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$121+ 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 10/21. Fares are subject to change and may not be available on all flights or dates of travel.
LEX — SJU
Oct 17 — Oct 241
Fri 10/17
Fri 10/24
1 adult, Economy
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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 September 17, 2025.

Round-trip from

$235
(Delta)

One-way from

$121
(American Airlines)

Popular in

August

Cheapest in

January

Average price

$523
From Lexington Blue Grass to Caribbean
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One-way flight from Lexington Blue Grass to Caribbean
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Highest demand for flights based on searches. 4% potential increase in price ($24 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($14 potential savings vs. average RT price).
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Average for round-trip flights in September 2025
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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 September 17, 2025.

This American Airlines deal was found by Cheapflights users on 9/17. 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.
Wed 10/156:00 amLEX - SJU
1 stop16h 10mAmerican Airlines
Wed 10/225:30 amSJU - LEX
2 stops11h 21mAmerican Airlines
Deal found 9/17$285
This American Airlines deal was found by Cheapflights users on 9/15. 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.
Sun 12/146:14 pmLEX - SJU
2 stops18h 16mAmerican Airlines
Thu 12/185:24 amSJU - LEX
2 stops17h 37mAmerican Airlines
Deal found 9/15$295
This American Airlines deal was found by Cheapflights users on 9/17. 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.
Mon 9/227:15 pmLEX - SJU
2 stops15h 56mAmerican Airlines
Wed 10/225:30 amSJU - LEX
2 stops9h 52mAmerican Airlines
Deal found 9/17$317
This American Airlines deal was found by Cheapflights users on 9/17. 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.
Mon 10/208:02 pmLEX - SJU
2 stops15h 04mAmerican Airlines
Wed 10/225:30 amSJU - LEX
2 stops9h 52mAmerican Airlines
Deal found 9/17$325
This American Airlines deal was found by Cheapflights users on 9/16. 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 10/227:10 pmLEX - SJU
2 stops15h 56mAmerican Airlines
Mon 10/277:10 amSJU - LEX
1 stop16h 58mAmerican Airlines
Deal found 9/16$342
This American Airlines deal was found by Cheapflights users on 9/16. 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 12/126:04 pmLEX - SJU
2 stops20h 43mAmerican Airlines
Sat 12/208:35 pmSJU - LEX
2 stops14h 55mAmerican Airlines
Deal found 9/16$364
This American Airlines deal was found by Cheapflights users on 9/15. 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.
Sat 12/68:09 pmLEX - SJU
2 stops16h 21mAmerican Airlines
Sun 12/146:25 amSJU - LEX
1 stop12h 19mAmerican Airlines
Deal found 9/15$365
This American Airlines deal was found by Cheapflights users on 9/16. 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 10/317:45 amLEX - PUJ
1 stop6h 45mAmerican Airlines
Fri 11/75:30 pmPUJ - LEX
2 stops20h 57mAmerican Airlines
Deal found 9/16$382
This American Airlines deal was found by Cheapflights users on 9/17. 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.
Fri 11/1411:21 amLEX - SJU
1 stop8h 27mAmerican Airlines
Mon 11/176:25 amSJU - LEX
1 stop12h 04mAmerican Airlines
Deal found 9/17$382
This American Airlines deal was found by Cheapflights users on 9/16. 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 9/307:15 pmLEX - SJU
2 stops15h 56mAmerican Airlines
Fri 10/33:05 pmSJU - LEX
1 stop9h 21mAmerican Airlines
Deal found 9/16$399
This United Airlines deal was found by Cheapflights users on 9/16. 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 10/317:05 amLEX - PUJ
2 stops9h 20mUnited Airlines
Fri 11/75:20 pmPUJ - LEX
2 stops20h 57mUnited Airlines
Deal found 9/16$408
This American Airlines deal was found by Cheapflights users on 9/14. 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 12/176:04 pmLEX - PUJ
1 stop16h 49mAmerican Airlines
Tue 12/235:23 pmPUJ - LEX
2 stops19h 00mAmerican Airlines
Deal found 9/14$409

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 September 17, 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

Sun 1/18

5:55 am-5:19 pm

1 stop10h 24m

San Juan Luis Munoz Marin Intl

Tue 1/20

7:30 am-12:40 pm

1 stop6h 10m

$266

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

Tue 1/20

5:00 pm-11:49 pm

1 stop5h 49m

San Juan Luis Munoz Marin Intl

Fri 1/23

6:15 am-2:29 pm

1 stop9h 14m

$266

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

Mon 1/19

5:55 am-1:00 pm

1 stop6h 05m

San Juan Luis Munoz Marin Intl

Mon 1/26

6:15 am-2:29 pm

1 stop9h 14m

$266

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

Sun 12/14

8:09 pm-1:01 pm

1 stop15h 52m

San Juan Luis Munoz Marin Intl

Thu 12/18

5:24 am-10:01 pm

2 stops17h 37m

$295

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

Sat 12/13

6:09 pm-1:30 pm

2 stops18h 21m

San Juan Luis Munoz Marin Intl

Wed 12/17

8:20 am-3:27 pm

1 stop8h 07m

$295

LexingtonPunta Cana

LEX - PUJ

LEXPUJ

Lexington Blue Grass

Sat 1/10

8:18 pm-11:40 am

1 stop14h 22m

Punta Cana

Thu 1/15

4:05 pm-9:49 pm

1 stop6h 44m

$353

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

Sun 1/18

5:32 pm-6:11 am

2 stops11h 39m

San Juan Luis Munoz Marin Intl

Thu 1/22

2:05 am-4:48 pm

2 stops15h 43m

$375

LexingtonPunta Cana

LEX - PUJ

LEXPUJ

Lexington Blue Grass

Fri 1/2

7:10 am-4:38 pm

1 stop8h 28m

Punta Cana

Thu 1/15

6:05 pm-11:55 pm

1 stop6h 50m

$378

LexingtonPunta Cana

LEX - PUJ

LEXPUJ

Lexington Blue Grass

Fri 1/2

6:55 pm-1:27 pm

2 stops17h 32m

Punta Cana

Thu 1/15

4:05 pm-9:49 pm

1 stop6h 44m

$383

LexingtonPunta Cana

LEX - PUJ

LEXPUJ

Lexington Blue Grass

Tue 3/3

3:45 pm-3:53 pm

2 stops23h 08m

Punta Cana

Fri 3/6

6:05 pm-9:25 am

1 stop16h 20m

$383

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/16

Showing 1-10 of 49 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, September is the cheapest month in which you can book a flight from Lexington to Caribbean (average of $254). Flying from Lexington to Caribbean in June is currently the most expensive (average of $339). 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 September 17, 2025.

Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Lexington to Caribbean as you normally would.

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 September 17, 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
8.0
Very good
7,961 reviews

Comfort

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
Delta
8.0
Very good
7,961 reviews
Delta
8.0
Very good
7,961 reviews

Comfort

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!
American Airlines
7.2
Good
10,000 reviews
Delta
8.0
Very good
7,961 reviews

Comfort

7.9

Boarding

8.2

Food

7.3

Crew

8.5

Entertainment

7.9

Overall

8.0

Reviews

1 / 20
10.0
Excellent

Kim,May 2025

PIH - SLC

This trip was fine even with delay I had plenty of time to get connection flight!

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 10h 24m. Fly via Delta or American 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 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 - Oranjestad Reina Beatrix 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, September is the cheapest month in which you can book a flight from Lexington to Caribbean (average of $254). Flying from Lexington to Caribbean in June is currently the most expensive (average of $339). 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 September 17, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$264Average$642FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$354Average$659FlexibilityNo cancel feeOn-time71%

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