU
8h 51m1 stop
United Airlines Logo
1:05 am - 9:05 amSJU-BNA
9h 00m1 stop
$246United Airlines
Find Deal
Thu, Oct 23 - Wed, Oct 29
Spirit Airlines Logo
9:47 pm - 3:11 pmBNA-STT
15h 24m1 stop
Spirit Airlines Logo
4:06 pm - 9:12 pmSTT-BNA
7h 06m1 stop
$255Spirit Airlines
Find Deal
Fri, Nov 7 - Mon, Nov 10
Spirit Airlines Logo
5:05 am - 12:59 pmBNA-STT
6h 54m1 stop
Spirit Airlines Logo
1:33 pm - 10:54 pmSTT-BNA
11h 21m1 stop
$258Spirit Airlines
Find Deal
Sat, Nov 1 - Sat, Nov 8

Frontier flights from Kentucky to Caribbean Islands

Our best Frontier deals on Kentucky to Caribbean Islands flight tickets
Frontier
Sep 26
BNA7:02 pmNashville Intl
6h 32m
1 stop
SJU2:34 amSan Juan Luis Munoz Marin Intl
Sep 29
SJU12:06 pmSan Juan Luis Munoz Marin Intl
8h 21m
1 stop
BNA7:27 pmNashville Intl
$258
Find similar
Frontier
Mar 3
CVG11:57 amCincinnati Cinci./N. Kentucky
9h 49m
1 stop
SJU10:46 pmSan Juan Luis Munoz Marin Intl
Mar 3
SJU3:55 amSan Juan Luis Munoz Marin Intl
11h 03m
1 stop
CVG1:58 pmCincinnati Cinci./N. Kentucky
$259
Find similar
Frontier
Oct 24
BNA5:25 pmNashville Intl
8h 05m
1 stop
SJU2:30 amSan Juan Luis Munoz Marin Intl
Nov 1
SJU1:59 amSan Juan Luis Munoz Marin Intl
13h 40m
1 stop
BNA2:39 pmNashville Intl
$262
Find similar

American Airlines flights from Kentucky to Caribbean Islands

Our best American Airlines deals on Kentucky to Caribbean Islands flight tickets
American Airlines
Nov 8
CVG4:11 pmCincinnati Cinci./N. Kentucky
6h 41m
1 stop
SJU11:52 pmSan Juan Luis Munoz Marin Intl
Nov 13
SJU4:44 pmSan Juan Luis Munoz Marin Intl
8h 14m
1 stop
CVG11:58 pmCincinnati Cinci./N. Kentucky
$225
Find similar
American Airlines
Feb 17
CVG2:09 pmCincinnati Cinci./N. Kentucky
13h 46m
1 stop
SJU4:55 amSan Juan Luis Munoz Marin Intl
Feb 25
SJU6:40 amSan Juan Luis Munoz Marin Intl
9h 57m
1 stop
CVG3:37 pmCincinnati Cinci./N. Kentucky
$235
Find similar
American Airlines
Oct 1
CVG6:49 pmCincinnati Cinci./N. Kentucky
16h 22m
2 stops
SJU11:11 amSan Juan Luis Munoz Marin Intl
Oct 7
SJU5:30 amSan Juan Luis Munoz Marin Intl
7h 05m
1 stop
CVG12:35 pmCincinnati Cinci./N. Kentucky
$245
Find similar

momondo Fare Finder

 
Customize your flight search to find flights from Kentucky to Caribbean Islands 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, momondo users made 832,500 searches. Data last updated September 24, 2025.
Use the filters below to find and compare flights from Kentucky to Caribbean Islands that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

NashvilleSan Juan

BNA - SJU

BNASJU

Nashville Intl

Wed 10/15

5:35 am-2:45 pm

1 stop8h 10m

San Juan Luis Munoz Marin Intl

Fri 11/14

7:40 am-5:15 pm

1 stop11h 35m

$215

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

Tue 2/24

12:40 pm-8:30 pm

1 stop6h 50m

San Juan Luis Munoz Marin Intl

Thu 3/5

6:15 am-11:37 am

1 stop6h 22m

$225

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

Sat 11/8

4:11 pm-11:52 pm

1 stop6h 41m

San Juan Luis Munoz Marin Intl

Thu 11/13

4:44 pm-11:58 pm

1 stop8h 14m

$225

NashvilleSan Juan

BNA - SJU

BNASJU

Nashville Intl

Thu 12/4

9:50 pm-12:29 pm

1 stop12h 39m

San Juan Luis Munoz Marin Intl

Sun 12/7

6:00 am-7:49 pm

1 stop15h 49m

$226

NashvilleSan Juan

BNA - SJU

BNASJU

Nashville Intl

Thu 12/11

2:06 pm-12:37 am

1 stop8h 31m

San Juan Luis Munoz Marin Intl

Sun 12/14

3:55 am-12:31 pm

1 stop10h 36m

$229

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

Tue 2/17

2:09 pm-4:55 am

1 stop13h 46m

San Juan Luis Munoz Marin Intl

Wed 2/25

6:40 am-3:37 pm

1 stop9h 57m

$235

NashvilleSan Juan

BNA - SJU

BNASJU

Nashville Intl

Mon 10/27

6:07 am-2:40 pm

1 stop7h 33m

San Juan Luis Munoz Marin Intl

Tue 10/28

1:05 am-9:05 am

1 stop9h 00m

$239

NashvilleSan Juan

BNA - SJU

BNASJU

Nashville Intl

Thu 10/23

10:47 am-8:38 pm

1 stop8h 51m

San Juan Luis Munoz Marin Intl

Wed 10/29

1:05 am-9:05 am

1 stop9h 00m

$246

NashvilleSaint Thomas Island

BNA - STT

BNASTT

Nashville Intl

Fri 11/7

9:47 pm-3:11 pm

1 stop15h 24m

Saint Thomas Island Cyril E King

Mon 11/10

4:06 pm-9:12 pm

1 stop7h 06m

$255

NashvilleSaint Thomas Island

BNA - STT

BNASTT

Nashville Intl

Sat 11/1

5:05 am-12:59 pm

1 stop6h 54m

Saint Thomas Island Cyril E King

Sat 11/8

1:33 pm-10:54 pm

1 stop11h 21m

$258

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
1
2

See travel insights to Caribbean Islands from

How to get the cheapest flight ticket from Kentucky to Caribbean Islands

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

What is the cheapest month to fly to Caribbean Islands?

The month of October is, on average, the cheapest month to fly to Caribbean Islands from Kentucky, with most prices found around $344. The month of January is another great option to travel to Caribbean Islands, with average flight prices from Kentucky averaging around $370.

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

The cheapest day to depart from Kentucky to Caribbean Islands is on a Tuesday. Travelers who choose to depart for Caribbean Islands on a Tuesday will often find tickets 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 Islands.

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

According to our data, the cheapest time of day to fly to Caribbean Islands is in the evening. momondo users have found flights departing from Kentucky to Caribbean Islands in the evening for as low as $339. Keep in mind that these prices may fluctuate based on what airline you choose and the time of year you plan to travel. Try not to purchase tickets in the afternoon because they tend to be around $441. Of course, these prices can vary depending on the time of year and what airport you fly to.

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

You are more likely to see cheaper flights to Caribbean Islands from Kentucky when booking weeks ahead of your departure date. In general, you can expect to find flights to Caribbean Islands for around $437 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Caribbean Islands from Kentucky for as low as $282 on momondo.

Can stopping save me money on Kentucky to Caribbean Islands flights?

No. A direct flight is the cheapest option for a flight between Kentucky to Caribbean Islands.

Cheap Kentucky to Caribbean Islands flight deals and tips

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

Fastest flight time

3h 35m

Direct flights

Sun

Airports in Caribbean Islands

2 airports
The fastest flight from Kentucky to Caribbean Islands takes 3h 35m
Direct flights go from Kentucky to Caribbean Islands on Sunday. There are no airlines offering direct flights.
There are 2 airports near Caribbean Islands: Punta Cana (PUJ), San Juan Luis Munoz Marin Intl (SJU)
Search flight deals

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

    Prices for flights from Kentucky to Caribbean Islands are updated daily.

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

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

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Kentucky to Caribbean Islands.

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

    The travel and health documents you'll need for your trip to Caribbean Islands may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Caribbean Islands. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • What is the most popular plane model from Kentucky to Caribbean Islands?

Best airlines flying from Kentucky to Caribbean Islands

Compare and see reviews for airlines that fly from Kentucky to Caribbean Islands with momondo
Airline
Rating
Free Cancellation
Price
Spirit AirlinesPriceFrom $152Free CancellationRating
6.3
8,041 reviews
Search Spirit Airlines flights
DeltaPriceFrom $206Free CancellationRating
7.9
7,973 reviews
Search Delta flights
SouthwestPriceFrom $225Free CancellationRating
8.0
4,244 reviews
Search Southwest flights
American AirlinesPriceFrom $261Free CancellationRating
7.2
10,000 reviews
Search American Airlines flights
United AirlinesPriceFrom $275Free CancellationRating
7.4
8,928 reviews
Search United Airlines flights

Why use momondo?

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

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 Islands from Kentucky.

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

Yes. momondo allows you to filter the results for Kentucky to Caribbean Islands flights to just show those with flexible booking policies.

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

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Caribbean Islands from Kentucky.

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

If you are not ready to book a flight from Kentucky to Caribbean Islands now, use our insights above to find helpful tips or alternatively set up a price alert, where momondo will track prices on flights to Caribbean Islands and let you know when they change.

An easier way to manage your Caribbean Islands trip

We make it super easy to schedule, organize and travel with friends or family. Trips is free — and available to use no matter where you book.
Start using Trips
Find my bookings

Get notified when prices go down

Daily price changes in your inbox - only with Price Alerts.
1 adult
Fri 10/24
Fri 10/31
By creating a price alert you accept our terms of use and privacy policy.

Find better results for your trip to Caribbean Islands

Popular cities in Caribbean Islands

Popular flights according to clicks in the last 7 days on momondo
Flights to New Yorkfrom $50
Flights to Londonfrom $328
Flights to Bangkokfrom $532
Flights to Tokyofrom $389
Flights to Los Angelesfrom $44
Flights to Parisfrom $336
Flights to Copenhagenfrom $365
Flights to Istanbulfrom $381
Flights to Manilafrom $523
Flights to Romefrom $305
Flights to Miamifrom $49
Flights to Chicagofrom $65