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$138+ 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 11/25. Fares are subject to change and may not be available on all flights or dates of travel.
LEX — SJU
Dec 11 — Dec 181
Thu 12/11
Thu 12/18
1 adult, Economy
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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 November 11, 2025.

This American Airlines deal was found by Cheapflights users on 11/9. 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 12/68:09 pmLEX - SJU
2 stops18h 48mAmerican Airlines
Mon 12/156:25 amSJU - LEX
1 stop12h 08mAmerican Airlines
Deal found 11/9$295
This United Airlines deal was found by Cheapflights users on 11/9. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/97:00 amLEX - PUJ
1 stop8h 02mUnited Airlines
Tue 12/162:55 pmPUJ - LEX
1 stop8h 35mUnited Airlines
Deal found 11/9$362
This American Airlines deal was found by Cheapflights users on 11/9. 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 12/68:09 pmLEX - SJU
2 stops13h 00mAmerican Airlines
Sun 12/146:25 amSJU - LEX
1 stop12h 19mAmerican Airlines
Deal found 11/9$365
This Kiwi.com deal was found by Cheapflights users on 11/9. 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 11/167:39 pmLEX - PUJ
1 stop18h 41mMultiple Airlines
Sat 11/225:45 pmPUJ - LEX
1 stop17h 41mMultiple Airlines
Deal found 11/9$373
This American Airlines deal was found by Cheapflights users on 11/9. 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 12/177:55 amLEX - PLS
1 stop6h 47mAmerican Airlines
Mon 12/223:33 pmPLS - LEX
1 stop8h 28mAmerican Airlines
Deal found 11/9$380
This United Airlines deal was found by Cheapflights users on 11/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/147:05 amLEX - SJU
2 stops13h 21mUnited Airlines
Thu 11/202:05 amSJU - LEX
2 stops12h 12mUnited Airlines
Deal found 11/10$399
This American Airlines deal was found by Cheapflights users on 11/9. 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 11/116:40 amLEX - SJU
2 stops13h 08mAmerican Airlines
Mon 11/176:25 amSJU - LEX
1 stop12h 04mAmerican Airlines
Deal found 11/9$407
This American Airlines deal was found by Cheapflights users on 11/10. 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 12/157:18 pmLEX - SJU
2 stops15h 41mAmerican Airlines
Fri 12/196:00 amSJU - LEX
1 stop13h 30mAmerican Airlines
Deal found 11/10$418
This United Airlines deal was found by Cheapflights users on 11/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/1210:40 amLEX - SJU
1 stop9h 20mUnited Airlines
Fri 11/142:05 amSJU - LEX
2 stops16h 05mUnited Airlines
Deal found 11/10$489
This American Airlines deal was found by Cheapflights users on 11/10. 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 12/247:00 amLEX - MBJ
1 stop29h 52mAmerican Airlines
Wed 12/3111:27 amMBJ - LEX
1 stop6h 06mAmerican Airlines
Deal found 11/10$507
This American Airlines deal was found by Cheapflights users on 11/10. 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 12/166:40 amLEX - STT
2 stops9h 08mAmerican Airlines
Wed 12/244:25 pmSTT - LEX
2 stops21h 58mAmerican Airlines
Deal found 11/10$509
This United Airlines deal was found by Cheapflights users on 11/10. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/257:05 amLEX - SJU
1 stop7h 35mUnited Airlines
Fri 11/282:05 amSJU - LEX
2 stops12h 12mUnited Airlines
Deal found 11/10$509

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 November 11, 2025.

Round-trip from

$235
(American Airlines)

One-way from

$138
(Kiwi.com)

Popular in

July

Cheapest in

October

Average price

$498
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. 19% potential increase in price ($127 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in November 2025
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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 November 11, 2025.
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

Mon 2/2

6:00 am-8:50 pm

1 stop13h 50m

San Juan Luis Munoz Marin Intl

Fri 2/6

7:00 am-6:52 pm

2 stops12h 52m

$235

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

Mon 2/2

8:35 am-10:22 pm

2 stops12h 47m

San Juan Luis Munoz Marin Intl

Thu 2/5

2:05 am-4:48 pm

2 stops15h 43m

$303

LexingtonProvidenciales

LEX - PLS

LEXPLS

Lexington Blue Grass

Mon 1/26

6:00 am-2:32 pm

1 stop8h 32m

Providenciales

Thu 1/29

12:52 pm-11:15 pm

1 stop10h 23m

$380

LexingtonProvidenciales

LEX - PLS

LEXPLS

Lexington Blue Grass

Fri 2/6

6:00 am-11:41 am

1 stop5h 41m

Providenciales

Mon 2/9

3:50 pm-2:28 pm

2 stops22h 38m

$385

LexingtonProvidenciales

LEX - PLS

LEXPLS

Lexington Blue Grass

Wed 12/17

7:55 am-2:42 pm

1 stop6h 47m

Providenciales

Mon 12/22

1:20 pm-10:30 am

2 stops21h 10m

$385

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

Fri 11/14

10:40 am-10:22 pm

2 stops10h 42m

San Juan Luis Munoz Marin Intl

Fri 11/21

4:52 pm-11:44 pm

1 stop7h 52m

$399

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

Fri 11/14

7:51 am-5:52 pm

2 stops9h 01m

San Juan Luis Munoz Marin Intl

Fri 11/21

2:50 pm-11:59 pm

2 stops10h 09m

$399

LexingtonPunta Cana

LEX - PUJ

LEXPUJ

Lexington Blue Grass

Fri 2/6

4:35 pm-11:54 am

2 stops18h 19m

Punta Cana

Mon 2/9

6:02 pm-12:16 pm

2 stops19h 14m

$406

LexingtonPunta Cana

LEX - PUJ

LEXPUJ

Lexington Blue Grass

Sun 2/22

7:07 pm-4:45 pm

1 stop20h 38m

Punta Cana

Mon 3/2

5:45 pm-12:05 pm

2 stops19h 20m

$420

LexingtonPunta Cana

LEX - PUJ

LEXPUJ

Lexington Blue Grass

Sat 1/17

7:23 pm-12:55 pm

1 stop16h 32m

Punta Cana

Sat 1/24

6:02 pm-12:19 pm

2 stops19h 17m

$421

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/10

Showing 1-10 of 48 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, January is the cheapest month in which you can book a flight from Lexington to Caribbean (average of $128). Flying from Lexington to Caribbean in June is currently the most expensive (average of $244). 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.

What is the cheapest time of day to fly from LEX to CB?

Find hourly flight availability from Lexington to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated November 11, 2025.

One of the essential ways to save on airfare from Lexington to Caribbean is to remain as flexible as possible. Flights that are in the evening tend to be the most expensive. A flight at noon could potentially save you up to 49% on airfare.

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 November 11, 2025.
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
8,007 reviews

Crew

8.5

Food

7.3

Overall

7.9

Boarding

8.1

Comfort

7.9

Entertainment

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
8,007 reviews
Delta
7.9
Good
8,007 reviews

Crew

8.5

Food

7.3

Overall

7.9

Boarding

8.1

Comfort

7.9

Entertainment

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
11,045 reviews
Delta
7.9
Good
8,007 reviews

Crew

8.5

Food

7.3

Overall

7.9

Boarding

8.1

Comfort

7.9

Entertainment

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 55m. Fly via American Airlines, United Airlines, or Delta to get the fastest option. Airlines will cover a distance of 1802 mi. This flight may include one or multiple stops.

  • What are the cheapest airlines to fly from Lexington to Caribbean one-way?

    The cheapest airline one-way is United Airlines, with whom users have recently found tickets for as low as $169. However, be on the lookout for offers from American Airlines and Delta, as they are both options that can get you from Lexington to Caribbean for a low price.

  • 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, January is the cheapest month in which you can book a flight from Lexington to Caribbean (average of $128). Flying from Lexington to Caribbean in June is currently the most expensive (average of $244). 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 November 11, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$274Average$641FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$340Average$631FlexibilityNo cancel feeOn-time71%

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