$143 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 9/26. 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

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$523
Santo Domingo
Santo Domingo1 stop$591
Montego Bay
Montego Bay1 stop$515
Oranjestad
Oranjestad2 stops$424
Nassau
Nassau1 stop$507
Simpson Bay
Simpson Bay1 stop$995
Providenciales
Providenciales1 stop$505
George Town
George Town1 stop$538
Punta Cana
Punta Cana1 stop$523
Santo Domingo
Santo Domingo1 stop$591
Montego Bay
Montego Bay1 stop$515
Oranjestad
Oranjestad2 stops$424
Nassau
Nassau1 stop$507
Simpson Bay
Simpson Bay1 stop$995
Providenciales
Providenciales1 stop$505
George Town
George Town1 stop$538

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, Sep 17 - Tue, Sep 23
Southwest Logo
7:50 am - 2:55 pmDAL-SJU
6h 05m1 stop
Southwest Logo
1:35 pm - 8:35 pmSJU-DAL
8h 00m1 stop
$335Southwest
Find Deal
Wed, Sep 3 - Fri, Sep 5
Southwest Logo
7:50 am - 2:55 pmDAL-SJU
6h 05m1 stop
Southwest Logo
5:50 am - 1:00 pmSJU-DAL
8h 10m1 stop
$349Southwest
Find Deal
Wed, Sep 17 - Tue, Sep 23
Southwest Logo
11:40 am - 10:30 pmDAL-SJU
9h 50m1 stop
Southwest Logo
11:50 am - 10:05 pmSJU-DAL
11h 15m1 stop
$351Southwest
Find Deal
Mon, Sep 15 - Thu, Sep 18
Southwest Logo
8:30 am - 6:45 pmDAL-SJU
9h 15m1 stop
Southwest Logo
2:40 pm - 9:40 pmSJU-DAL
8h 00m2 stops
$357Southwest
Find Deal
Fri, Oct 17 - Wed, Oct 22
Delta Logo
6:00 am - 4:33 pmDAL-SJU
9h 33m1 stop
Delta Logo
5:43 pm - 11:55 pmSJU-DAL
7h 12m1 stop
$450Delta
Find Deal
Mon, Nov 24 - Wed, Nov 26
Delta Logo
6:37 pm - 12:38 pmDAL-PUJ
16h 01m1 stop
Delta Logo
3:20 pm - 2:00 pmPUJ-DAL
24h 40m2 stops
$526Delta
Find Deal
Mon, Sep 15 - Wed, Sep 24
Delta Logo
6:00 am - 12:45 pmDAL-PLS
5h 45m1 stop
Delta Logo
2:10 pm - 11:49 pmPLS-DAL
10h 39m1 stop
$536Delta
Find Deal
Wed, Sep 10 - Sun, Sep 14
WestJet Logo
3:52 pm - 2:19 pmDAL-SXM
21h 27m2 stops
WestJet Logo
2:10 pm - 11:49 pmSXM-DAL
34h 39m2 stops
$3,556WestJet
Find Deal
Wed, Oct 1 - Sun, Oct 5
WestJet Logo
8:45 am - 2:19 pmDAL-SXM
28h 34m2 stops
WestJet Logo
2:10 pm - 5:54 pmSXM-DAL
28h 44m2 stops
$3,597WestJet
Find Deal
Wed, Sep 10 - Sun, Sep 14
WestJet Logo
3:52 pm - 2:19 pmDAL-SXM
21h 27m2 stops
WestJet Logo
2:10 pm - 5:39 pmSXM-DAL
28h 29m2 stops
$3,646WestJet
Find Deal
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 $310, 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 $303 (return) on average. On the other hand, the most expensive months are December and May, when the average cost of round-trip tickets is $904 and $545 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 seasonNovember
Cheapest flight$143
Best time to beat the crowds with an average 15% drop in price.
Most popular time to fly and prices are also 0% lower on average.
Flight from Dallas Love Field to Punta Cana

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.
8.0
SouthwestOverall score based on 4241 reviews
8.6Crew
7.0Food
8.1Boarding
8.0Comfort
7.5Entertainment
Airline reviews

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

2.0 MediocreAnonymous, Jul 2025AUS - RDU
Read more Southwest reviews

southwest just starting charging for luggage. hadnt realized it until it was too late. now out $70 when i couldve bought a carry on if i wouldve known. free bags was one of the only reasons i chose southwest over another airline (the other being no assigned seats, which is apparently also being changed). stupid business decision. wont be flying southwest anymore.

The quality of Southwest Airlines continues to degrade each time I fly with them. If it were not for the free luggage, I would probably choose another airline. Their prices are a little bit competitive, but way too high for the quality of the service. Southwest is not unique in this way. Domestic flight in the United States of America has continued to be a lower and lower quality product. Very sad when you compare the quality of domestic airlines to that of many international airlines around the world.

Very smooth checking in our luggage with a super pleasant SW agent. I enjoyed a fun entertaining movie.

WiFi did not work. For as outrageous as these flights cost, when they’re advertised with certain services/ features they should be in working order

Worst experience I had on Southwest. Still better than most, but the seating was barely tolerable.

The Southwest employees (all two of them) were very nice and cheerful despite the fact the line to self-check a bag (simply drop it off) was hundreds of people long. Thank God I arrived early to the airport because I stood in this line for at least an hour. Once on the flight that had been delayed by an hour, we had no Wi-Fi and thus no entertainment. Finally, I hope the investor strong arm tactics against Southwest pay off in a short-term windfall to your C-Suite because the rest of you are screwed. I have been a faithful Southwest customer for 15 years due to everything you just got rid of. I'm flying to Idaho and Washington in October, both places I used to simply book with Southwest without a second thought now with Frontier (Washington) and United (Idaho) because they offer everything the "new" Southwest does but cheaper and at better times, destinations, etc. This really makes me sad...

It was okay. The plane was delayed from earlier in the day, but they kept updating the departure time, sometimes later, sometimes earlier. That was stressful. Once we finally got on and took off, it was fine. I was supposed to have a connection in Chicago to Los Angeles, and the time for so late I was rebooked to arrive in LA 3 hours late. The departure time to Chicago later became early enough to have taken my original connection and arrive earlier but that wasn't an option.

It was one and half hour late... Not sure if any other experience matters.

Delayed flight. Nicest crew member was a SW pilot flying seated next to me who kindly move to seat the final passenger. Flight extra delayed. My cup of refreshment of ginger ale was so packed with ice it was literally 2 sips.

Flight crew and cabin crew were great. I had to rearrange flights because my original flight was 3hrs delayed for weather, the rub is the flight I moved to boarded on time then we sat at the gate for 2 hours because scheduling stole our first officer for another flight, TWICE. Then our actual FO was an hour delayed. To make it worse my original flight went from a 3 hour delay to departing 15min EARLY. Just poor scheduling operations all around.

My experience on any Delta flight is always overshadowed by the time Delta removed me from a flight for no apparent reason.

Delayed and took off even later than the scheduled delay time

For a 69 year old with health problems I had the worse experience, no wheelchair when I entered a lady told me to sit and wait while a gentleman told me I had to walk to the Delta station, which I did. I had a carry on and a bag, and I was traveling with my service dog, which was on his carrier and the lady charged me for my carry on luggage, beside all the waiting cause of the delay, I had to walk to get my luggage cause no wheelchair showed up, I am so disappointed. I will get in touch with the company. I got home at 3:00 am, not good for my health situation.

Only issue was with seating. The economy fare we purchased did say there was no guarantee the three people in our party would be seated together, and we were not. At the gate, the agent told us more specifically, the fare we purchased meant we would be seated in middle seats only. This should just be made more obvious.

Great experience on Delta. Staff from baggage check to flight attendants were very courteous and professional. My only issue was a personal preference for pretzels instead of the chips and cookies that were offered.

There was no problems, just a little uncomfortable with seats that do not lay back a little

Always good but we must do something about people in rows ahead of you that don't put their seats back up when they are suppose to. And It's rough to not be able to even lean over to get something out of my purse.

Flight was delayed, 30+ bags had to be gate checked. Crew were very friendly!

Everything was good until we were boarding our connection flight in Atlanta, we were told to gate check our carry-on, but when we got inside the plane, there was plenty of room in the overhead.

Did not know my son and I had different seating arrangements. He was fine, but it was disappointing.

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