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Caribbean

$133+ 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 3/10. Fares are subject to change and may not be available on all flights or dates of travel.
LEX — SJU
Mar 22 — Mar 291
Sun 3/22
Sun 3/29
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 February 20, 2026.

This American Airlines deal was found by Cheapflights users on 2/19. 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 4/2212:18 pm
LEX
-
SJU
1 stop8h 33m
American Airlines
Wed 4/296:00 am
SJU
-
LEX
1 stop17h 52m
American Airlines
Deal found 2/19$266
This Kiwi.com deal was found by Cheapflights users on 2/19. 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 4/239:31 am
LEX
-
SJU
1 stop11h 18m
Multiple Airlines
Wed 4/293:36 pm
SJU
-
LEX
1 stop17h 05m
Multiple Airlines
Deal found 2/19$290
This American Airlines deal was found by Cheapflights users on 2/18. 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 12/146:00 am
LEX
-
SJU
2 stops13h 56m
American Airlines
Wed 12/236:15 pm
SJU
-
LEX
1 stop17h 15m
American Airlines
Deal found 2/18$299
This American Airlines deal was found by Cheapflights users on 2/17. 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.
Thu 3/195:50 pm
LEX
-
MBJ
2 stops16h 17m
American Airlines
Thu 3/261:27 pm
MBJ
-
LEX
2 stops20h 24m
American Airlines
Deal found 2/17$322
This American Airlines deal was found by Cheapflights users on 2/19. 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 4/206:00 am
LEX
-
SJU
2 stops12h 10m
American Airlines
Tue 4/2810:03 am
SJU
-
LEX
2 stops13h 49m
American Airlines
Deal found 2/19$332
This American Airlines deal was found by Cheapflights users on 2/19. 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 4/212:15 pm
LEX
-
SJU
1 stop8h 47m
American Airlines
Thu 4/303:19 pm
SJU
-
LEX
1 stop8h 33m
American Airlines
Deal found 2/19$338
This Delta deal was found by Cheapflights users on 2/19. 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.
Sun 5/246:57 am
LEX
-
MBJ
1 stop9h 32m
Delta
Thu 5/2812:55 pm
MBJ
-
LEX
1 stop8h 10m
Delta
Deal found 2/19$342
This American Airlines deal was found by Cheapflights users on 2/19. 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 7/188:11 pm
LEX
-
MBJ
1 stop15h 44m
American Airlines
Sat 7/255:17 pm
MBJ
-
LEX
2 stops16h 16m
American Airlines
Deal found 2/19$350
This Kiwi.com deal was found by Cheapflights users on 2/18. 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.
Wed 3/1811:55 am
LEX
-
SJU
1 stop10h 04m
Multiple Airlines
Wed 3/257:54 pm
SJU
-
LEX
1 stop12h 51m
Multiple Airlines
Deal found 2/18$364
This American Airlines deal was found by Cheapflights users on 2/18. 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 7/128:11 pm
LEX
-
MBJ
2 stops16h 31m
American Airlines
Fri 7/175:17 pm
MBJ
-
LEX
2 stops16h 16m
American Airlines
Deal found 2/18$365
This American Airlines deal was found by Cheapflights users on 2/18. 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 5/95:51 pm
LEX
-
PLS
2 stops18h 34m
American Airlines
Thu 5/142:12 pm
PLS
-
LEX
1 stop9h 40m
American Airlines
Deal found 2/18$368
This American Airlines deal was found by Cheapflights users on 2/20. 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 4/126:00 am
LEX
-
SJU
1 stop16h 05m
American Airlines
Sat 4/183:19 pm
SJU
-
LEX
1 stop8h 33m
American Airlines
Deal found 2/20$372

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 February 20, 2026.

Round-trip from

$266
(American Airlines)

One-way from

$133
(Delta)

Popular in

August

Cheapest in

March

Average price

$470
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. 21% potential increase in price ($148 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 February 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 February 20, 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

Sat 5/2

3:28 pm-4:32 am

2 stops13h 04m

San Juan Luis Munoz Marin Intl

Sat 5/9

6:00 am-5:14 pm

2 stops11h 14m

$299

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

Wed 4/22

12:18 pm-8:51 pm

1 stop8h 33m

San Juan Luis Munoz Marin Intl

Tue 4/28

10:03 am-11:52 pm

2 stops13h 49m

$299

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

Thu 4/23

9:31 am-8:49 pm

1 stop11h 18m

San Juan Luis Munoz Marin Intl

Tue 4/28

1:59 am-8:41 am

2 stops30h 42m

$303

LexingtonMontego Bay

LEX - MBJ

LEXMBJ

Lexington Blue Grass

Thu 3/19

5:50 pm-9:07 am

2 stops16h 17m

Montego Bay Sangster Intl

Thu 3/26

1:27 pm-10:51 am

2 stops20h 24m

$322

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

Mon 4/20

6:00 am-6:10 pm

2 stops12h 10m

San Juan Luis Munoz Marin Intl

Tue 4/28

10:03 am-11:52 pm

2 stops13h 49m

$332

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

Tue 4/21

6:00 am-6:10 pm

2 stops12h 10m

San Juan Luis Munoz Marin Intl

Wed 4/29

3:19 pm-11:52 pm

1 stop8h 33m

$338

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

Tue 4/21

6:00 am-6:10 pm

2 stops12h 10m

San Juan Luis Munoz Marin Intl

Thu 4/30

3:19 pm-11:52 pm

1 stop8h 33m

$338

LexingtonMontego Bay

LEX - MBJ

LEXMBJ

Lexington Blue Grass

Sun 5/24

6:57 am-3:29 pm

1 stop9h 32m

Montego Bay Sangster Intl

Thu 5/28

12:55 pm-10:05 pm

1 stop8h 10m

$342

LexingtonMontego Bay

LEX - MBJ

LEXMBJ

Lexington Blue Grass

Sun 7/12

8:11 pm-11:42 am

2 stops16h 31m

Montego Bay Sangster Intl

Fri 7/17

5:17 pm-10:33 am

2 stops16h 16m

$365

LexingtonProvidenciales

LEX - PLS

LEXPLS

Lexington Blue Grass

Sat 5/9

6:36 pm-2:15 pm

2 stops19h 39m

Providenciales

Thu 5/14

1:25 pm-10:58 am

2 stops21h 33m

$368

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/17

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, July is the cheapest month in which you can book a flight from Lexington to Caribbean (average of $109). Flying from Lexington to Caribbean in June is currently the most expensive (average of $249). 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 February 20, 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
8,228 reviews

Comfort

7.9

Boarding

8.1

Entertainment

7.8

Crew

8.5

Food

7.2

Overall

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
8,228 reviews
Delta
7.9
Good
8,228 reviews

Comfort

7.9

Boarding

8.1

Entertainment

7.8

Crew

8.5

Food

7.2

Overall

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
11,334 reviews
Delta
7.9
Good
8,228 reviews

Comfort

7.9

Boarding

8.1

Entertainment

7.8

Crew

8.5

Food

7.2

Overall

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 8h 18m. Fly via American Airlines, Delta, or United Airlines to get the fastest option. Airlines will cover a distance of 1802 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 - Nassau Intl 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, July is the cheapest month in which you can book a flight from Lexington to Caribbean (average of $109). Flying from Lexington to Caribbean in June is currently the most expensive (average of $249). 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 February 20, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$163Average$710FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$296Average$635FlexibilityNo cancel feeOn-time71%

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