Cheap flights from Kentucky to Caribbean Islands from $104

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 8/25. 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
1 adult, Economy, 0 bags

Discover deals from 900+ travel sites with momondo.

Find the cheapest flights from Kentucky to Caribbean Islands

Cheap round-trip flights

Enter your travel dates to find the best prices.
United Airlines Logo
7:25 am - 3:42 pm
SDF
-
SJU
8h 17m
1 stop
United Airlines Logo
3:56 pm - 11:59 pm
SJU
-
SDF
8h 03m
1 stop
$220United Airlines
Sun, Aug 30 - Wed, Sep 2
United Airlines Logo
7:10 am - 8:38 pm
SDF
-
SJU
13h 28m
2 stops
United Airlines Logo
2:20 pm - 10:15 pm
SJU
-
SDF
7h 55m
1 stop
$223United Airlines
Sat, Aug 29 - Mon, Aug 31
Delta Logo
1:17 pm - 10:29 pm
SDF
-
SJU
9h 12m
1 stop
Delta Logo
12:56 pm - 9:33 pm
SJU
-
SDF
8h 37m
1 stop
$226Delta
Wed, Aug 12 - Wed, Aug 19
Multiple Airlines Logo
7:15 pm - 12:41 am
TYS
-
SJU
29h 26m
1 stop
Multiple Airlines Logo
7:00 am - 4:25 pm
SJU
-
TYS
9h 25m
1 stop
$226Multiple Airlines
Fri, Aug 14 - Thu, Aug 20
Multiple Airlines Logo
7:15 pm - 12:56 am
TYS
-
SJU
29h 41m
1 stop
Multiple Airlines Logo
7:00 am - 4:25 pm
SJU
-
TYS
9h 25m
1 stop
$236Multiple Airlines
Mon, Aug 17 - Thu, Aug 20
Frontier Logo
11:00 am - 12:41 am
CVG
-
SJU
13h 41m
1 stop
Frontier Logo
6:00 am - 8:25 pm
SJU
-
CVG
14h 25m
1 stop
$251Frontier
Thu, Aug 13 - Fri, Aug 14
Frontier Logo
11:00 am - 12:41 am
CVG
-
SJU
13h 41m
1 stop
Frontier Logo
5:37 pm - 10:05 am
SJU
-
CVG
16h 28m
1 stop
$252Frontier
Wed, Aug 12 - Wed, Aug 19
Southwest Logo
3:35 pm - 10:45 pm
SDF
-
SJU
7h 10m
1 stop
Southwest Logo
6:00 am - 1:35 pm
SJU
-
SDF
7h 35m
1 stop
$258Southwest
Sun, Aug 9 - Fri, Aug 14
Southwest Logo
4:10 pm - 11:05 pm
SDF
-
SJU
6h 55m
1 stop
Southwest Logo
5:00 am - 3:30 pm
SJU
-
SDF
10h 30m
2 stops
$273Southwest
Fri, Sep 25 - Mon, Sep 28
Delta Logo
5:14 am - 11:43 am
BNA
-
PUJ
5h 29m
1 stop
Delta Logo
2:50 pm - 8:40 pm
PUJ
-
BNA
6h 50m
1 stop
$454Delta
Tue, Aug 25 - Thu, Aug 27

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American Airlines flights from Kentucky to Caribbean Islands

Our best American Airlines deals on Kentucky to Caribbean Islands flight tickets
American Airlines
Aug 15
CVG8:16 amCincinnati Cinci./N. Kentucky
15h 27m
1 stop
SJU11:43 pmSan Juan Luis Munoz Marin Intl
Aug 20
SJU12:55 amSan Juan Luis Munoz Marin Intl
8h 29m
1 stop
CVG9:24 amCincinnati Cinci./N. Kentucky
$268
American Airlines
Sep 2
SDF8:16 amLouisville Intl
6h 35m
1 stop
SJU2:51 pmSan Juan Luis Munoz Marin Intl
Sep 7
SJU7:03 amSan Juan Luis Munoz Marin Intl
15h 56m
1 stop
SDF10:59 pmLouisville Intl
$276
American Airlines
Aug 22
CVG11:23 amCincinnati Cinci./N. Kentucky
10h 32m
2 stops
SJU9:55 pmSan Juan Luis Munoz Marin Intl
Sep 5
SJU7:03 amSan Juan Luis Munoz Marin Intl
10h 05m
2 stops
CVG5:08 pmCincinnati Cinci./N. Kentucky
$293

Delta flights from Kentucky to Caribbean Islands

Our best Delta deals on Kentucky to Caribbean Islands flight tickets
Delta
Aug 12
SDF1:17 pmLouisville Intl
9h 12m
1 stop
SJU10:29 pmSan Juan Luis Munoz Marin Intl
Aug 19
SJU12:56 pmSan Juan Luis Munoz Marin Intl
8h 37m
1 stop
SDF9:33 pmLouisville Intl
$226
Delta
Sep 25
SDF6:00 amLouisville Intl
5h 45m
1 stop
SJU11:45 amSan Juan Luis Munoz Marin Intl
Sep 30
SJU5:59 pmSan Juan Luis Munoz Marin Intl
6h 00m
1 stop
SDF11:59 pmLouisville Intl
$283
Delta
Aug 10
CVG4:20 pmCincinnati Cinci./N. Kentucky
6h 09m
1 stop
SJU10:29 pmSan Juan Luis Munoz Marin Intl
Aug 16
SJU5:49 pmSan Juan Luis Munoz Marin Intl
6h 36m
1 stop
CVG12:25 amCincinnati Cinci./N. Kentucky
$291

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 June 27, 2026.
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

Cheapest round-trip

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

Sun 8/30

7:25 am-3:42 pm

1 stop8h 17m

San Juan Luis Munoz Marin Intl

Wed 9/2

3:56 pm-11:59 pm

1 stop8h 03m

$220

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

Sat 8/29

7:10 am-8:38 pm

2 stops13h 28m

San Juan Luis Munoz Marin Intl

Mon 8/31

2:20 pm-10:15 pm

1 stop7h 55m

$223

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

Wed 8/12

1:17 pm-10:29 pm

1 stop9h 12m

San Juan Luis Munoz Marin Intl

Wed 8/19

12:56 pm-9:33 pm

1 stop8h 37m

$226

KnoxvilleSan Juan

TYS - SJU

TYSSJU

Knoxville McGhee Tyson

Fri 8/14

7:15 pm-12:41 am

1 stop29h 26m

San Juan Luis Munoz Marin Intl

Thu 8/20

7:00 am-4:25 pm

1 stop9h 25m

$226

KnoxvilleSan Juan

TYS - SJU

TYSSJU

Knoxville McGhee Tyson

Mon 8/17

7:15 pm-12:56 am

1 stop29h 41m

San Juan Luis Munoz Marin Intl

Thu 8/20

7:00 am-4:25 pm

1 stop9h 25m

$236

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

Thu 8/13

11:00 am-12:41 am

1 stop13h 41m

San Juan Luis Munoz Marin Intl

Fri 8/14

6:00 am-8:25 pm

1 stop14h 25m

$251

CincinnatiSan Juan

CVG - SJU

CVGSJU

Cincinnati Cinci./N. Kentucky

Wed 8/12

11:00 am-12:41 am

1 stop13h 41m

San Juan Luis Munoz Marin Intl

Wed 8/19

5:37 pm-10:05 am

1 stop16h 28m

$252

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

Sun 8/9

3:35 pm-10:45 pm

1 stop7h 10m

San Juan Luis Munoz Marin Intl

Fri 8/14

6:00 am-1:35 pm

1 stop7h 35m

$258

LouisvilleSan Juan

SDF - SJU

SDFSJU

Louisville Intl

Fri 9/25

4:10 pm-11:05 pm

1 stop6h 55m

San Juan Luis Munoz Marin Intl

Mon 9/28

5:00 am-3:30 pm

2 stops10h 30m

$273
Quickest round-trip

NashvillePunta Cana

BNA - PUJ

BNAPUJ

Nashville Intl

Tue 8/25

5:14 am-11:43 am

1 stop5h 29m

Punta Cana

Thu 8/27

2:50 pm-8:40 pm

1 stop6h 50m

$454

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 20 resultsSorted by cheapest first
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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 January is, on average, the cheapest month to fly to Caribbean Islands from Kentucky, with most prices found around $160. The month of September is another great option to travel to Caribbean Islands, with average flight prices from Kentucky averaging around $163.

How far in advance should I book a flight from Kentucky 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 $431 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 $387 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 45m

Direct flights

Every day

Airports in Caribbean Islands

99 airports
The fastest flight from Kentucky to Caribbean Islands takes 3h 45m
Direct flights go from Kentucky to Caribbean Islands every day.
There are 99 airports in Caribbean Islands. From Kentucky there are direct flights to Punta Cana (PUJ), San Juan Luis Munoz Marin Intl (SJU).

Frequently asked questions about flying from Kentucky to Caribbean Islands

  • 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
DeltaPriceFrom $160Free CancellationRating
7.8
8,451 reviews
Search Delta flights
SouthwestPriceFrom $225Free CancellationRating
7.9
4,246 reviews
Search Southwest flights
American AirlinesPriceFrom $238Free CancellationRating
7.1
11,779 reviews
Search American Airlines flights
United AirlinesPriceFrom $259Free CancellationRating
7.4
9,896 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.

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1 adult
Mon 7/27
Mon 8/3

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