$206 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 8/20. 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

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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$415
Montego Bay
Montego Bay2 stops$317
Oranjestad
Oranjestad1 stop$621
Nassau
Nassau1 stop$493
Kingston
Kingston1 stop$703
Simpson Bay
Simpson Bay2 stops$503
Providenciales
Providenciales2 stops$444
Bridgetown
Bridgetown2 stops$667
George Town
George Town1 stop$470
St. John's
St. John's2 stops$703
Punta Cana
Punta Cana1 stop$415
Montego Bay
Montego Bay2 stops$317
Oranjestad
Oranjestad1 stop$621
Nassau
Nassau1 stop$493
Kingston
Kingston1 stop$703
Simpson Bay
Simpson Bay2 stops$503
Providenciales
Providenciales2 stops$444
Bridgetown
Bridgetown2 stops$667
George Town
George Town1 stop$470
St. John's
St. John's2 stops$703

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

Tue, Apr 21 - Tue, Apr 28
Delta Logo
4:53 pm - 11:12 pm
LEX
-
SJU
6h 19m
1 stop
Delta Logo
7:30 am - 1:34 pm
SJU
-
LEX
6h 04m
1 stop
$246Delta
Tue, Apr 21 - Tue, Apr 28
American Airlines Logo
6:00 am - 10:05 pm
LEX
-
SJU
16h 05m
1 stop
American Airlines Logo
11:43 am - 11:52 pm
SJU
-
LEX
12h 09m
2 stops
$266American Airlines
Sat, Apr 25 - Fri, May 1
United Airlines Logo
10:15 am - 8:34 pm
LEX
-
SJU
10h 19m
1 stop
United Airlines Logo
1:00 am - 5:02 pm
SJU
-
LEX
16h 02m
2 stops
$292United Airlines
Wed, Apr 22 - Wed, Apr 29
American Airlines Logo
6:00 am - 10:05 pm
LEX
-
SJU
16h 05m
1 stop
American Airlines Logo
11:43 am - 11:52 pm
SJU
-
LEX
12h 09m
2 stops
$299American Airlines
Wed, Mar 25 - Wed, Apr 1
Multiple Airlines Logo
8:26 pm - 8:53 am
LEX
-
SJU
12h 27m
1 stop
Multiple Airlines Logo
7:54 pm - 8:29 am
SJU
-
LEX
12h 35m
1 stop
$314Multiple Airlines
Sat, Apr 11 - Wed, Apr 15
American Airlines Logo
5:51 pm - 11:51 am
LEX
-
MBJ
19h 00m
2 stops
American Airlines Logo
3:20 pm - 11:52 pm
MBJ
-
LEX
7h 32m
1 stop
$317American Airlines
Sat, Apr 11 - Wed, Apr 15
American Airlines Logo
4:15 pm - 2:15 pm
LEX
-
MBJ
23h 00m
1 stop
American Airlines Logo
3:20 pm - 11:52 pm
MBJ
-
LEX
7h 32m
1 stop
$318American Airlines
Wed, Mar 25 - Wed, Apr 1
Multiple Airlines Logo
8:26 pm - 12:48 am
LEX
-
SJU
28h 22m
2 stops
Multiple Airlines Logo
7:54 pm - 8:29 am
SJU
-
LEX
12h 35m
1 stop
$320Multiple Airlines
Tue, Apr 28 - Wed, May 6
Delta Logo
7:19 am - 1:21 pm
LEX
-
PUJ
6h 02m
1 stop
Delta Logo
3:57 pm - 11:54 pm
PUJ
-
LEX
7h 57m
1 stop
$415Delta
Sat, May 9 - Fri, May 15
United Airlines Logo
7:35 pm - 1:30 pm
LEX
-
MBJ
18h 55m
2 stops
United Airlines Logo
2:40 pm - 8:14 pm
MBJ
-
LEX
28h 34m
2 stops
$432United Airlines
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 $305 (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 $867 respectively.

Good to know

Low seasonNovember
Cheapest flight$206
Best time to beat the crowds with an average 11% 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 8242 reviews
7.2Food
8.1Boarding
7.8Entertainment
8.5Crew
7.9Comfort
Airline reviews

Everything was good except wifi and a leaking drink chiller. The floor was all wet and my bag was soaked. Did not notice until debarking. Have not heard back from Delta. Even though this was leg one of an international flight in first class, they denied access to their Sky Club - very disappointing!

6.0 GoodAnonymous, Feb 2026
RDU - SEA
Read more Delta reviews

Everything was good except wifi and a leaking drink chiller. The floor was all wet and my bag was soaked. Did not notice until debarking. Have not heard back from Delta. Even though this was leg one of an international flight in first class, they denied access to their Sky Club - very disappointing!

The staff was fine. The plane was extremely tight, and I paid for the wifi and it did not work at all. I was actually going to ask for a refund.

two hour delay and the Delta representative on the PA system was unable to understand

An awesome flight crew. FC seat cushion just doesn’t cut it for a 3+ hour flight.

2+hrs delay without any reason provided and a cramped flight

We waited an hour on the runway to get a gate in Orlando

Flight was delayed by 3-hours and their fix was… complimentary pretzels.

Flight was delayed due to crew being not on time

Flight crew issues delayed my flight by 2 1/2 hours. Causing me to miss my connection.

The staff on board and gate was nice - a welcome change from the usual. We also arrived early, which was a great benefit, given that it takes 30 minutes plus to get bags at SRQ.

Lack of gluten free options in food service. I have Celiac disease and it appears you no longer offer special meals for people with dietary restrictions. I am a frequent flyer traveling into and out of Omaha airport. I have noticed over the course of several months that although our flight typically arrives ahead of schedule (awesome job AA!) - we typically sit on the runway for several minutes waiting for the ground crew to get in place. Not sure if it is a ground crew issue or a gate availability issue (due to construction at this airport). Seems to be more of a ground crew being on time issue.

Arrived early picked up my bag in a few minutes- great trip - thank you

Flight boarded, departed and landed on time. Excellent service from flight attendant in FIRST

Boarding is always an ordeal. Less dogs on flights. I am highly allergic to dogs and cats. Why are there so many animals these days?

Flight to Tampa was delayed taking off due to plane arriving late but no other issues

There was a delay with the plan which cause the flight to leave later and once arrived in Chicago there was another delay and some passengers missed their connecting flights

Massimo, flight attendant was very authentic, attentive - wonderful. Food/wrap was just okay.

Worst experience ever. Flight could not land in Charlotte for what we were told was a ground stop. Had to be diverted to Raleigh to refuel. Strangely during ground stop, our connecting flight had no issue taking off on time causing us to miss our flight. We were told there were no other flights that day to our final destination and that two days out was the next one. The only flights to get us there were from Chicago the next morning. Completely opposite direction but it was a direct flight. So we get flown to Chicago and have to find a hotel in our own dime. The flight in the morning was also delayed. Thankfully only a short time. The non too of all this, our luggage did not arrive by the time we were there. Communication was terrible, through the entire trip. Complete incompetence. Will never fly American again.

Horrible. Got delayed many hours because their pilot wasn't trained for night landing at the airport and a rain delay made it a night landing. We have to wait hours for a qualified crew. They give us 12 dollar meal vouchers but most everything in the airport was closed and definitely more expensive than the vouchers.

I am an AA flyer for a very long time... AA has yet to disappoint.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports