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Caribbean Islands

$171+ 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 4/1. Fares are subject to change and may not be available on all flights or dates of travel.
LEX — SJU
Jan 3 — Jan 101
Sat 1/3
Sat 1/10
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 December 4, 2025.

This Kiwi.com deal was found by Cheapflights users on 12/4. 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 12/149:22 pmLEX - SJU
2 stops26h 23mMultiple Airlines
Fri 12/196:00 amSJU - LEX
1 stop27h 41mMultiple Airlines
Deal found 12/4$392
This American Airlines deal was found by Cheapflights users on 12/2. 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 12/1511:23 amLEX - SJU
2 stops11h 29mAmerican Airlines
Fri 12/192:31 pmSJU - LEX
2 stops10h 30mAmerican Airlines
Deal found 12/2$399
This Delta deal was found by Cheapflights users on 12/2. 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 12/177:10 amLEX - PLS
1 stop5h 35mDelta
Mon 12/222:10 pmPLS - LEX
1 stop9h 49mDelta
Deal found 12/2$410
This American Airlines deal was found by Cheapflights users on 12/2. 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 12/2$419
This Delta deal was found by Cheapflights users on 12/4. 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.
Thu 12/187:10 amLEX - PLS
1 stop5h 35mDelta
Mon 12/222:10 pmPLS - LEX
1 stop7h 41mDelta
Deal found 12/4$440
This American Airlines deal was found by Cheapflights users on 12/2. 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
2 stops12h 05mAmerican Airlines
Deal found 12/2$455
This Delta deal was found by Cheapflights users on 12/3. 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.
Sat 12/61:06 pmLEX - SJU
1 stop9h 14mDelta
Sun 12/147:00 amSJU - LEX
1 stop10h 28mDelta
Deal found 12/3$458
This Kiwi.com deal was found by Cheapflights users on 12/3. 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 12/299:02 pmLEX - SJU
2 stops13h 56mMultiple Airlines
Wed 1/78:08 pmSJU - LEX
1 stop15h 53mMultiple Airlines
Deal found 12/3$460
This Kiwi.com deal was found by Cheapflights users on 12/3. 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 12/411:18 amLEX - SJU
1 stop24h 14mMultiple Airlines
Thu 12/115:09 pmSJU - LEX
1 stop28h 03mMultiple Airlines
Deal found 12/3$476
This American Airlines deal was found by Cheapflights users on 12/3. 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 12/146:10 pmLEX - SJU
2 stops14h 59mAmerican Airlines
Sun 12/216:44 amSJU - LEX
1 stop16h 21mAmerican Airlines
Deal found 12/3$479
This United Airlines deal was found by Cheapflights users on 12/3. 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 12/107:00 amLEX - SJU
2 stops13h 26mUnited Airlines
Wed 12/178:30 amSJU - LEX
2 stops15h 00mUnited Airlines
Deal found 12/3$489
This United Airlines deal was found by Cheapflights users on 12/4. 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 12/177:00 amLEX - PLS
2 stops9h 00mUnited Airlines
Mon 12/225:06 pmPLS - LEX
2 stops27h 58mUnited Airlines
Deal found 12/4$495

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 December 4, 2025.

Round-trip from

$235
(Delta)

One-way from

$171
(American Airlines)

Popular in

July

Cheapest in

October

Average price

$624
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. 19% potential increase in price ($129 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 2% potential price decrease ($16 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in December 2025
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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 December 4, 2025.
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

Sun 2/22

3:46 pm-11:58 pm

1 stop7h 12m

San Juan Luis Munoz Marin Intl

Wed 2/25

6:15 am-11:50 am

1 stop6h 35m

$235

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

Sat 2/21

5:00 pm-11:58 pm

1 stop5h 58m

San Juan Luis Munoz Marin Intl

Wed 2/25

6:15 am-11:50 am

1 stop6h 35m

$235

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

Sat 2/21

5:00 pm-11:58 pm

1 stop5h 58m

San Juan Luis Munoz Marin Intl

Tue 2/24

6:15 am-11:50 am

1 stop6h 35m

$235

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

Tue 2/24

6:00 am-4:06 pm

1 stop9h 06m

San Juan Luis Munoz Marin Intl

Fri 2/27

5:14 pm-11:33 pm

1 stop7h 19m

$295

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

Tue 1/6

7:41 am-12:30 pm

2 stops27h 49m

San Juan Luis Munoz Marin Intl

Wed 1/28

6:00 am-11:23 pm

1 stop18h 23m

$295

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

Tue 2/10

6:39 pm-12:27 pm

2 stops16h 48m

San Juan Luis Munoz Marin Intl

Sat 2/14

7:00 pm-10:45 am

2 stops16h 45m

$295

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

Tue 1/6

6:39 pm-6:22 pm

2 stops22h 43m

San Juan Luis Munoz Marin Intl

Thu 1/29

1:58 pm-9:28 pm

1 stop8h 30m

$295

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

Mon 1/5

6:09 am-11:34 pm

2 stops16h 25m

San Juan Luis Munoz Marin Intl

Wed 1/28

6:00 am-11:23 pm

2 stops18h 23m

$295

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

Sun 2/1

7:41 am-10:26 pm

1 stop13h 45m

San Juan Luis Munoz Marin Intl

Thu 2/5

4:28 pm-11:23 pm

1 stop7h 55m

$295

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

Thu 2/19

5:45 pm-11:55 am

2 stops17h 10m

San Juan Luis Munoz Marin Intl

Tue 2/24

6:00 am-4:10 pm

1 stop11h 10m

$295

Flights are sorted by cheapest round-trip flights first.

Deals found on 12/3

Showing 1-10 of 50 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, January is the cheapest month in which you can book a flight from Lexington to Caribbean Islands (average of $128). Flying from Lexington to Caribbean Islands 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 EPX?

Find hourly flight availability from Lexington to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated December 4, 2025.

Unlike in the evening, when flights are generally more expensive, you can save up to 48% on flights from Lexington to Caribbean Islands by exploring options for tickets at noon.

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 December 4, 2025.
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
8,011 reviews

Boarding

8.1

Crew

8.5

Food

7.3

Comfort

7.9

Entertainment

7.9

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
8,011 reviews
Delta
7.9
Good
8,011 reviews

Boarding

8.1

Crew

8.5

Food

7.3

Comfort

7.9

Entertainment

7.9

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
11,045 reviews
Delta
7.9
Good
8,011 reviews

Boarding

8.1

Crew

8.5

Food

7.3

Comfort

7.9

Entertainment

7.9

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 Delta, American Airlines, and United Airlines 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 13h 01m. 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 - Punta Cana, Lexington Blue Grass - San Juan Luis Munoz Marin Intl or Lexington Blue Grass - Montego Bay Sangster Intl 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, January is the cheapest month in which you can book a flight from Lexington to Caribbean Islands (average of $128). Flying from Lexington to Caribbean Islands 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 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 December 4, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$267Average$640FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$332Average$654FlexibilityNo cancel feeOn-time71%

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