$124 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 5/5. 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$487
Santo Domingo
Santo Domingo1 stop$650
Montego Bay
Montego Bay1 stop$464
Oranjestad
Oranjestad2 stops$511
Nassau
Nassau1 stop$356
Simpson Bay
Simpson Bay1 stop$301
Providenciales
Providenciales1 stop$506
George Town
George Town2 stops$435
Punta Cana
Punta Cana1 stop$487
Santo Domingo
Santo Domingo1 stop$650
Montego Bay
Montego Bay1 stop$464
Oranjestad
Oranjestad2 stops$511
Nassau
Nassau1 stop$356
Simpson Bay
Simpson Bay1 stop$301
Providenciales
Providenciales1 stop$506
George Town
George Town2 stops$435

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

Sun, May 10 - Tue, May 19
Delta Logo
6:00 am - 4:33 pm
DAL
-
SJU
9h 33m
1 stop
Delta Logo
5:43 pm - 11:56 pm
SJU
-
DAL
7h 13m
1 stop
$256Delta
Tue, Apr 28 - Wed, May 6
Delta Logo
12:25 pm - 11:13 pm
DAL
-
SJU
9h 48m
1 stop
Delta Logo
2:45 pm - 10:33 pm
SJU
-
DAL
8h 48m
1 stop
$260Delta
Mon, May 11 - Wed, May 13
Southwest Logo
1:05 pm - 11:40 pm
DAL
-
SJU
9h 35m
1 stop
Southwest Logo
8:10 am - 4:10 pm
SJU
-
DAL
9h 00m
1 stop
$290Southwest
Tue, May 19 - Fri, May 22
Southwest Logo
6:05 am - 1:30 pm
DAL
-
SXM
6h 25m
1 stop
Southwest Logo
2:25 pm - 10:45 pm
SXM
-
DAL
9h 20m
1 stop
$301Southwest
Mon, May 11 - Sat, May 16
Southwest Logo
6:00 am - 1:30 pm
DAL
-
SXM
6h 30m
1 stop
Southwest Logo
2:35 pm - 11:20 pm
SXM
-
DAL
9h 45m
1 stop
$321Southwest
Tue, May 5 - Wed, May 13
Delta Logo
3:53 pm - 11:13 pm
DAL
-
SJU
6h 20m
1 stop
Delta Logo
1:14 pm - 9:10 pm
SJU
-
DAL
8h 56m
1 stop
$322Delta
Tue, May 5 - Tue, May 12
Southwest Logo
9:00 am - 9:05 pm
DAL
-
SJU
11h 05m
1 stop
Southwest Logo
5:05 am - 1:35 pm
SJU
-
DAL
9h 30m
1 stop
$332Southwest
Sat, May 16 - Tue, May 19
Delta Logo
7:12 am - 4:33 pm
DAL
-
SJU
8h 21m
1 stop
Delta Logo
5:43 pm - 11:56 pm
SJU
-
DAL
7h 13m
1 stop
$345Delta
Tue, May 5 - Wed, May 13
Delta Logo
6:05 am - 2:05 pm
DAL
-
SXM
7h 00m
1 stop
Delta Logo
3:20 pm - 11:56 pm
SXM
-
DAL
9h 36m
1 stop
$345Delta
Tue, May 5 - Sat, May 9
Southwest Logo
9:00 am - 9:05 pm
DAL
-
SJU
11h 05m
2 stops
Southwest Logo
5:45 am - 3:35 pm
SJU
-
DAL
10h 50m
1 stop
$347Southwest
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$124
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 Nassau

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 4334 reviews
8.6Crew
8.0Comfort
8.1Boarding
7.0Food
7.5Entertainment
Airline reviews

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

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

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.

It was good from LAX to Phoenix, But the connection in Phoenix to Tulsa was not that great. The staff on both flights were great. The choice of free entertainment was ok nothing to brag about. The 45 min delay because of some electrical issue wasn't great from Phoenix to Tulsa. We sat there with hardly any air, The seat I had was between windows so the side of the plane pushed in on you. My being a bigger man it then made the seating area uncomfortable. The seats on the plane had no power to connect to recharge your phone or anything. I would recommend that they should look into a slot or clamp to hold your phone to enjoy while watching the entertainment choices hands-free. Also make it possible to raise the inner seat by the window be able to raise the arm rest up to make more room for larger people to set more comfortably. I would also say other then that stop price gouging the airfare or nickel and diming everything. Not fair for people having to fly for emergencies and be paying for higher prices due to the season or holidays. Your making your money either way and the cost of flying is still going to be the same regardless if there's 100 people or 200 people.

Had a great flight. Delayed takeoff, but comfortable. Snacks were good.

Love them will get a Southwest card to track my points and keep flying with them. My family and I were pleased with the services.

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

Everything was great until I lost my water bottle and they can’t seem to locate it. I know I left it on the plane though.

WiFi didn’t work most of the time. The usb chargers would work only occasionally for 5 mins and wouldn’t charge after that. Had to keep trying repeatedly at each of the seats in the row.

The crew bent over backwards to thank us for flying and make us comfortable. The food service was quick and efficient. The Captain communicated and said goodbye and thank you as we departed. They really stood out!

Okay considering we had weather delays which the Pilot notified us of immediately!

Generally on time departures and arrivals, clean planes, sky miles membership provides great benefits (complimentary upgrades, etc).

Flight from Fort Wayne to Atlanta was the smallest in terms of cabin space that I've ever seen. A carry on I've used for 20 years BARELY fit in overhead compartment. I'm 5'10" and felt very cramped. Not the best experience.

I am writing to express my dissatisfaction with the poor service and unprofessional staff we encountered when traveling with an infant. Our flight was delayed, and the gate staff failed to manage the boarding process appropriately. Due to incorrect, unavailable, or missing 'pink tag' stroller and car seat check-in procedures at the gate, we were forced to board last. Furthermore, the gate staff was rude and dismissive, causing significant distress to our infant. To make matters worse, one of our checked items—an infant sleeper/lounger—was returned to us broken. Given the unsafe handling of essential equipment and unprofessional treatment, I expect a prompt resolution regarding compensation for the damaged items.

We departed and landed early which was a nice surprise. The boarding process was slow.

N Everything was perfect from boarding to assistance to baggage in Tampa

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports