HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Caribbean

$191+ Cheap flights from Lexington (LEX) to Caribbean

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 2/26. Fares are subject to change and may not be available on all flights or dates of travel.
LEX — SJU
Feb 14 — Feb 211
Sat 2/14
Sat 2/21
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Lexington to Caribbean with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Lexington to Caribbean

Keep the following information in mind while searching for Lexington to Caribbean flight deals. Data was last updated January 15, 2026.

Round-trip from

$256
(American Airlines)

One-way from

$191
(American Airlines)

Popular in

December

Cheapest in

March

Average price

$559
From Lexington Blue Grass to Caribbean
Search Deals
One-way flight from Lexington Blue Grass to Caribbean
Search Deals
Highest demand for flights based on searches. 13% potential increase in price ($83 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($34 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

Find flight deals from Lexington to Caribbean

Cheapest flights from Lexington to Caribbean
Explore the most affordable flight options available from Lexington to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 15, 2026.

This American Airlines deal was found by Cheapflights users on 1/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/231:14 pm
LEX
-
SJU
2 stops9h 26m
American Airlines
Fri 2/276:33 am
SJU
-
LEX
1 stop17h 39m
American Airlines
Deal found 1/13$256
This Kiwi.com deal was found by Cheapflights users on 1/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/2211:59 am
LEX
-
SJU
1 stop26h 32m
Multiple Airlines
Tue 3/32:59 am
SJU
-
LEX
2 stops30h 34m
Multiple Airlines
Deal found 1/13$311
This American Airlines deal was found by Cheapflights users on 1/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/281:58 pm
LEX
-
SJU
1 stop8h 33m
American Airlines
Thu 3/56:33 am
SJU
-
LEX
1 stop11h 04m
American Airlines
Deal found 1/14$316
This Delta deal was found by Cheapflights users on 1/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/296:00 am
LEX
-
SJU
1 stop10h 17m
Delta
Thu 2/57:30 am
SJU
-
LEX
1 stop7h 17m
Delta
Deal found 1/13$338
This American Airlines deal was found by Cheapflights users on 1/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/410:27 am
LEX
-
SJU
2 stops12h 07m
American Airlines
Wed 3/186:33 am
SJU
-
LEX
1 stop15h 24m
American Airlines
Deal found 1/14$346
This Faresmojo deal was found by Cheapflights users on 1/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/3110:05 am
LEX
-
SJU
1 stop10h 02m
JetBlue
Sat 8/151:06 pm
SJU
-
LEX
1 stop5h 48m
JetBlue
Deal found 1/13$356
This Kiwi.com deal was found by Cheapflights users on 1/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/2211:59 am
LEX
-
SJU
2 stops21h 18m
Multiple Airlines
Wed 2/254:31 pm
SJU
-
LEX
1 stop19h 35m
Multiple Airlines
Deal found 1/13$357
This Delta deal was found by Cheapflights users on 1/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/2512:36 pm
LEX
-
SJU
1 stop10h 22m
Delta
Tue 3/36:15 am
SJU
-
LEX
1 stop6h 35m
Delta
Deal found 1/13$381
This American Airlines deal was found by Cheapflights users on 1/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/16:00 am
LEX
-
SJU
1 stop16h 05m
American Airlines
Mon 5/44:30 pm
SJU
-
LEX
1 stop6h 16m
American Airlines
Deal found 1/13$382
This Kiwi.com deal was found by Cheapflights users on 1/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/49:45 pm
LEX
-
STT
1 stop15h 46m
Multiple Airlines
Wed 5/134:40 pm
STT
-
LEX
1 stop18h 21m
Multiple Airlines
Deal found 1/14$384
This American Airlines deal was found by Cheapflights users on 1/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/16:39 pm
LEX
-
NAS
1 stop16h 40m
American Airlines
Fri 2/61:12 pm
NAS
-
LEX
1 stop10h 03m
American Airlines
Deal found 1/13$414
This American Airlines deal was found by Cheapflights users on 1/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/316:17 pm
LEX
-
NAS
1 stop17h 02m
American Airlines
Tue 2/32:22 pm
NAS
-
LEX
1 stop8h 53m
American Airlines
Deal found 1/13$422

Cheapflights Fare Finder

 
Customize your flight search to find flights from Lexington to Caribbean 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, Cheapflights users made 2,558,603 searches. Data last updated January 15, 2026.
Use the filters below to find and compare flights from Lexington to Caribbean that are best for you.

