$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 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

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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$429
Montego Bay
Montego Bay2 stops$357
Oranjestad
Oranjestad2 stops$666
Nassau
Nassau1 stop$458
Kingston
Kingston2 stops$707
Simpson Bay
Simpson Bay2 stops$401
Providenciales
Providenciales2 stops$358
Bridgetown
Bridgetown1 stop$692
George Town
George Town2 stops$375
St. John's
St. John's2 stops$745
Punta Cana
Punta Cana1 stop$429
Montego Bay
Montego Bay2 stops$357
Oranjestad
Oranjestad2 stops$666
Nassau
Nassau1 stop$458
Kingston
Kingston2 stops$707
Simpson Bay
Simpson Bay2 stops$401
Providenciales
Providenciales2 stops$358
Bridgetown
Bridgetown1 stop$692
George Town
George Town2 stops$375
St. John's
St. John's2 stops$745

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

Sat, May 2 - Tue, May 5
United Airlines Logo
10:10 am - 8:34 pm
LEX
-
SJU
10h 24m
1 stop
United Airlines Logo
1:00 am - 1:18 pm
SJU
-
LEX
12h 18m
2 stops
$316United Airlines
Sat, Jul 18 - Sat, Jul 25
American Airlines Logo
8:10 pm - 1:09 pm
LEX
-
MBJ
17h 59m
2 stops
American Airlines Logo
5:17 pm - 12:39 pm
MBJ
-
LEX
18h 22m
2 stops
$357American Airlines
Sat, May 9 - Wed, May 13
American Airlines Logo
5:51 pm - 12:25 pm
LEX
-
PLS
18h 34m
2 stops
American Airlines Logo
1:25 pm - 11:56 pm
PLS
-
LEX
10h 31m
2 stops
$358American Airlines
Sat, May 9 - Wed, May 13
American Airlines Logo
4:15 pm - 1:12 pm
LEX
-
PLS
20h 57m
1 stop
American Airlines Logo
3:00 pm - 10:46 pm
PLS
-
LEX
7h 46m
1 stop
$360American 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
2:55 pm - 4:05 pm
MBJ
-
LEX
24h 10m
1 stop
$363American Airlines
Sat, May 2 - Wed, May 6
United Airlines Logo
10:10 am - 8:34 pm
LEX
-
SJU
10h 24m
1 stop
United Airlines Logo
3:56 pm - 11:49 pm
SJU
-
LEX
7h 53m
1 stop
$366United Airlines
Tue, Jun 9 - Fri, Jun 12
Multiple Airlines Logo
1:17 pm - 3:58 pm
LEX
-
SJU
26h 41m
1 stop
Multiple Airlines Logo
8:27 pm - 11:12 am
SJU
-
LEX
14h 45m
1 stop
$376Multiple Airlines
Tue, Jun 9 - Sat, Jun 13
Delta Logo
7:05 am - 1:31 pm
LEX
-
SJU
6h 26m
1 stop
Delta Logo
5:56 pm - 12:04 am
SJU
-
LEX
6h 08m
1 stop
$416Delta
Mon, May 18 - Tue, May 26
Multiple Airlines Logo
9:45 pm - 4:40 pm
LEX
-
PUJ
18h 55m
1 stop
Multiple Airlines Logo
9:25 am - 11:32 am
PUJ
-
LEX
26h 07m
1 stop
$437Multiple Airlines
Tue, Jul 7 - Tue, Jul 14
Delta Logo
7:05 am - 2:12 pm
LEX
-
UVF
7h 07m
1 stop
Delta Logo
3:33 pm - 11:55 pm
UVF
-
LEX
8h 22m
1 stop
$937Delta
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 $360 (return) on average. On the other hand, the most expensive months are August and December, when the average cost of round-trip tickets is $1,148 and $831 respectively.

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 9% 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 8356 reviews
7.8Entertainment
8.5Crew
7.2Food
8.1Boarding
7.9Comfort
Airline reviews

Excellent service, I love the soft blush pink mood lighting on the 767-400ER during meal service. The overhead gasper vents on the 767-400ER were also very strong with a lot of airflow to keep me comfortable on my flight.

10.0 ExcellentChristopher, Mar 2026
JFK - MXP
Read more Delta reviews

Excellent service, I love the soft blush pink mood lighting on the 767-400ER during meal service. The overhead gasper vents on the 767-400ER were also very strong with a lot of airflow to keep me comfortable on my flight.

This was the worse experience. They delayed our flight twice and we still had to find another flight to get home sooner which was alos delayed. Also, the flight attendant named Ginny on DL9890 leaving at 4:13pm on 3/23/26 was extremely rude.

I love Delta the flight attendants were personable and the flight arrived 1/2 earlier thanks expected. All a plus. The gate agent was a bit flustered but even with that I still had a good experience. Her supervisor assisted me.

Got to fly my favorite plane, the Boeing 767-400ER, to Milan. The soft blush pink mood lighting during meal service was very beautiful and gorgeous. The service was top-notch, and our flights were on time. I highly recommend Delta.

I am still at the Airport! Delayed Delayed and Delyaed

I took seat 15A in anticipation of window seat, there is no window.

The first class flight attendant was awful to everyone. Very rude; no customer service. She should not be working in first class.

Snacks and included beverages were appreciated. Boarding went smoothly. Plenty of overhead bin space. Seats get very uncomfortable after a couple of hours. After waiting 10 painful minutes for my walker, a very nice Delta guest agent pushed me in a wheelchair to the gate. It was finally delivered to me after another 15 minutes . Our checked bag was on the carousel long b4 I was able to retrieve it. Fortunately it was still there but somewhere along the way the straps we used to secure it were removed and and were not reattached. Wish I had made note of the agents name.

It was fine. 55 minute flight. No snacks or beverage service offered. Boarding went smoothly and my walker was waiting for me on the jet way.

Smaller plane for a longer flight than my first one. Doesn’t make sense.

The flight changed gates multiple times and flight had to be delayed multiple times

We called Kayak for a change due to the TSA situation in Atlanta. What we got was a canceled return flight (in error) and we had to find the mistake. Not happy with Kayak who blamed it on AA.

Tv screens and movie selection v good. Friendly staff. They were really worried about max capacity and room for carryons. That is never fun but i had no problem finding space when I boarded.

I was in last row so that is never great bc the person in front of me leaned his seat all the way back into me.

Delayed for mechanical and no updates on what was happening and how long the delay might be.

My flight from LGA was cancelled and my rebooked flight from JFK was delayed numerous times. I will now be getting home after 2am.

Flight was delayed half hour before boarding, but when I checked flight aware the plane that would Pick us up had a delay of more than an hour. AA should let us know in advance to avoid waiting several hours in the airport

On the return flight, arriving in Denver we sat on the tarmac in Denver for over 20 minutes.

Typical AA - late by 90+ mn. Gate changed twice... Changed the departure time 6 times No explanation, no communication on reasons for delay I travel with AA twice a year... and it is consistently very poor.. I will continue to use AA only when i have to.

The flight attendant in business class was excellent! Professional, friendly and attentive.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports