$118 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 8/18. 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 Cana2 stops$498
Santo Domingo
Santo Domingo1 stop$388
Montego Bay
Montego Bay1 stop$542
Oranjestad
Oranjestad2 stops$586
Nassau
Nassau2 stops$438
Simpson Bay
Simpson Bay1 stop$385
Providenciales
Providenciales2 stops$602
George Town
George Town2 stops$535
Punta Cana
Punta Cana2 stops$498
Santo Domingo
Santo Domingo1 stop$388
Montego Bay
Montego Bay1 stop$542
Oranjestad
Oranjestad2 stops$586
Nassau
Nassau2 stops$438
Simpson Bay
Simpson Bay1 stop$385
Providenciales
Providenciales2 stops$602
George Town
George Town2 stops$535

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

Wed, Aug 19 - Wed, Aug 26
Southwest Logo
12:20 pm - 10:00 pm
DAL
-
SJU
8h 40m
2 stops
Southwest Logo
6:00 am - 5:20 pm
SJU
-
DAL
12h 20m
1 stop
$358Southwest
Mon, Aug 10 - Tue, Aug 18
Delta Logo
6:00 am - 1:42 pm
DAL
-
SJU
6h 42m
1 stop
Delta Logo
7:00 am - 1:52 pm
SJU
-
DAL
7h 52m
1 stop
$359Delta
Fri, Aug 21 - Fri, Aug 21
Southwest Logo
8:45 am - 4:55 pm
DAL
-
SJU
7h 10m
1 stop
Southwest Logo
8:55 pm - 9:05 am
SJU
-
DAL
13h 10m
1 stop
$378Southwest
Thu, Sep 3 - Mon, Sep 7
Southwest Logo
10:00 am - 10:10 pm
DAL
-
SJU
11h 10m
1 stop
Southwest Logo
8:55 pm - 8:50 am
SJU
-
DAL
12h 55m
1 stop
$383Southwest
Sun, Aug 23 - Fri, Aug 28
Southwest Logo
6:00 am - 2:05 pm
DAL
-
SXM
7h 05m
1 stop
Southwest Logo
3:05 pm - 10:10 pm
SXM
-
DAL
8h 05m
1 stop
$385Southwest
Fri, Aug 7 - Fri, Aug 14
Southwest Logo
8:45 am - 8:05 pm
DAL
-
SJU
10h 20m
1 stop
Southwest Logo
8:55 pm - 9:05 am
SJU
-
DAL
13h 10m
1 stop
$387Southwest
Wed, Aug 5 - Wed, Aug 12
Delta Logo
6:00 am - 1:28 pm
DAL
-
SDQ
6h 28m
1 stop
Delta Logo
2:53 pm - 10:26 pm
SDQ
-
DAL
8h 33m
1 stop
$388Delta
Sat, Aug 22 - Fri, Aug 28
Southwest Logo
7:00 pm - 2:05 pm
DAL
-
SXM
18h 05m
2 stops
Southwest Logo
3:05 pm - 10:10 pm
SXM
-
DAL
8h 05m
1 stop
$390Southwest
Wed, Sep 30 - Wed, Oct 7
Southwest Logo
10:50 am - 7:00 pm
DAL
-
SJU
7h 10m
1 stop
Southwest Logo
6:45 am - 12:35 pm
SJU
-
DAL
6h 50m
1 stop
$392Southwest
Fri, Aug 14 - Fri, Aug 14
Southwest Logo
8:45 am - 4:55 pm
DAL
-
SJU
7h 10m
1 stop
Southwest Logo
8:55 pm - 9:05 am
SJU
-
DAL
13h 10m
1 stop
$397Southwest
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 May, when tickets cost $257 (return) on average. On the other hand, the most expensive months are April and June, when the average cost of round-trip tickets is $652 and $526 respectively.

Good to know

Low seasonApril
Cheapest flight$118
Best time to beat the crowds but there is an average 27% increase in price.
Most popular time to fly and prices are also 15% 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.
7.9
SouthwestOverall score based on 4245 reviews
8.1Boarding
7.5Entertainment
8.6Crew
7.0Food
8.0Comfort
Airline reviews

Flight was constantly delayed with significant changes in time, it was supposed to get to Colorado Springs at 8:30 PM but it got there after midnight.

2.0 MediocreMarcela, Jun 2026
DAL - COS
Read more Southwest reviews

Flight was constantly delayed with significant changes in time, it was supposed to get to Colorado Springs at 8:30 PM but it got there after midnight.

I don't know why flying out of Sarasota requires two plane changes.

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

Great flight. Good snacks and drinks. Grateful it was free. The flight from Nashville to louisville, i think her name was Tracy (not sure that's right) super awesome, nice and cheerful. She really enjoyed being at work today! She was the person who scanned the boarding pass on flight wn941. She should be recommended for a raise !

I elected to pay for the upgrades and found very little difference

Flight was hours late, unable to sit next to spouse, I have had so much better experiences. Substantially better, only saving grace was that it was a short flight.

I was assigned seat 7E, yet my boarding was Group 5, which caused me to have to put my luggage in the back of the plance above `19 or 20 aisle, as passengers who had boarded earlier took the overhead bins in the front. SW needs to monitor bin space and ensure that bin space above the seat are aligned to those sitting near their seats. Also the seating assignments needs to align with group number. Maybe board those last first and so on? Having said the ALL the passengers on the plane were gracious enough to allow me and other passengers in this dilema to retrieve our luggage and helped us along the way. I always love the flight staff, as always their fantastic and I can't rave about them enough!

The flight crew was extremely rude and especially not helpful when our flight was delayed.

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.

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

Flight got canceled 4 times, missed my connecting flight due to delays, have to wait to go home tomorrow

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

The WiFi was not working. That made for a long flight.

Flight was delayed due to crew being not on time

Flight was delayed. No information on why it was delayed. After we boarded the flight, , the crew made announcement that the captain hs not arrived and he will take 15 mins more to arrive. Passengers were just sitting patiently for the captain to arrive and start, Terrible experience.

Timing, quality of service, promptness and courtesy of the staff

There was no wifi available on this flight. And there were no screens, no onboard entertainment, no entertainment options at all. It was like travelling in the 1990s again, except without even a main screen for options. Seats, as usual, were tight and uncomfortable.

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

Wasn't a Delta issue I don't think, but seems there was a Delta flight at each of the 2 Dallas airports at the same exact time, both to Atlanta. I was evidently booked on the one at Love Airport, but the Carey transport shuttle took me to DFW instead and I ended up missing the flight by just a few minutes. Was able to book a Southwest flight from Love Airport, but was a big loss of time and an inconvenience.

App was rather sporadic in working along with Wi-Fi no longer could text and passenger seated next to me was sicker than a dog from LAXLIH also disappointed I couldn’t buy access to sky club with my bonvoy Amex

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports