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Caribbean

$162+ 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 3/7. Fares are subject to change and may not be available on all flights or dates of travel.
LEX — SJU
Feb 27 — Mar 61
Fri 2/27
Fri 3/6
1 adult, Economy
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Cheap 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 28, 2026.

This American Airlines deal was found by Cheapflights users on 1/26. 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 1/26$256
This American Airlines deal was found by Cheapflights users on 1/27. 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.
Tue 2/245:00 am
LEX
-
SJU
1 stop14h 39m
American Airlines
Tue 3/33:39 pm
SJU
-
LEX
1 stop8h 47m
American Airlines
Deal found 1/27$296
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
Thu 2/199:39 am
LEX
-
STT
1 stop29h 55m
Multiple Airlines
Wed 2/255:40 pm
STT
-
LEX
1 stop18h 26m
Multiple Airlines
Deal found 1/27$324
This American Airlines deal was found by Cheapflights users on 1/25. 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
Sun 5/36:00 am
SJU
-
LEX
1 stop17h 52m
American Airlines
Deal found 1/25$336
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 3/164:22 pm
LEX
-
STT
1 stop21h 04m
Multiple Airlines
Tue 3/242:36 pm
STT
-
LEX
1 stop29h 00m
Multiple Airlines
Deal found 1/27$348
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 5/109:51 am
LEX
-
STT
1 stop29h 43m
Multiple Airlines
Wed 5/204:40 pm
STT
-
LEX
1 stop21h 35m
Multiple Airlines
Deal found 1/27$354
This Faresmojo deal was found by Cheapflights users on 1/26. 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 stop6h 38m
JetBlue
Sat 8/157:30 am
SJU
-
LEX
1 stop7h 29m
JetBlue
Deal found 1/26$356
This Kiwi.com deal was found by Cheapflights users on 1/27. 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 4/129:31 am
LEX
-
STT
2 stops27h 55m
Multiple Airlines
Wed 4/224:40 pm
STT
-
LEX
1 stop16h 01m
Multiple Airlines
Deal found 1/27$367
This Kiwi.com deal was found by Cheapflights users on 1/26. 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 3/164:22 pm
LEX
-
SJU
1 stop16h 31m
Multiple Airlines
Fri 3/277:54 pm
SJU
-
LEX
2 stops18h 56m
Multiple Airlines
Deal found 1/26$370
This American Airlines deal was found by Cheapflights users on 1/26. 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 3/46:40 am
LEX
-
SJU
2 stops12h 59m
American Airlines
Wed 3/183:00 pm
SJU
-
LEX
1 stop18h 24m
American Airlines
Deal found 1/26$375
This American Airlines deal was found by Cheapflights users on 1/27. 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 4/15:50 pm
LEX
-
PLS
2 stops18h 40m
American Airlines
Thu 4/91:25 pm
PLS
-
LEX
2 stops21h 33m
American Airlines
Deal found 1/27$390
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
Thu 4/169:31 am
LEX
-
STT
2 stops26h 55m
Multiple Airlines
Wed 4/224:40 pm
STT
-
LEX
1 stop16h 01m
Multiple Airlines
Deal found 1/27$410

Find 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 28, 2026.

Round-trip from

$256
(American Airlines)

One-way from

$162
(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 ($84 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

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 28, 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

Tue 2/24

5:00 am-3:49 pm

2 stops9h 49m

San Juan Luis Munoz Marin Intl

Tue 3/3

3:39 pm-11:26 pm

1 stop8h 47m

$256

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

Tue 2/24

3:46 pm-11:58 pm

1 stop7h 12m

San Juan Luis Munoz Marin Intl

Tue 3/3

6:15 am-2:59 pm

1 stop9h 44m

$256

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

Fri 5/1

12:44 pm-8:24 pm

1 stop7h 40m

San Juan Luis Munoz Marin Intl

Mon 5/4

6:15 am-1:34 pm

1 stop7h 19m

$256

LexingtonSaint Thomas Island

LEX - STT

LEXSTT

Lexington Blue Grass

Thu 2/19

9:39 am-4:34 pm

1 stop29h 55m

Saint Thomas Island Cyril E King

Wed 2/25

5:40 pm-11:06 am

1 stop18h 26m

$324

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

Tue 6/16

8:11 pm-9:33 am

2 stops13h 22m

San Juan Luis Munoz Marin Intl

Tue 6/23

6:00 am-11:59 pm

1 stop17h 59m

$375

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

Mon 3/16

10:27 am-10:58 pm

2 stops12h 31m

San Juan Luis Munoz Marin Intl

Tue 3/24

6:00 am-5:11 pm

2 stops11h 11m

$375

LexingtonProvidenciales

LEX - PLS

LEXPLS

Lexington Blue Grass

Wed 4/1

5:50 pm-12:30 pm

2 stops18h 40m

Providenciales

Thu 4/9

1:25 pm-10:58 am

2 stops21h 33m

$390

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

Fri 6/12

4:10 pm-11:41 pm

1 stop7h 31m

San Juan Luis Munoz Marin Intl

Wed 6/17

12:39 am-12:53 pm

1 stop12h 14m

$415

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

Wed 3/4

6:40 am-8:39 pm

2 stops12h 59m

San Juan Luis Munoz Marin Intl

Wed 3/18

7:40 am-5:16 pm

1 stop9h 36m

$415

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

Mon 2/9

6:00 am-1:06 pm

1 stop6h 06m

San Juan Luis Munoz Marin Intl

Fri 2/13

6:15 am-2:59 pm

1 stop9h 44m

$420

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/25

Showing 1-10 of 50 results
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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 $149). 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 28, 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
8,123 reviews

Boarding

8.1

Food

7.2

Overall

7.9

Comfort

7.9

Crew

8.5

Entertainment

7.8

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
8,123 reviews
Delta
7.9
Good
8,123 reviews

Boarding

8.1

Food

7.2

Overall

7.9

Comfort

7.9

Crew

8.5

Entertainment

7.8

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
11,201 reviews
Delta
7.9
Good
8,123 reviews

Boarding

8.1

Food

7.2

Overall

7.9

Comfort

7.9

Crew

8.5

Entertainment

7.8

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 7h 12m. Fly via American Airlines, Delta, or United Airlines to get the fastest option. Airlines will cover a distance of 1757 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 $149). 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

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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 28, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$163Average$621FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$299Average$654FlexibilityNo cancel feeOn-time71%

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