$152 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 2/23. 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$543
Santo Domingo
Santo Domingo1 stop$659
Montego Bay
Montego Bay1 stop$528
Oranjestad
Oranjestad1 stop$577
Nassau
Nassau1 stop$472
Simpson Bay
Simpson Bay1 stop$567
Providenciales
Providenciales1 stop$413
George Town
George Town1 stop$484
Punta Cana
Punta Cana1 stop$543
Santo Domingo
Santo Domingo1 stop$659
Montego Bay
Montego Bay1 stop$528
Oranjestad
Oranjestad1 stop$577
Nassau
Nassau1 stop$472
Simpson Bay
Simpson Bay1 stop$567
Providenciales
Providenciales1 stop$413
George Town
George Town1 stop$484

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, Apr 21 - Tue, Apr 28
Southwest Logo
2:05 pm - 10:40 pm
DAL
-
SJU
7h 35m
1 stop
Southwest Logo
5:05 am - 1:35 pm
SJU
-
DAL
9h 30m
1 stop
$364Southwest
Tue, Apr 7 - Tue, Apr 14
Southwest Logo
9:00 am - 9:05 pm
DAL
-
SJU
11h 05m
2 stops
Southwest Logo
11:25 am - 7:55 pm
SJU
-
DAL
9h 30m
2 stops
$365Southwest
Sun, May 17 - Wed, May 20
Delta Logo
10:20 am - 10:54 pm
DAL
-
SJU
11h 34m
1 stop
Delta Logo
12:50 pm - 8:35 pm
SJU
-
DAL
8h 45m
1 stop
$366Delta
Wed, Feb 18 - Wed, Feb 25
Southwest Logo
7:35 am - 7:05 pm
DAL
-
SJU
9h 30m
2 stops
Southwest Logo
6:10 am - 2:45 pm
SJU
-
DAL
10h 35m
2 stops
$382Southwest
Thu, May 7 - Sun, May 10
Southwest Logo
9:20 pm - 9:10 am
DAL
-
SJU
10h 50m
1 stop
Southwest Logo
11:40 am - 8:00 pm
SJU
-
DAL
9h 20m
1 stop
$383Southwest
Sun, Mar 8 - Thu, Mar 12
Southwest Logo
8:50 pm - 9:25 am
DAL
-
SJU
11h 35m
1 stop
Southwest Logo
8:50 pm - 8:15 am
SJU
-
DAL
12h 25m
1 stop
$390Southwest
Fri, May 15 - Mon, May 18
Southwest Logo
9:20 pm - 8:55 am
DAL
-
SJU
10h 35m
1 stop
Southwest Logo
10:00 am - 6:30 pm
SJU
-
DAL
9h 30m
2 stops
$391Southwest
Wed, Feb 25 - Fri, Feb 27
Southwest Logo
1:05 pm - 12:35 am
DAL
-
SJU
9h 30m
2 stops
Southwest Logo
10:50 am - 7:05 pm
SJU
-
DAL
10h 15m
1 stop
$400Southwest
Sun, May 17 - Thu, May 21
Delta Logo
10:20 am - 10:54 pm
DAL
-
SJU
11h 34m
1 stop
Delta Logo
12:50 pm - 8:35 pm
SJU
-
DAL
8h 45m
1 stop
$401Delta
Wed, Apr 15 - Wed, Apr 22
Southwest Logo
12:05 pm - 10:40 pm
DAL
-
SJU
9h 35m
1 stop
Southwest Logo
2:00 pm - 9:15 pm
SJU
-
DAL
8h 15m
1 stop
$405Southwest
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 March, when tickets cost $305 (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 $645 respectively.

Good to know

Low seasonJanuary
Cheapest flight$152
Best time to beat the crowds with an average 30% drop in price.
Most popular time to fly and prices are also 15% 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 4268 reviews
7.5Entertainment
8.1Boarding
7.0Food
8.0Comfort
8.6Crew
Airline reviews

Everything went smoothly and we even arrived a little bit early.

10.0 ExcellentAmy, Jan 2026
DEN - STL
Read more Southwest reviews

Everything went smoothly and we even arrived a little bit early.

Great vacation. Can't wait till next year for another one.

Great flight but super high price. Glad it was a business trip and not personal

On time. Friendly staff. Took to long to pre bord all the specialty groups. Cramped small plane

The seats were comfortable, and the boarding process was pretty smooth.

3 hour delay. Had to change plans and was still delayed.

The staff was very friendly, professional, and courteous. The overall flight was a great experience.

The crew canceled the complementary snack and drink in anticipation of turbulence that never materialized. I was counting on the drink (water) to take the the doses of medication - prescribed for my heart condition - that were due during the flight. Since no snack or meal was served on this flight, I cannot rate the food quality. Otherwise, this flight was excellent.

Departure was delayed more than 1/2 hour while we waited for luggage (only) transfer from another flight/plane. Once approved for takeoff, the flight was excellent.

We got exit row seats both flights. Everything was running on time

Excellent flight and got us around tough weather. Only issue was seat TV did not work and crew tried to reboot.

Very large passenger too space from my own seat. Arm board couldn’t be lowered because of his size. It wads very uncomfortable trip, as the flight was full couldn’t move anywhere having back pain because of the position in which I was the entire flight.

was sitting in the jet bridge for 10 minutes in -20 degree weather waiting for my bag

Outdated equipment in disrepair, wifi inoperable. Broken seats, taped air vents, generally poor condition, the 717 showed its age and lack of upkeep.

My flight out of Baton Rouge to Atlanta was delayed by a half hour. This got us into Atlanta airport 30 minutes late. I ran through the airport to get to my connecting flight. As I approached the boarding gate, I saw the boarding door was still open and a passenger was being checked in. But when I got to the gate, the boarding agent told me they had already given away my seat and there were no empty seats on that flight. So I had to take a later flight. That has never happened to me before. Very frustrating.

Connection through Atlanta was difficult. Mechanical issue on plane caused a two hour delay. New gate was a mile away.

No WiFi. Comfort plus should have alcohol provided, crew only offered water or tea. Who the heck wants tea?

The flight was delayed and oversold. I volunteered to give up my seat for compensation. Thinking I could get a good night's sleep instead of arriving home at 2 am. It took over an hour to get the new reservation confirmed, three different gate attendants, and two red coats. It took even longer to confirm the overnight hotel, and when I arrived, the line was 45 minutes long, with two people checking in, and at least 15 people slowly, very slowly—no food except frozen convenience food, no coupon for food from airlines. Slept, headed back to the airport, and that flight had an equipment change and a gate change just as they were about to board. It took an additional hour to board as they cleaned the plane from storage.

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.

Good seat comfort ORF to ATL. Bad seat ATL to SEA (terrible lumbar support, hard, ouch)..

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports