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$118+ 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 1/26. Fares are subject to change and may not be available on all flights or dates of travel.
LEX — SJU
Jan 1 — Jan 81
Thu 1/1
Thu 1/8
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 December 2, 2025.

This American Airlines deal was found by Cheapflights users on 11/30. 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
1 stop15h 56mAmerican Airlines
Sun 12/146:25 amSJU - LEX
1 stop12h 19mAmerican Airlines
Deal found 11/30$399
This Kiwi.com deal was found by Cheapflights users on 12/1. 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.
Tue 12/233:22 pmLEX - SJU
1 stop29h 43mMultiple Airlines
Sat 12/277:35 amSJU - LEX
1 stop25h 53mMultiple Airlines
Deal found 12/1$403
This American Airlines deal was found by Cheapflights users on 11/30. 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 12/1511:23 amLEX - SJU
2 stops11h 29mAmerican Airlines
Fri 12/198:25 amSJU - LEX
1 stop10h 08mAmerican Airlines
Deal found 11/30$459
This Delta deal was found by Cheapflights users on 12/1. 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.
Mon 12/86:05 amLEX - MBJ
1 stop8h 08mDelta
Thu 12/113:38 pmMBJ - LEX
1 stop8h 30mDelta
Deal found 12/1$473
This American Airlines deal was found by Cheapflights users on 12/1. 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 12/84:35 pmLEX - MBJ
2 stops20h 25mAmerican Airlines
Thu 12/113:12 pmMBJ - LEX
1 stop8h 02mAmerican Airlines
Deal found 12/1$478
This Delta deal was found by Cheapflights users on 11/30. 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 12/258:10 amLEX - MBJ
1 stop12h 31mDelta
Tue 12/3012:30 pmMBJ - LEX
1 stop9h 21mDelta
Deal found 11/30$503
This American Airlines deal was found by Cheapflights users on 12/1. 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 12/164:35 pmLEX - MBJ
2 stops17h 38mAmerican Airlines
Mon 12/2211:07 amMBJ - LEX
2 stops10h 58mAmerican Airlines
Deal found 12/1$508
This Delta deal was found by Cheapflights users on 11/30. 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.
Mon 12/153:41 pmLEX - SJU
1 stop6h 39mDelta
Fri 12/193:10 pmSJU - LEX
1 stop8h 40mDelta
Deal found 11/30$512
This American Airlines deal was found by Cheapflights users on 12/1. 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 12/57:18 pmLEX - SJU
2 stops15h 41mAmerican Airlines
Sun 12/76:00 amSJU - LEX
2 stops12h 40mAmerican Airlines
Deal found 12/1$520
This Delta deal was found by Cheapflights users on 11/30. 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 12/258:10 amLEX - MBJ
1 stop12h 31mDelta
Mon 12/298:00 amMBJ - LEX
1 stop6h 56mDelta
Deal found 11/30$533
This American Airlines deal was found by Cheapflights users on 12/1. 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 12/48:09 pmLEX - PUJ
1 stop15h 44mAmerican Airlines
Sun 12/712:51 pmPUJ - LEX
1 stop10h 07mAmerican Airlines
Deal found 12/1$549
This Delta deal was found by Cheapflights users on 11/30. 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 12/258:10 amLEX - MBJ
1 stop12h 31mDelta
Thu 1/18:00 amMBJ - LEX
1 stop6h 56mDelta
Deal found 11/30$561

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 December 2, 2025.

Round-trip from

$235
(Delta)

One-way from

$118
(Delta)

Popular in

July

Cheapest in

October

Average price

$624
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 ($129 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 December 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 December 2, 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 2/23

6:00 am-11:44 pm

1 stop16h 44m

San Juan Luis Munoz Marin Intl

Thu 2/26

2:38 pm-11:33 pm

1 stop9h 55m

$235

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

Sun 1/25

8:00 am-9:39 pm

1 stop12h 39m

San Juan Luis Munoz Marin Intl

Thu 1/29

4:28 pm-11:23 pm

1 stop7h 55m

$295

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

Mon 1/12

8:07 am-9:39 pm

1 stop12h 32m

San Juan Luis Munoz Marin Intl

Wed 1/14

6:00 am-4:14 pm

1 stop11h 14m

$295

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

Tue 1/6

6:39 pm-5:01 pm

2 stops21h 22m

San Juan Luis Munoz Marin Intl

Thu 1/15

6:30 am-11:15 pm

2 stops17h 45m

$295

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

Fri 1/9

6:00 am-11:56 pm

2 stops16h 56m

San Juan Luis Munoz Marin Intl

Thu 1/15

6:30 am-5:53 pm

1 stop12h 23m

$295

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

Thu 1/8

6:39 pm-1:41 pm

2 stops18h 02m

San Juan Luis Munoz Marin Intl

Wed 1/14

6:30 am-6:09 pm

1 stop12h 39m

$295

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

Sun 2/1

7:41 am-10:26 pm

1 stop13h 45m

San Juan Luis Munoz Marin Intl

Thu 2/5

4:28 pm-11:23 pm

1 stop7h 55m

$295

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

Sat 1/10

6:00 am-11:56 pm

2 stops16h 56m

San Juan Luis Munoz Marin Intl

Thu 1/15

6:30 am-11:15 pm

2 stops17h 45m

$295

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

Tue 5/19

7:30 am-8:38 pm

2 stops13h 08m

San Juan Luis Munoz Marin Intl

Wed 5/27

7:45 am-4:55 pm

1 stop9h 10m

$312

LexingtonPunta Cana

LEX - PUJ

LEXPUJ

Lexington Blue Grass

Mon 1/19

9:30 pm-6:00 pm

1 stop19h 30m

Punta Cana

Fri 1/23

1:10 pm-8:40 pm

1 stop8h 30m

$344

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/30

Showing 1-10 of 58 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 December 2, 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 48% 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 December 2, 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
8,010 reviews

Entertainment

7.9

Comfort

7.9

Crew

8.5

Food

7.3

Overall

7.9

Boarding

8.1

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
8,010 reviews
Delta
7.9
Good
8,010 reviews

Entertainment

7.9

Comfort

7.9

Crew

8.5

Food

7.3

Overall

7.9

Boarding

8.1

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
11,041 reviews
Delta
7.9
Good
8,010 reviews

Entertainment

7.9

Comfort

7.9

Crew

8.5

Food

7.3

Overall

7.9

Boarding

8.1

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 11h 02m. Fly via American Airlines or Delta to get the fastest option. Airlines will cover a distance of 990 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 - Montego Bay Sangster 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 December 2, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$267Average$640FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$332Average$654FlexibilityNo cancel feeOn-time71%

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