$171 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 4/1. 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$344
Montego Bay
Montego Bay2 stops$508
Oranjestad
Oranjestad1 stop$590
Nassau
Nassau1 stop$393
Kingston
Kingston2 stops$688
Simpson Bay
Simpson Bay1 stop$501
Providenciales
Providenciales1 stop$364
Bridgetown
Bridgetown1 stop$601
George Town
George Town1 stop$419
St. John's
St. John's2 stops$737
Punta Cana
Punta Cana1 stop$344
Montego Bay
Montego Bay2 stops$508
Oranjestad
Oranjestad1 stop$590
Nassau
Nassau1 stop$393
Kingston
Kingston2 stops$688
Simpson Bay
Simpson Bay1 stop$501
Providenciales
Providenciales1 stop$364
Bridgetown
Bridgetown1 stop$601
George Town
George Town1 stop$419
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

Sat, Feb 21 - Wed, Feb 25
Delta Logo
5:00 pm - 11:58 pmLEX-SJU
5h 58m1 stop
Delta Logo
6:15 am - 11:50 amSJU-LEX
6h 35m1 stop
$235Delta
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Tue, Feb 24 - Fri, Feb 27
United Airlines Logo
10:35 am - 9:00 pmLEX-SJU
9h 25m1 stop
United Airlines Logo
2:05 am - 1:20 pmSJU-LEX
12h 15m2 stops
$259United Airlines
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Sun, Jan 4 - Wed, Jan 28
Multiple Airlines Logo
9:18 am - 12:29 pmLEX-SJU
26h 11m1 stop
Multiple Airlines Logo
4:40 pm - 11:01 amSJU-LEX
19h 21m1 stop
$272Multiple Airlines
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Sun, Jan 11 - Wed, Jan 14
Multiple Airlines Logo
11:51 am - 3:35 pmLEX-SJU
26h 44m1 stop
Multiple Airlines Logo
4:40 pm - 11:01 amSJU-LEX
19h 21m1 stop
$284Multiple Airlines
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Tue, Jan 6 - Thu, Jan 15
American Airlines Logo
6:39 pm - 5:01 pmLEX-SJU
21h 22m2 stops
American Airlines Logo
6:30 am - 11:15 pmSJU-LEX
17h 45m2 stops
$295American Airlines
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Sun, Mar 1 - Wed, Mar 4
Delta Logo
12:36 pm - 11:58 pmLEX-SJU
10h 22m1 stop
Delta Logo
6:15 am - 11:50 amSJU-LEX
6h 35m1 stop
$302Delta
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Sun, Jan 4 - Sat, Jan 24
Multiple Airlines Logo
9:18 am - 12:29 pmLEX-SJU
26h 11m1 stop
Multiple Airlines Logo
10:52 am - 11:01 amSJU-LEX
25h 09m2 stops
$307Multiple Airlines
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Fri, Jan 9 - Sat, Jan 10
Multiple Airlines Logo
9:30 pm - 9:47 amLEX-SJU
11h 17m1 stop
Multiple Airlines Logo
3:55 am - 8:51 pmSJU-LEX
17h 56m1 stop
$311Multiple Airlines
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Mon, Feb 16 - Thu, Feb 19
American Airlines Logo
6:00 am - 5:25 pmLEX-SJU
10h 25m1 stop
American Airlines Logo
8:30 am - 5:15 pmSJU-LEX
9h 45m1 stop
$320American Airlines
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Sat, May 2 - Wed, May 6
Air Canada Logo
2:00 pm - 1:40 pmLEX-BGI
23h 40m2 stops
Air Canada Logo
2:40 pm - 4:55 pmBGI-LEX
26h 15m2 stops
$2,476Air Canada
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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 July and August, when the average cost of round-trip tickets is $689 and $678 respectively.

What’s the cheapest day of the week to fly from Lexington to Caribbean?

The average price of all round-trip flights from Lexington to Caribbean clicked on KAYAK for each day over the last 12 months.

If you are looking for a flight deal from Lexington to Caribbean, look for departures on Tuesdays and avoid leaving on a Monday, as it's usually the priciest day. When flying back from Caribbean, Thursday is the cheapest day to fly and Saturday is the most expensive.

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$171
Best time to beat the crowds with an average 12% drop in price.
Most popular time to fly with an average 2% increase in price.
Flight from Lexington to San Juan Airport

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.

  • What is the cheapest time of day to fly to Caribbean?

    The cheapest time of day to fly to Caribbean is generally in the morning, when round-trip flights cost $477 on average. Morning departures are around 6% cheaper than evening flights, on average. The most expensive time of day to fly to Caribbean is generally in the afternoon, which is peak travel time and where the average cost of a ticket is $521.

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 8011 reviews
8.5Crew
7.3Food
7.9Entertainment
7.9Comfort
8.1Boarding
Airline reviews

I fly Delta all the time, have Platinum Medallion status. But this route seems to have major problems with delays and seems to never leave on time! Have only taken it twice in the last two weeks, and each time it had delays of more than 1 hour... very disappointed!!!!

4.0 OkayCarl, Dec 2025FLL - LGA
Read more Delta reviews

I fly Delta all the time, have Platinum Medallion status. But this route seems to have major problems with delays and seems to never leave on time! Have only taken it twice in the last two weeks, and each time it had delays of more than 1 hour... very disappointed!!!!

Getting to the flight was arduous and lengthy. The flight itself was good but the food option wasn’t a good selection. I need to do a Kosher option on my return. Flight crew were nice

Good seats in Main cabin, excellent service and excellent landing

My flight was cancelled with no explanation after I had already cleared security. I was given 4 options to rebook, only one being non-stop like I had paid for. I grabbed it. It was 4 plus hours later and then took off even later. Biggest complaint is that I booked early and had an aisle seat. They gave me a "window" seat in front of the exit row, so the seat did not decline. I weigh all of 103 #s and it was tight for me! For what I paid, I feel I was kind of ripped off. I think they should have given me the empty comfort seat for the inconvenience. There was no apology nor any explanation as to why the flight was cancelled. My guess is it benefitted Delta in some way.

Very smooth, on-time, and pleasantly uneventful flight. The team at the gate and on board were professional and genuinely courteous. The pilot kept us well updated throughout, and both takeoff and landing were steady and enjoyable without any drama. Just a good, solid flight. Thank you! 💗

Staff was exceptional! Everyone was kind, professional and friendly making the trip very pleasant. Thank you!

No lunch on a x-country flight scheduled for 10:50 am departure, arrived 5+ hrs later. That requires a black box label before you pay for the tickets. Worst, when I checked in online, it's specifically said that lunch was served on his flight for economy Plus passengers.

We had a lot of really rough weather but that was not Delta's fault. Pilot was amazing.

First, Delta needs more flights to/from Miami. Second, a 1000pm leaving at 1230pm is unacceptable from their biggest airport world hub. Another aircraft could have been used such as the aircraft scheduled to be used in the morning for that exact same route. Yes, I did get me there but the lack of sleep the next day didn't help me enjoy my entire trip since I was busy with activities during the weekend. This can be and is expected from Spirit (going bankrupt) and Frontier (despite they're nickel and dimers). But from Delta's World Hub? That's totally unacceptable!

This flight was straightforward and without difficulty. Service was OK, but I continue to be underwhelmed by level of attention given to Sky Priority passengers.

AA delayed the flight for 3 hours and 50 minutes, but delayed the last 2 hours, 30 minutes at a time, so if we knew before, could have stayed at home and worked instead of being at the airport wasting time... The plane's crew was excellent, not their fault.

After arriving in Dallas, the aircraft taxied for an unusually long time and was unable to park at the gate, which caused a significant delay and made me miss my connecting flight. I then had to wait in a very long line to be rebooked, and I was told that no hotel or meal accommodations would be provided. What is even more unacceptable is that my luggage was mishandled and has still not been located. My suitcase contains important medications that I urgently need, and I have been unable to access them due to the airline’s mishandling. This situation has caused me considerable stress and inconvenience, and I need this issue to be resolved immediately.

RIC Staff was not enough. Elderly passengers had to wait 30 minutes to deplane, so we could board and still had to walk as no chairs were provided. And, passenger in front of my seat assignment rammed seat against my legs entire flight time. Was mildly bruised and left thigh still sore.

Liked that it was on time. Staff professional and friendly.

Things were delayed a little. But that didn’t affect my plans. It was fine. I was surprised it was so full thanksgiving day. The crew were friendly and professional.

I appreciated that it was on time, safe and professional. I didn’t like that I wasn’t in a place where I had a window at my window seat. It would have been nice to know that in advance. If it was mentioned in the ticketing, I didn’t notice it.

My flight was delayed about three hours. I got home at 3:30 in the morning very bad experience.

I like that the crew kept us informed but we moved back and forth from gate to gate before the aircraft arrived.

The flight was delayed multiple times, again no fault of American but again the extra cost, for everything makes it feel like a cheap airline! Especially when flights are outrageously expensive already

Horrible. Both legs of my flight were delayed more than 6 hours. No compensation, no screens on the plane, and the plane was not clean.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports