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Caribbean Islands

$138+ 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 8/26. Fares are subject to change and may not be available on all flights or dates of travel.
LEX — SJU
Aug 12 — Aug 191
Tue 8/12
Tue 8/19
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 August 7, 2025.

Round-trip from

$215
(American Airlines)

One-way from

$138
(American Airlines)

Popular in

June

Cheapest in

January

Average price

$438
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 ($26 potential increase over avg. RT price).
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Cheapest flight prices on average. 1% potential price decrease ($7 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 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 August 7, 2025.

This American Airlines deal was found by Cheapflights users on 8/5. 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 9/166:47 amLEX - SJU
2 stops11h 27mAmerican Airlines
Wed 9/243:55 pmSJU - LEX
2 stops18h 37mAmerican Airlines
Deal found 8/5$215
This Delta deal was found by Cheapflights users on 8/5. 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.
Tue 9/166:00 amLEX - SJU
1 stop10h 31mDelta
Wed 9/247:30 amSJU - LEX
1 stop9h 35mDelta
Deal found 8/5$271
This American Airlines deal was found by Cheapflights users on 8/6. 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 stops15h 56mAmerican Airlines
Sat 10/115:30 amSJU - LEX
2 stops11h 59mAmerican Airlines
Deal found 8/6$276
This American Airlines deal was found by Cheapflights users on 8/7. 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 9/67:15 pmLEX - SJU
2 stops17h 35mAmerican Airlines
Thu 9/116:10 amSJU - LEX
2 stops18h 10mAmerican Airlines
Deal found 8/7$317
This American Airlines deal was found by Cheapflights users on 8/6. 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 11/86:00 amLEX - SJU
2 stops14h 32mAmerican Airlines
Sun 11/166:25 amSJU - LEX
1 stop12h 03mAmerican Airlines
Deal found 8/6$337
This Delta deal was found by Cheapflights users on 8/5. 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 10/243:46 pmLEX - SJU
1 stop6h 13mDelta
Tue 10/285:43 pmSJU - LEX
1 stop6h 22mDelta
Deal found 8/5$352
This Kiwi.com deal was found by Cheapflights users on 8/7. 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 8/177:47 pmLEX - SJU
1 stop26h 01mMultiple Airlines
Wed 8/203:59 amSJU - LEX
1 stop16h 31mMultiple Airlines
Deal found 8/7$354
This American Airlines deal was found by Cheapflights users on 8/7. 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 10/56:28 amLEX - SJU
2 stops17h 11mAmerican Airlines
Thu 10/91:35 pmSJU - LEX
2 stops9h 40mAmerican Airlines
Deal found 8/7$357
This United Airlines deal was found by Cheapflights users on 8/5. 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.
Tue 9/167:00 amLEX - SJU
2 stops13h 38mUnited Airlines
Tue 9/231:05 amSJU - LEX
2 stops12h 19mUnited Airlines
Deal found 8/5$361
This Kiwi.com deal was found by Cheapflights users on 8/4. 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 8/319:19 amLEX - MBJ
1 stop26h 55mMultiple Airlines
Wed 9/312:19 pmMBJ - LEX
1 stop22h 07mMultiple Airlines
Deal found 8/4$371
This American Airlines deal was found by Cheapflights users on 8/5. 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 12/64:04 pmLEX - SJU
1 stop6h 26mAmerican Airlines
Mon 12/156:40 amSJU - LEX
1 stop15h 05mAmerican Airlines
Deal found 8/5$378
This American Airlines deal was found by Cheapflights users on 8/5. 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 8/157:22 pmLEX - SJU
2 stops15h 47mAmerican Airlines
Thu 8/216:00 amSJU - LEX
2 stops11h 41mAmerican Airlines
Deal found 8/5$379

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 August 7, 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 9/16

6:47 am-6:14 pm

2 stops11h 27m

San Juan Luis Munoz Marin Intl

Wed 9/24

3:55 pm-10:32 am

2 stops18h 37m

$215

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

Tue 9/16

6:00 am-4:31 pm

1 stop10h 31m

San Juan Luis Munoz Marin Intl

Wed 9/24

7:30 am-5:05 pm

1 stop9h 35m

$271

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-5:29 pm

2 stops11h 59m

$276

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

Sat 9/6

7:15 pm-12:50 pm

2 stops17h 35m

San Juan Luis Munoz Marin Intl

Thu 9/11

6:10 am-12:20 am

2 stops18h 10m

$317

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

Wed 1/21

7:30 am-10:22 pm

2 stops13h 52m

San Juan Luis Munoz Marin Intl

Tue 1/27

2:05 am-1:13 pm

2 stops12h 08m

$327

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

Sat 11/8

6:00 am-9:32 pm

2 stops14h 32m

San Juan Luis Munoz Marin Intl

Sun 11/16

6:25 am-5:28 pm

1 stop12h 03m

$337

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

Fri 10/24

3:46 pm-9:59 pm

1 stop6h 13m

San Juan Luis Munoz Marin Intl

Tue 10/28

5:43 pm-12:05 am

1 stop6h 22m

$352

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

Sun 1/18

1:30 pm-11:49 pm

1 stop9h 19m

San Juan Luis Munoz Marin Intl

Mon 1/26

3:21 pm-9:39 pm

1 stop7h 18m

$353

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

Sun 8/17

7:47 pm-9:48 pm

1 stop26h 01m

San Juan Luis Munoz Marin Intl

Wed 8/20

3:59 am-8:30 pm

1 stop16h 31m

$354

LexingtonSan Juan

LEX - SJU

LEXSJU

Lexington Blue Grass

Mon 1/19

12:57 pm-11:40 pm

1 stop9h 43m

San Juan Luis Munoz Marin Intl

Mon 1/26

6:50 pm-1:11 pm

2 stops19h 21m

$355

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/5

Showing 1-10 of 48 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 August 7, 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 August 7, 2025.
See what other customers who have flown with Delta, United Airlines, 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
7,987 reviews

Crew

8.5

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Overall

8.0

Food

7.3

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
7,987 reviews
Delta
8.0
Very good
7,987 reviews

Crew

8.5

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Overall

8.0

Food

7.3

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!
United Airlines
7.4
Good
8,916 reviews
Delta
8.0
Very good
7,987 reviews

Crew

8.5

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Overall

8.0

Food

7.3

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
7,987 reviews

Crew

8.5

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Overall

8.0

Food

7.3

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!
WestJet
7.2
Good
3,002 reviews
Delta
8.0
Very good
7,987 reviews

Crew

8.5

Entertainment

7.9

Comfort

7.9

Boarding

8.2

Overall

8.0

Food

7.3

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.

  • 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 $138. Users have also found prices from $185 and $216 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 - Oranjestad Reina Beatrix 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 August 7, 2025.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$267Average$673FlexibilityNo cancel feeOn-timeN/A
American AirlinesCheapest$354Average$686FlexibilityNo cancel feeOn-time71%

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