$106 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 12/9. 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 Cana2 stops$578
Santo Domingo
Santo Domingo1 stop$486
Montego Bay
Montego Bay1 stop$633
Oranjestad
Oranjestad2 stops$580
Nassau
Nassau1 stop$512
Simpson Bay
Simpson Bay1 stop$545
Providenciales
Providenciales1 stop$483
George Town
George Town2 stops$521
Punta Cana
Punta Cana2 stops$578
Santo Domingo
Santo Domingo1 stop$486
Montego Bay
Montego Bay1 stop$633
Oranjestad
Oranjestad2 stops$580
Nassau
Nassau1 stop$512
Simpson Bay
Simpson Bay1 stop$545
Providenciales
Providenciales1 stop$483
George Town
George Town2 stops$521

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

Mon, Dec 8 - Thu, Dec 11
Southwest Logo
1:00 pm - 10:05 pmDAL-SJU
7h 05m1 stop
Southwest Logo
3:55 pm - 10:10 pmSJU-DAL
8h 15m1 stop
$236Southwest
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Mon, Dec 8 - Thu, Dec 11
Southwest Logo
1:00 pm - 12:35 amDAL-SJU
9h 35m1 stop
Southwest Logo
5:45 am - 1:05 pmSJU-DAL
9h 20m2 stops
$261Southwest
Find Deal
Mon, Jan 19 - Thu, Jan 22
Southwest Logo
12:55 pm - 12:40 amDAL-SJU
9h 45m1 stop
Southwest Logo
6:10 am - 4:55 pmSJU-DAL
12h 45m1 stop
$279Southwest
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Mon, Dec 8 - Thu, Dec 11
Southwest Logo
2:00 pm - 12:35 amDAL-SJU
8h 35m2 stops
Southwest Logo
5:45 am - 1:05 pmSJU-DAL
9h 20m2 stops
$301Southwest
Find Deal
Sat, Jan 31 - Wed, Feb 11
Southwest Logo
1:15 pm - 12:10 amDAL-SJU
8h 55m1 stop
Southwest Logo
5:40 am - 1:05 pmSJU-DAL
9h 25m2 stops
$304Southwest
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Sun, Dec 14 - Tue, Dec 16
Southwest Logo
2:00 pm - 12:35 amDAL-SJU
8h 35m2 stops
Southwest Logo
5:45 am - 2:45 pmSJU-DAL
11h 00m1 stop
$311Southwest
Find Deal
Mon, Feb 23 - Thu, Feb 26
Southwest Logo
2:30 pm - 12:40 amDAL-SJU
8h 10m2 stops
Southwest Logo
6:30 am - 5:40 pmSJU-DAL
13h 10m2 stops
$319Southwest
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Sat, Jan 24 - Sat, Jan 31
Southwest Logo
12:10 pm - 11:00 pmDAL-SJU
8h 50m1 stop
Southwest Logo
8:40 am - 6:00 pmSJU-DAL
11h 20m1 stop
$329Southwest
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Tue, Dec 9 - Tue, Dec 16
Delta Logo
6:05 am - 5:28 pmDAL-SJU
9h 23m1 stop
Delta Logo
7:00 am - 1:15 pmSJU-DAL
8h 15m1 stop
$337Delta
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Sun, Jan 4 - Wed, Jan 7
Delta Logo
6:05 am - 1:02 pmDAL-NAS
5h 57m1 stop
Delta Logo
2:56 pm - 10:29 pmNAS-DAL
8h 33m1 stop
$529Delta
Find Deal
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 March, when tickets cost $304 (return) on average. On the other hand, the most expensive months are December and January, when the average cost of round-trip tickets is $785 and $609 respectively.

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

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

Your flight ticket price will generally be cheaper if you fly to Caribbean on a Wednesday and more expensive on a Sunday. On your return trip to Dallas Love Field, you should consider flying back on a Thursday, and avoid Tuesdays for better deals.

Good to know

Low seasonOctober
Cheapest flight$106
Best time to beat the crowds but there is an average 3% increase in price.
Most popular time to fly and prices are also 8% 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.

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

    The cheapest time of day to fly to Caribbean 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 is generally in the evening, which is peak travel time and where the average cost of a ticket is $512.

Reviews of the top 3 airlines serving 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 4245 reviews
8.0Comfort
7.5Entertainment
8.1Boarding
8.6Crew
7.0Food
Airline reviews

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

10.0 ExcellentIlevba, Nov 2025DCA - DAL
Read more Southwest reviews

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.

Everything a cheap airline should be at normal airline rates.

Plane crashed into a bus or some other vehicle on the ground while pulling out of the gate. No injuries, but wing tip was damaged and returned to gate for “maintenance issues” and we departed 5 hours later because the plane went out of service and new plane was flown in from a nearby airport, Midway.

Ever since Southwest starting charging for bags, passengers don't want to pay to check their bags, so the gate agents have to beg people to check their roller bags now because there's "not enough space". This was a terrible business move by Southwest.

Full cans of soda would be nice. A choice between two snacks would be appreciated.

Tried watching free movie and it kept freezing so I couldn’t finish.

Our flight from SFO to MSP was right on time on 11/15/2025. No delays. As we approached MSP at about 8 pm, we circled in the air until 8:40 pm so I don't call that efficient for MSP. I think the captain should announce the delay and why. (as if we all don't know that we are just circling around the area, slowing down, speeding up, slowing down.) Thank you. Marilyn Fischer

Service in business class was not impressive. I ordered coffee with dinner and then watched other people get 2 refills before I got my 1 cup of coffee, and only after I pressed the attendant button overhead. Furthermore, the seats in the forward cabin need maintenance on this 737-800: the upholstery is detaching from the seat frame, at least on the backs of seats 1C, 1D.

Plenty of leg room, temperature was great and staff was excellent. Would do it more often.

The ticket agents in West Palm Beach on Friday afternoon Nov. 7th were incredible in getting us on an earlier plane to Atlanta during the government shutdown. Had the taken our original flight we would have missed our connection. She did this on her own, We didn't even have to ask, and she did it all with a smile and showing genuine concern that we would be taken care of. We are very grateful and thankful. We fly often, and now we will be sure to fly Delta.

Flight delayed then cancelled. Misplaced luggage. Still do not have. Rented car 1100 mile drive. I had to buy some overnight Hotels clothes toiletries gas food at my expense. Still not home. Not sure where luggage is. Over 4 hours on hold to Felta

I truly love flying with Delta. They have always treated me with the upmost respect

Our flight attendant in FIRST CLASS was one of the worst I’ve ever had. She was not at all pleasant, nor particularly good at her service.

Everything went well and was good. Nothing exceptional, but no complaints either. Cheap seats are pretty comfortable.

Staff were friendly and happy. Delta could make sure passengers that don't have the app know of changes. Without Kayak I would not have known about the change of gate or the delay. Kayak was faster to notify me.

They ended up paying for the bag twice, but the counter wouldn't take my baggage receipt. Left it to me to resolve. Not sure how to resolve the issue.

Always comes in handy when I want a quick weekend getaway.

The entire staff from check in agents to flight attendants were pleasant and professional. Would suggest a complimentary water.

Spirit is low fare air line. Food also cost you. No free food.

Everyone was kind for the most part. I did travel with children and paid for seats and even then it was not as suitable. I tried calling their customer service prior to check in and I was told they couldn't help me because I didn't purchase my tickets with them.

I think the staff was nice. They took time to explain safety protocols. Boarding was great. They started early and our flight left a little early which was convenient. Having free games to play would have been better

Just total easy flight experience!! What could you do better..? Hmmm..? There was nothing I can remember. Spirit was a far more comfortable and easy process than American, United & Delta. I'll always look for Spirit and I've told a few people about, since flying this past trip!! I'm a SPIRIT FAN!! Thank You, SPIRIT AIRLINES!! Very, VERY well done, 100%!! See you...SOON!! -Best, Linda R.

The flight was 3.5 hrs delayed. I was not notified prior to arriving to the airport via spirit app. or via boarding pass that I already had loaded on my phone. The agent that i saw at the counter didn’t mention anything about the delay either. I only saw the update after logging in to my email account.

Better than my las vagas experience, but still dissapointed with the airline support service.

Unfortunately, spirits crew had us boarding and parking the plane often, would wait long periods of time before allowing the people attending the flight on the plane to know what was going on this caused for my plane to not only get diverted but then canceled at an airport 2 hours away and basically stranded with charter buses MAYBE being hired. I was left with no choice but to stay overnight and use a comp room in Altantic City to then arrive home the next day. This trip was the first time seeing my partner since he joined the Air Force and this stressful ride caused unwarranted tears on what was supposed to be an east flight home. I understand weather is unpredictable but to have passengers deboard to then reboard an hour later to taxi on the runway for another hour to then basically leave an entire fight stranded. I waited almost 30 minutes at the airport and not one employee could tell me about a charter bus so I had to leave and make accommodations to stay overnight and get a ride home.

Great! We boarded on time! Everything went so smoothly! The flight was so smooth

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports