$163 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 5/18. 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 Cana2 stops$461
Montego Bay
Montego Bay2 stops$357
Oranjestad
Oranjestad1 stop$661
Nassau
Nassau1 stop$464
Kingston
Kingston2 stops$934
Simpson Bay
Simpson Bay1 stop$550
Providenciales
Providenciales1 stop$461
Bridgetown
Bridgetown1 stop$688
George Town
George Town1 stop$457
St. John's
St. John's2 stops$993
Punta Cana
Punta Cana2 stops$461
Montego Bay
Montego Bay2 stops$357
Oranjestad
Oranjestad1 stop$661
Nassau
Nassau1 stop$464
Kingston
Kingston2 stops$934
Simpson Bay
Simpson Bay1 stop$550
Providenciales
Providenciales1 stop$461
Bridgetown
Bridgetown1 stop$688
George Town
George Town1 stop$457
St. John's
St. John's2 stops$993

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, May 19 - Thu, May 28
American Airlines Logo
6:00 am - 6:10 pm
LEX
-
SJU
12h 10m
2 stops
American Airlines Logo
6:00 am - 4:05 pm
SJU
-
LEX
10h 05m
2 stops
$326American Airlines
Sun, May 17 - Tue, May 26
Multiple Airlines Logo
11:51 am - 6:59 pm
LEX
-
SJU
7h 08m
1 stop
Multiple Airlines Logo
6:00 am - 8:47 am
SJU
-
LEX
50h 47m
2 stops
$331Multiple Airlines
Sat, May 23 - Sat, May 30
Multiple Airlines Logo
11:27 am - 6:24 am
LEX
-
SJU
18h 57m
2 stops
Multiple Airlines Logo
8:04 pm - 2:15 pm
SJU
-
LEX
18h 11m
1 stop
$334Multiple Airlines
Fri, May 22 - Sat, May 30
Multiple Airlines Logo
9:46 pm - 6:24 am
LEX
-
SJU
32h 38m
2 stops
Multiple Airlines Logo
8:04 pm - 2:15 pm
SJU
-
LEX
18h 11m
1 stop
$337Multiple Airlines
Sun, May 17 - Wed, May 27
Multiple Airlines Logo
11:51 am - 6:59 pm
LEX
-
SJU
7h 08m
1 stop
Multiple Airlines Logo
8:32 am - 2:15 pm
SJU
-
LEX
29h 43m
2 stops
$338Multiple Airlines
Tue, May 19 - Thu, May 28
United Airlines Logo
7:00 am - 9:24 pm
LEX
-
SJU
14h 24m
2 stops
United Airlines Logo
3:56 pm - 11:59 pm
SJU
-
LEX
8h 03m
1 stop
$346United Airlines
Sat, Jun 6 - Fri, Jun 12
American Airlines Logo
8:10 pm - 11:45 am
LEX
-
MBJ
16h 35m
2 stops
American Airlines Logo
5:17 pm - 10:42 am
MBJ
-
LEX
16h 25m
2 stops
$357American Airlines
Sat, Aug 29 - Sat, Sep 5
Delta Logo
6:00 am - 3:00 pm
LEX
-
STT
9h 00m
1 stop
Delta Logo
4:10 pm - 11:55 pm
STT
-
LEX
7h 45m
1 stop
$479Delta
Thu, Jun 4 - Mon, Jun 8
United Airlines Logo
5:15 am - 2:57 pm
LEX
-
NAS
9h 42m
1 stop
United Airlines Logo
3:59 pm - 10:30 pm
NAS
-
LEX
6h 31m
1 stop
$489United Airlines
Fri, Jun 5 - Tue, Jun 9
Delta Logo
7:02 am - 2:10 pm
LEX
-
PLS
7h 08m
1 stop
Delta Logo
3:45 pm - 10:03 pm
PLS
-
LEX
6h 18m
1 stop
$496Delta
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 September, when tickets cost $163 (return) on average. On the other hand, the most expensive months are April and June, when the average cost of round-trip tickets is $406 and $348 respectively.

Good to know

Low seasonNovember
Cheapest flight$163
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly with an average 13% 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 8465 reviews
7.9Comfort
7.2Food
8.1Boarding
7.8Entertainment
8.5Crew
Airline reviews

The flight was operated by Latam. The aircraft had a technical issue and the flight was delayed for the next day. They grounded other passengers to get their airplane assigned to my flight. Most of he ground staff don't speak English (Orlando Airport), but were very polite.The crew on the other hand could speak English and Portuguese. On board service was good.

6.0 GoodSilvestre, Apr 2026
MCO - GRU
Read more Delta reviews

The flight was operated by Latam. The aircraft had a technical issue and the flight was delayed for the next day. They grounded other passengers to get their airplane assigned to my flight. Most of he ground staff don't speak English (Orlando Airport), but were very polite.The crew on the other hand could speak English and Portuguese. On board service was good.

The agent at check in and at the gate were less than thrilled to be at work. I'm not a fan of Kayak's placement on the plane. I got put in the middle seat and none of my preferences were used.

In ATL they have two sets of departure screens. Follow what is on your airline's departure board - the ATL Airport Authority departure board had completely incorrect details about the gate assignment for my flight, which would have made me miss boarding.

Flight was delayed it was hot while sitting on the plane, one engine was working on the plane until they had to do some jimmy rigging down the runway in order for the other engine to charge up. It was ridiculous

The flight was very good and the staff was very friendly and helpful!

The only thing I would say is we tried to get on a standby earlier flight, but with our fair we couldn’t. That seems senseless to leave with open seats..

Very easy to use and convenient, you can perform any action within the same portal

In a world of delays, Delta was on time both ways! Boarding was fast and efficient. Staff was friendly. AND wifi worked.

WiFi didn’t work. Flight delayed 3 hours Crew members were illiterate Seat lean back did not work.

Flight was delayed, we could have been notified earlier and in a consistent manner. App was not refreshing for another passenger to get the latest flight status. We could have stayed and waited at the hotel instead of waiting at the airport had we known the flight was going to delayed for more than 5 hours. The toilet is too tight, and needs to be cleaned more frequently (every hour). The entertainment screen froze, the touch screen not responding to touch. We were upgraded to comfort, it is more comfortable than regular economy seats.

I would like a refund for the extra cost the seat I paid for. An oversized person sat next to me and I couldn’t fit on my seat and had to move to another seat.

Boarding gate at LAX was too crowded—two gates next to one another

The flight was delayed about an hour for a maintenance specialist to approve the maintenance repair

This flight was delayed but it worked in my favor because my Atlanta to Dallas flight was delayed.

This was a hard flight. 3 delays out of OKC (1 on the Tarmac). Delay in Atlanta coming to Dallas. total travel time was the equivalent of driving from OKC to Atlanta.

Like: flights are on time, good boarding process Can improve: planes are old, improve entertainment and make space more comfortable

Had to wait for a gate for a long time, then waited on the run way for a long time before leaving. The actual flights part was good.

The airplane was an old model, the overhead didn’t have enough room for people’s items and made boarding and boarding disappointing and stressful. Crew allowed passengers to bring more than the permitted baggage sizes.

Flying in the United States with the major airlines has become so underwhelming. A 2-3hr flight in most other parts of the world with the major carriers of the area comes with newer, CLEANER aircraft and significantly better in flight service in terms of both staff attitude and a actual meal service.

On time departure and early arrival. Flight attendant very nice.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports