$161 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 1/13. 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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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$566
Santo Domingo
Santo Domingo1 stop$762
Montego Bay
Montego Bay1 stop$581
Oranjestad
Oranjestad1 stop$564
Nassau
Nassau1 stop$469
Simpson Bay
Simpson Bay1 stop$743
Providenciales
Providenciales1 stop$430
George Town
George Town1 stop$507
Punta Cana
Punta Cana1 stop$566
Santo Domingo
Santo Domingo1 stop$762
Montego Bay
Montego Bay1 stop$581
Oranjestad
Oranjestad1 stop$564
Nassau
Nassau1 stop$469
Simpson Bay
Simpson Bay1 stop$743
Providenciales
Providenciales1 stop$430
George Town
George Town1 stop$507

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

Wed, Jan 14 - Thu, Jan 22
Southwest Logo
4:00 pm - 12:35 am
DAL
-
SJU
6h 35m1 stop
Southwest Logo
5:40 am - 1:05 pm
SJU
-
DAL
9h 25m2 stops
$411Southwest
Fri, Jan 23 - Tue, Jan 27
Southwest Logo
2:35 pm - 12:35 am
DAL
-
SJU
8h 00m2 stops
Southwest Logo
10:20 am - 4:10 pm
SJU
-
DAL
7h 50m1 stop
$413Southwest
Tue, Mar 10 - Tue, Mar 17
Southwest Logo
9:45 am - 7:30 pm
DAL
-
SJU
8h 45m2 stops
Southwest Logo
5:15 am - 4:00 pm
SJU
-
DAL
11h 45m2 stops
$415Southwest
Sun, Jan 11 - Tue, Jan 13
Southwest Logo
7:10 am - 1:45 pm
DAL
-
PLS
5h 35m1 stop
Southwest Logo
2:40 pm - 9:00 pm
PLS
-
DAL
7h 20m1 stop
$430Southwest
Thu, Jan 22 - Mon, Jan 26
Southwest Logo
2:35 pm - 12:35 am
DAL
-
SJU
8h 00m2 stops
Southwest Logo
2:35 pm - 9:40 pm
SJU
-
DAL
9h 05m2 stops
$432Southwest
Thu, Feb 19 - Thu, Feb 26
Delta Logo
6:00 am - 3:04 pm
DAL
-
STT
7h 04m1 stop
Delta Logo
1:52 pm - 10:31 pm
STT
-
DAL
10h 39m1 stop
$479Delta
Sun, Feb 8 - Tue, Feb 17
Delta Logo
6:00 am - 1:31 pm
DAL
-
NAS
6h 31m1 stop
Delta Logo
2:59 pm - 10:31 pm
NAS
-
DAL
8h 32m1 stop
$529Delta
Sun, Mar 15 - Wed, Mar 18
Delta Logo
12:12 pm - 11:44 am
DAL
-
NAS
22h 32m2 stops
Delta Logo
6:10 pm - 9:42 am
NAS
-
DAL
16h 32m1 stop
$533Delta
Sun, Feb 8 - Thu, Feb 12
WestJet Logo
11:15 am - 2:46 pm
DAL
-
UVF
49h 31m2 stops
WestJet Logo
3:40 pm - 5:49 pm
UVF
-
DAL
28h 09m2 stops
$4,209WestJet
Sun, Feb 8 - Thu, Feb 12
WestJet Logo
11:15 am - 2:46 pm
DAL
-
UVF
49h 31m2 stops
WestJet Logo
3:40 pm - 5:49 pm
UVF
-
DAL
28h 09m2 stops
$4,280WestJet
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 $381, 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 $304 (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 $625 respectively.

What’s the cheapest day of the week to fly from Dallas Love Field to Caribbean Islands?

The average price of all round-trip flights from Dallas Love Field Airport to Caribbean Islands clicked on KAYAK for each day over the last 12 months.

When flying from Dallas Love Field to Caribbean Islands, you should consider leaving on a Wednesday and avoid Sundays if you are looking for the best rates. For your return to Dallas Love Field, you’ll find the best rates on Thursdays and the most expensive ones on Tuesdays.

Good to know

Low seasonOctober
Cheapest flight$161
Best time to beat the crowds but there is an average 2% increase in price.
Most popular time to fly and prices are also 9% 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.

  • What is the cheapest time of day to fly to Caribbean Islands?

    The cheapest time of day to fly to Caribbean Islands is generally at night, when round-trip flights cost $292 on average. Morning departures are around 7% cheaper than evening flights, on average. The most expensive time of day to fly to Caribbean Islands is generally in the evening, which is peak travel time and where the average cost of a ticket is $512.

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.
7.9
SouthwestOverall score based on 4250 reviews
7.0Food
8.0Comfort
7.5Entertainment
8.6Crew
8.1Boarding
Airline reviews

They sent a notice that they were boarding an hour early. We had to leave the club and run to the gate. They said sorry, that came from corporate and was a mistake. They did not have enough seating because the flight before it had not taken off on time. They moved our gate and delayed it for an hour.

2.0 MediocreRobert, Dec 2025
LAS - TPA
Read more Southwest reviews

They sent a notice that they were boarding an hour early. We had to leave the club and run to the gate. They said sorry, that came from corporate and was a mistake. They did not have enough seating because the flight before it had not taken off on time. They moved our gate and delayed it for an hour.

The boarding and seat assignment system no longer works for me, but I know it is being replaced. Otherwise, I am good with the overall experience.

The lead steward kept singing about "San Francisco" and hotel California---more annoying than humorous....needs work. Flight was smooth and on time.

Still a fan of open seating. Flight was on schedule and arrived on time. The 737 MAX is very comfortable.

Airline travel is always too cramped to really be pleasant, but the cabin crew on this flight did a pretty good job of making up for it by putting on some music during boarding and sprinkling a few funny remarks into the safety briefing and announcements, and just generally being friendly and helpful. It definitely reminded me of why I prefer the in-flight experience on Southwest!

No delays and arrived to destination 30 min early. Staff was super friendly.

San Diego airport is brand new, spacious, airy and very smooth checkin at SW baggage drop.

It was rough. The staff was unprofessional, the choice of on board drinks terrible, it was cramped in space at every airport, they always ran out of overhead bin space so they pressured people to check bags for free or we couldn’t leave on the plane— so I did check my bag to help, and they nearly lost my bag. My bag did not arrive on the luggage belt, another man on my flight and I had to waste our time going to the baggage office to search for our bags. I would only fly southwest again if it was my last choice. Also, my flights were consistently delayed over and over again— at one point they straight up told us we were waiting for the pilot to arrive.

Crew could have been friendlier, maybe I'm spoiled by SW crews. In flight wifi was good. Would be nice to have more food offerings on a 4 plus hour flight

Had to get off plane from prior flight even though I had to reboard same plane to continue to my final destination.

None of the airplane features were available during the flight.

Original flight was cancelled and when i was rebooked by the airline, they couldn't seat me in the same type of seat as I had originally booked (went from window/aisle to middle/middle and one was a bulkhead seat, and other wasn't in the same class)

Lady Pilot was perfect in every way wheels up to wheels down communication, professionalism, excellent on time departure and on time arrival, excellent communication! Fantastic job with Superb attitude!!

The food is terrible. The staff is wonderful. Comfort is good.

Left on time, a bit delayed due to headwinds most of the trip.

I fly Delta all the time, have Platinum Medallion status. But this route seems to have major problems with delays and seems to never leave on time! Have only taken it twice in the last two weeks, and each time it had delays of more than 1 hour... very disappointed!!!!

Getting to the flight was arduous and lengthy. The flight itself was good but the food option wasn’t a good selection. I need to do a Kosher option on my return. Flight crew were nice

Good seats in Main cabin, excellent service and excellent landing

My flight was cancelled with no explanation after I had already cleared security. I was given 4 options to rebook, only one being non-stop like I had paid for. I grabbed it. It was 4 plus hours later and then took off even later. Biggest complaint is that I booked early and had an aisle seat. They gave me a "window" seat in front of the exit row, so the seat did not decline. I weigh all of 103 #s and it was tight for me! For what I paid, I feel I was kind of ripped off. I think they should have given me the empty comfort seat for the inconvenience. There was no apology nor any explanation as to why the flight was cancelled. My guess is it benefitted Delta in some way.

Very smooth, on-time, and pleasantly uneventful flight. The team at the gate and on board were professional and genuinely courteous. The pilot kept us well updated throughout, and both takeoff and landing were steady and enjoyable without any drama. Just a good, solid flight. Thank you! 💗

Everything you need to know for your flight to Caribbean Islands

Information on your arrival and departure airports