$158 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 4/27. 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 Love Field to Caribbean

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$507
Santo Domingo
Santo Domingo1 stop$650
Montego Bay
Montego Bay1 stop$500
Oranjestad
Oranjestad2 stops$515
Nassau
Nassau1 stop$403
Simpson Bay
Simpson Bay1 stop$301
Providenciales
Providenciales1 stop$522
George Town
George Town1 stop$514
Punta Cana
Punta Cana1 stop$507
Santo Domingo
Santo Domingo1 stop$650
Montego Bay
Montego Bay1 stop$500
Oranjestad
Oranjestad2 stops$515
Nassau
Nassau1 stop$403
Simpson Bay
Simpson Bay1 stop$301
Providenciales
Providenciales1 stop$522
George Town
George Town1 stop$514

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

Di, Mai 5 - Do, Mai 7
Delta Logo
3:53 pm - 11:13 pm
DAL
-
SJU
6h 20m
1 stop
Delta Logo
1:14 pm - 11:56 pm
SJU
-
DAL
11h 42m
1 stop
$256Delta
So, Mai 10 - Do, Mai 14
Southwest Logo
6:00 am - 2:25 pm
DAL
-
SXM
7h 25m
1 stop
Southwest Logo
2:25 pm - 10:45 pm
SXM
-
DAL
9h 20m
1 stop
$301Southwest
So, Mai 10 - Do, Mai 14
Southwest Logo
6:00 am - 2:25 pm
DAL
-
SXM
7h 25m
1 stop
Southwest Logo
2:25 pm - 9:20 am
SXM
-
DAL
19h 55m
2 stops
$306Southwest
Mo, Apr 27 - Do, Apr 30
Southwest Logo
4:35 pm - 11:55 pm
DAL
-
SJU
6h 20m
1 stop
Southwest Logo
3:45 pm - 10:45 pm
SJU
-
DAL
8h 00m
1 stop
$316Southwest
Di, Mai 5 - Fr, Mai 8
Delta Logo
12:25 pm - 8:24 pm
DAL
-
SJU
6h 59m
1 stop
Delta Logo
5:43 pm - 11:56 pm
SJU
-
DAL
7h 13m
1 stop
$320Delta
So, Mai 3 - Mi, Mai 6
Delta Logo
6:05 am - 4:23 pm
DAL
-
SJU
9h 18m
1 stop
Delta Logo
12:55 pm - 10:33 pm
SJU
-
DAL
10h 38m
1 stop
$326Delta
Sa, Mai 2 - Mi, Mai 6
Delta Logo
2:59 pm - 11:13 pm
DAL
-
SJU
7h 14m
1 stop
Delta Logo
2:45 pm - 10:33 pm
SJU
-
DAL
8h 48m
1 stop
$345Delta
Mi, Aug 12 - Do, Aug 20
Delta Logo
6:00 am - 1:56 pm
DAL
-
SXM
6h 56m
1 stop
Delta Logo
3:21 pm - 10:27 pm
SXM
-
DAL
8h 06m
1 stop
$345Delta
Mo, Mai 11 - Do, Mai 14
Southwest Logo
4:35 pm - 11:55 pm
DAL
-
SJU
6h 20m
1 stop
Southwest Logo
1:00 pm - 8:35 pm
SJU
-
DAL
8h 35m
1 stop
$350Southwest
Sa, Mai 2 - Mi, Mai 6
Delta Logo
10:17 am - 8:24 pm
DAL
-
SJU
9h 07m
1 stop
Delta Logo
12:55 pm - 10:33 pm
SJU
-
DAL
10h 38m
1 stop
$351Delta
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 January, when tickets cost $275 (return) on average. On the other hand, the most expensive months are December and September, when the average cost of round-trip tickets is $795 and $730 respectively.

Good to know

Low seasonApril
Cheapest flight$158
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly and prices are also 12% 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 4329 reviews
8.6Crew
7.0Food
7.5Entertainment
8.0Comfort
8.1Boarding
Airline reviews

The new boarding process was easy and straightforward. Very pleasant.

