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Caribbean Islands

$208+ 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 11/2. Fares are subject to change and may not be available on all flights or dates of travel.
LEX — SJU
Oct 30 — Nov 61
Thu 10/30
Thu 11/6
1 adult, Economy
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Cheap 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 September 30, 2025.

Round-trip from

$282
(American Airlines)

One-way from

$208
(American Airlines)

Popular in

August

Cheapest in

January

Average price

$523
From Lexington Blue Grass to Caribbean Islands
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One-way flight from Lexington Blue Grass to Caribbean Islands
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Highest demand for flights based on searches. 4% potential increase in price ($22 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 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 September 30, 2025.

This American Airlines deal was found by Cheapflights users on 9/29. 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 12/27:18 pmLEX - SJU
2 stops13h 49mAmerican Airlines
Fri 12/58:20 amSJU - LEX
2 stops10h 13mAmerican Airlines
Deal found 9/29$282
This American Airlines deal was found by Cheapflights users on 9/30. 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 10/147:10 pmLEX - SJU
2 stops15h 56mAmerican Airlines
Thu 10/305:30 amSJU - LEX
2 stops11h 21mAmerican Airlines
Deal found 9/30$317
This American Airlines deal was found by Cheapflights users on 9/29. 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 12/66:10 pmLEX - SJU
2 stops14h 57mAmerican Airlines
Sun 12/146:25 amSJU - LEX
1 stop12h 19mAmerican Airlines
Deal found 9/29$325
This American Airlines deal was found by Cheapflights users on 9/29. 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 12/148:09 pmLEX - SJU
2 stops12h 58mAmerican Airlines
Tue 12/166:25 amSJU - LEX
2 stops10h 02mAmerican Airlines
Deal found 9/29$360
This American Airlines deal was found by Cheapflights users on 9/30. 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 11/135:00 amLEX - SJU
1 stop14h 58mAmerican Airlines
Tue 11/186:25 amSJU - LEX
1 stop12h 04mAmerican Airlines
Deal found 9/30$372
This Delta deal was found by Cheapflights users on 9/30. 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.
Fri 11/146:00 amLEX - PUJ
1 stop8h 38mDelta
Fri 11/215:03 pmPUJ - LEX
1 stop8h 01mDelta
Deal found 9/30$378
This American Airlines deal was found by Cheapflights users on 9/30. 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 11/145:59 pmLEX - PUJ
2 stops16h 41mAmerican Airlines
Fri 11/215:27 pmPUJ - LEX
2 stops18h 20mAmerican Airlines
Deal found 9/30$383
This American Airlines deal was found by Cheapflights users on 9/29. 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
1 stop9h 46mAmerican Airlines
Tue 12/166:25 amSJU - LEX
1 stop12h 08mAmerican Airlines
Deal found 9/29$405
This American Airlines deal was found by Cheapflights users on 9/29. 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 10/188:02 pmLEX - SJU
2 stops15h 04mAmerican Airlines
Mon 10/205:30 amSJU - LEX
1 stop17h 45mAmerican Airlines
Deal found 9/29$407
This American Airlines deal was found by Cheapflights users on 9/30. 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 12/138:09 pmLEX - NAS
1 stop16h 04mAmerican Airlines
Tue 12/166:45 pmNAS - LEX
2 stops16h 08mAmerican Airlines
Deal found 9/30$407
This American Airlines deal was found by Cheapflights users on 9/29. 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 12/138:02 pmLEX - SJU
2 stops25h 03mAmerican Airlines
Wed 12/176:00 amSJU - LEX
2 stops18h 14mAmerican Airlines
Deal found 9/29$410
This American Airlines deal was found by Cheapflights users on 9/30. 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 12/157:18 pmLEX - SJU
2 stops13h 49mAmerican Airlines
Fri 12/196:15 pmSJU - LEX
1 stop17h 15mAmerican Airlines
Deal found 9/30$412

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 September 30, 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

Tue 12/2

7:18 pm-11:59 am

2 stops15h 41m

San Juan Luis Munoz Marin Intl

Fri 12/5

8:20 am-5:33 pm

2 stops10h 13m

$282

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

Tue 10/14

7:10 pm-11:06 am

2 stops15h 56m

San Juan Luis Munoz Marin Intl

Thu 10/30

5:30 am-4:51 pm

2 stops11h 21m

$317

LexingtonPunta Cana

LEX - PUJ

LEXPUJ

Lexington Blue Grass

Sat 1/10

7:23 pm-12:55 pm

1 stop16h 32m

Punta Cana

Thu 1/15

2:31 pm-4:14 pm

1 stop26h 43m

$359

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

Sun 12/14

8:09 pm-10:07 am

2 stops12h 58m

San Juan Luis Munoz Marin Intl

Tue 12/16

6:25 am-3:27 pm

2 stops10h 02m

$360

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

Sun 12/14

8:09 pm-10:07 am

2 stops12h 58m

San Juan Luis Munoz Marin Intl

Wed 12/17

6:00 am-11:14 pm

2 stops18h 14m

$360

LexingtonPunta Cana

LEX - PUJ

LEXPUJ

Lexington Blue Grass

Sun 1/18

5:55 am-2:20 pm

1 stop7h 25m

Punta Cana

Sat 1/24

6:05 pm-11:55 pm

1 stop6h 50m

$378

LexingtonPunta Cana

LEX - PUJ

LEXPUJ

Lexington Blue Grass

Fri 11/14

6:00 am-3:38 pm

1 stop8h 38m

Punta Cana

Fri 11/21

5:03 pm-12:04 am

1 stop8h 01m

$378

LexingtonPunta Cana

LEX - PUJ

LEXPUJ

Lexington Blue Grass

Sun 1/18

6:39 pm-12:11 pm

1 stop16h 32m

Punta Cana

Sat 1/24

5:33 pm-12:19 pm

2 stops19h 46m

$383

LexingtonPunta Cana

LEX - PUJ

LEXPUJ

Lexington Blue Grass

Fri 11/14

5:59 pm-11:40 am

2 stops16h 41m

Punta Cana

Fri 11/21

5:27 pm-10:47 am

2 stops18h 20m

$383

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

Mon 12/15

11:23 am-10:09 pm

1 stop9h 46m

San Juan Luis Munoz Marin Intl

Tue 12/16

6:00 am-3:27 pm

2 stops10h 27m

$405

Flights are sorted by cheapest round-trip flights first.

Deals found on 9/29

Showing 1-10 of 43 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, September is the cheapest month in which you can book a flight from Lexington to Caribbean Islands (average of $254). Flying from Lexington to Caribbean Islands 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 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 September 30, 2025.

When flying from Lexington to Caribbean Islands, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

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 September 30, 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
8.0
Very good
7,964 reviews

Food

7.3

Crew

8.5

Entertainment

7.9

Overall

8.0

Comfort

7.9

Boarding

8.2

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
7,964 reviews
Delta
8.0
Very good
7,964 reviews

Food

7.3

Crew

8.5

Entertainment

7.9

Overall

8.0

Comfort

7.9

Boarding

8.2

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
7,964 reviews

Food

7.3

Crew

8.5

Entertainment

7.9

Overall

8.0

Comfort

7.9

Boarding

8.2

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 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, Delta, and United Airlines fly from Lexington to Caribbean Islands in about 6h 41m. The time it takes to get you to your destination can typically vary by up to 9h. Airlines will cover a distance of 1408 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the cheapest airlines to fly from Lexington to Caribbean Islands one-way?

    For one-way options, check prices for American Airlines. According to our data, you can fly for as low as $208. Users have also found prices from $253 and $293 on United Airlines and Delta, respectively.

  • 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 - 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, September is the cheapest month in which you can book a flight from Lexington to Caribbean Islands (average of $254). Flying from Lexington to Caribbean Islands 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 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 September 30, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$264Average$631FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$340Average$643FlexibilityNo cancel feeOn-time71%

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