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Caribbean Islands

$128+ Cheap flights from Lexington (LEX) to Caribbean Islands

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 3/10. Fares are subject to change and may not be available on all flights or dates of travel.
LEX — SJU
Feb 25 — Mar 41
Wed 2/25
Wed 3/4
1 adult, Economy
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Cheap flight deals from Lexington to Caribbean Islands

Cheapest flights from Lexington to Caribbean Islands
Explore the most affordable flight options available from Lexington to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 26, 2026.

This American Airlines deal was found by Cheapflights users on 1/26. 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 2/235:07 pm
LEX
-
SJU
1 stop11h 17m
American Airlines
Fri 2/276:33 am
SJU
-
LEX
1 stop17h 39m
American Airlines
Deal found 1/26$256
This American Airlines deal was found by Cheapflights users on 1/25. 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 4/116:00 am
LEX
-
SJU
1 stop16h 05m
American Airlines
Sat 4/187:25 am
SJU
-
LEX
1 stop9h 49m
American Airlines
Deal found 1/25$296
This American Airlines deal was found by Cheapflights users on 1/25. 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 2/284:59 pm
LEX
-
SJU
2 stops16h 01m
American Airlines
Tue 3/35:42 pm
SJU
-
LEX
2 stops20h 36m
American Airlines
Deal found 1/25$324
This American Airlines deal was found by Cheapflights users on 1/25. 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 5/16:00 am
LEX
-
SJU
1 stop16h 05m
American Airlines
Sun 5/36:00 am
SJU
-
LEX
1 stop17h 52m
American Airlines
Deal found 1/25$336
This Faresmojo deal was found by Cheapflights users on 1/26. 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 Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/3110:05 am
LEX
-
SJU
1 stop6h 38m
JetBlue
Sat 8/157:30 am
SJU
-
LEX
1 stop7h 29m
JetBlue
Deal found 1/26$356
This Kiwi.com deal was found by Cheapflights users on 1/26. 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.
Mon 3/164:22 pm
LEX
-
SJU
1 stop16h 31m
Multiple Airlines
Fri 3/277:54 pm
SJU
-
LEX
2 stops18h 56m
Multiple Airlines
Deal found 1/26$370
This American Airlines deal was found by Cheapflights users on 1/26. 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 3/46:40 am
LEX
-
SJU
2 stops12h 59m
American Airlines
Wed 3/183:00 pm
SJU
-
LEX
1 stop18h 24m
American Airlines
Deal found 1/26$375
This American Airlines deal was found by Cheapflights users on 1/26. 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 4/15:50 pm
LEX
-
PLS
2 stops18h 40m
American Airlines
Thu 4/91:25 pm
PLS
-
LEX
2 stops21h 33m
American Airlines
Deal found 1/26$390
This Kiwi.com deal was found by Cheapflights users on 1/23. 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 3/111:56 am
LEX
-
PUJ
1 stop27h 40m
Multiple Airlines
Wed 4/154:47 pm
PUJ
-
LEX
1 stop15h 54m
Multiple Airlines
Deal found 1/23$414
This American Airlines deal was found by Cheapflights users on 1/25. 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 6/164:10 pm
LEX
-
SJU
1 stop7h 31m
American Airlines
Tue 6/232:25 pm
SJU
-
LEX
1 stop9h 34m
American Airlines
Deal found 1/25$414
This American Airlines deal was found by Cheapflights users on 1/25. 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 2/97:41 am
LEX
-
SJU
1 stop13h 45m
American Airlines
Fri 2/136:33 am
SJU
-
LEX
1 stop17h 39m
American Airlines
Deal found 1/25$420
This American Airlines deal was found by Cheapflights users on 1/24. 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 2/86:39 pm
LEX
-
NAS
1 stop16h 40m
American Airlines
Sat 2/1412:48 pm
NAS
-
LEX
1 stop11h 05m
American Airlines
Deal found 1/24$434

Find flight deals from Lexington to Caribbean Islands

Keep the following information in mind while searching for Lexington to Caribbean Islands flight deals. Data was last updated January 26, 2026.

Round-trip from

$256
(American Airlines)

One-way from

$128
(Delta)

Popular in

December

Cheapest in

March

Average price

$559
From Lexington Blue Grass to Caribbean Islands
Search Deals
One-way flight from Lexington Blue Grass to Caribbean Islands
Search Deals
Highest demand for flights based on searches. 13% potential increase in price ($84 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 6% potential price decrease ($34 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in January 2026
Search Deals

Cheapflights Fare Finder

 
Customize your flight search to find flights from Lexington to Caribbean Islands 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 January 26, 2026.
Use the filters below to find and compare flights from Lexington to Caribbean Islands that are best for you.

Fly from

Lexington

Fly to

Caribbean Islands

Route

Depart

Return

Price

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

Tue 2/24

6:40 am-8:39 pm

2 stops12h 59m

San Juan Luis Munoz Marin Intl

Tue 3/3

5:25 pm-9:28 am

1 stop17h 03m

$256

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

Tue 2/24

3:46 pm-11:58 pm

1 stop7h 12m

San Juan Luis Munoz Marin Intl

Tue 3/3

6:15 am-2:59 pm

1 stop9h 44m

$256

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

Fri 5/1

12:44 pm-8:24 pm

1 stop7h 40m

San Juan Luis Munoz Marin Intl

Mon 5/4

6:15 am-1:34 pm

1 stop7h 19m

$256

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

Mon 2/23

1:14 pm-9:49 pm

1 stop7h 35m

San Juan Luis Munoz Marin Intl

Fri 2/27

6:33 am-11:12 pm

1 stop17h 39m

$256

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

Sat 4/11

6:00 am-10:05 pm

1 stop16h 05m

San Juan Luis Munoz Marin Intl

Sat 4/18

7:25 am-5:14 pm

1 stop9h 49m

$296

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

Sat 2/28

5:00 am-12:52 am

2 stops18h 52m

San Juan Luis Munoz Marin Intl

Tue 3/3

5:25 pm-9:28 am

1 stop17h 03m

$324

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

Fri 5/8

6:00 am-10:05 pm

1 stop16h 05m

San Juan Luis Munoz Marin Intl

Mon 5/11

6:00 am-11:52 pm

1 stop17h 52m

$336

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

Tue 6/16

8:11 pm-9:33 am

2 stops13h 22m

San Juan Luis Munoz Marin Intl

Tue 6/23

2:25 pm-11:59 pm

1 stop9h 34m

$375

LexingtonProvidenciales

LEX - PLS

LEXPLS

Lexington Blue Grass

Wed 4/1

5:50 pm-2:10 pm

2 stops20h 20m

Providenciales

Thu 4/9

1:25 pm-10:58 am

2 stops21h 33m

$390

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

Wed 3/4

6:40 am-8:39 pm

2 stops12h 59m

San Juan Luis Munoz Marin Intl

Wed 3/18

6:33 am-9:57 pm

1 stop15h 24m

$415

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/25

Showing 1-10 of 52 results
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Best time to book a flight from Lexington to Caribbean Islands

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

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

Currently, February is the cheapest month in which you can book a flight from Lexington to Caribbean Islands (average of $149). Flying from Lexington to Caribbean Islands in June is currently the most expensive (average of $252). 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.

Reviews of airlines servicing Caribbean Islands

Get insights into the airlines that provide service to Caribbean Islands. 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 Islands. Reviews last updated January 26, 2026.
See what other customers who have flown with Delta and American Airlines from Lexington to Caribbean Islands have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Delta
7.9
Good
8,111 reviews

Comfort

7.9

Food

7.2

Boarding

8.1

Crew

8.5

Entertainment

7.8

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
8,111 reviews
Delta
7.9
Good
8,111 reviews

Comfort

7.9

Food

7.2

Boarding

8.1

Crew

8.5

Entertainment

7.8

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
11,189 reviews
Delta
7.9
Good
8,111 reviews

Comfort

7.9

Food

7.2

Boarding

8.1

Crew

8.5

Entertainment

7.8

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 Islands. 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 Islands?

    Lexington Blue Grass (LEX) is the airport you will fly out of if you book a flight from Lexington to Caribbean Islands. 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 Islands?

    Airlines like American Airlines and Delta fly from Lexington to Caribbean Islands in about 7h 12m. The time it takes to get you to your destination can typically vary by up to 5h 47m. Airlines will cover a distance of 1757 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the most popular routes from Lexington to Caribbean Islands?

    When deciding which route to take from Lexington to Caribbean Islands consider Lexington Blue Grass - San Juan Luis Munoz Marin Intl, Lexington Blue Grass - Punta Cana or Lexington Blue Grass - Saint Thomas Island Cyril E King as they are the most popular.

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

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

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

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

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

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

    Currently, February is the cheapest month in which you can book a flight from Lexington to Caribbean Islands (average of $149). Flying from Lexington to Caribbean Islands in June is currently the most expensive (average of $252). 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 Islands

Discover the top 2 airlines that operate flights from Lexington to Caribbean Islands. 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 January 26, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$163Average$621FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$299Average$654FlexibilityNo cancel feeOn-time71%

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