Fly from

Lexington

Fly to

Caribbean

Route

Depart

Return

Price

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

Wed 2/25

1:58 pm-11:31 pm

1 stop8h 33m

San Juan Luis Munoz Marin Intl

Fri 2/27

6:33 am-11:12 pm

1 stop17h 39m

$256

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

Tue 2/24

6:40 am-9:34 pm

2 stops13h 54m

San Juan Luis Munoz Marin Intl

Fri 2/27

6:33 am-11:12 pm

1 stop17h 39m

$256

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

Mon 2/23

1:14 pm-9:49 pm

1 stop7h 35m

San Juan Luis Munoz Marin Intl

Thu 2/26

8:40 am-5:16 pm

1 stop9h 36m

$256

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

Sat 2/28

1:58 pm-11:31 pm

1 stop8h 33m

San Juan Luis Munoz Marin Intl

Thu 3/5

6:33 am-4:37 pm

1 stop11h 04m

$316

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

Thu 1/29

10:31 am-5:17 pm

1 stop5h 46m

San Juan Luis Munoz Marin Intl

Thu 2/5

7:30 am-1:47 pm

1 stop7h 17m

$338

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

Sun 4/12

6:00 am-10:05 pm

1 stop16h 05m

San Juan Luis Munoz Marin Intl

Wed 4/15

1:31 pm-11:52 pm

2 stops10h 21m

$346

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

Sun 2/22

11:59 am-10:17 am

2 stops21h 18m

San Juan Luis Munoz Marin Intl

Wed 2/25

4:31 pm-11:06 am

1 stop19h 35m

$357

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

Wed 2/25

6:40 am-3:20 pm

1 stop7h 40m

San Juan Luis Munoz Marin Intl

Mon 3/2

4:10 pm-9:28 am

1 stop18h 18m

$386

LexingtonNassau

LEX - NAS

LEXNAS

Lexington Blue Grass

Sun 2/1

6:39 pm-11:19 am

1 stop16h 40m

Nassau Intl

Fri 2/6

1:12 pm-11:15 pm

1 stop10h 03m

$414

LexingtonSaint Thomas Island

LEX - STT

LEXSTT

Lexington Blue Grass

Mon 5/4

9:45 pm-3:34 pm

2 stops17h 49m

Saint Thomas Island Cyril E King

Wed 5/13

4:40 pm-11:01 am

1 stop18h 21m

$424

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/14

Showing 1-10 of 43 results
1
2
3
...
5

Best time to book a flight from Lexington to Caribbean

Have a flexible travel schedule? Discover the best time to fly to Caribbean from Lexington with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Lexington to Caribbean

What is the cheapest month to book a flight from Lexington to Caribbean?

Currently, February is the cheapest month in which you can book a flight from Lexington to Caribbean (average of $148). Flying from Lexington to Caribbean in June is currently the most expensive (average of $252). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

Reviews of airlines servicing Caribbean

Get insights into the airlines that provide service to Caribbean. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean. Reviews last updated January 15, 2026.
Get a feel of what it's like to fly with Delta and American Airlines from Lexington to Caribbean by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,051 reviews

Crew

8.5

Entertainment

7.8

Food

7.2

Overall

7.9

Boarding

8.1

Comfort

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
Delta
7.9
Good
8,051 reviews
Delta
7.9
Good
8,051 reviews

Crew

8.5

Entertainment

7.8

Food

7.2

Overall

7.9

Boarding

8.1

Comfort

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.
American Airlines
7.2
Good
11,136 reviews
Delta
7.9
Good
8,051 reviews

Crew

8.5

Entertainment

7.8

Food

7.2

Overall

7.9

Boarding

8.1

Comfort

7.9

Reviews

1 / 20
6.0
Good

Jim,Nov 2025

AVL - ATL

The exit row seats without a seat in front are great for leg room but don’t have a fold out entertainment console so you’re forced to use the screen several feet in front of you (there is, at least, a remote). Best to bring a tablet loaded with entertainment or a book.

Related info for your journey

Find useful and relevant information for your journey from Lexington to Caribbean. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly from for flights from Lexington to Caribbean?

    Lexington Blue Grass (LEX) is the airport you will fly out of if you book a flight from Lexington to Caribbean. It is only a 5.6 mi journey to Blue Grass (LEX) from Lexington’s city center.

  • How long is the flight from Lexington to Caribbean?

    There are many flights that can get you from Lexington to Caribbean in 5h 43m. Fly via American Airlines, United Airlines, or Delta to get the fastest option. Airlines will cover a distance of 1662 mi. This flight may include one or multiple stops.

  • What are the most popular routes from Lexington to Caribbean?

    When deciding which route to take from Lexington to Caribbean consider Lexington Blue Grass - Punta Cana, Lexington Blue Grass - San Juan Luis Munoz Marin Intl or Lexington Blue Grass - Saint Thomas Island Cyril E King as they are the most popular.

  • Can I find deals for flights from Lexington to Caribbean that include hotel bookings?

    Yes. In addition to deals on Lexington to Caribbean flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Lexington to Caribbean?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Lexington to Caribbean.

  • Can I find deals for business class flights from Lexington to Caribbean?

    Yes. Cheapflights offers flight deals from Lexington to Caribbean by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Lexington to Caribbean?

    Currently, February is the cheapest month in which you can book a flight from Lexington to Caribbean (average of $148). Flying from Lexington to Caribbean in June is currently the most expensive (average of $252). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Lexington to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.
Cincinnati to Orlando flights
Cincinnati to Las Vegas flights
Cincinnati to Fort Lauderdale flights
Cincinnati to Tampa flights
Cincinnati to Fort Myers flights
Cincinnati to John F Kennedy Intl flights
Cincinnati to Sky Harbor Intl flights
Cincinnati to LaGuardia flights
Cincinnati to Newark flights
Cincinnati to Denver flights
Nashville to Los Angeles flights
Cincinnati to Miami flights
Cincinnati to Los Angeles flights
Nashville to Miami flights
Nashville to John F Kennedy Intl flights
Nashville to Newark flights
Nashville to LaGuardia flights
Cincinnati to Orlando Sanford Intl flights
Cincinnati to Dallas/Fort Worth flights
Nashville to Seattle flights
Nashville to Fort Lauderdale flights
Nashville to Las Vegas flights
Cincinnati to Hobby flights
Louisville to Miami flights
Cincinnati to Cancún flights
Cincinnati to St Petersburg flights
Nashville to Denver flights
Nashville to Dallas/Fort Worth flights
Nashville to Orlando flights
Cincinnati to Sarasota flights
Cincinnati to Seattle flights
Nashville to Cancún flights
Louisville to Las Vegas flights
Cincinnati to George Bush Intcntl flights
Nashville to Hobby flights
Nashville to O'Hare Intl flights
Cincinnati to Boston flights
Nashville to Reagan-National flights
Louisville to LaGuardia flights
Nashville to Tampa flights
Nashville to Heathrow flights
Lexington to Orlando flights
Nashville to San Francisco flights
Louisville to Newark flights
Cincinnati to Austin flights
Louisville to Orlando flights
Cincinnati to Atlanta flights
Cincinnati to Salt Lake City flights
Nashville to Salt Lake City flights
Louisville to Fort Lauderdale flights

Top 2 airlines flying from Lexington to Caribbean

Discover the top 2 airlines that operate flights from Lexington to Caribbean. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated January 15, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$163Average$638FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$299Average$659FlexibilityNo cancel feeOn-time71%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.