$146 Find Cheap Flights from Dallas Love Field 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 Love Field to Caribbean departing on 2/23. 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 Love Field to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$623
Santo Domingo
Santo Domingo1 stop$790
Montego Bay
Montego Bay1 stop$604
Oranjestad
Oranjestad1 stop$577
Nassau
Nassau1 stop$525
Simpson Bay
Simpson Bay1 stop$535
Providenciales
Providenciales1 stop$467
George Town
George Town2 stops$468
Punta Cana
Punta Cana1 stop$623
Santo Domingo
Santo Domingo1 stop$790
Montego Bay
Montego Bay1 stop$604
Oranjestad
Oranjestad1 stop$577
Nassau
Nassau1 stop$525
Simpson Bay
Simpson Bay1 stop$535
Providenciales
Providenciales1 stop$467
George Town
George Town2 stops$468

Book Cheap Love Field 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 Love Field 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 Love Field to Caribbean

Tue, Feb 3 - Thu, Feb 12
Delta Logo
6:00 am - 5:17 pm
DAL
-
SJU
9h 17m1 stop
Delta Logo
3:55 pm - 10:31 pm
SJU
-
DAL
8h 36m1 stop
$292Delta
Wed, Feb 18 - Wed, Mar 4
Southwest Logo
4:00 pm - 12:35 am
DAL
-
SJU
6h 35m1 stop
Southwest Logo
6:10 am - 4:55 pm
SJU
-
DAL
12h 45m1 stop
$317Southwest
Thu, Feb 5 - Fri, Feb 6
Southwest Logo
11:10 am - 9:50 pm
DAL
-
SJU
8h 40m1 stop
Southwest Logo
8:00 pm - 8:10 am
SJU
-
DAL
14h 10m1 stop
$342Southwest
Wed, Feb 18 - Wed, Feb 25
Delta Logo
2:27 pm - 11:58 pm
DAL
-
SJU
7h 31m1 stop
Delta Logo
6:15 am - 1:38 pm
SJU
-
DAL
9h 23m1 stop
$348Delta
Tue, Feb 3 - Wed, Feb 4
Southwest Logo
4:00 pm - 12:35 am
DAL
-
SJU
6h 35m1 stop
Southwest Logo
10:20 am - 4:10 pm
SJU
-
DAL
7h 50m1 stop
$349Southwest
Tue, Jan 27 - Thu, Jan 29
Southwest Logo
9:00 am - 11:10 pm
DAL
-
SJU
12h 10m1 stop
Southwest Logo
6:10 am - 4:55 pm
SJU
-
DAL
12h 45m1 stop
$352Southwest
Mon, Jan 26 - Fri, Jan 30
Southwest Logo
9:00 am - 11:10 pm
DAL
-
SJU
12h 10m1 stop
Southwest Logo
10:20 am - 7:00 pm
SJU
-
DAL
10h 40m1 stop
$354Southwest
Mon, Feb 2 - Sat, Feb 7
Southwest Logo
12:40 pm - 8:55 pm
DAL
-
SJU
6h 15m1 stop
Southwest Logo
6:00 am - 2:30 pm
SJU
-
DAL
10h 30m2 stops
$357Southwest
Wed, Feb 25 - Fri, Mar 6
Southwest Logo
1:05 pm - 12:35 am
DAL
-
SJU
9h 30m2 stops
Southwest Logo
8:00 am - 6:40 pm
SJU
-
DAL
12h 40m1 stop
$364Southwest
Fri, Feb 13 - Fri, Feb 20
Southwest Logo
8:50 pm - 10:00 am
DAL
-
SJU
11h 10m1 stop
Southwest Logo
6:00 am - 12:15 pm
SJU
-
DAL
8h 15m1 stop
$374Southwest
Booking Insights

KAYAK's insights & trends for Love Field to Caribbean flights

Get data-powered insights and trends into flights from Love Field 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 Dallas Love Field Airport to Caribbean?

To calculate monthly average prices, KAYAK takes all prices for each month over the last year for round-trip flights from Dallas Love Field Airport 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 Dallas Love Field Airport to Caribbean is March, when tickets cost $304 (return) on average. On the other hand, the most expensive months are December and May, when the average cost of round-trip tickets is $795 and $645 respectively.

