$137 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 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

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$489
Santo Domingo
Santo Domingo1 stop$574
Montego Bay
Montego Bay1 stop$508
Oranjestad
Oranjestad2 stops$582
Nassau
Nassau1 stop$452
Simpson Bay
Simpson Bay1 stop$567
Providenciales
Providenciales1 stop$413
George Town
George Town1 stop$484
Punta Cana
Punta Cana1 stop$489
Santo Domingo
Santo Domingo1 stop$574
Montego Bay
Montego Bay1 stop$508
Oranjestad
Oranjestad2 stops$582
Nassau
Nassau1 stop$452
Simpson Bay
Simpson Bay1 stop$567
Providenciales
Providenciales1 stop$413
George Town
George Town1 stop$484

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, May 4 - Fri, May 8
Delta Logo
6:05 am - 4:23 pm
DAL
-
SJU
9h 18m
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
5:35 am - 2:00 pm
SJU
-
DAL
9h 25m
1 stop
$353Southwest
Tue, Mar 3 - Wed, Mar 4
Southwest Logo
8:55 am - 7:05 pm
DAL
-
SJU
8h 10m
1 stop
Southwest Logo
5:40 am - 1:00 pm
SJU
-
DAL
9h 20m
2 stops
$359Southwest
Wed, Feb 25 - Wed, Mar 4
Southwest Logo
9:00 am - 11:10 pm
DAL
-
SJU
12h 10m
1 stop
Southwest Logo
5:40 am - 1:05 pm
SJU
-
DAL
9h 25m
2 stops
$364Southwest
Fri, Apr 10 - Tue, Apr 14
Southwest Logo
4:35 pm - 11:55 pm
DAL
-
SJU
6h 20m
1 stop
Southwest Logo
2:00 pm - 9:15 pm
SJU
-
DAL
8h 15m
1 stop
$365Southwest
Mon, Feb 23 - Fri, Feb 27
Southwest Logo
12:55 pm - 10:25 pm
DAL
-
SJU
7h 30m
1 stop
Southwest Logo
7:00 am - 12:25 pm
SJU
-
DAL
7h 25m
1 stop
$368Southwest
Fri, Apr 24 - Tue, Apr 28
Southwest Logo
9:20 pm - 8:55 am
DAL
-
SJU
10h 35m
1 stop
Southwest Logo
5:05 am - 3:55 pm
SJU
-
DAL
11h 50m
2 stops
$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
Sat, Feb 21 - Sat, Feb 28
Delta Logo
6:00 am - 3:20 pm
DAL
-
AUA
7h 20m
1 stop
Delta Logo
1:45 pm - 10:31 pm
AUA
-
DAL
10h 46m
1 stop
$633Delta
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 $378, 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 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 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 4267 reviews
8.6Crew
8.0Comfort
8.1Boarding
7.5Entertainment
7.0Food
Airline reviews

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

10.0 ExcellentAnonymous, Jan 2026
PHX - MDW
Read more Southwest reviews

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.

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.

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

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

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports