$83 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 5/26. 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$411
Santo Domingo
Santo Domingo2 stops$640
Montego Bay
Montego Bay1 stop$453
Oranjestad
Oranjestad1 stop$496
Nassau
Nassau2 stops$420
Simpson Bay
Simpson Bay1 stop$345
Providenciales
Providenciales1 stop$265
George Town
George Town1 stop$271
Punta Cana
Punta Cana1 stop$411
Santo Domingo
Santo Domingo2 stops$640
Montego Bay
Montego Bay1 stop$453
Oranjestad
Oranjestad1 stop$496
Nassau
Nassau2 stops$420
Simpson Bay
Simpson Bay1 stop$345
Providenciales
Providenciales1 stop$265
George Town
George Town1 stop$271

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

ma., mai 4 - on., 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
$260Delta
ma., mai 18 - fr., mai 22
Delta Logo
6:00 am - 2:10 pm
DAL
-
PLS
7h 10m
1 stop
Delta Logo
2:05 pm - 9:10 pm
PLS
-
DAL
8h 05m
1 stop
$265Delta
sø., aug. 2 - on., aug. 12
Delta Logo
6:00 am - 11:31 am
DAL
-
GCM
5h 31m
1 stop
Delta Logo
12:56 pm - 10:27 pm
GCM
-
DAL
9h 31m
1 stop
$271Delta
ti., apr. 28 - fr., mai 8
Southwest Logo
2:05 pm - 10:40 pm
DAL
-
SJU
7h 35m
1 stop
Southwest Logo
5:05 am - 11:25 am
SJU
-
DAL
7h 20m
1 stop
$320Southwest
ti., apr. 14 - to., apr. 16
Southwest Logo
2:05 pm - 10:40 pm
DAL
-
SJU
7h 35m
1 stop
Southwest Logo
1:00 pm - 8:35 pm
SJU
-
DAL
8h 35m
1 stop
$322Southwest
ma., apr. 20 - on., apr. 29
Delta Logo
6:05 am - 2:05 pm
DAL
-
SXM
7h 00m
1 stop
Delta Logo
1:35 pm - 10:33 pm
SXM
-
DAL
9h 58m
1 stop
$345Delta
sø., mai 3 - on., mai 6
Southwest Logo
8:45 pm - 9:10 am
DAL
-
SJU
11h 25m
1 stop
Southwest Logo
5:35 am - 2:00 pm
SJU
-
DAL
9h 25m
1 stop
$346Southwest
sø., mai 3 - to., mai 7
Southwest Logo
8:45 pm - 9:10 am
DAL
-
SJU
11h 25m
1 stop
Southwest Logo
8:40 pm - 8:25 am
SJU
-
DAL
12h 45m
1 stop
$348Southwest
ti., apr. 14 - on., apr. 29
Southwest Logo
2:05 pm - 10:40 pm
DAL
-
SJU
7h 35m
1 stop
Southwest Logo
5:35 am - 2:00 pm
SJU
-
DAL
9h 25m
1 stop
$349Southwest
ma., apr. 20 - on., apr. 29
Delta Logo
3:53 pm - 12:10 pm
DAL
-
SXM
19h 17m
2 stops
Delta Logo
1:35 pm - 10:33 pm
SXM
-
DAL
9h 58m
1 stop
$350Delta
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 $675 respectively.

Good to know

Low seasonJanuary
Cheapest flight$83
Best time to beat the crowds with an average 30% drop in price.
Most popular time to fly and prices are also 10% lower on average.
Flight from Dallas Love Field to George Town

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 4331 reviews
8.1Boarding
8.0Comfort
7.0Food
8.6Crew
7.5Entertainment
Airline reviews

Southwest continues to do less for more money. Flight attendants used to be fun and friendly. But now it’s like they don’t even see you. Such a shame.

6.0 GoodDavid, Mar 2026
RSW - BWI
Read more Southwest reviews

Southwest continues to do less for more money. Flight attendants used to be fun and friendly. But now it’s like they don’t even see you. Such a shame.

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 liked it better when you were truer to your roots Am paying more for less fun

Southwest was greaat! The most expensive but the least upsetting for those we were flying to see.

I flew twice this week on Southwest, was delayed over 2 hours both ways. From Pittsburgh to Chicago it was due to weather but the gate agents, pilot etc were great at updating everyone. Today from Midway to Pittsburgh the plane had come from an international location, kept getting delayed, no information was given until we were delayed for the third time. It was ridiculous, whoever scheduled that plane to fly to Pittsburgh after didn’t consider a lot of things.

Boarding was easy. The seats are small and fairly uncomfortable

I was supposed to be on a later flight. When I showed up at the gate, the woman working there was extremely helpful getting moved up to this earlier flight.

We had a 5 hour delay on the tarmac in Baltimore

Long layover between flights to Long Island from BWI - need better coordination between flights

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

This was the worse experience. They delayed our flight twice and we still had to find another flight to get home sooner which was alos delayed. Also, the flight attendant named Ginny on DL9890 leaving at 4:13pm on 3/23/26 was extremely rude.

I love Delta the flight attendants were personable and the flight arrived 1/2 earlier thanks expected. All a plus. The gate agent was a bit flustered but even with that I still had a good experience. Her supervisor assisted me.

Got to fly my favorite plane, the Boeing 767-400ER, to Milan. The soft blush pink mood lighting during meal service was very beautiful and gorgeous. The service was top-notch, and our flights were on time. I highly recommend Delta.

I am still at the Airport! Delayed Delayed and Delyaed

I took seat 15A in anticipation of window seat, there is no window.

The first class flight attendant was awful to everyone. Very rude; no customer service. She should not be working in first class.

Snacks and included beverages were appreciated. Boarding went smoothly. Plenty of overhead bin space. Seats get very uncomfortable after a couple of hours. After waiting 10 painful minutes for my walker, a very nice Delta guest agent pushed me in a wheelchair to the gate. It was finally delivered to me after another 15 minutes . Our checked bag was on the carousel long b4 I was able to retrieve it. Fortunately it was still there but somewhere along the way the straps we used to secure it were removed and and were not reattached. Wish I had made note of the agents name.

It was fine. 55 minute flight. No snacks or beverage service offered. Boarding went smoothly and my walker was waiting for me on the jet way.

Smaller plane for a longer flight than my first one. Doesn’t make sense.

The cabin temperature was nice and cool. The wifi was not working.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports