$133 Find Cheap Flights from Lexington to Caribbean

This is the cheapest one-way flight price found by a KAYAK user in the last 72 hours by searching for a flight from Lexington to Caribbean departing on 3/29. Fares are subject to change and may not be available on all flights or dates of travel. Click the price to replicate the search for this deal.
1 adult
1 adult, Economy, 0 bags

KAYAK searches hundreds of travel sites at once for deals on flights to Caribbean

Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 23% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Free to useThere are no hidden charges or fees.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
Flight Deals

Cheap Flights from Lexington to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$449
Montego Bay
Montego Bay2 stops$349
Oranjestad
Oranjestad1 stop$510
Nassau
Nassau2 stops$467
Kingston
Kingston2 stops$741
Simpson Bay
Simpson Bay1 stop$581
Providenciales
Providenciales2 stops$368
Bridgetown
Bridgetown2 stops$1,835
George Town
George Town2 stops$435
St. John's
St. John's2 stops$660
Punta Cana
Punta Cana1 stop$449
Montego Bay
Montego Bay2 stops$349
Oranjestad
Oranjestad1 stop$510
Nassau
Nassau2 stops$467
Kingston
Kingston2 stops$741
Simpson Bay
Simpson Bay1 stop$581
Providenciales
Providenciales2 stops$368
Bridgetown
Bridgetown2 stops$1,835
George Town
George Town2 stops$435
St. John's
St. John's2 stops$660

Book Cheap Lexington to Caribbean Plane Tickets

 
Here are some of the best deals found on KAYAK recently from the most popular airlines for round-trip flights from Lexington to Caribbean that are departing in the next months. While these flights were available on KAYAK in the last 72 hours, prices and availability are subject to change and deals may expire.
Discover the best prices for you by selecting your travel dates on KAYAK.

Recent round-trip flight deals from Lexington to Caribbean

Thu, Apr 9 - Tue, Apr 14
American Airlines Logo
6:00 am - 10:05 pm
LEX
-
SJU
16h 05m
1 stop
American Airlines Logo
3:19 pm - 11:52 pm
SJU
-
LEX
8h 33m
1 stop
$266American Airlines
Sun, Apr 12 - Sat, Apr 18
American Airlines Logo
6:00 am - 10:05 pm
LEX
-
SJU
16h 05m
1 stop
American Airlines Logo
3:19 pm - 11:52 pm
SJU
-
LEX
8h 33m
1 stop
$299American Airlines
Wed, Apr 22 - Mon, Apr 27
American Airlines Logo
6:00 am - 10:05 pm
LEX
-
SJU
16h 05m
1 stop
American Airlines Logo
6:00 am - 11:52 pm
SJU
-
LEX
17h 52m
1 stop
$339American Airlines
Sun, May 17 - Sun, May 24
American Airlines Logo
5:51 pm - 11:51 am
LEX
-
MBJ
19h 00m
2 stops
American Airlines Logo
5:17 pm - 12:55 pm
MBJ
-
LEX
18h 38m
2 stops
$349American Airlines
Sun, Mar 8 - Fri, Mar 13
United Airlines Logo
7:00 am - 1:55 pm
LEX
-
PLS
6h 55m
1 stop
United Airlines Logo
3:01 pm - 1:15 pm
PLS
-
LEX
22h 14m
2 stops
$400United Airlines
Sun, Mar 8 - Fri, Mar 13
United Airlines Logo
7:00 am - 1:55 pm
LEX
-
PLS
6h 55m
1 stop
United Airlines Logo
2:23 pm - 1:15 pm
PLS
-
LEX
22h 52m
1 stop
$402United Airlines
Sun, Mar 1 - Tue, Mar 31
Multiple Airlines Logo
11:56 am - 3:31 pm
LEX
-
SJU
26h 35m
1 stop
Multiple Airlines Logo
8:24 pm - 8:29 am
SJU
-
LEX
36h 05m
2 stops
$429Multiple Airlines
Sun, Mar 1 - Sat, Mar 7
Multiple Airlines Logo
11:56 am - 12:02 pm
LEX
-
MBJ
24h 06m
1 stop
Multiple Airlines Logo
1:00 pm - 7:33 am
MBJ
-
LEX
18h 33m
1 stop
$436Multiple Airlines
Tue, Apr 28 - Wed, May 6
Delta Logo
6:00 am - 1:21 pm
LEX
-
PUJ
7h 21m
1 stop
Delta Logo
2:46 pm - 11:54 pm
PUJ
-
LEX
9h 08m
1 stop
$449Delta
Wed, Apr 29 - Tue, May 5
Delta Logo
7:19 am - 2:48 pm
LEX
-
STT
7h 29m
1 stop
Delta Logo
3:05 pm - 11:54 pm
STT
-
LEX
8h 49m
1 stop
$468Delta
Booking Insights

KAYAK's insights & trends for Lexington to Caribbean flights

Get data-powered insights and trends into flights from Lexington to Caribbean to help you find the cheapest flights, the best time to fly and much more.

What is the cheapest month to fly from Lexington to Caribbean?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Lexington to Caribbean, removes the top 0.1% to account for outliers, and then takes the median of all values for each month.

The cheapest month for flights from Lexington to Caribbean is March, when tickets cost $330 (return) on average. On the other hand, the most expensive months are August and December, when the average cost of round-trip tickets is $913 and $895 respectively.

Good to know

Low seasonNovember
Cheapest flight$133
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly with an average 1% increase in price.
Flight from Lexington to San Juan

FAQs - booking Caribbean flights

  • How does KAYAK find such low prices on flights from Lexington to Caribbean?

    KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Lexington to Caribbean.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Lexington to Caribbean?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Lexington to Caribbean is likely to change within 7 days, so travelers know whether to wait or book now.

  • What is the Hacker Fare option on flights from Lexington to Caribbean?

    Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly from Lexington to Caribbean with an airline and back with another airline.

  • What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Lexington to Caribbean?

    Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying from Lexington to Caribbean up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Reviews of the top airlines flying from Lexington to Caribbean

 
Need help choosing which airline to fly with from Lexington to Caribbean? KAYAK airline reviews give an overall score for each airline based on loads of factors, including comfort, boarding, in-flight entertainment and more, to make your decision easier. See airline scores according to verified KAYAK customer reviews.
7.9
DeltaOverall score based on 8204 reviews
7.2Food
8.5Crew
8.1Boarding
7.9Comfort
7.8Entertainment
Airline reviews

Everything I mentioned earlier - the airbus was more comfortable indeed and the experience was further enhanced.

10.0 ExcellentSoosnata, Feb 2026
LAX - HNL
Read more Delta reviews

Everything I mentioned earlier - the airbus was more comfortable indeed and the experience was further enhanced.

Delta continues to set the benchmark for traveler-friendly service with minimal disruption and clear communication within the mainland US (coast to coast). I am consistently pleased to be a Delta customer, and this experience once again met my expectations. There was a brief delay departing from MIA due to a technical issue that required the aircraft to return to the gate. However, the situation was handled professionally and transparently. Fortunately, my planned layover allowed ample buffer time, so the adjustment caused no stress. Overall, another smooth and reassuring experience.

Good experience and the flight landed early. There was no food I had or entertainment.

Flight was delayed and no reasons provided. After the passengers were boarded, the crew made announcement that the captain has jot arrived and he would take another 15 mins. All passengers patiently sat until the captain came and started. Terrible experience!

Flight was delayed. No information on why it was delayed. After we boarded the flight, , the crew made announcement that the captain hs not arrived and he will take 15 mins more to arrive. Passengers were just sitting patiently for the captain to arrive and start, Terrible experience.

Totally worth the miles to upgrade to Delta Comfort. Plenty of legroom.

This was my first time flying Delta ever and I had a great experience!

Smallest leg room I've ever had on a plane.

They took all carry-on luggage from Groups 6 -9 - I was group 5 and waiting in line to board - they made me check my luggage too. That then went to baggage claim and delayed departure from the airport. There was overhead room in my seating area - Delta over reacted. Also, had a gentleman next to me that took up 1/2 my seat.

Excellent!!! Aeromexico is a great airline. What was not that good is the service provided by Kayak. It is never clear and not easy to manage.

The smell from the bathroom kept wafting through the cabin. It made people sick.

The flight was really crowded. Flight attendants were just ok.

Boarding delayed 20 minutes for no reason, no wifi, in flight entertainment, or snacks / waters?

Didn't get a seat assignment until the last minute even though i picked a seat.

American has been able to implement an algorithm that makes it possible for nearly every one of my evening flights to be late. Congratulations!

I was on a small regional flight from Detroit to Philadelphia. When we landed the outside cruise needed to turn something off with the engine, which took quite a long time. Then, when they allowed us to get off the plane it was outside. They took their time, unloading all the luggage and waited till they unloaded all the luggage before they brought it over to us. It was 9 o’clock at night freezing cold out, and there was no proactive hustle to try to get people their luggage. It was really one of the worst experiences I think I’ve ever had with American until a manager came over. I don’t think they were going to even consider pulling the luggage over to the people that had been waiting outside for at least 10 minutes in the freezing cold.

The flight was fine, once we got underway. It was more than hour delayed

Beverage service was not good. Also just one service in 5 hr 30 min flight. No ask fir water ir anything beside one time beverage service.

Waited for oxygen tanks for 30 minutes after boarding was complete.

The seats are too uncomfortable for anyone over 5ft 8in. I'm 5'10" with a back and hip issue and I was in pai for the full duration of the flight.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports