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$180+ 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 1/3. Fares are subject to change and may not be available on all flights or dates of travel.
LEX — SJU
dic. 18 — dic. 251
jue. 12/18
jue. 12/25
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 noviembre 18, 2025.

This American Airlines deal was found by Cheapflights users on 11/18. 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.
lun. 12/157:18 pmLEX - SJU
2 stops13h 51mAmerican Airlines
jue. 12/181:30 amSJU - LEX
1 stop12h 53mAmerican Airlines
Deal found 11/18$288
This American Airlines deal was found by Cheapflights users on 11/17. 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.
vie. 12/57:18 pmLEX - SJU
2 stops15h 41mAmerican Airlines
lun. 12/86:25 amSJU - LEX
1 stop12h 08mAmerican Airlines
Deal found 11/17$317
This United Airlines deal was found by Cheapflights users on 11/18. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 12/47:00 amLEX - SJU
2 stops14h 22mUnited Airlines
lun. 12/82:05 amSJU - LEX
2 stops16h 05mUnited Airlines
Deal found 11/18$337
This Kiwi.com deal was found by Cheapflights users on 11/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 12/59:02 pmLEX - SJU
2 stops14h 30mMultiple Airlines
sáb. 12/64:10 amSJU - LEX
1 stop7h 18mMultiple Airlines
Deal found 11/17$363
This Kiwi.com deal was found by Cheapflights users on 11/15. 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.
lun. 12/11:18 pmLEX - SJU
1 stop9h 26mMultiple Airlines
vie. 12/56:59 pmSJU - LEX
2 stops40h 29mMultiple Airlines
Deal found 11/15$367
This American Airlines deal was found by Cheapflights users on 11/18. 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.
sáb. 12/68:09 pmLEX - SJU
1 stop17h 06mAmerican Airlines
dom. 12/147:00 amSJU - LEX
1 stop15h 45mAmerican Airlines
Deal found 11/18$370
This United Airlines deal was found by Cheapflights users on 11/15. 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.
vie. 12/57:00 amLEX - SJU
1 stop7h 40mUnited Airlines
mar. 12/92:05 amSJU - LEX
2 stops12h 17mUnited Airlines
Deal found 11/15$376
This American Airlines deal was found by Cheapflights users on 11/15. 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.
lun. 12/18:10 pmLEX - SJU
1 stop16h 28mAmerican Airlines
vie. 12/56:25 amSJU - LEX
1 stop12h 08mAmerican Airlines
Deal found 11/15$399
This Kiwi.com deal was found by Cheapflights users on 11/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 12/159:02 pmLEX - MBJ
2 stops15h 08mMultiple Airlines
lun. 12/221:05 pmMBJ - LEX
1 stop25h 27mMultiple Airlines
Deal found 11/17$472
This Delta deal was found by Cheapflights users on 11/17. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 12/246:20 amLEX - MBJ
1 stop6h 27mDelta
mié. 12/312:12 pmMBJ - LEX
1 stop8h 55mDelta
Deal found 11/17$473
This American Airlines deal was found by Cheapflights users on 11/17. 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.
mar. 12/167:16 pmLEX - STT
2 stops17h 36mAmerican Airlines
mié. 12/244:25 pmSTT - LEX
2 stops20h 08mAmerican Airlines
Deal found 11/17$509
This American Airlines deal was found by Cheapflights users on 11/18. 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.
mar. 12/236:09 amLEX - NAS
2 stops14h 19mAmerican Airlines
mié. 12/314:55 pmNAS - LEX
1 stop5h 06mAmerican Airlines
Deal found 11/18$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 noviembre 18, 2025.

Round-trip from

$235
(American Airlines)

One-way from

$180
(Kiwi.com)

Popular in

July

Cheapest in

October

Average price

$456
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 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 noviembre 18, 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

lun. 1/19

6:00 am-1:08 pm

1 stop6h 08m

San Juan Luis Munoz Marin Intl

jue. 1/22

11:38 am-11:15 pm

2 stops12h 37m

$235

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

mar. 2/3

6:00 am-2:59 pm

1 stop7h 59m

San Juan Luis Munoz Marin Intl

jue. 3/5

6:00 am-10:10 pm

1 stop17h 10m

$235

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

dom. 1/25

5:32 pm-6:11 am

2 stops11h 39m

San Juan Luis Munoz Marin Intl

lun. 1/26

2:05 am-1:25 pm

2 stops12h 20m

$264

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

mar. 2/3

10:30 am-9:00 pm

1 stop9h 30m

San Juan Luis Munoz Marin Intl

mié. 3/4

2:05 am-4:55 pm

2 stops15h 50m

$312

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

vie. 12/5

7:18 pm-11:59 am

2 stops15h 41m

San Juan Luis Munoz Marin Intl

mié. 12/10

11:00 am-9:29 pm

2 stops11h 29m

$317

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

lun. 1/19

10:30 am-10:22 pm

2 stops10h 52m

San Juan Luis Munoz Marin Intl

mié. 1/21

2:05 am-1:25 pm

2 stops12h 20m

$325

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

jue. 12/4

7:00 am-10:22 pm

2 stops14h 22m

San Juan Luis Munoz Marin Intl

mar. 12/9

8:30 am-8:39 pm

2 stops13h 09m

$337

LexingtonPunta Cana

LEX - PUJ

LEXPUJ

Lexington Blue Grass

sáb. 1/10

7:23 pm-12:55 pm

1 stop16h 32m

Punta Cana

jue. 1/15

2:51 pm-11:15 pm

1 stop9h 24m

$362

LexingtonPunta Cana

LEX - PUJ

LEXPUJ

Lexington Blue Grass

dom. 1/18

6:39 pm-12:11 pm

1 stop16h 32m

Punta Cana

sáb. 1/24

6:02 pm-12:19 pm

2 stops19h 17m

$366

LexingtonPunta Cana

LEX - PUJ

LEXPUJ

Lexington Blue Grass

sáb. 1/17

7:23 pm-12:55 pm

1 stop16h 32m

Punta Cana

sáb. 1/24

6:02 pm-12:19 pm

2 stops19h 17m

$391

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/17

Showing 1-10 of 47 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 noviembre 18, 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 noviembre 18, 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
8,003 reviews

Crew

8.5

Boarding

8.1

Food

7.3

Comfort

7.9

Entertainment

7.9

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
8,003 reviews
Delta
7.9
Good
8,003 reviews

Crew

8.5

Boarding

8.1

Food

7.3

Comfort

7.9

Entertainment

7.9

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
11,045 reviews
Delta
7.9
Good
8,003 reviews

Crew

8.5

Boarding

8.1

Food

7.3

Comfort

7.9

Entertainment

7.9

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 6h 08m. Fly via American Airlines, United Airlines, or Delta 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 - San Juan Luis Munoz Marin Intl, Lexington Blue Grass - Punta Cana 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 noviembre 18, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$274Average$641FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$340Average$646FlexibilityNo cancel feeOn-time71%

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