$118 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 3/30. 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$428
Montego Bay
Montego Bay1 stop$473
Oranjestad
Oranjestad2 stops$590
Nassau
Nassau2 stops$423
Kingston
Kingston2 stops$688
Simpson Bay
Simpson Bay1 stop$584
Providenciales
Providenciales1 stop$364
Bridgetown
Bridgetown2 stops$636
George Town
George Town2 stops$442
St. John's
St. John's2 stops$737
Punta Cana
Punta Cana1 stop$428
Montego Bay
Montego Bay1 stop$473
Oranjestad
Oranjestad2 stops$590
Nassau
Nassau2 stops$423
Kingston
Kingston2 stops$688
Simpson Bay
Simpson Bay1 stop$584
Providenciales
Providenciales1 stop$364
Bridgetown
Bridgetown2 stops$636
George Town
George Town2 stops$442
St. John's
St. John's2 stops$737

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

Wed, Feb 4 - Fri, Feb 6
United Airlines Logo
9:00 am - 10:22 pm
LEX
-
SJU
12h 22m2 stops
United Airlines Logo
2:05 am - 1:25 pm
SJU
-
LEX
12h 20m2 stops
$235United Airlines
Thu, Jan 29 - Thu, Feb 5
American Airlines Logo
12:49 pm - 11:56 pm
LEX
-
SJU
10h 07m2 stops
American Airlines Logo
8:20 am - 11:15 pm
SJU
-
LEX
15h 55m1 stop
$298American Airlines
Sun, Mar 1 - Thu, Mar 5
American Airlines Logo
10:27 am - 11:34 pm
LEX
-
SJU
12h 07m2 stops
American Airlines Logo
4:10 pm - 9:28 am
SJU
-
LEX
18h 18m1 stop
$325American Airlines
Mon, Jan 26 - Thu, Jan 29
American Airlines Logo
7:17 pm - 11:41 am
LEX
-
PLS
16h 24m1 stop
American Airlines Logo
3:50 pm - 11:15 pm
PLS
-
LEX
7h 25m1 stop
$364American Airlines
Thu, Jan 22 - Tue, Jan 27
American Airlines Logo
7:00 am - 8:50 pm
LEX
-
SJU
12h 50m1 stop
American Airlines Logo
7:00 am - 6:09 pm
SJU
-
LEX
12h 09m1 stop
$365American Airlines
Thu, Jan 15 - Sat, Jan 31
Multiple Airlines Logo
11:51 am - 11:35 pm
LEX
-
SJU
34h 44m2 stops
Multiple Airlines Logo
4:40 pm - 11:01 am
SJU
-
LEX
19h 21m1 stop
$378Multiple Airlines
Thu, Jan 15 - Sat, Jan 24
Multiple Airlines Logo
11:51 am - 11:35 pm
LEX
-
SJU
34h 44m2 stops
Multiple Airlines Logo
4:40 pm - 11:01 am
SJU
-
LEX
19h 21m1 stop
$397Multiple Airlines
Mon, Mar 30 - Mon, Apr 6
Delta Logo
6:00 am - 2:30 pm
LEX
-
PLS
8h 30m1 stop
Delta Logo
3:45 pm - 11:53 pm
PLS
-
LEX
8h 08m1 stop
$451Delta
Wed, Mar 4 - Mon, Mar 9
Delta Logo
6:00 am - 12:29 pm
LEX
-
GCM
6h 29m1 stop
Delta Logo
1:12 pm - 11:53 pm
GCM
-
LEX
9h 41m1 stop
$456Delta
Sun, Mar 1 - Wed, Mar 4
Air Canada Logo
2:03 pm - 4:20 pm
LEX
-
CUR
25h 17m2 stops
Air Canada Logo
5:15 pm - 4:55 pm
CUR
-
LEX
24h 40m2 stops
$1,747Air Canada
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 October, when tickets cost $370 (return) on average. On the other hand, the most expensive months are December and July, when the average cost of round-trip tickets is $895 and $689 respectively.

How far in advance should I book a flight from Lexington to Caribbean?

To calculate weekly average prices, KAYAK takes all prices for each week before departure 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 average of all the values for each week.

To get a below average price on the flight from Lexington to Caribbean, you should book around 1 week before departure. For the absolute cheapest price, our data suggests you should book 22 weeks before departure.

Good to know

Low seasonNovember
Cheapest flight$118
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly with an average 6% 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 8013 reviews
7.9Comfort
7.8Entertainment
7.2Food
8.5Crew
8.1Boarding
Airline reviews

A 12 hour flight during the day with one real meal service - are you kidding? Also the breakfast was one of the worst and not what was listed

4.0 OkayAvik, Dec 2025
SEA - ICN
Read more Delta reviews

A 12 hour flight during the day with one real meal service - are you kidding? Also the breakfast was one of the worst and not what was listed

Flight was delayed several times. At one point, they "pulled back" 15 minutes from the delayed boarding and sent a text saying we would board sooner than previously advised. The flight then was delayed again. And when we boarded, there was an unspecified technical issue which had us waiting in the plane for about an hour.

Delta is a good airline. I've never had an issue with Delta. I'll continue to fly with them until they show me that I shouldn't.

The only thing nice I can say is the flight crew was really nice and apologetic about the situation. They shared as much information as they had and advised us on what we could do about missing connecting flights. The boarding process was so slow. The gate agent was working by herself and should have had someone working with her. It took almost an hour to board because she was trying to board a full flight of people and provide customer service to everyone who was flying standby and/or had questions. It was really chaotic. This didn't help the fact that we were delayed and folks were missing connections the longer it took.

The gate attendants and the crew were terrible. Because of high winds, they needed to carry more fuel, so they had to get volunteers to take the next flight at 6 am the next day. They did a terrible job of it - our flight ended up taking off just under 3 hours of the scheduled time. I hope to never fly Delta again.

Did not realize internet screen was hidden between seats and no info printed!!!!

2 of the seats in row 31 the entertainment system was not working, and one seat the tray table did not go all the way down. Flight arrived early and departed on time which was great.

Very good flight crew and very nice people staff were incredible especially the gate agent

Waited at the usual crowded gate at DCA where one ends up standing up because there aren't enough seats.

The flight was delayed for about 2 hrs. Other than it, it was good.

Crew were all friendly and helpful. It was a short flight so just a beverage service with a cookie. After we were boarded the plane took about 45 minutes to leave the gate but it was New Year’s Eve so not shocking there was some delay. Overall good experience and very grateful.

After the door had been closed, the cockpit makes an announcement that catering is running late and it is not the airline's fault. It is their fault in the sense that we had to sit for 2 hours or more when we could have stayed in the terminal. Poor communications between catering and airline. This caused a young man to lose his temper and he went storming out hitting objects. He had complained to the gate agent that he had already waited at the gate 7 hours and when can the airplane leave? Airilnes do a poor job of explaining delays, maintenance issues, etc. whereas being truthful may gain more sympathy or understanding.

The flight was very smooth and the meal in business class was great.

The captain brought my 6 year old son into the cockpit and allowed him to ask questions, sit in the captain’s chair and talk about all the gears and levers. Made the trip very special for him.

I take this flight about 6-8 times per year. It is convenient and saves an hour or two by skipping PDX, SEA, PHX, or ORD (but it takes longer to get bags to the carousel than Alaska Airlines). I wish the food service were better (but they might cut back on it because it is a red-eye). The WifI seems to go down about an hour out of Anchorage, and then comes back about an hour later...so be warned if this is an issue for you.

Better service. No food options, but we did get drinks and a cookie.

Boarding was organized and timely. Food was mediocre, especially for first class travel.

We were 4+ hours delayed. AA is absolutely obnoxious. They just kept pushing back the time to the point where we did not get into Vegas until after midnight when we were supposed to arrive like 845pm.

My last flight on 25 Dec, it’s Christmas Day, everyone happy and very good mood. I really enjoy traveling with Americans Airlines from Miami to Minneapolis my home town after long flight from lhe to Doha then Miami. Thank you again to make my travels comfortable and relaxed. Best regards

The boarding process needs to be fixed. The zone don't work, especially when there is hardly anyone in zones 3, 4,and 5, leaving the majority of the passengers backed up in the aisle, especially because passengers seated near the front are blocking passengers who are seated in the rear of the plane. It would also help if the size of carry on bags was more strictly enforced.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports