$158 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 4/27. 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$612
Santo Domingo
Santo Domingo1 stop$650
Montego Bay
Montego Bay1 stop$456
Oranjestad
Oranjestad2 stops$538
Nassau
Nassau2 stops$345
Simpson Bay
Simpson Bay1 stop$301
Providenciales
Providenciales2 stops$588
George Town
George Town1 stop$541
Punta Cana
Punta Cana1 stop$612
Santo Domingo
Santo Domingo1 stop$650
Montego Bay
Montego Bay1 stop$456
Oranjestad
Oranjestad2 stops$538
Nassau
Nassau2 stops$345
Simpson Bay
Simpson Bay1 stop$301
Providenciales
Providenciales2 stops$588
George Town
George Town1 stop$541

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 - Thu, May 7
Delta Logo
3:53 pm - 11:13 pm
DAL
-
SJU
6h 20m
1 stop
Delta Logo
5:43 pm - 11:56 pm
SJU
-
DAL
7h 13m
1 stop
$256Delta
Sun, May 10 - Fri, May 15
Southwest Logo
6:00 am - 2:25 pm
DAL
-
SXM
7h 25m
1 stop
Southwest Logo
2:25 pm - 10:45 pm
SXM
-
DAL
9h 20m
1 stop
$301Southwest
Tue, May 5 - Wed, May 13
Delta Logo
3:53 pm - 11:13 pm
DAL
-
SJU
6h 20m
1 stop
Delta Logo
2:48 pm - 11:56 pm
SJU
-
DAL
10h 08m
1 stop
$326Delta
Tue, May 12 - Tue, May 19
Southwest Logo
9:00 am - 6:30 pm
DAL
-
NAS
8h 30m
2 stops
Southwest Logo
2:10 pm - 9:00 pm
NAS
-
DAL
7h 50m
1 stop
$345Southwest
Tue, May 5 - Sat, May 9
Delta Logo
12:25 pm - 11:13 pm
DAL
-
SJU
9h 48m
1 stop
Delta Logo
5:43 pm - 11:56 pm
SJU
-
DAL
7h 13m
1 stop
$351Delta
Mon, May 4 - Wed, May 6
Southwest Logo
4:35 pm - 11:55 pm
DAL
-
SJU
6h 20m
1 stop
Southwest Logo
5:35 am - 2:55 pm
SJU
-
DAL
10h 20m
2 stops
$366Southwest
Fri, May 8 - Sat, May 16
Southwest Logo
4:30 pm - 11:55 pm
DAL
-
SJU
6h 25m
1 stop
Southwest Logo
6:25 am - 2:50 pm
SJU
-
DAL
9h 25m
1 stop
$371Southwest
Tue, Jul 28 - Thu, Jul 30
Delta Logo
7:10 am - 4:45 pm
DAL
-
SJU
8h 35m
1 stop
Delta Logo
5:56 pm - 11:57 pm
SJU
-
DAL
7h 01m
1 stop
$374Delta
Sun, May 10 - Sat, May 16
Southwest Logo
6:00 am - 1:20 pm
DAL
-
NAS
6h 20m
1 stop
Southwest Logo
8:45 am - 1:25 pm
NAS
-
DAL
5h 40m
1 stop
$375Southwest
Tue, May 12 - Wed, May 13
Southwest Logo
9:00 am - 6:30 pm
DAL
-
NAS
8h 30m
2 stops
Southwest Logo
8:45 am - 2:00 pm
NAS
-
DAL
6h 15m
1 stop
$376Southwest
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 $730 respectively.

Good to know

Low seasonApril
Cheapest flight$158
Best time to beat the crowds with an average 9% drop in price.
Most popular time to fly and prices are also 12% lower on average.
Flight from Dallas Love Field to San Juan

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 4330 reviews
7.0Food
8.6Crew
8.0Comfort
7.5Entertainment
8.1Boarding
Airline reviews

Southwest is kind of a slum airline. It’s gotten more expensive over the years for less and less service. I am a Southwest Chase Visa card holder and was forced to choose a seat in the 26th row in the middle seat. However my wife who is a rewards member but doesn’t hold a card or anything else, gets randomly assigned a normally paid seat in row 6! How does that work?

4.0 OkayDavid, Apr 2026
COS - DAL
Read more Southwest reviews

Southwest is kind of a slum airline. It’s gotten more expensive over the years for less and less service. I am a Southwest Chase Visa card holder and was forced to choose a seat in the 26th row in the middle seat. However my wife who is a rewards member but doesn’t hold a card or anything else, gets randomly assigned a normally paid seat in row 6! How does that work?

For the first time in a long time, the Wi-Fi actually worked the entire flight! The flight crew was amazing as usual.

The seat was not comfortable. 1D. My back was sore all night and the next day.

Great flight. I didn't get a drink because I was asleep whole on the flight.

Great flight from Seattle to Phoenix and to Chicago-Midway from Phoenix

The new boarding process was easy and straightforward. Very pleasant.

The flight was okay. The pilots did an amazing job and kept us updated on the flight. The flight attendants were okay. They found time to be chatty with each other rather than focus on the guests. One of the attendants was a little less warm when asking about my bag I had on my lap that I was using during latter part of the mid- flight. Mind you, it was not the departure descent. I’m respectful to each and every attendant, it was the tone in her voice reminding me to place my carryon bag on the floor. I hope to have a better experience next time.

The entire travel day was a disaster from beginning to end. Woke up at two in the morning to make it to San Juan airport in time for a 5:30 am flight to Milwaukee which connected in Baltimore. Massive delays lead to me missing original connection out of Baltimore. Sixteen hours of delays/rebooking/layover time later, arrived in Milwaukee to find that only one of two checked bags made it there (despite the fact that Southwest brought another 737 jet to San Juan to fly us out to our original Baltimore connection—-not squeezed into another booked flight). The flight from Baltimore to Milwaukee was barely half full, so there was no logical reason to ship my bags out of Baltimore on a different flight to Chicago to then ship to Milwaukee. Southwest decided that my bags should not have been on the same connecting flight I WAS ON to Milwaukee, and then proceeded to accidentally leave my larger bag with the important items in Chicago. Terrible logic and support all around. Extremely angered and disappointed with SW. What a clownish operation your company has become!

It was as expected and I was grateful for the wheel chair help and ease of use.

One of the best airlines for fast boarding, on time arrivals, and top notch service!

Crew was nice, meal was good. Entertainment had to be rebooted 3 times and still did not work. Turns out there was residue on screen, it needed to be cleaned to prevent the touchscreen buttons from continuously activating. I had entertainment for the last 45 minutes of a 5 hour 45 minute flight. Really unacceptable for first class. Flight attendent indicated your cleaning solution creates this problem. Seems as if this is widely known, you should be using a different product or cleaning better. Really really disappointing which simply added to the wi fi on your planes with reliably never ever works.

The baggage belt was not updated on the Delta App and was displayed on the wrong belt board. Was not expecting this to happen.

The plan was delayed and left DC 90 minutes late. However, it showed a 20 minute delay on the delta app, then a 12 min delay. It turned out to be an hour delay. I found out where the plane was with flightaware. Stop keeping customers in the dark about what is going on.

Everything went smoothly, although the usual gripes about airline travel were still present: the boarding process is inefficient, the snack selection is limited, and so on. Since there was extra space on the flight, the gate agent rearranged many people's seats to put people on the aisles and windows, leaving the middle seats empty, as much as possible, which was pretty great.

Landed without a gate ready. Plane is extremely old and dirty.

All the amenities was wonderful, if they could keep their prices that low. I'd fly with them all the time.

Very old plane with no inflight entertainment. I purchased the internet pass and it was nearly unusable.

My tray was broken so i had no place to work or eat except my lap. Flight attendant said I would get an email with some credit or miles, it was a complete waste of time as I could only function at about 20% of normal. I have not received anything yet.

Short trip, no food and therefore no expectation for much interaction with staff who were pleasant and professional. My critique is on comfort of the seats. Exit rows and comfort seats do not provide enough personal space for 3 side-by-side seats, especially when in the middle row. Some passengers are not considerate of the middle seat and there should be signs that state something to the effect of: "please consider giving middle seats use of the armrests."

My flight yesterday evening was delayed 3.5 hours with no water or food service. Poor experience

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports