HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Caribbean

$156+ Cheap flights from Love Field (DAL) to Caribbean

This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/11. Fares are subject to change and may not be available on all flights or dates of travel.
DAL — SJU
Aug 19 — Aug 261
Tue 8/19
Tue 8/26
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from Love Field to Caribbean with Cheapflights

1. Tell us where you want to go

Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”

2. Select your favorite providers

We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.

3. Compare prices and book

Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.

Cheap flight deals from Love Field to Caribbean

Keep the following information in mind while searching for Love Field to Caribbean flight deals. Data was last updated August 14, 2025.

Round-trip from

$330
(Southwest)

One-way from

$156
(Southwest)

Popular in

November

Cheapest in

October

Average price

$365
From Dallas Love Field to Caribbean
Search Deals
One-way flight from Dallas Love Field to Caribbean
Search Deals
Highest demand for flights based on searches. 4% potential increase in price ($16 potential increase over avg. RT price).
Search Deals
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Search Deals
Average for round-trip flights in August 2025
Search Deals

Find flight deals from Love Field to Caribbean

Cheapest flights from Love Field to Caribbean
Explore the most affordable flight options available from Love Field to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 14, 2025.

This Southwest deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/311:30 amDAL - SJU
1 stop9h 50mSouthwest
Tue 11/45:45 amSJU - DAL
2 stops9h 10mSouthwest
Deal found 8/11$330
This Southwest deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/1712:55 pmDAL - SJU
2 stops8h 50mSouthwest
Tue 9/235:00 amSJU - DAL
2 stops9h 30mSouthwest
Deal found 8/14$335
This Southwest deal was found by Cheapflights users on 8/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/77:00 amDAL - SJU
1 stop9h 15mSouthwest
Thu 10/91:05 pmSJU - DAL
1 stop9h 00mSouthwest
Deal found 8/11$349
This Southwest deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/23:50 pmDAL - SJU
1 stop7h 55mSouthwest
Tue 10/710:50 amSJU - DAL
1 stop10h 55mSouthwest
Deal found 8/13$351
This Southwest deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/207:40 pmDAL - SJU
1 stop13h 15mSouthwest
Sun 10/269:20 pmSJU - DAL
1 stop11h 50mSouthwest
Deal found 8/14$360
This Southwest deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/161:20 pmDAL - SJU
1 stop7h 35mSouthwest
Wed 10/226:10 amSJU - DAL
1 stop11h 00mSouthwest
Deal found 8/13$363
This Southwest deal was found by Cheapflights users on 8/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/1412:35 pmDAL - SJU
2 stops11h 00mSouthwest
Thu 9/185:00 amSJU - DAL
2 stops8h 30mSouthwest
Deal found 8/14$374
This Southwest deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/193:30 pmDAL - SJU
1 stop7h 20mSouthwest
Sun 9/216:30 amSJU - DAL
1 stop8h 55mSouthwest
Deal found 8/12$375
This Southwest deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/37:00 amDAL - SJU
1 stop12h 30mSouthwest
Sat 12/63:10 pmSJU - DAL
1 stop7h 15mSouthwest
Deal found 8/13$377
This Southwest deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/110:25 amDAL - SJU
1 stop12h 20mSouthwest
Sat 11/83:10 pmSJU - DAL
1 stop7h 15mSouthwest
Deal found 8/12$381
This Southwest deal was found by Cheapflights users on 8/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/33:50 pmDAL - SJU
1 stop7h 55mSouthwest
Tue 10/710:50 amSJU - DAL
1 stop10h 55mSouthwest
Deal found 8/13$383
This Southwest deal was found by Cheapflights users on 8/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/36:55 amDAL - PLS
1 stop5h 50mSouthwest
Fri 11/72:40 pmPLS - DAL
1 stop9h 15mSouthwest
Deal found 8/12$400

Cheapflights Fare Finder

 
Customize your flight search to find flights from Love Field to Caribbean that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 14, 2025.
Use the filters below to find and compare flights from Dallas Love Field Airport to Caribbean that are best for you.

Fly from

Love Field

Fly to

Caribbean

Route

Depart

Return

Price

DallasSan Juan

DAL - SJU

DALSJU

Dallas Love Field

Mon 11/3

11:30 am-11:20 pm

1 stop9h 50m

San Juan Luis Munoz Marin Intl

Tue 11/4

5:45 am-12:55 pm

2 stops9h 10m

$330

DallasSan Juan

DAL - SJU

DALSJU

Dallas Love Field

Mon 9/22

10:06 am-10:00 pm

1 stop10h 54m

San Juan Luis Munoz Marin Intl

Fri 9/26

5:41 pm-11:49 pm

1 stop7h 08m

$335

DallasSan Juan

DAL - SJU

DALSJU

Dallas Love Field

Tue 9/30

9:05 am-5:25 pm

1 stop7h 20m

San Juan Luis Munoz Marin Intl

Thu 10/2

7:05 am-4:10 pm

1 stop10h 05m

$335

DallasSan Juan

DAL - SJU

DALSJU

Dallas Love Field

Mon 9/15

10:06 am-10:00 pm

1 stop10h 54m

San Juan Luis Munoz Marin Intl

Fri 9/19

2:26 pm-11:49 pm

1 stop10h 23m

$335

DallasSan Juan

DAL - SJU

DALSJU

Dallas Love Field

Mon 10/20

7:40 pm-9:55 am

1 stop13h 15m

San Juan Luis Munoz Marin Intl

Sun 10/26

9:20 pm-8:10 am

1 stop11h 50m

$335

DallasSan Juan

DAL - SJU

DALSJU

Dallas Love Field

Tue 9/16

12:55 pm-10:45 pm

2 stops8h 50m

San Juan Luis Munoz Marin Intl

Fri 9/19

5:50 am-5:15 pm

1 stop12h 25m

$335

DallasSan Juan

DAL - SJU

DALSJU

Dallas Love Field

Mon 9/22

10:45 am-6:45 pm

1 stop7h 00m

San Juan Luis Munoz Marin Intl

Fri 9/26

5:50 am-5:15 pm

1 stop12h 25m

$335

DallasProvidenciales

DAL - PLS

DALPLS

Dallas Love Field

Mon 11/3

6:55 am-1:45 pm

1 stop5h 50m

Providenciales

Fri 11/7

2:40 pm-10:55 pm

1 stop9h 15m

$400

DallasSanto Domingo

DAL - SDQ

DALSDQ

Dallas Love Field

Tue 9/9

6:00 am-1:22 pm

1 stop6h 22m

Santo Domingo Las Americas

Wed 9/10

2:47 pm-11:49 pm

1 stop10h 02m

$483

DallasProvidenciales

DAL - PLS

DALPLS

Dallas Love Field

Sat 11/1

6:15 am-2:25 pm

1 stop7h 10m

Providenciales

Wed 11/5

2:40 pm-10:10 pm

1 stop8h 30m

$485

Flights are sorted by cheapest round-trip flights first.

Deals found on 8/12

Showing 1-10 of 60 results
1
2
3
...
6

Best time to book a flight from Love Field to Caribbean

Have a flexible travel schedule? Discover the best time to fly to Caribbean from Love Field with our price prediction graph.
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.

Cheapflights Insights

Everything you need to know about your flight from Dallas Love Field Airport to Caribbean

What is the cheapest month to book a flight from Dallas Love Field Airport to Caribbean?

Currently, September is the cheapest month in which you can book a flight from Dallas Love Field Airport to Caribbean (average of $254). Flying from Dallas Love Field Airport to Caribbean in June is currently the most expensive (average of $339). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

What is the cheapest time of day to fly from DAL to CB?

Find hourly flight availability from Love Field to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 14, 2025.

When flying from Dallas Love Field Airport to Caribbean, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.

Reviews of airlines servicing Caribbean

Get insights into the airlines that provide service to Caribbean. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean. Reviews last updated August 14, 2025.
See what other customers who have flown with Southwest, Delta, and Spirit Airlines from Dallas Love Field Airport to Caribbean have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Southwest
8.0
Very good
4,244 reviews

Comfort

8.0

Entertainment

7.5

Crew

8.6

Food

7.0

Boarding

8.1

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Southwest
8.0
Very good
4,244 reviews
Southwest
8.0
Very good
4,244 reviews

Comfort

8.0

Entertainment

7.5

Crew

8.6

Food

7.0

Boarding

8.1

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Delta
8.0
Very good
7,980 reviews
Southwest
8.0
Very good
4,244 reviews

Comfort

8.0

Entertainment

7.5

Crew

8.6

Food

7.0

Boarding

8.1

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.
Spirit Airlines
6.3
Okay
8,045 reviews
Southwest
8.0
Very good
4,244 reviews

Comfort

8.0

Entertainment

7.5

Crew

8.6

Food

7.0

Boarding

8.1

Overall

8.0

Reviews

1 / 20
8.0
Excellent

Walter,Aug 2025

OAK - SAN

Dozens of flights and I've never seen a row's beverages forgotten. I even went back and asked the attendant to check on them and nothing. I really hope it didn't have something to do with the Black mother with her kid in the row. Otherwise it was a typical Southwest flight, rapid boarding, tolerable leg room.

Related info for your journey

Find useful and relevant information for your journey from Love Field to Caribbean. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What are the most popular routes from Dallas Love Field Airport to Caribbean?

    While some choose either Dallas Love Field - Castries Hewanorra or Dallas Love Field - Montego Bay Sangster Intl, Dallas Love Field - San Juan Luis Munoz Marin Intl is the most popular route from Dallas Love Field Airport to Caribbean.

  • Can I find deals for flights from Love Field to Caribbean that include hotel bookings?

    Yes. In addition to deals on Love Field to Caribbean flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from Love Field to Caribbean?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from Love Field to Caribbean.

  • Can I find deals for business class flights from Love Field to Caribbean?

    Yes. Cheapflights offers flight deals from Love Field to Caribbean by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

  • What is the cheapest month to book a flight from Dallas Love Field Airport to Caribbean?

    Currently, September is the cheapest month in which you can book a flight from Dallas Love Field Airport to Caribbean (average of $254). Flying from Dallas Love Field Airport to Caribbean in June is currently the most expensive (average of $339). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for Love Field to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.
Dallas/Fort Worth to O'Hare Intl flights
Dallas/Fort Worth to Seattle flights
Dallas/Fort Worth to LaGuardia flights
Dallas/Fort Worth to Las Vegas flights
Dallas/Fort Worth to John F Kennedy Intl flights
Dallas/Fort Worth to Midway flights
Dallas/Fort Worth to Newark flights
Dallas/Fort Worth to Los Angeles flights
Dallas/Fort Worth to Denver flights
Dallas/Fort Worth to Cancún flights
Dallas/Fort Worth to Reagan-National flights
Dallas/Fort Worth to Boston flights
Dallas/Fort Worth to Orlando flights
Dallas/Fort Worth to Baltimore flights
Dallas/Fort Worth to San Francisco flights
Dallas/Fort Worth to Portland flights
Dallas/Fort Worth to Sky Harbor Intl flights
Dallas/Fort Worth to Fort Lauderdale flights
Dallas/Fort Worth to Ontario flights
Dallas/Fort Worth to Narita flights
Dallas/Fort Worth to Mexico City flights
Dallas/Fort Worth to Miami flights
Dallas/Fort Worth to Dulles Intl flights
Love Field to Las Vegas flights
Dallas/Fort Worth to Detroit flights
Love Field to Seattle flights
Dallas/Fort Worth to Heathrow flights
Dallas/Fort Worth to Haneda flights
Dallas/Fort Worth to Luis Munoz Marin Intl flights
Dallas/Fort Worth to Charles de Gaulle flights
Dallas/Fort Worth to Cozumel flights
Dallas/Fort Worth to Minneapolis flights
Dallas/Fort Worth to San Diego flights
Love Field to O'Hare Intl flights
Dallas/Fort Worth to Atlanta flights
Dallas/Fort Worth to Honolulu flights
Dallas/Fort Worth to Madrid flights
Love Field to LaGuardia flights
Dallas/Fort Worth to Burbank flights
Love Field to Midway flights
Dallas/Fort Worth to Tampa flights
Dallas/Fort Worth to Santa Ana flights
Dallas/Fort Worth to Columbus flights
Love Field to Cancún flights
Dallas/Fort Worth to Nashville flights
Dallas/Fort Worth to Salt Lake City flights
Dallas/Fort Worth to Frankfurt flights
Dallas/Fort Worth to Leonardo da Vinci/Fiumicino flights
Dallas/Fort Worth to Incheon Intl flights
Love Field to Miami flights

Top 3 airlines flying from Love Field to Caribbean

Discover the top 3 airlines that operate flights from Love Field to Caribbean. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 14, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$156Average$230FlexibilityNo cancel feeOn-time65%
DeltaCheapest$258Average$359FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$271Average$689FlexibilityNo cancel feeOn-time63%

100% Free

Cheapflights is completely free to use, so you can start saving the moment you arrive.

Book with Flexibility

Our users can plan ahead with confidence and find flights with no change fees

Travel Smart

Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.