10.0 ExcellentAnonymous, Apr 2026
LAS - OKC
Read more Southwest reviews

The new boarding process was easy and straightforward. Very pleasant.

The flight was okay. The pilots did an amazing job and kept us updated on the flight. The flight attendants were okay. They found time to be chatty with each other rather than focus on the guests. One of the attendants was a little less warm when asking about my bag I had on my lap that I was using during latter part of the mid- flight. Mind you, it was not the departure descent. I’m respectful to each and every attendant, it was the tone in her voice reminding me to place my carryon bag on the floor. I hope to have a better experience next time.

The entire travel day was a disaster from beginning to end. Woke up at two in the morning to make it to San Juan airport in time for a 5:30 am flight to Milwaukee which connected in Baltimore. Massive delays lead to me missing original connection out of Baltimore. Sixteen hours of delays/rebooking/layover time later, arrived in Milwaukee to find that only one of two checked bags made it there (despite the fact that Southwest brought another 737 jet to San Juan to fly us out to our original Baltimore connection—-not squeezed into another booked flight). The flight from Baltimore to Milwaukee was barely half full, so there was no logical reason to ship my bags out of Baltimore on a different flight to Chicago to then ship to Milwaukee. Southwest decided that my bags should not have been on the same connecting flight I WAS ON to Milwaukee, and then proceeded to accidentally leave my larger bag with the important items in Chicago. Terrible logic and support all around. Extremely angered and disappointed with SW. What a clownish operation your company has become!

It was as expected and I was grateful for the wheel chair help and ease of use.

One of the best airlines for fast boarding, on time arrivals, and top notch service!

The new seat assignment thing is wierd. If you don’t pay for a seat they always assign you a middle seat regardless of how many people are on the flight. Idk… the new company that bought Southwest is trying to make it more profitable, but I’m just not seeing it. The flight attendants aren’t having as much fun anymore. It just feels like the airline is slowly dying. IMO. We shall see if Southwest is the next Toy’s R Us.

Terrible. Even though there’s assigned seating now, they are still the slowest boarding airline of anyone.

The Air hostess were very rude on my flight from Houston to Austin . Their regular communication itself felt a they are shouting at people.

Communication about the delayed flight was poor. We were told to move gates three times but that was bad information. We went from gate 128 to gate 126 and then to gate 123 and back to gate 126. Communication about the delay was bad. Ended up being 1 1/2 hour late getting home.

Plane was late. Zero service for 2+ hour flight and it was not that bumpy.

Boarding was good. The flight was on time ( arrival was 20 minutes early). Inflight service was average ( US airlines have not mastered the skills of customer service yet). The food was mediocre. “ breakfast “ was downright awful and insulting. It was a piece of dough with mon descript filling that was supposed to be cheese omelette).

The tray table was broken and the food was terrible.

The gentleman at the gate I think his name is RIE was exceptional

While they turned off most cabin lights to allow people to sleep, I was bothered by how bright the side lights still were. It was still quite bright for me in a window seat, when I wish I could have slept!

One of the flight attendants was a little cranky. I appreciated the free wifi and plug to charge my laptop

No entertainment. Plane was so small had to pink tag a carry on ive used for 20 years easily on board. The fact the flight got in at midnight, had to wait for crew in fort wayne to allow the plane to approach the gate, THEN had to wait for bag on jet bridge made experience irritating at best.

Crew was great. Near on time departure and early arrival. Snacks are always meh. Not a fan of the "pay for everything including miles " proposal unless base flight rate going to be 100 bucks.

Would have been better if there was a nonstop flight from Tampa to Norfolk or Tampa to New Port News.

Overall Good! The weather delayed our takeoff from Atlanta and our arrival in Miami! If Mother Nature can mess up a flight she will do it every time!

The flight was smooth, the crew was great but the plane was quite old

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports