$151 Find Cheap Flights from Dallas Love Field to Caribbean Islands

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 Islands departing on 5/5. 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

KAYAK searches hundreds of travel sites at once for deals on flights to Caribbean Islands

 
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Dallas to Caribbean Islands, as well as popular online travel agencies
These are the airlines KAYAK users have selected most often from within our search results in flight searches from Dallas to Caribbean Islands, as well as popular online travel agencies
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Flight Deals

Cheap Flights from Love Field to Caribbean Islands

Cheapest round-trip prices found by our users on KAYAK in the last 72 hours
Punta Cana
Punta Cana1 stop$461
Santo Domingo
Santo Domingo1 stop$649
Montego Bay
Montego Bay1 stop$484
Oranjestad
Oranjestad2 stops$531
Nassau
Nassau1 stop$450
Simpson Bay
Simpson Bay1 stop$326
Providenciales
Providenciales1 stop$507
George Town
George Town1 stop$486
Punta Cana
Punta Cana1 stop$461
Santo Domingo
Santo Domingo1 stop$649
Montego Bay
Montego Bay1 stop$484
Oranjestad
Oranjestad2 stops$531
Nassau
Nassau1 stop$450
Simpson Bay
Simpson Bay1 stop$326
Providenciales
Providenciales1 stop$507
George Town
George Town1 stop$486

Book Cheap Love Field to Caribbean Islands 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 Islands 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 Islands

Mon, Apr 13 - Fri, Apr 17
Southwest Logo
11:30 am - 11:25 pm
DAL
-
SJU
10h 55m
1 stop
Southwest Logo
2:00 pm - 10:45 pm
SJU
-
DAL
9h 45m
1 stop
$322Southwest
Sat, May 2 - Wed, May 6
Southwest Logo
6:00 am - 1:40 pm
DAL
-
SXM
6h 40m
1 stop
Southwest Logo
2:25 pm - 8:30 am
SXM
-
DAL
19h 05m
2 stops
$326Southwest
Mon, Apr 13 - Fri, Apr 17
Southwest Logo
3:15 pm - 11:55 pm
DAL
-
SJU
7h 40m
2 stops
Southwest Logo
2:00 pm - 10:45 pm
SJU
-
DAL
9h 45m
1 stop
$346Southwest
Fri, Apr 24 - Fri, May 8
Southwest Logo
9:10 pm - 8:55 am
DAL
-
SJU
10h 45m
1 stop
Southwest Logo
5:05 am - 11:25 am
SJU
-
DAL
7h 20m
1 stop
$363Southwest
Mon, Apr 20 - Fri, Apr 24
Southwest Logo
3:45 pm - 11:25 pm
DAL
-
SJU
6h 40m
1 stop
Southwest Logo
3:45 pm - 10:45 pm
SJU
-
DAL
8h 00m
1 stop
$364Southwest
Fri, May 1 - Mon, May 4
Southwest Logo
1:05 pm - 11:40 pm
DAL
-
SJU
9h 35m
1 stop
Southwest Logo
1:00 pm - 8:35 pm
SJU
-
DAL
8h 35m
1 stop
$370Southwest
Sun, May 17 - Wed, May 20
Southwest Logo
8:45 pm - 9:10 am
DAL
-
SJU
11h 25m
1 stop
Southwest Logo
8:10 am - 4:10 pm
SJU
-
DAL
9h 00m
1 stop
$371Southwest
Mon, May 11 - Wed, May 20
Delta Logo
6:44 pm - 1:51 pm
DAL
-
SXM
18h 07m
1 stop
Delta Logo
3:20 pm - 11:56 pm
SXM
-
DAL
9h 36m
1 stop
$375Delta
Sat, Apr 25 - Thu, Apr 30
Southwest Logo
6:00 am - 1:40 pm
DAL
-
SXM
6h 40m
1 stop
Southwest Logo
2:25 pm - 10:45 pm
SXM
-
DAL
9h 20m
1 stop
$380Southwest
Sun, May 17 - Wed, May 20
Delta Logo
6:00 am - 1:51 pm
DAL
-
SXM
6h 51m
1 stop
Delta Logo
3:20 pm - 11:56 pm
SXM
-
DAL
9h 36m
1 stop
$488Delta
Booking Insights

KAYAK's insights & trends for Love Field to Caribbean Islands flights

Get data-powered insights and trends into flights from Love Field to Caribbean Islands to help you find the cheapest flights, the best time to fly and much more.

Can I save money by flying with a layover from Dallas Love Field Airport to Caribbean Islands?

The average round-trip price for all non-stop flights, flights with one layover, and flights with two layovers for the route found by users searching on KAYAK in the last 2 weeks.

No, with an average price for the route of $394, prices are generally cheapest when you fly direct.

What is the cheapest month to fly from Dallas Love Field Airport to Caribbean Islands?

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 Islands, 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 Islands 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$151
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 Nassau

FAQs - booking Caribbean Islands flights

  • How does KAYAK find such low prices on flights from Dallas Love Field to Caribbean Islands?

    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 Islands.

  • 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 Islands?

    KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight from Dallas Love Field to Caribbean Islands 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 Islands?

    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 Islands 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 Islands?

    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 Islands 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 Islands

 
See real verified KAYAK customer reviews for airlines flying from Dallas to Caribbean Islands. Airline scores are aggregated from all reviews left by passengers on KAYAK after flying with an airline. KAYAK doesn’t show reviews that are older than 5 years. Learn how KAYAK collects reviews.
Need help choosing which airline to fly with from Love Field to Caribbean Islands? 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 4320 reviews
8.0Comfort
8.1Boarding
7.5Entertainment
8.6Crew
7.0Food
Airline reviews

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

4.0 OkayKenny, Mar 2026
TPA - BWI
Read more Southwest reviews

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

The new seating arrangement is so over priced for what you get.

The problem with the seat assignments is that there were a lot of rows in the front that were empty but my row at the back was full. Just not so pleasant.

No food or entertainment, just a quick 40 minute flight. A little bumpy due to Santa Ana winds but pilot has no control over that. Good flight and landing!

Good but I prefer choose your own seat. With the new assigned seats they should board from the back I see no advantage to this new boarding. Just like every other airline

I realize they are still working out kinks with the new boarding process, but by the time I boarded in group 5, most of the bins were full. All airlines should better enforce small bags and jackets going under the seats until everyone has boarded.

WiFi was not working and didn’t have a beverage service

Snacks are always pretzels. Why can't you also offer peanuts ?

Flight boarded late after announcing on time boarding. Flight arrived only a little late despite late departure. Had trouble connecting to WiFi

Perhaps when you’re sitting in 1st class and the crew closes the bathroom for the pilots, there could be a notification other than holding your hands up as a blockade when you get there and you’re told the restrooms are closed please turn around … especially at night when visibility is poor and you’re met by a flight attendants with their arms up

First class is comfortable. Enjoyed a movie and was able to relax compared to coach.

Loved flying First Class. Very comfortable. The seat was amazing. Enjoyed a movie and was able to relax so much better than in coach.

We landed and sat on the tarmac for 45 minutes because they only have one gate at the airport and there was another plane running late so we had to wait

The WiFi was not working. That made for a long flight.

With Aeromexico it ended up good but with Delta it was bad because we did everything through Delta... Showed up at the Delta terminal... It was the wrong place! Nothing ever told us to go to the Aeromexico terminal. It said "in partnership with Aeromexico" but I was never instructed to check in with them or go to their terminal. We had to haul @$$ running through the airport and almost didn't make it thanks to this poor communication. 👎🏽

Absolutely no communication on why there's a delay and multiple flight time reschedules. I would have canceled the flight and drove back home if I known it was going to be rescheduled 3 or 4 times.

Another late night flight and MORE men belligerently drinking and yelling. I had to move from first to economy because they were so obnoxious and disruptive. Crazy to go from a cozy chair to cardboard when you were supposed to be in first. Delta allows was too much drinking which leads to belligerent behavior.

I was in first class and literally the men behind me were so aggressively loud I moved myself to economy. This has become so common on Delta - people using audio without headphones, and men on 12am / late night flights drinking and yelling to talk to each other which prevents anyone around them from resting. Pretty crazy to have to move from first to economy (poorer service, less comfort...). Wild wild. Looking into other airlines.

Love delta smaller commuter plane so no entertainment and paid wifi on MKE-LGA leg was extremely unreliable and slow

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports