$128 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 7/11. 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 Cana1 stop$487
Santo Domingo
Santo Domingo1 stop$594
Montego Bay
Montego Bay1 stop$534
Oranjestad
Oranjestad1 stop$359
Nassau
Nassau2 stops$458
Simpson Bay
Simpson Bay1 stop$513
Providenciales
Providenciales2 stops$562
George Town
George Town2 stops$584
Punta Cana
Punta Cana1 stop$487
Santo Domingo
Santo Domingo1 stop$594
Montego Bay
Montego Bay1 stop$534
Oranjestad
Oranjestad1 stop$359
Nassau
Nassau2 stops$458
Simpson Bay
Simpson Bay1 stop$513
Providenciales
Providenciales2 stops$562
George Town
George Town2 stops$584

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

Tue, Jun 2 - Fri, Jun 5
Delta Logo
6:44 pm - 12:00 pm
DAL
-
AUA
16h 16m
1 stop
Delta Logo
1:15 pm - 11:56 pm
AUA
-
DAL
11h 41m
1 stop
$359Delta
Tue, Jun 2 - Fri, Jun 5
Delta Logo
12:22 pm - 12:40 pm
DAL
-
AUA
23h 18m
2 stops
Delta Logo
1:15 pm - 11:56 pm
AUA
-
DAL
11h 41m
1 stop
$364Delta
Sun, Jun 7 - Thu, Jun 18
Delta Logo
6:09 am - 8:00 pm
DAL
-
KIN
13h 51m
1 stop
Delta Logo
9:00 am - 5:55 pm
KIN
-
DAL
8h 55m
1 stop
$420Delta
Tue, Oct 20 - Tue, Oct 20
Southwest Logo
6:00 am - 1:35 pm
DAL
-
SJU
6h 35m
1 stop
Southwest Logo
3:40 pm - 9:20 pm
SJU
-
DAL
6h 40m
1 stop
$421Southwest
Wed, Aug 26 - Mon, Aug 31
Southwest Logo
12:20 pm - 10:00 pm
DAL
-
SJU
8h 40m
2 stops
Southwest Logo
5:30 am - 3:05 pm
SJU
-
DAL
10h 35m
1 stop
$426Southwest
Fri, Jun 12 - Thu, Jun 18
Delta Logo
12:18 pm - 8:00 pm
DAL
-
KIN
7h 42m
1 stop
Delta Logo
9:00 am - 5:55 pm
KIN
-
DAL
8h 55m
1 stop
$446Delta
Thu, Aug 13 - Mon, Aug 17
Southwest Logo
11:40 am - 10:15 pm
DAL
-
SJU
9h 35m
2 stops
Southwest Logo
6:30 am - 2:40 pm
SJU
-
DAL
9h 10m
2 stops
$451Southwest
Fri, Oct 9 - Tue, Oct 13
Southwest Logo
4:05 pm - 12:35 am
DAL
-
SJU
7h 30m
1 stop
Southwest Logo
3:40 pm - 9:20 pm
SJU
-
DAL
6h 40m
1 stop
$456Southwest
Sat, Sep 5 - Wed, Sep 9
Southwest Logo
5:15 pm - 12:15 pm
DAL
-
NAS
18h 00m
2 stops
Southwest Logo
1:10 pm - 8:30 pm
NAS
-
DAL
8h 20m
1 stop
$458Southwest
Sun, Jul 26 - Tue, Jul 28
Southwest Logo
5:10 pm - 12:25 am
DAL
-
SJU
6h 15m
1 stop
Southwest Logo
8:35 pm - 7:50 am
SJU
-
DAL
12h 15m
1 stop
$459Southwest
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 May, when tickets cost $257 (return) on average. On the other hand, the most expensive months are April and September, when the average cost of round-trip tickets is $652 and $585 respectively.

Good to know

Low seasonApril
Cheapest flight$128
Best time to beat the crowds with an average 2% drop in price.
Most popular time to fly and prices are also 3% 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 4285 reviews
8.0Comfort
7.0Food
8.6Crew
8.1Boarding
7.5Entertainment
Airline reviews

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

4.0 OkayAnonymous, May 2026
MDW - LAX
Read more Southwest reviews

The first time I flew in the extra legroom section. It was difficult to notice a difference. I had bad luck with my neighbors. The crew was okay. Southwest has reduced the live TV options.

The flight was smooth. The Southwest experience has degraded overall, but this one was okay.

No gluten free snacks. Seats felt worn or bare bones even though it was a new 737 MAX 8.

One major problem that was very unprofessional and uncalled for. Plane landed and we had to wait 20 minutes to get off the plane since they were waiting for someone to come to the gate to drive the jetway. Southwest couldn't have someone available and waiting for the plane to land? Is there only one person in Hobby airport who knows to drive the jetway? Was he at lunch? In the bar? Uncomfortable and uncalled for!

The checking experience in Orlando was terrible, almost missed the flight. Too many travelers and Southwest completely understaffed.

I'm glad it wasn't only 75% full because I could get a good seat

if I was good. Not happy that I have to pay extra money to get the seat I need for lake room, but I guess that’s a sign of the times.

Seats were very comfortable. They tilted back. Drinks and snacks were free and served 3 times. Attendants were awesome.

Plane was clean and comfortable. Flight attendants and gate staff were professional, friendly and efficient. Boarding and deplaning were orderly and efficient. All in all, the typical excellent Southwest experience.

Truly terrible. Will never willingly fly southwest again. Seats are worse than before they switched to assigned seating. One flight attendant was the opposite of helpful (rude, unhelpful, dismissive, and as my stranger seatmate said unprompted: a total prick). This caused me, 15 minutes into the flight, to book an alternate return flight home on a competing airline (first class 1.2k purchase instead of my existing planned flight) just so I would not have to ever be on that aircraft, with that terrible service person, with those horrific seats ever again.

I continue to be satisfied with Delta’s excellent service out of LGA. The digit id works well and gets me through security in no time. Whenever possible, I choose Delta.

Was revoked with Jet Blue due to delay from Kenya Air

The Boarding process was great. Particularly since my wife and I require assistance. The flight attendants were amazing. We travel frequently; they honestly were a cut above. 😀

Enjoyed it very much. Especially liked the free WiFi that Delta offers.

Smooth flight. Left on time, and got in 15 minutes early. Onboard video was great

For some reason, TSA Atlanta didn’t have my bag on the flight on time and they don’t have to provide Delta a reason for that.

WiFi didn’t work on two of four planes. Flight attendants were not overly friendly or welcoming. Planes were extremely slow to board and deplane.

Delta does a great job with entertainment and free wifi. I can still be in touch with my colleagues while in the air.

Aside from a completely packed plane, I really have no complaints.

Bus to plane was delayed for no apparent reason and our luggage was still on the belt when they shut it off. Took about 20 minutes to turn it back on to get our luggage.

Everything you need to know for your flight to Caribbean

Information on your arrival and departure airports