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$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 11/25. Fares are subject to change and may not be available on all flights or dates of travel.
LEX — SJU
Nov 27 — Dec 41
Thu 11/27
Thu 12/4
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 October 28, 2025.

This American Airlines deal was found by Cheapflights users on 10/26. 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.
Tue 12/26:07 pmLEX - SJU
2 stops22h 45mAmerican Airlines
Fri 12/53:58 pmSJU - LEX
1 stop8h 16mAmerican Airlines
Deal found 10/26$295
This American Airlines deal was found by Cheapflights users on 10/26. 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.
Thu 11/2011:17 amLEX - SJU
2 stops21h 53mAmerican Airlines
Thu 11/276:42 pmSJU - LEX
2 stops23h 56mAmerican Airlines
Deal found 10/26$297
This American Airlines deal was found by Cheapflights users on 10/27. 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.
Sat 12/68:09 pmLEX - SJU
2 stops13h 00mAmerican Airlines
Sun 12/146:25 amSJU - LEX
1 stop12h 19mAmerican Airlines
Deal found 10/27$341
This American Airlines deal was found by Cheapflights users on 10/26. 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 11/246:03 amLEX - SJU
2 stops16h 49mAmerican Airlines
Thu 11/276:42 pmSJU - LEX
2 stops23h 56mAmerican Airlines
Deal found 10/26$368
This American Airlines deal was found by Cheapflights users on 10/26. 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 11/197:16 pmLEX - SJU
2 stops13h 54mAmerican Airlines
Thu 11/276:42 pmSJU - LEX
2 stops23h 56mAmerican Airlines
Deal found 10/26$371
This American Airlines deal was found by Cheapflights users on 10/27. 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.
Mon 12/157:18 pmLEX - SJU
2 stops15h 41mAmerican Airlines
Fri 12/197:00 amSJU - LEX
2 stops11h 33mAmerican Airlines
Deal found 10/27$378
This Kiwi.com deal was found by Cheapflights users on 10/26. 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.
Tue 11/253:38 pmLEX - SJU
1 stop7h 06mMultiple Airlines
Wed 12/37:10 amSJU - LEX
2 stops28h 18mMultiple Airlines
Deal found 10/26$383
This American Airlines deal was found by Cheapflights users on 10/26. 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.
Sun 11/238:10 pmLEX - SJU
2 stops13h 00mAmerican Airlines
Wed 12/36:00 amSJU - LEX
2 stops16h 29mAmerican Airlines
Deal found 10/26$395
This American Airlines deal was found by Cheapflights users on 10/26. 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.
Sun 11/2311:17 amLEX - SJU
2 stops21h 53mAmerican Airlines
Thu 11/273:41 pmSJU - LEX
2 stops29h 03mAmerican Airlines
Deal found 10/26$398
This Delta deal was found by Cheapflights users on 10/28. 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.
Wed 10/296:00 amLEX - SJU
1 stop10h 33mDelta
Sat 11/15:43 pmSJU - LEX
1 stop6h 22mDelta
Deal found 10/28$399
This American Airlines deal was found by Cheapflights users on 10/28. 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 12/2211:17 amPLS - LEX
1 stop10h 44mAmerican Airlines
Deal found 10/28$404
This Kiwi.com deal was found by Cheapflights users on 10/26. 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.
Sun 11/2311:16 amLEX - SJU
1 stop11h 27mMultiple Airlines
Wed 12/37:10 amSJU - LEX
2 stops28h 18mMultiple Airlines
Deal found 10/26$406

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 October 28, 2025.

Round-trip from

$295
(American Airlines)

One-way from

$133
(Kiwi.com)

Popular in

December

Cheapest in

January

Average price

$413
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. 2% potential increase in price ($17 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 5% potential price decrease ($28 potential savings vs. average RT price).
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Average for round-trip flights in October 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 October 28, 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 12/15

7:18 pm-11:59 am

2 stops15h 41m

San Juan Luis Munoz Marin Intl

Fri 12/19

6:00 am-11:22 pm

1 stop18h 22m

$341

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-9:28 pm

1 stop8h 36m

$368

LexingtonProvidenciales

LEX - PLS

LEXPLS

Lexington Blue Grass

Wed 12/17

7:55 am-2:42 pm

1 stop6h 47m

Providenciales

Mon 12/22

11:17 am-10:01 pm

1 stop10h 44m

$404

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

Fri 11/7

7:51 am-8:48 pm

1 stop11h 57m

San Juan Luis Munoz Marin Intl

Fri 11/14

6:25 am-5:29 pm

1 stop12h 04m

$419

LexingtonNassau

LEX - NAS

LEXNAS

Lexington Blue Grass

Thu 1/22

6:00 am-12:13 pm

1 stop6h 13m

Nassau Intl

Tue 1/27

2:22 pm-11:15 pm

1 stop8h 53m

$445

LexingtonNassau

LEX - NAS

LEXNAS

Lexington Blue Grass

Thu 1/8

7:00 am-12:13 pm

1 stop5h 13m

Nassau Intl

Mon 1/12

1:12 pm-11:15 pm

1 stop10h 03m

$445

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

Wed 12/3

3:41 pm-11:20 pm

1 stop6h 39m

San Juan Luis Munoz Marin Intl

Tue 12/9

6:38 pm-12:08 am

1 stop6h 30m

$450

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

Sat 12/6

8:09 pm-1:05 pm

1 stop15h 56m

San Juan Luis Munoz Marin Intl

Sun 12/14

6:25 am-5:44 pm

1 stop12h 19m

$455

LexingtonPunta Cana

LEX - PUJ

LEXPUJ

Lexington Blue Grass

Sat 2/21

7:10 am-4:40 pm

1 stop8h 30m

Punta Cana

Sat 2/28

6:05 pm-9:25 am

1 stop16h 20m

$456

LexingtonPunta Cana

LEX - PUJ

LEXPUJ

Lexington Blue Grass

Tue 2/24

7:10 am-3:25 pm

1 stop7h 15m

Punta Cana

Fri 2/27

6:05 pm-9:25 am

1 stop16h 20m

$456

Flights are sorted by cheapest round-trip flights first.

Deals found on 10/27

Showing 1-10 of 45 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 October 28, 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 October 28, 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
7,994 reviews

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.9

Overall

7.9

Food

7.3

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
Delta
7.9
Good
7,994 reviews
Delta
7.9
Good
7,994 reviews

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.9

Overall

7.9

Food

7.3

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.
American Airlines
7.2
Good
11,032 reviews
Delta
7.9
Good
7,994 reviews

Boarding

8.2

Comfort

7.9

Crew

8.5

Entertainment

7.9

Overall

7.9

Food

7.3

Reviews

1 / 20
8.0
Excellent

Matthew,Oct 2025

GSP - ATL

This is always a full flight since it is the connecting route to primary destinations through Atlanta. That said, the crew handles the full load well. Not much more to say, it is a short flight with no in-flight services due to the length.

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 39m. 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 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 $191. 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 - 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 October 28, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$274Average$640FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$340Average$633FlexibilityNo cancel feeOn-time71%

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