Good to know

Low seasonJanuary
Cheapest flight$146
Best time to beat the crowds with an average 30% drop in price.
Most popular time to fly and prices are also 15% lower on average.
Flight from Dallas Love Field to San Juan

FAQs - booking Caribbean flights

  • How does KAYAK find such low prices on flights from Dallas Love Field 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 Dallas Love Field to Caribbean.

  • How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Dallas Love Field to Caribbean?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Dallas Love Field 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 Dallas Love Field 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 Dallas Love Field 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 Dallas Love Field 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 Dallas Love Field 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 Love Field to Caribbean

 
Need help choosing which airline to fly with from Love Field 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
SouthwestOverall score based on 4248 reviews
8.6Crew
8.1Boarding
7.5Entertainment
7.0Food
8.0Comfort
Airline reviews

Pretty seamless, just a tad bit late in taking off and landing.

8.0 ExcellentSudhir, Jan 2026
MCI - LGA
Read more Southwest reviews

Pretty seamless, just a tad bit late in taking off and landing.

Flight was fine other than there was a gate change that I was not notified of. By chance I happened to check my phone and saw the change, otherwise, we would have missed our connecting flight.

Haven’t flown on SW in years. Flight was on time departing and arriving. Served vegan butter onion flavored pretzels which were bad. Coke served was in a tiny paper cup. Crew was not engaging. Felt like they were going through the motions. Old plane, tight seats and no leg room.

Check-in, Boarding and flight were smooth. All the employees and crew was very nice and funny. They gave the kids crayons and workbooks to keep them occupied which was a big win. I’ve flown Southwest many times and that’s the first time I’ve seen that and it is a great addition.

Flight was on time. Wi-fi was a little spotty/slow. Boarding and exit were efficient.

Okay, not wonderful. Short flight. Wi-fi didn't work properly. Stuck waiting for a gate to open upon arrival for 20 or so minutes.

They sent a notice that they were boarding an hour early. We had to leave the club and run to the gate. They said sorry, that came from corporate and was a mistake. They did not have enough seating because the flight before it had not taken off on time. They moved our gate and delayed it for an hour.

The boarding and seat assignment system no longer works for me, but I know it is being replaced. Otherwise, I am good with the overall experience.

The lead steward kept singing about "San Francisco" and hotel California---more annoying than humorous....needs work. Flight was smooth and on time.

Still a fan of open seating. Flight was on schedule and arrived on time. The 737 MAX is very comfortable.

DTW line is too long. The flights from DTW to BWI are always delayed for unknown reasons.

Delta canceled our flight and we had to scramble to find another airline to get home. Phoenix is not a delta hub so they didn’t have another plane. It would have been a red eye though Salt Lake City. Getting in at 5am. No bueno.

This flight was no comparison to our prior flight. I'm thinking it all has to do with the age of the aircraft.

This flight was a first class choice and left much to be desired. Seat backs on seats were falling apart and torn. Seats actually didn't come to a "full & upright position". Pull out table was sprung. Not any significant leg room. All in all we were on an obviously older plane and felt overcharged for what we received as first class.

A 12 hour flight during the day with one real meal service - are you kidding? Also the breakfast was one of the worst and not what was listed

Flight was delayed several times. At one point, they "pulled back" 15 minutes from the delayed boarding and sent a text saying we would board sooner than previously advised. The flight then was delayed again. And when we boarded, there was an unspecified technical issue which had us waiting in the plane for about an hour.

Delta is a good airline. I've never had an issue with Delta. I'll continue to fly with them until they show me that I shouldn't.

The only thing nice I can say is the flight crew was really nice and apologetic about the situation. They shared as much information as they had and advised us on what we could do about missing connecting flights. The boarding process was so slow. The gate agent was working by herself and should have had someone working with her. It took almost an hour to board because she was trying to board a full flight of people and provide customer service to everyone who was flying standby and/or had questions. It was really chaotic. This didn't help the fact that we were delayed and folks were missing connections the longer it took.

The gate attendants and the crew were terrible. Because of high winds, they needed to carry more fuel, so they had to get volunteers to take the next flight at 6 am the next day. They did a terrible job of it - our flight ended up taking off just under 3 hours of the scheduled time. I hope to never fly Delta again.

Did not realize internet screen was hidden between seats and no info printed!!!!

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports