$137 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 4/28. 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$489
Santo Domingo
Santo Domingo1 stop$1,314
Montego Bay
Montego Bay1 stop$493
Oranjestad
Oranjestad2 stops$582
Nassau
Nassau1 stop$512
Simpson Bay
Simpson Bay1 stop$513
Providenciales
Providenciales1 stop$413
George Town
George Town1 stop$409
Punta Cana
Punta Cana1 stop$489
Santo Domingo
Santo Domingo1 stop$1,314
Montego Bay
Montego Bay1 stop$493
Oranjestad
Oranjestad2 stops$582
Nassau
Nassau1 stop$512
Simpson Bay
Simpson Bay1 stop$513
Providenciales
Providenciales1 stop$413
George Town
George Town1 stop$409

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, May 4 - Thu, May 14
Delta Logo
12:25 pm - 8:24 pm
DAL
-
SJU
6h 59m
1 stop
Delta Logo
6:15 am - 2:59 pm
SJU
-
DAL
9h 44m
1 stop
$328Delta
Thu, Apr 30 - Mon, May 4
Southwest Logo
9:20 pm - 9:10 am
DAL
-
SJU
10h 50m
1 stop
Southwest Logo
8:40 pm - 8:30 am
SJU
-
DAL
12h 50m
1 stop
$346Southwest
Fri, May 8 - Wed, May 13
Southwest Logo
8:35 pm - 10:25 am
DAL
-
SJU
12h 50m
1 stop
Southwest Logo
2:00 pm - 11:10 pm
SJU
-
DAL
10h 10m
2 stops
$353Southwest
Tue, Mar 3 - Wed, Mar 4
Southwest Logo
12:40 pm - 8:55 pm
DAL
-
SJU
6h 15m
1 stop
Southwest Logo
5:40 am - 1:05 pm
SJU
-
DAL
9h 25m
2 stops
$359Southwest
Mon, Feb 23 - Thu, Feb 26
Southwest Logo
12:55 pm - 10:25 pm
DAL
-
SJU
7h 30m
1 stop
Southwest Logo
6:00 am - 12:15 pm
SJU
-
DAL
8h 15m
1 stop
$364Southwest
Fri, Feb 20 - Wed, Feb 25
Southwest Logo
8:50 pm - 10:00 am
DAL
-
SJU
11h 10m
1 stop
Southwest Logo
6:10 am - 2:45 pm
SJU
-
DAL
10h 35m
2 stops
$368Southwest
Fri, Apr 24 - Wed, Apr 29
Southwest Logo
9:20 pm - 8:55 am
DAL
-
SJU
10h 35m
1 stop
Southwest Logo
5:05 am - 1:35 pm
SJU
-
DAL
9h 30m
1 stop
$371Southwest
Fri, Feb 20 - Fri, Feb 27
Southwest Logo
8:50 pm - 10:00 am
DAL
-
SJU
11h 10m
1 stop
Southwest Logo
3:15 pm - 8:55 pm
SJU
-
DAL
7h 40m
1 stop
$372Southwest
Tue, Mar 3 - Wed, Mar 4
Southwest Logo
9:00 am - 11:10 pm
DAL
-
SJU
12h 10m
1 stop
Southwest Logo
6:10 am - 4:55 pm
SJU
-
DAL
12h 45m
1 stop
$377Southwest
Mon, Feb 16 - Wed, Feb 25
Delta Logo
6:00 am - 2:50 pm
DAL
-
SXM
6h 50m
1 stop
Delta Logo
1:38 pm - 10:31 pm
SXM
-
DAL
10h 53m
1 stop
$513Delta
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$137
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 Providenciales

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 4267 reviews
8.6Crew
7.0Food
8.0Comfort
7.5Entertainment
8.1Boarding
Airline reviews

WIFI was great. My selection for seating is an aisle, but during my trip, I never had an aisle seat. If we can get that corrected, I will be thrilled. No snack or drink on this flight.

10.0 ExcellentJoseph, Jan 2026
BWI - RIC
Read more Southwest reviews

WIFI was great. My selection for seating is an aisle, but during my trip, I never had an aisle seat. If we can get that corrected, I will be thrilled. No snack or drink on this flight.

WIFI was great. My selection for seating is an aisle, but during my trip, I never had an aisle seat. If we can get that corrected, I will be thrilled.

The wifi on the plane is great. The only issue that I have is that I prefer an aisle seat and on my trips this week, I was either in the middle or window. If we can work to secure aisle seating, I will be thrilled. Nice trip.

All good except once again bags took an hour at Midway Airport Happens all the time. Ridiculous

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.

I didn't take this flight. I changed the flight. Why am I getting surveys and notifications on flights that I change. Seems like a defect with Kayak.

Delta One is extraordinary. I fly business when somebody hires me. I just wonder why there is such a chasm between business class and the insanely inhumane and nonsensical coach. The seats are not large enough to fit even my tiny wife. We fly 10% of what we did because we don’t want to pay 5-10 k but for $400 it’s unbearable. It seems like the accountants took over and made stupid decisions. Screw in 20 extra seats and make it so unbearable that people fly 90% less. Just put the damn price up and put some proper chairs in. But business, yay.

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

It was last minute due to weather - considering - it was amazing! Good smiles, friendly staff and they were making sure we knew what was going on when and where.

delta last minute gave me a boarding pass for a different flight with no confirmation that they were changing it

The flight was comfortable and uneventful, which is what I desire

The service from the flight attendants were of supreme quality. They greeted and treated everyone with a wide smile. This is totally absent nowadays. Kudos to them!!!!

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

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports