$145 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 6/6. 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$600
Santo Domingo
Santo Domingo1 stop$720
Montego Bay
Montego Bay1 stop$535
Oranjestad
Oranjestad2 stops$606
Nassau
Nassau1 stop$553
Simpson Bay
Simpson Bay2 stops$475
Providenciales
Providenciales1 stop$607
George Town
George Town2 stops$595
Punta Cana
Punta Cana2 stops$600
Santo Domingo
Santo Domingo1 stop$720
Montego Bay
Montego Bay1 stop$535
Oranjestad
Oranjestad2 stops$606
Nassau
Nassau1 stop$553
Simpson Bay
Simpson Bay2 stops$475
Providenciales
Providenciales1 stop$607
George Town
George Town2 stops$595

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

Thu, May 14 - Fri, May 15
Southwest Logo
9:10 pm - 9:10 am
DAL
-
SJU
11h 00m
1 stop
Southwest Logo
3:45 pm - 10:45 pm
SJU
-
DAL
8h 00m
1 stop
$381Southwest
Mon, Jul 13 - Wed, Jul 15
Southwest Logo
3:10 pm - 12:15 am
DAL
-
SJU
8h 05m
1 stop
Southwest Logo
6:00 am - 2:10 pm
SJU
-
DAL
9h 10m
1 stop
$400Southwest
Tue, Aug 4 - Mon, Aug 10
Southwest Logo
10:50 am - 7:00 pm
DAL
-
SJU
7h 10m
1 stop
Southwest Logo
8:55 pm - 8:50 am
SJU
-
DAL
12h 55m
1 stop
$413Southwest
Fri, Oct 30 - Fri, Oct 30
Southwest Logo
9:10 am - 6:10 pm
DAL
-
SJU
8h 00m
1 stop
Southwest Logo
9:45 pm - 9:20 am
SJU
-
DAL
12h 35m
1 stop
$421Southwest
Thu, Aug 13 - Mon, Aug 17
Southwest Logo
9:10 am - 10:50 pm
DAL
-
SJU
12h 40m
1 stop
Southwest Logo
6:00 am - 11:15 am
SJU
-
DAL
6h 15m
1 stop
$426Southwest
Tue, Jun 30 - Thu, Jul 9
Southwest Logo
4:00 pm - 11:45 pm
DAL
-
SJU
6h 45m
1 stop
Southwest Logo
7:00 am - 5:55 pm
SJU
-
DAL
11h 55m
1 stop
$435Southwest
Mon, Jul 6 - Tue, Jul 14
Southwest Logo
4:10 pm - 11:35 pm
DAL
-
SJU
6h 25m
1 stop
Southwest Logo
8:35 pm - 7:50 am
SJU
-
DAL
12h 15m
1 stop
$440Southwest
Wed, Aug 5 - Sun, Aug 9
Southwest Logo
12:25 pm - 10:00 pm
DAL
-
SJU
8h 35m
2 stops
Southwest Logo
9:25 pm - 9:20 am
SJU
-
DAL
12h 55m
1 stop
$443Southwest
Sun, Jul 5 - Thu, Jul 9
Delta Logo
6:40 pm - 1:53 pm
DAL
-
SXM
18h 13m
1 stop
Delta Logo
3:20 pm - 3:03 pm
SXM
-
DAL
24h 43m
1 stop
$569Delta
Fri, Jul 3 - Thu, Jul 9
Delta Logo
6:40 pm - 1:53 pm
DAL
-
SXM
18h 13m
1 stop
Delta Logo
3:20 pm - 9:16 am
SXM
-
DAL
18h 56m
1 stop
$580Delta
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 June, when tickets cost $156 (return) on average. On the other hand, the most expensive months are September and December, when the average cost of round-trip tickets is $585 and $516 respectively.

Good to know

Low seasonApril
Cheapest flight$145
Best time to beat the crowds with an average 11% drop in price.
Most popular time to fly and prices are also 2% lower on average.
Flight from Dallas Love Field to Simpson Bay

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.

Reviews of the top airlines flying 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.
7.9
SouthwestOverall score based on 4310 reviews
8.6Crew
7.5Entertainment
7.0Food
8.1Boarding
8.0Comfort
Airline reviews

Not having a five hour delay with little notice! The crew was very kind, though, and just as tired as we passengers were. The flight didn't depart until nearly 1 am...and no reason was ever given.

2.0 MediocreAnonymous, May 2026
SEA - SMF
Read more Southwest reviews

Not having a five hour delay with little notice! The crew was very kind, though, and just as tired as we passengers were. The flight didn't depart until nearly 1 am...and no reason was ever given.

The entire experience from boarding to landing was amazing! The crew were very friendly. Will definitely be back.

no service at all due to turbulence. they should've at least given us snacks, there were only 10 people on the entire flight.

First time I've had to use the disabled accommodations. And I could not have had a better experience with Southwest, i was having trouble getting from one terminal to another due to my heart failure. And the next thing I know a Southwest agent had made sure. I had a wheelchair at all my flights. Can't thank them enough.

Delayed flight, lack of information, boarding process is a mess as is the carryon luggage causing issues when leaving the plane….just a poor experience.

Comfortable. Easy. No problems. Just wish they had gf options for snacks.

The crew was very kind and made going to Hawaii relaxing and fun to look forward to! Thank you Southwest for a pleasant flight!

This leg was much better, but we did have to have a 3 hour lay o er after coming from a very exhausting hiccup with our flight from BNA to Den

We waited in the airplane for over 45 min for a southwest employee to make the flight. This cause over half the plane to miss their connecting flight in Denver. When we confronted the desk upon arrival, they told us the only flight they had was the next day leaving at 8:50 pm!!! Or they offered to get us to Burbank or LA, but after that we were on our own to get back to Santa Barbara. I paid for a flight from sba to bna bna to sba. My re entry into mom mode has been 💯 rough because of southwest mistake with my flight. And now I’m leaving to Reno tomorrow for a vballl tournament and just discovered that my leg in Vegas has me and my 3 kids on a stand by flight even though I had booked these ticket last year November!! Do better southwest!

Southwest is kind of a slum airline. It’s gotten more expensive over the years for less and less service. I am a Southwest Chase Visa card holder and was forced to choose a seat in the 26th row in the middle seat. However my wife who is a rewards member but doesn’t hold a card or anything else, gets randomly assigned a normally paid seat in row 6! How does that work?

Seats in Delta Main are unbelievably close to the seat in front of. Hard to get a backpack under the seat.

The flight was operated by Latam. The aircraft had a technical issue and the flight was delayed for the next day. They grounded other passengers to get their airplane assigned to my flight. Most of he ground staff don't speak English (Orlando Airport), but were very polite.The crew on the other hand could speak English and Portuguese. On board service was good.

The agent at check in and at the gate were less than thrilled to be at work. I'm not a fan of Kayak's placement on the plane. I got put in the middle seat and none of my preferences were used.

In ATL they have two sets of departure screens. Follow what is on your airline's departure board - the ATL Airport Authority departure board had completely incorrect details about the gate assignment for my flight, which would have made me miss boarding.

Flight was delayed it was hot while sitting on the plane, one engine was working on the plane until they had to do some jimmy rigging down the runway in order for the other engine to charge up. It was ridiculous

The flight was very good and the staff was very friendly and helpful!

The only thing I would say is we tried to get on a standby earlier flight, but with our fair we couldn’t. That seems senseless to leave with open seats..

Very easy to use and convenient, you can perform any action within the same portal

In a world of delays, Delta was on time both ways! Boarding was fast and efficient. Staff was friendly. AND wifi worked.

WiFi didn’t work. Flight delayed 3 hours Crew members were illiterate Seat lean back did not work.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports