$123 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 4/22. 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$415
Montego Bay
Montego Bay1 stop$312
Oranjestad
Oranjestad1 stop$607
Nassau
Nassau2 stops$514
Kingston
Kingston1 stop$782
Simpson Bay
Simpson Bay1 stop$478
Providenciales
Providenciales1 stop$363
Bridgetown
Bridgetown1 stop$652
George Town
George Town2 stops$389
St. John's
St. John's2 stops$705
Punta Cana
Punta Cana1 stop$415
Montego Bay
Montego Bay1 stop$312
Oranjestad
Oranjestad1 stop$607
Nassau
Nassau2 stops$514
Kingston
Kingston1 stop$782
Simpson Bay
Simpson Bay1 stop$478
Providenciales
Providenciales1 stop$363
Bridgetown
Bridgetown1 stop$652
George Town
George Town2 stops$389
St. John's
St. John's2 stops$705

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, Mar 24 - Wed, Apr 15
American Airlines Logo
10:27 am - 10:58 pm
LEX
-
SJU
12h 31m
2 stops
American Airlines Logo
6:00 am - 11:52 pm
SJU
-
LEX
17h 52m
1 stop
$266American Airlines
Sun, Apr 12 - Sat, Apr 18
American Airlines Logo
6:00 am - 2:29 pm
LEX
-
SJU
8h 29m
1 stop
American Airlines Logo
7:25 am - 2:57 pm
SJU
-
LEX
7h 32m
1 stop
$299American Airlines
Tue, Apr 14 - Tue, Apr 21
American Airlines Logo
6:00 am - 2:15 pm
LEX
-
MBJ
9h 15m
1 stop
American Airlines Logo
3:20 pm - 11:52 pm
MBJ
-
LEX
7h 32m
1 stop
$312American Airlines
Sat, Jul 18 - Sat, Jul 25
American Airlines Logo
8:11 pm - 10:55 am
LEX
-
MBJ
15h 44m
1 stop
American Airlines Logo
5:17 pm - 10:33 am
MBJ
-
LEX
16h 16m
2 stops
$317American Airlines
Sun, Apr 12 - Sat, Apr 18
Multiple Airlines Logo
9:31 am - 6:55 pm
LEX
-
SJU
9h 24m
1 stop
Multiple Airlines Logo
3:47 pm - 8:41 am
SJU
-
LEX
16h 54m
2 stops
$323Multiple Airlines
Sat, Apr 11 - Wed, Apr 22
Delta Logo
5:12 pm - 11:15 pm
LEX
-
SJU
6h 03m
1 stop
Delta Logo
12:55 pm - 11:54 pm
SJU
-
LEX
10h 59m
1 stop
$330Delta
Wed, Apr 15 - Wed, Apr 22
United Airlines Logo
6:01 pm - 4:05 pm
LEX
-
PLS
22h 04m
2 stops
United Airlines Logo
5:15 pm - 9:20 am
PLS
-
LEX
16h 05m
2 stops
$381United Airlines
Wed, May 6 - Sun, May 10
United Airlines Logo
7:50 pm - 4:05 pm
LEX
-
PLS
20h 15m
2 stops
United Airlines Logo
5:15 pm - 9:20 am
PLS
-
LEX
16h 05m
2 stops
$393United Airlines
Tue, Apr 28 - Wed, May 6
Delta Logo
6:00 am - 1:21 pm
LEX
-
PUJ
7h 21m
1 stop
Delta Logo
3:57 pm - 11:54 pm
PUJ
-
LEX
7h 57m
1 stop
$415Delta
Sun, May 24 - Sat, May 30
Multiple Airlines Logo
3:05 pm - 2:36 pm
LEX
-
AUA
23h 31m
1 stop
Multiple Airlines Logo
3:41 pm - 2:15 pm
AUA
-
LEX
22h 34m
1 stop
$607Multiple 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 December and August, when the average cost of round-trip tickets is $831 and $678 respectively.

Good to know

Low seasonNovember
Cheapest flight$123
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly with an average 2% 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 8245 reviews
8.1Boarding
8.5Crew
7.9Comfort
7.8Entertainment
7.2Food
Airline reviews

The whole experience was excellent. As it most often is with Delta

10.0 ExcellentRay, Mar 2026
LGA - MCO
Read more Delta reviews

The whole experience was excellent. As it most often is with Delta

Cabin was not pressurized properly. Several passengers had respiratory difficulties.

I was happy that I was able to get a last minute flight but unfortunately my seat was a middle seat. Even with Delta Comfort I wasn't comfortable

There’s not much to say about a one hour flight. This is a connection from LA to RNO that I missed the previous night due to a mechanical check delay on my originating flight from JFK to LAX. The short flight itself was fine. Instructions from the pilot and crew were per usual. The coffee was barely lukewarm, which possibly was purposeful so we would down it quickly. Bags were already on carousel upon reaching baggage claim, which was excellent.

Flight was warm for first few hours and quite rough

Seat was extremely hard which made even a short 1 hour 20 minute flight fairly uncomfortable.

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.

Good crew and flight was on time. It’s a small plane with limited overhead luggage space. They said the overhead space was full and I had to check my bag. There was still space when I got on. Waiting for my checked luggage added 30 minutes to my trip. Not the end of the world but also not great.

My seat was assigned last row behind restrooms No legroom’s I’m very Pettit Still was not comfortable Food choice was excellent

Delayed initially because they couldn’t print the flight details. Poor instruction on delay. When I got on the plane the flight attendant argued with me about whether my carry on would fit (it did, although she didn’t acknowledge that). No greeting (other than arguing with me) getting on or off the plane.

Overall good. The pilots and flight attendants are excellent! The equipment was the issue on my First flight as they had to wait for a part to be installed. So the take off was at least 30 minutes later.

The worst Airline ever. They centered my second flight and leave me in NY. They don’t have any representatives at the airport and they don’t respond to calls. Basically I got stuck. I will never purchase through there again.

It was an older plane. First Class was not especially roomy or comfortable. It was a short flight so there were no meal but they did offer mixed nuts which used to be normal but now is rare. Crew member was very polite and professional.

The chicken wrap was tiny ($13 for what looked like a 1/3 of a normal wrap?) and disgusting.

It was a train wreck but on an airplane. First off, flight was delayed then we board only to hear two announcements, First weather delays in Orlando and second backup battery warning on emergency lights. After sitting on the plane for almost 2 hours they have us deplane due to the maintenance issue. We were told they were getting another plane. In the mean time, I notice another American- Orlando flight and ask the gate agent if I can switch. He says he cant help me and I'd have to walk to A13 from A37. Really!? I get down there and get a seat only to get an announcement my original flight was RE-boarding. The Then inflight there's no communication and I notice on flightaware were circling over the Gulf of America. I call the flight attendant and of course she has no clue and apparently 5m later the pilot finally tells us about another delay. Why does American always have these service and delay issues? They are my LAST choice in flights now!

Mediocre would be best description. Food bland. Seat biz class uncomfortable to sleep. Crew never dimmed lights completely in an overnight flight to Europe. Would avoid AA if possible.

For my arriving destination, we were delayed multiple times to the point that we arrived 6 hours after we were originally scheduled. On my flight home, they overbooked and involuntarily removed passengers (including me) from the plane. It was not a good experience.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports