$156 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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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$465
Montego Bay
Montego Bay1 stop$557
Oranjestad
Oranjestad1 stop$544
Nassau
Nassau2 stops$440
Kingston
Kingston2 stops$709
Simpson Bay
Simpson Bay2 stops$645
Providenciales
Providenciales2 stops$390
Bridgetown
Bridgetown1 stop$647
George Town
George Town1 stop$463
St. John's
St. John's2 stops$740
Punta Cana
Punta Cana1 stop$465
Montego Bay
Montego Bay1 stop$557
Oranjestad
Oranjestad1 stop$544
Nassau
Nassau2 stops$440
Kingston
Kingston2 stops$709
Simpson Bay
Simpson Bay2 stops$645
Providenciales
Providenciales2 stops$390
Bridgetown
Bridgetown1 stop$647
George Town
George Town1 stop$463
St. John's
St. John's2 stops$740

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, Feb 24 - Tue, Mar 3
American Airlines Logo
5:00 am - 3:49 pm
LEX
-
SJU
9h 49m
2 stops
American Airlines Logo
5:25 pm - 9:28 am
SJU
-
LEX
17h 03m
1 stop
$256American Airlines
Sat, May 2 - Sat, May 9
United Airlines Logo
7:00 am - 8:38 pm
LEX
-
SJU
13h 38m
2 stops
United Airlines Logo
7:20 am - 6:47 pm
SJU
-
LEX
11h 27m
2 stops
$281United Airlines
Sat, Apr 25 - Sat, May 2
United Airlines Logo
10:15 am - 8:34 pm
LEX
-
SJU
10h 19m
1 stop
United Airlines Logo
7:20 am - 8:14 pm
SJU
-
LEX
12h 54m
2 stops
$290United Airlines
Wed, Feb 25 - Fri, Feb 27
American Airlines Logo
6:40 am - 8:39 pm
LEX
-
SJU
12h 59m
2 stops
American Airlines Logo
6:33 am - 11:12 pm
SJU
-
LEX
17h 39m
1 stop
$296American Airlines
Sun, Mar 1 - Sat, Mar 7
Multiple Airlines Logo
11:56 am - 1:05 am
LEX
-
SJU
36h 09m
2 stops
Multiple Airlines Logo
4:41 pm - 7:33 am
SJU
-
LEX
15h 52m
1 stop
$313Multiple Airlines
Wed, Feb 18 - Tue, Feb 24
United Airlines Logo
10:35 am - 10:22 pm
LEX
-
SJU
10h 47m
2 stops
United Airlines Logo
2:05 am - 4:50 pm
SJU
-
LEX
15h 45m
2 stops
$318United Airlines
Sat, May 2 - Sat, May 9
American Airlines Logo
7:11 am - 10:05 pm
LEX
-
SJU
14h 54m
2 stops
American Airlines Logo
6:00 am - 3:18 pm
SJU
-
LEX
9h 18m
1 stop
$324American Airlines
Sat, Apr 11 - Sat, Apr 18
Multiple Airlines Logo
10:52 am - 1:26 pm
LEX
-
STT
26h 34m
1 stop
Multiple Airlines Logo
4:40 pm - 8:41 am
STT
-
LEX
16h 01m
1 stop
$405Multiple Airlines
Tue, Apr 28 - Wed, May 6
Delta Logo
6:00 am - 11:43 am
LEX
-
PUJ
5h 43m
1 stop
Delta Logo
1:10 pm - 9:21 pm
PUJ
-
LEX
8h 11m
1 stop
$465Delta
Fri, Feb 27 - Tue, Mar 3
Delta Logo
7:13 am - 5:02 pm
LEX
-
NAS
9h 49m
1 stop
Delta Logo
4:23 pm - 11:09 pm
NAS
-
LEX
6h 46m
1 stop
$466Delta
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 August, when the average cost of round-trip tickets is $936 and $913 respectively.

Good to know

Low seasonNovember
Cheapest flight$156
Best time to beat the crowds with an average 13% drop in price.
Most popular time to fly with an average 4% 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 8089 reviews
7.9Comfort
8.1Boarding
8.5Crew
7.2Food
7.8Entertainment
Airline reviews

Good seat comfort ORF to ATL. Bad seat ATL to SEA (terrible lumbar support, hard, ouch)..

8.0 ExcellentAnonymous, Jan 2026
ORF - ATL
Read more Delta reviews

Good seat comfort ORF to ATL. Bad seat ATL to SEA (terrible lumbar support, hard, ouch)..

Because I was moved to an exit row, the snacks in economy comfort, the selection of snacks was better.

I upgraded to first. Quick and easy boarding. Comfortable seat with power and a nice IPA.

Probably not the fault of Delta but there was delay after delay after delay and I ended up getting home 4 hours later then I should have at 1:30 in the morning

Easiest airport experience ever in my life at MSP with Delta check-in and flight attendant gave us a bottle of champagne in celebration of our 10-year wedding anniversary, so overall amazing!

No in flight service, no explanation - FC got service, C+ did not, unsure about Economy. No turbulence to speak of, so I guess another way to cut cost, or promote health and well being of Delta employees? Also, boarding in MEM combined zones, and with overhead space already full on both flights after Zone 2/ Diamond, presents a huge challenge to find a space for a bag. Delta, other than point A to B, is no longer reasonable to fly - very poor experiences, not even taking into account the chastising at the gate and rude crews, across the board.

It would have been better if the flight wasn't delayed by 2.5 hours

Delta’s staff is unmatched. From the gate agents, to the pilots, to the flight attendants… all top of the industry.

Delta flight Delay for ,more that two hours i.e original flight was 6.30 PM and it starts at 8.45 PM, When we connect Delta team for meal vouchers as it is late arrival in designation,But we did not get it as per delta policy , which is not good for mid night arrival,

Inexperienced boarding crew allowed too many bags on to a full flight and delayed takeoff causing a missed connection and unplanned overnight stay. There was a hotel at the airport but Delta would not pay for it offering only to shuttle me to an area hotel. Never even offerred so much as an apology by anyone working for Delta.

There were no TV screens - even in Business class. 5 delays, and only given $12 meal voucher! Terrible!

It was good. But the gate team made me check my carry on when there was plenty of space for my luggage on the plane. Otherwise our trip was fine.

The entertainment options were at best, fair. It was exactly the same as my outbound flight. It would have been more entertaining if there were some series from Apple TV, HBO, Showtime or other carriers for me to catch up with.

Concern Regarding Significant Gate Delay and Jet Bridge Issue Dear Customer Relations Team, I am writing to express my disappointment with the experience I had on my recent flight AA 2414 on Sunday January 18, 2026. What should have been a routine departure turned into a frustrating and avoidable delay due to an issue with the jet bridge at the gate. As a result, the flight was delayed by approximately 90 minutes while multiple gate changes were attempted. The lack of clear communication during this period made the situation even more challenging. Passengers were left uncertain about the cause of the delay, the expected timeline, and the next steps. This not only disrupted travel plans but also created unnecessary stress for everyone on board. I understand that operational issues can arise, but a malfunctioning jet bridge and the resulting extended delay suggest an area where procedures or equipment maintenance may need attention. I hope you will review this incident to prevent similar disruptions in the future. I would appreciate acknowledgment of this concern and consideration of appropriate compensation for the inconvenience and lost time caused by this delay. Thank you for taking the time to review my experience. I look forward to hearing from you. Sincerely, Dion Dillard

They made me pay $40 to check a bag that was listed as free when I bought my ticket. Then before boarding they offered to check any bags free.

It was a good trip. Flight Attendants were friendly and responsive.

Qatar airways ,boarding arrangements at Hamid international airport could been better

Crew in Columbia was not prepared for landing. It was a bit of a disaster and getting bags took forever.

My seat tv didn’t work the whole trip. And the seat space is too small despite being seated at the front.

The seat cushions were very worn so they were extremely uncomfortable.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports