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$180+ Cheap flights from Caribbean to Lexington (LEX)

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 2/28. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — LEX
Jan 17 — Jan 241
Sat 1/17
Sat 1/24
1 adult, Economy
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Cheap flight deals from Caribbean to Lexington

Best flights from Caribbean to Lexington
Discover carefully curated flight deals from Caribbean to Lexington that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated December 18, 2025.

This American Airlines deal was found by Cheapflights users on 12/15. 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.
Fri 2/136:00 amSJU - LEX
1 stop11h 10mAmerican Airlines
Mon 2/165:02 pmLEX - SJU
1 stop10h 58mAmerican Airlines
Deal found 12/15$260
This Kiwi.com deal was found by Cheapflights users on 12/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/236:00 amSJU - LEX
1 stop15h 56mMultiple Airlines
Fri 2/279:46 pmLEX - SJU
2 stops27h 39mMultiple Airlines
Deal found 12/16$404
This United Airlines deal was found by Cheapflights users on 12/14. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/282:05 amSJU - LEX
2 stops15h 43mUnited Airlines
Sat 1/318:35 amLEX - SJU
2 stops15h 01mUnited Airlines
Deal found 12/14$524
This American Airlines deal was found by Cheapflights users on 12/16. 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.
Mon 2/2312:31 pmSJU - LEX
2 stops12h 02mAmerican Airlines
Fri 2/276:00 amLEX - SJU
1 stop16h 44mAmerican Airlines
Deal found 12/16$525
This American Airlines deal was found by Cheapflights users on 12/17. 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 2/2312:50 pmSTT - LEX
2 stops11h 43mAmerican Airlines
Fri 2/275:45 pmLEX - STT
2 stops17h 36mAmerican Airlines
Deal found 12/17$579

Find flight deals from Caribbean to Lexington

Keep the following information in mind while searching for Caribbean to Lexington flight deals. Data was last updated December 18, 2025.

Round-trip from

$404
(Kiwi.com)

One-way from

$180
(Kiwi.com)
From Caribbean to Lexington Blue Grass
Search Deals
One-way flight from Caribbean to Lexington Blue Grass
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Caribbean to Lexington 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 18, 2025.
Use the filters below to find and compare flights from Caribbean to Lexington that are best for you.

Fly from

Caribbean

Fly to

Lexington

Route

Depart

Return

Price

San JuanLexington

SJU - LEX

SJULEX

San Juan Luis Munoz Marin Intl

Fri 2/13

6:00 am-4:10 pm

1 stop11h 10m

Lexington Blue Grass

Mon 2/16

5:02 pm-5:00 am

1 stop10h 58m

$260

San JuanLexington

SJU - LEX

SJULEX

San Juan Luis Munoz Marin Intl

Mon 2/23

6:00 am-8:56 pm

1 stop15h 56m

Lexington Blue Grass

Fri 2/27

9:46 pm-2:25 am

2 stops27h 39m

$404

San JuanLexington

SJU - LEX

SJULEX

San Juan Luis Munoz Marin Intl

Wed 1/28

2:05 am-4:48 pm

2 stops15h 43m

Lexington Blue Grass

Sat 1/31

8:35 am-12:36 am

2 stops15h 01m

$524

San JuanLexington

SJU - LEX

SJULEX

San Juan Luis Munoz Marin Intl

Mon 2/23

12:31 pm-11:33 pm

2 stops12h 02m

Lexington Blue Grass

Fri 2/27

6:00 am-11:44 pm

1 stop16h 44m

$525

Saint Thomas IslandLexington

STT - LEX

STTLEX

Saint Thomas Island Cyril E King

Mon 2/23

12:50 pm-11:33 pm

2 stops11h 43m

Lexington Blue Grass

Fri 2/27

5:45 pm-12:21 pm

2 stops17h 36m

$579

San JuanLexington

SJU - LEX

SJULEX

San Juan Luis Munoz Marin Intl

Fri 1/9

6:30 am-5:53 pm

1 stop12h 23m

$184

San JuanLexington

SJU - LEX

SJULEX

San Juan Luis Munoz Marin Intl

Sat 3/21

3:22 pm-8:45 am

1 stop17h 23m

$189

Saint Thomas IslandLexington

STT - LEX

STTLEX

Saint Thomas Island Cyril E King

Sun 3/1

3:36 pm-8:56 pm

1 stop30h 20m

$235

Saint Thomas IslandLexington

STT - LEX

STTLEX

Saint Thomas Island Cyril E King

Sun 2/22

3:36 pm-8:56 pm

1 stop30h 20m

$241

San JuanLexington

SJU - LEX

SJULEX

San Juan Luis Munoz Marin Intl

Fri 1/9

9:23 pm-1:17 pm

2 stops40h 54m

$247

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/16

Showing 1-10 of 21 results
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Best time to book a flight from Caribbean to Lexington

Have a flexible travel schedule? Discover the best time to fly to Lexington from Caribbean 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 Caribbean to Lexington

What is the cheapest month to book a flight from Caribbean to Lexington?

Currently, February is the cheapest month in which you can book a flight from Caribbean to Lexington (average of $97). Flying from Caribbean to Lexington in June is currently the most expensive (average of $251). 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.

Related info for your journey

Find useful and relevant information for your journey from Caribbean to Lexington. 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 into for flights to Lexington from Caribbean?

    For a flight from Caribbean to Lexington, you will be flying into Blue Grass. Lexington Blue Grass (LEX) is just 5.6 mi from the center of the city.

  • How long is the flight from Caribbean to Lexington?

    There are many flights that can get you from Caribbean to Lexington in 11h 10m. Fly via American Airlines to get the fastest option. The distance between Caribbean and Lexington is about 1757 mi.

  • Can I find deals for flights from Caribbean to Lexington that include hotel bookings?

    Yes. In addition to deals on Caribbean to Lexington flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Caribbean to Lexington?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Caribbean to Lexington.

  • Can I find deals for business class flights from Caribbean to Lexington?

    Yes. Cheapflights offers flight deals from Caribbean to Lexington 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 Caribbean to Lexington?

    Currently, February is the cheapest month in which you can book a flight from Caribbean to Lexington (average of $97). Flying from Caribbean to Lexington in June is currently the most expensive (average of $251). 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

Traveling to a place near Lexington?

Book flights to Lexington if you plan to visit one of these locations
Somerset
Berea
Georgetown
Frankfort

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