$123 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 5/4. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Caribbean

Travelers love KAYAK
41,299,237 searches in the past 7 days on KAYAK

Save 23% or moreCompare multiple travel sites with one search.

Track pricesNot ready to book? Create a price alert for when prices drop.

Free to useThere are no hidden charges or fees.

Filter your dealsChoose cabin class, free Wi-Fi and more.

Flight Deals
Booking Insights
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$489
Santo Domingo
Santo Domingo1 stop$602
Montego Bay
Montego Bay1 stop$552
Oranjestad
Oranjestad1 stop$518
Nassau
Nassau1 stop$452
Simpson Bay
Simpson Bay1 stop$310
Providenciales
Providenciales1 stop$461
George Town
George Town1 stop$384
Punta Cana
Punta Cana1 stop$489
Santo Domingo
Santo Domingo1 stop$602
Montego Bay
Montego Bay1 stop$552
Oranjestad
Oranjestad1 stop$518
Nassau
Nassau1 stop$452
Simpson Bay
Simpson Bay1 stop$310
Providenciales
Providenciales1 stop$461
George Town
George Town1 stop$384

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, May 5 - Tue, May 12
Southwest Logo
6:05 am - 1:30 pm
DAL
-
SXM
6h 25m
1 stop
Southwest Logo
2:25 pm - 8:30 am
SXM
-
DAL
19h 05m
2 stops
$310Southwest
Tue, Apr 21 - Wed, Apr 29
Delta Logo
3:53 pm - 11:12 pm
DAL
-
SJU
6h 19m
1 stop
Delta Logo
6:15 am - 3:03 pm
SJU
-
DAL
9h 48m
1 stop
$336Delta
Mon, Apr 20 - Fri, Apr 24
Delta Logo
6:05 am - 4:23 pm
DAL
-
SJU
9h 18m
1 stop
Delta Logo
6:15 am - 3:03 pm
SJU
-
DAL
9h 48m
1 stop
$341Delta
Tue, Apr 14 - Tue, Apr 28
Southwest Logo
6:00 am - 2:50 pm
DAL
-
SJU
7h 50m
1 stop
Southwest Logo
5:35 am - 4:10 pm
SJU
-
DAL
11h 35m
1 stop
$343Southwest
Fri, Apr 17 - Thu, Apr 23
Southwest Logo
9:10 pm - 8:55 am
DAL
-
SJU
10h 45m
1 stop
Southwest Logo
10:00 am - 7:00 pm
SJU
-
DAL
10h 00m
1 stop
$346Southwest
Tue, Apr 7 - Thu, Apr 9
Southwest Logo
3:50 pm - 11:40 pm
DAL
-
SJU
6h 50m
1 stop
Southwest Logo
8:40 pm - 8:25 am
SJU
-
DAL
12h 45m
1 stop
$350Southwest
Mon, Apr 13 - Sat, Apr 25
Southwest Logo
6:00 am - 1:10 pm
DAL
-
SJU
6h 10m
1 stop
Southwest Logo
5:15 am - 3:45 pm
SJU
-
DAL
11h 30m
1 stop
$351Southwest
Fri, Apr 24 - Tue, Apr 28
Southwest Logo
1:05 pm - 11:40 pm
DAL
-
SJU
9h 35m
1 stop
Southwest Logo
5:35 am - 4:10 pm
SJU
-
DAL
11h 35m
1 stop
$361Southwest
Tue, May 5 - Tue, May 19
Southwest Logo
9:00 am - 9:05 pm
DAL
-
SJU
11h 05m
1 stop
Southwest Logo
5:35 am - 3:10 pm
SJU
-
DAL
10h 35m
2 stops
$364Southwest
Sat, Mar 21 - Sat, Mar 28
LATAM Airlines Logo
6:40 pm - 1:58 pm
DAL
-
UVF
18h 18m
1 stop
LATAM Airlines Logo
3:18 pm - 9:42 am
UVF
-
DAL
19h 24m
1 stop
$1,203LATAM Airlines
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 May, when the average cost of round-trip tickets is $795 and $625 respectively.

Good to know

Low seasonJanuary
Cheapest flight$123
Best time to beat the crowds with an average 29% drop in price.
Most popular time to fly and prices are also 8% lower on average.
Flight from Dallas Love Field to Simpson Bay

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 4304 reviews
8.6Crew
7.5Entertainment
7.0Food
8.0Comfort
8.1Boarding
Airline reviews

Flight boarded late after announcing on time boarding. Flight arrived only a little late despite late departure. Had trouble connecting to WiFi

4.0 OkayEmma, Mar 2026
LAX - PHX
Read more Southwest reviews

Flight boarded late after announcing on time boarding. Flight arrived only a little late despite late departure. Had trouble connecting to WiFi

Mediocre. Boarding is now unpleasant. The employees, once friendly and nice, are now regularly speaking sternly to passengers, badgering them to do things right so they can take off on time and gate check bags because they don't have enough overhead bin space. The pretzel snack was crushed flat and broken into even smaller pieces, which happens frequently lately. Drink service was suspended before they reached my row.

The last 3 flights between BWI and BDL canceled the beverage service mid- way. Just say up front that the fight is too short. Thanks!

It was canceled. Supposedly weather. But there was no snow in Baltimore. At least we found out before driving to airport

I have not flown Southwest in awhile and had a very pleasant experience. From ticketing to boarding to the flight. The flight left on time and landed ahead of schedule. It won't be so long next time!!

The Southwest experience has definitely taken a dive from its early days. You can no longer deferentiate from other airlines. Air travel is too expensive. Southwest is no longer budget friendly. They have lost me as a loyal customer.

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.

An entire day of delays. Cost lots of money. Meals and a hotel.

The WiFi and crew on the plane were good, however, the boarding experience was awful. I paid for the Choice Preferred and was boarded in group 5 so all overhead storage was full. They found room for our luggage, but further back making getting off the plane a nightmare. Also, we were in row 6 and the seats were extremely uncomfortable. Both my daughter and I had no leg room and couldn’t wait to get off the plane.

The charges were ridiculous for an hour flight and the turbulence was very scary.

Cabin was not pressurized properly. Several passengers had respiratory difficulties.

I was happy that I was able to get a last minute flight but unfortunately my seat was a middle seat. Even with Delta Comfort I wasn't comfortable

There’s not much to say about a one hour flight. This is a connection from LA to RNO that I missed the previous night due to a mechanical check delay on my originating flight from JFK to LAX. The short flight itself was fine. Instructions from the pilot and crew were per usual. The coffee was barely lukewarm, which possibly was purposeful so we would down it quickly. Bags were already on carousel upon reaching baggage claim, which was excellent.

Flight was warm for first few hours and quite rough

Seat was extremely hard which made even a short 1 hour 20 minute flight fairly uncomfortable.

Everything was good except wifi and a leaking drink chiller. The floor was all wet and my bag was soaked. Did not notice until debarking. Have not heard back from Delta. Even though this was leg one of an international flight in first class, they denied access to their Sky Club - very disappointing!

The staff was fine. The plane was extremely tight, and I paid for the wifi and it did not work at all. I was actually going to ask for a refund.

two hour delay and the Delta representative on the PA system was unable to understand

An awesome flight crew. FC seat cushion just doesn’t cut it for a 3+ hour flight.

2+hrs delay without any reason provided and a cramped flight

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports