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Find cheap flights from Lexington to Caribbean from $365

This is the cheapest round-trip flight price found by a KAYAK user in the last 72 hours by searching for a flight from Lexington to Caribbean departing on 6/20. 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
0 bags
Sat 6/29
Sat 7/6

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Best Caribbean Flight Deals

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours

Punta Cana
Punta Cana1 stop$452
Montego Bay
Montego Bay1 stop$447
Oranjestad
Oranjestad1 stop$545
Nassau
Nassau1 stop$400
Simpson Bay
Simpson Bay2 stops$441
Providenciales
Providenciales2 stops$425
George Town
George Town1 stop$488
St. John's
St. John's2 stops$682

Good to know

Low season

November

High season

March

Cheapest flight

$365
Best time to beat the crowds with an average 1% drop in price.
Most popular time to fly with an average 5% 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 to Caribbean from Lexington 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 to Caribbean with an airline and back to Lexington 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 to Caribbean from Lexington up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

See more FAQs

Top tips for finding cheap flights to Caribbean

  • Morning departure is around 21% more expensive than an evening flight, on average*.
*Average of the lowest prices shown in KAYAK’s search results for departures within the next 30 days

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.
8.0
DeltaOverall score based on 10457 reviews
7.9Comfort
8.6Crew
8.2Boarding
8.0Entertainment
7.4Food
Airline reviews

I've flown many many times on Northwest and then Delta. The crew on this flight were absolutely the best I've had the pleasure of being looked after by.

10.0 ExcellentAnonymous, May 2024MSP - YVR
Read more about Delta reviews

I've flown many many times on Northwest and then Delta. The crew on this flight were absolutely the best I've had the pleasure of being looked after by.

Flew first class so everything was great. But maybe because the flights were red eye, no meals were served, just chips. I flew Alaska Air 1st class at 9PM (2 hour flight) and they served beef short rib sliders!

Had to change aircraft due to a faulty door. Surprisingly it only caused about an hour and a half of delay. Delta handled this situation as well as can be expected.

Awful. Flight was continuously getting delayed and gates kept changing without any reason. Flight was delayed for more then 3 hours

Paid premium for Delta only to be on safe but tired old 767 with ancient cabin in mediocre condition. Poor wifi and horrible inflight entertainment. Hardly a premium experience. Should have flown SW and had fun flight crew and no pretense

Our flight to Zurich was delayed by almost 3 hours, so we missed our next flight. There was no indication it would be delayed this much. We were told the gate had changed and then it apparently took over 2 hours to load the "catering" on the plane. We were not compensated in any way for the trouble.

Rated entertainment as Mediocre as there were major problems with the Infotainment system that took probably a half hour for them to fix.

Your crew could maybe answer the call bell at least one of the times I pressed it. I pressed it first time with 2.5 hours left in our flight bc my partner was hungry and wanted a sandwich. We finally got the sandwich with 40 mins left in the flight.

Half the bathrooms assigned to economy were out of action

Delta crushed it. Flight attendant in first was attentive and just never stopped. Honestly one of the best domestic flights I’ve been on.

very very tight seats unfriendly crew who do not seem to care about the comfort of their passengers and do not know how to smile poor ground staff support at LHR and PHX

The boarding process and flight were great. However, I waited about 40 minutes for my luggage. It did not come up on the designated belt. Instead, everyone’s bags were on a cart. Not sure what the issue was, but we were not informed until another passenger went looking for her bags and found them.

There were delays on both ends. It made it less than excellent. This plane was great though

AA1537 the AC was not working properly. It was very hot and uncomfortable.

So uncomfortable to sit in the tiny space on a long, international. Food was rough. Please, less white flour and processed food.

Worst experience flying American Airlines. I fly with them often, so I was super disappointed in the service I received at gate 30 in LGA on May 24, mid-day. The flight was delayed twice. I was patiently waiting in the American Airlines lounge when I received the notice on my app that the plane was boarding 45 minutes before its newly re-scheduled take off of 4 pm (from the orginal 1:45 pm then 3:00 pm). It took me 5 min to travel from the lounge to the gate and when I arrived there at 3:20 flight gate attendant told me the flight had closed and that they announced for passengers multiple times. I showed them the notification on my app and they were really rude and unempathetic. The person who rescheduled my flight at customer service wasn't any happier but was at least helpful in getting me on the next flight.

Flight was 1/2 hour delayed leaving Phoenix. Otherwise it was an average flight. Flight crew on this trip was very nice.

Our flight was delayed 2.5 hrs due to plane being too hot! After 1.5 hrs, airline decided to use another plane but had to wait for gate, baggage transfer & beverage transfer. Anyone could tell after first half hour that another plane was required and although did not affect us many would miss connecting flights at Heathrow. I have found the stewards are not the friendliest in the industry and the food is questionable, even as I like airplane food normally, the best of the 2 flights was the yogurt & granola for breakfast.

Everything was great except for the wifi was junk. Crew was super friendly and helpful

Was lucky to have a employee at the AA checkin counter that had compassion and understood they ordeal that we went through with our original flight being diverted, needing to stay in the aircraft and then flying to the original destination; adding hours to the trip and forcing us to miss our connection and our rebooked connection. She was able to get up on standby on the highest priority on the next flight to the closest airport we need to be at and it all worked out despite being many hours late.

Book cheap flights from Lexington to Caribbean

Recent round-trip flight deals

6/20Thu
1 stop
10h 51mLEX-SJU
6/23Sun
2 stops
13h 25mSJU-LEX
$365
7/10Wed
1 stopDelta
7h 42mLEX-SJU
7/17Wed
1 stopDelta
8h 23mSJU-LEX
$374
7/10Wed
1 stopDelta
7h 42mLEX-SJU
7/18Thu
1 stopDelta
10h 08mSJU-LEX
$384
7/15Mon
1 stopDelta
9h 44mLEX-SJU
7/18Thu
1 stopDelta
10h 08mSJU-LEX
$394
6/20Thu
2 stops
15h 06mLEX-SJU
6/23Sun
2 stops
13h 25mSJU-LEX
$395
7/27Sat
1 stopDelta
7h 49mLEX-SJU
8/5Mon
1 stopDelta
7h 51mSJU-LEX
$414
9/21Sat
2 stopsAmerican Airlines
19h 07mLEX-PLS
9/28Sat
2 stopsAmerican Airlines
20h 41mPLS-LEX
$425
9/21Sat
1 stopAmerican Airlines
20h 19mLEX-PLS
9/28Sat
2 stopsAmerican Airlines
19h 01mPLS-LEX
$432
8/7Wed
2 stopsUnited Airlines
24h 09mLEX-PLS
8/11Sun
2 stopsUnited Airlines
29h 29mPLS-LEX
$559
10/21Mon
2 stopsUnited Airlines
22h 40mLEX-PUJ
10/24Thu
2 stopsUnited Airlines
23h 29mPUJ-LEX
$621

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Last minute flights from Lexington to Caribbean

Last minute flight, train and bus deals

6/3Mon
multi-stop
17h 21mLEX-PUJ
6/10Mon
multi-stop
30h 31mPUJ-LEX
$639
6/3Mon
multi-stopAmerican Airlines
18h 03mLEX-SJU
6/10Mon
multi-stopAmerican Airlines
13h 37mSJU-LEX
$643
5/31Fri
multi-stopAmerican Airlines
9h 19mLEX-SJU
6/3Mon
multi-stopAmerican Airlines
12h 03mSJU-LEX
$665
5/31Fri
multi-stopAmerican Airlines
10h 35mLEX-SJU
6/3Mon
multi-stopAmerican Airlines
10h 19mSJU-LEX
$666
6/2Sun
multi-stopAmerican Airlines
14h 47mLEX-PUJ
6/9Sun
multi-stopAmerican Airlines
7h 52mPUJ-LEX
$758
6/3Mon
multi-stopAmerican Airlines
16h 31mLEX-SJU
6/10Mon
multi-stopAmerican Airlines
16h 37mSJU-LEX
$761
6/2Sun
multi-stopAmerican Airlines
16h 16mLEX-PUJ
6/9Sun
multi-stopAmerican Airlines
7h 52mPUJ-LEX
$763
6/3Mon
multi-stop
26h 43mLEX-PUJ
6/10Mon
multi-stop
27h 39mPUJ-LEX
$765
6/3Mon
multi-stop
28h 52mLEX-PUJ
6/10Mon
multi-stop
30h 31mPUJ-LEX
$776
6/2Sun
multi-stopAmerican Airlines
17h 28mLEX-PUJ
6/9Sun
multi-stopAmerican Airlines
18h 24mPUJ-LEX
$783

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