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$108+ 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 11/15. Fares are subject to change and may not be available on all flights or dates of travel.
LEX — SJU
Aug 25 — Sep 11
Mon 8/25
Mon 9/1
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 August 20, 2025.

Round-trip from

$215
(American Airlines)

One-way from

$108
(Delta)

Popular in

June

Cheapest in

January

Average price

$517
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. 3% potential increase in price ($18 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($8 potential savings vs. average RT price).
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Average for round-trip flights in August 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 August 20, 2025.

This American Airlines deal was found by Cheapflights users on 8/19. 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 10/47:15 pmLEX - SJU
2 stops17h 32mAmerican Airlines
Sat 10/115:30 amSJU - LEX
1 stop15h 55mAmerican Airlines
Deal found 8/19$215
This American Airlines deal was found by Cheapflights users on 8/20. 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 9/185:57 pmLEX - SJU
2 stops17h 14mAmerican Airlines
Tue 9/236:10 amSJU - LEX
2 stops16h 53mAmerican Airlines
Deal found 8/20$282
This Mytrip deal was found by Cheapflights users on 8/20. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/1812:16 pmLEX - SJU
2 stops25h 55mMultiple Airlines
Tue 9/236:44 amSJU - LEX
1 stop9h 04mMultiple Airlines
Deal found 8/20$320
This American Airlines deal was found by Cheapflights users on 8/18. 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.
Sat 11/85:00 amLEX - SJU
1 stop15h 32mAmerican Airlines
Sun 11/166:25 amSJU - LEX
1 stop12h 03mAmerican Airlines
Deal found 8/18$349
This Kiwi.com deal was found by Cheapflights users on 8/18. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/109:49 pmLEX - SJU
1 stop16h 23mMultiple Airlines
Tue 10/143:19 pmSJU - LEX
1 stop23h 29mMultiple Airlines
Deal found 8/18$356
This American Airlines deal was found by Cheapflights users on 8/20. 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 9/2012:54 pmLEX - SJU
2 stops10h 43mAmerican Airlines
Tue 9/234:43 pmSJU - LEX
1 stop6h 20mAmerican Airlines
Deal found 8/20$357
This American Airlines deal was found by Cheapflights users on 8/19. 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 8/276:00 amLEX - SJU
1 stop9h 00mAmerican Airlines
Fri 9/57:05 pmSJU - LEX
2 stops19h 00mAmerican Airlines
Deal found 8/19$399
This Kiwi.com deal was found by Cheapflights users on 8/19. 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.
Thu 8/289:19 amLEX - SJU
1 stop30h 12mMultiple Airlines
Fri 9/55:13 pmSJU - LEX
2 stops42h 13mMultiple Airlines
Deal found 8/19$420
This Mytrip deal was found by Cheapflights users on 8/18. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/27:25 pmLEX - NAS
1 stop15h 05mMultiple Airlines
Thu 10/911:30 amNAS - LEX
1 stop7h 15mMultiple Airlines
Deal found 8/18$444
This American Airlines deal was found by Cheapflights users on 8/19. 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 9/177:47 amLEX - PUJ
1 stop7h 38mAmerican Airlines
Wed 9/244:25 pmPUJ - LEX
1 stop6h 38mAmerican Airlines
Deal found 8/19$453
This American Airlines deal was found by Cheapflights users on 8/18. 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.
Fri 10/176:00 amLEX - PUJ
1 stop8h 52mAmerican Airlines
Mon 10/204:39 pmPUJ - LEX
2 stops17h 40mAmerican Airlines
Deal found 8/18$457
This United Airlines deal was found by Cheapflights users on 8/19. 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.
Mon 9/296:01 pmLEX - PUJ
2 stops21h 24mUnited Airlines
Fri 10/34:35 pmPUJ - LEX
2 stops23h 13mUnited Airlines
Deal found 8/19$465

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 August 20, 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

Sat 10/4

7:15 pm-11:11 am

2 stops15h 56m

San Juan Luis Munoz Marin Intl

Sat 10/11

5:30 am-9:25 pm

1 stop15h 55m

$215

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

Tue 1/13

1:30 pm-11:49 pm

1 stop9h 19m

San Juan Luis Munoz Marin Intl

Tue 1/20

2:10 pm-11:55 pm

1 stop10h 45m

$270

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

Tue 1/13

12:33 pm-11:40 pm

2 stops10h 07m

San Juan Luis Munoz Marin Intl

Tue 1/20

6:30 am-2:32 pm

2 stops9h 02m

$282

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

Tue 2/10

12:33 pm-11:40 pm

2 stops10h 07m

San Juan Luis Munoz Marin Intl

Tue 2/24

6:40 am-2:31 pm

2 stops8h 51m

$282

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

Thu 9/18

5:57 pm-11:11 am

2 stops17h 14m

San Juan Luis Munoz Marin Intl

Tue 9/23

6:10 am-11:03 pm

2 stops16h 53m

$282

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

Fri 9/19

7:15 pm-12:50 pm

2 stops17h 35m

San Juan Luis Munoz Marin Intl

Tue 9/23

6:10 am-11:03 pm

2 stops16h 53m

$282

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

Sat 9/20

7:15 pm-12:50 pm

2 stops17h 35m

San Juan Luis Munoz Marin Intl

Tue 9/23

6:10 am-11:03 pm

2 stops16h 53m

$282

LexingtonSaint Thomas Island

LEX - STT

LEXSTT

Lexington Blue Grass

Sun 10/12

7:25 pm-9:56 am

1 stop14h 31m

Saint Thomas Island Cyril E King

Fri 10/17

11:01 am-7:58 am

3 stops20h 57m

$375

LexingtonNassau

LEX - NAS

LEXNAS

Lexington Blue Grass

Thu 10/2

7:25 pm-10:30 am

1 stop15h 05m

Nassau Intl

Thu 10/9

11:30 am-6:45 pm

1 stop7h 15m

$444

LexingtonPunta Cana

LEX - PUJ

LEXPUJ

Lexington Blue Grass

Wed 9/17

7:47 am-3:25 pm

1 stop7h 38m

Punta Cana

Wed 9/24

4:25 pm-11:03 pm

1 stop6h 38m

$453

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/18

Showing 1-10 of 60 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 August 20, 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 August 20, 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
7,982 reviews

Comfort

7.9

Overall

8.0

Boarding

8.2

Crew

8.5

Food

7.3

Entertainment

7.9

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
7,982 reviews
Delta
8.0
Very good
7,982 reviews

Comfort

7.9

Overall

8.0

Boarding

8.2

Crew

8.5

Food

7.3

Entertainment

7.9

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
7,982 reviews

Comfort

7.9

Overall

8.0

Boarding

8.2

Crew

8.5

Food

7.3

Entertainment

7.9

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 9h 19m. Fly via American 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 cheapest airlines to fly from Lexington to Caribbean one-way?

    The cheapest airline one-way is Delta, with whom users have recently found tickets for as low as $108. However, be on the lookout for offers from American Airlines and United Airlines, 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 - Saint Thomas Island Cyril E King or Lexington Blue Grass - Punta Cana 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 August 20, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$267Average$662FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$354Average$678FlexibilityNo cancel feeOn-time71%

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