$100 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 4/14. 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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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$669
Montego Bay
Montego Bay1 stop$488
Oranjestad
Oranjestad1 stop$577
Nassau
Nassau2 stops$452
Simpson Bay
Simpson Bay2 stops$522
Providenciales
Providenciales1 stop$463
George Town
George Town2 stops$464
Punta Cana
Punta Cana1 stop$489
Santo Domingo
Santo Domingo1 stop$669
Montego Bay
Montego Bay1 stop$488
Oranjestad
Oranjestad1 stop$577
Nassau
Nassau2 stops$452
Simpson Bay
Simpson Bay2 stops$522
Providenciales
Providenciales1 stop$463
George Town
George Town2 stops$464

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

Mon, Apr 27 - Wed, May 6
Southwest Logo
1:15 pm - 11:40 pm
DAL
-
SJU
9h 25m
2 stops
Southwest Logo
11:25 am - 7:55 pm
SJU
-
DAL
9h 30m
2 stops
$364Southwest
Wed, Apr 29 - Thu, May 7
Southwest Logo
11:55 am - 9:05 pm
DAL
-
SJU
8h 10m
1 stop
Southwest Logo
2:00 pm - 10:45 pm
SJU
-
DAL
9h 45m
1 stop
$382Southwest
Wed, Mar 4 - Sun, Mar 8
Southwest Logo
6:55 am - 2:55 pm
DAL
-
STT
6h 00m
1 stop
Southwest Logo
2:50 pm - 7:35 am
STT
-
DAL
17h 45m
2 stops
$383Southwest
Thu, May 7 - Thu, May 7
Southwest Logo
6:00 am - 2:55 pm
DAL
-
SJU
7h 55m
1 stop
Southwest Logo
8:40 pm - 8:25 am
SJU
-
DAL
12h 45m
1 stop
$400Southwest
Mon, Mar 9 - Mon, Mar 16
Southwest Logo
8:55 pm - 9:20 am
DAL
-
SJU
11h 25m
1 stop
Southwest Logo
8:50 pm - 8:25 am
SJU
-
DAL
12h 35m
1 stop
$402Southwest
Fri, May 1 - Thu, May 7
Southwest Logo
1:15 pm - 11:55 pm
DAL
-
SJU
9h 40m
2 stops
Southwest Logo
10:00 am - 6:40 pm
SJU
-
DAL
9h 40m
2 stops
$405Southwest
Mon, May 11 - Mon, May 18
Southwest Logo
1:15 pm - 11:40 pm
DAL
-
SJU
9h 25m
2 stops
Southwest Logo
10:00 am - 6:30 pm
SJU
-
DAL
9h 30m
2 stops
$418Southwest
Fri, May 15 - Mon, May 18
Southwest Logo
4:35 pm - 11:55 pm
DAL
-
SJU
6h 20m
1 stop
Southwest Logo
8:40 pm - 8:30 am
SJU
-
DAL
12h 50m
1 stop
$423Southwest
Sun, Mar 8 - Thu, Mar 12
Delta Logo
6:05 am - 1:54 pm
DAL
-
SXM
6h 49m
1 stop
Delta Logo
12:55 pm - 10:45 pm
SXM
-
DAL
10h 50m
1 stop
$577Delta
Sun, Mar 8 - Thu, Mar 12
Delta Logo
6:05 am - 1:54 pm
DAL
-
SXM
6h 49m
1 stop
Delta Logo
3:20 pm - 11:27 am
SXM
-
DAL
21h 07m
2 stops
$582Delta
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 $657 respectively.

Good to know

Low seasonJanuary
Cheapest flight$100
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 Saint Thomas Island

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 4289 reviews
7.5Entertainment
8.6Crew
8.1Boarding
8.0Comfort
7.0Food
Airline reviews

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.

4.0 OkayAnonymous, Feb 2026
BOI - LAS
Read more Southwest reviews

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.

Still need to work out the kinks on the new assigned seating boarding process. Otherwise, a very good flight.

WiFi did not work. Boarding with the new seating assignments took too long. The temperature in the terminal was obnoxious. +/- 80°

The seats are now more narrow. I paid for front row the seats in the front are even more narrow than before.

Only downside was the legroom and seat width, which is always a problem unless I spend more for a premium seat.

My flight from Denver to Minneapolis was excellent. My flight from Minneapolis to Denver was one of the worst I flights I have ever experienced. I had a window seat, the gentleman in the middle seat was morbidly obese and SW should have made him purchase two seats. His elbow dug into my arm most of the way even after I asked to please be careful. I was literally squashed between the him and the window with no wiggle room. The plane was full so it was not possible to ask for a different seat. I realize I should have complained to the flight attendant but I didn't feel anything could be done to rectify the situation. I fly SW often, I will continue to do so as this was my first negative experience.

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!

I appreciate the staff who allowed me to board though I arrived a little late! Regarding the assigned seating, I had booked my flight before this change and wasn't aware of the change at the time, and so I didn't select a seat at booking as I didn't realize it was relevant. Better communication about the change would have been helpful for preparing.

Flight attendants very hospitable and friendly. Pilot flew a smooth take off and landing.

Everything I mentioned earlier - the airbus was more comfortable indeed and the experience was further enhanced.

Delta continues to set the benchmark for traveler-friendly service with minimal disruption and clear communication within the mainland US (coast to coast). I am consistently pleased to be a Delta customer, and this experience once again met my expectations. There was a brief delay departing from MIA due to a technical issue that required the aircraft to return to the gate. However, the situation was handled professionally and transparently. Fortunately, my planned layover allowed ample buffer time, so the adjustment caused no stress. Overall, another smooth and reassuring experience.

Good experience and the flight landed early. There was no food I had or entertainment.

Flight was delayed and no reasons provided. After the passengers were boarded, the crew made announcement that the captain has jot arrived and he would take another 15 mins. All passengers patiently sat until the captain came and started. Terrible experience!

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.

Totally worth the miles to upgrade to Delta Comfort. Plenty of legroom.

This was my first time flying Delta ever and I had a great experience!

Smallest leg room I've ever had on a plane.

They took all carry-on luggage from Groups 6 -9 - I was group 5 and waiting in line to board - they made me check my luggage too. That then went to baggage claim and delayed departure from the airport. There was overhead room in my seating area - Delta over reacted. Also, had a gentleman next to me that took up 1/2 my seat.

Excellent!!! Aeromexico is a great airline. What was not that good is the service provided by Kayak. It is never clear and not easy to manage.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports