Caribbean

$123+ 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 4/7. Fares are subject to change and may not be available on all flights or dates of travel.
DAL — SJU
Mar 24 — Mar 311
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Cheap 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 February 22, 2026.

This Delta deal was found by Cheapflights users on 2/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/1312:25 pm
DAL
-
SJU
1 stop6h 59m
Delta
Wed 4/227:30 am
SJU
-
DAL
1 stop11h 20m
Delta
Deal found 2/22$287
This Delta deal was found by Cheapflights users on 2/22. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/116:05 am
DAL
-
SJU
1 stop9h 13m
Delta
Tue 4/146:15 am
SJU
-
DAL
1 stop9h 48m
Delta
Deal found 2/22$311
This Delta deal was found by Cheapflights users on 2/20. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/46:00 am
DAL
-
SXM
1 stop7h 00m
Delta
Fri 8/73:25 pm
SXM
-
DAL
1 stop8h 06m
Delta
Deal found 2/20$335
This Southwest deal was found by Cheapflights users on 2/18. 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 4/139:20 pm
DAL
-
SJU
1 stop12h 15m
Southwest
Wed 4/2211:25 am
SJU
-
DAL
2 stops9h 30m
Southwest
Deal found 2/18$364
This Southwest deal was found by Cheapflights users on 2/18. 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 4/211:45 pm
DAL
-
SJU
2 stops8h 55m
Southwest
Wed 4/2211:25 am
SJU
-
DAL
2 stops9h 30m
Southwest
Deal found 2/18$377
This Southwest deal was found by Cheapflights users on 2/18. 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 4/227:05 pm
DAL
-
SJU
1 stop13h 05m
Southwest
Wed 4/2911:25 am
SJU
-
DAL
1 stop9h 30m
Southwest
Deal found 2/18$382
This Southwest deal was found by Cheapflights users on 2/19. 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 4/149:00 am
DAL
-
SJU
2 stops11h 05m
Southwest
Wed 4/2211:25 am
SJU
-
DAL
2 stops9h 20m
Southwest
Deal found 2/19$384
This Delta deal was found by Cheapflights users on 2/19. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/56:00 am
DAL
-
KIN
1 stop13h 00m
Delta
Sun 3/89:00 am
KIN
-
DAL
1 stop13h 45m
Delta
Deal found 2/19$394
This Southwest deal was found by Cheapflights users on 2/18. 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 5/207:05 pm
DAL
-
SJU
1 stop13h 05m
Southwest
Thu 5/211:00 pm
SJU
-
DAL
1 stop8h 35m
Southwest
Deal found 2/18$397
This Delta deal was found by Cheapflights users on 2/21. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/1512:12 pm
DAL
-
SJU
1 stop10h 03m
Delta
Wed 3/186:15 am
SJU
-
DAL
1 stop9h 58m
Delta
Deal found 2/21$414
This Southwest deal was found by Cheapflights users on 2/18. 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 4/267:40 am
DAL
-
SJU
1 stop6h 00m
Southwest
Thu 4/301:00 pm
SJU
-
DAL
1 stop8h 35m
Southwest
Deal found 2/18$415
This Southwest deal was found by Cheapflights users on 2/18. 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 2/256:55 am
DAL
-
STT
1 stop6h 00m
Southwest
Thu 2/262:10 pm
STT
-
DAL
1 stop10h 00m
Southwest
Deal found 2/18$416

Find 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 February 22, 2026.

Round-trip from

$287
(Delta)

One-way from

$123
(Delta)

Popular in

December

Cheapest in

October

Average price

$346
From Dallas Love Field to Caribbean
One-way flight from Dallas Love Field to Caribbean
Highest demand for flights based on searches. 11% potential increase in price ($46 potential increase over avg. RT price).
Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
Average for round-trip flights in February 2026

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 February 22, 2026.
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 4/13

9:20 pm-10:35 am

1 stop12h 15m

San Juan Luis Munoz Marin Intl

Wed 4/22

11:25 am-7:55 pm

2 stops9h 30m

$364

DallasSan Juan

DAL - SJU

DALSJU

Dallas Love Field

Tue 4/14

6:05 am-1:20 pm

1 stop6h 15m

San Juan Luis Munoz Marin Intl

Wed 4/22

8:10 am-2:00 pm

1 stop6h 50m

$384

DallasKingston

DAL - KIN

DALKIN

Dallas Love Field

Thu 3/5

6:00 am-8:00 pm

1 stop13h 00m

Kingston Norman Manley

Sun 3/8

9:00 am-10:45 pm

1 stop13h 45m

$394

DallasSimpson Bay

DAL - SXM

DALSXM

Dallas Love Field

Mon 4/20

6:00 am-1:30 pm

1 stop6h 30m

Simpson Bay Princess Juliana

Sat 4/25

2:35 pm-11:20 pm

1 stop9h 45m

$423

DallasSan Juan

DAL - SJU

DALSJU

Dallas Love Field

Sat 4/25

12:50 pm-11:15 pm

2 stops9h 25m

San Juan Luis Munoz Marin Intl

Thu 4/30

2:00 pm-10:45 pm

1 stop9h 45m

$440

DallasSan Juan

DAL - SJU

DALSJU

Dallas Love Field

Wed 3/25

10:20 am-7:30 pm

1 stop8h 10m

San Juan Luis Munoz Marin Intl

Thu 4/2

8:50 pm-8:15 am

1 stop12h 25m

$446

DallasSan Juan

DAL - SJU

DALSJU

Dallas Love Field

Tue 3/31

4:15 pm-12:15 am

1 stop7h 00m

San Juan Luis Munoz Marin Intl

Tue 4/7

2:00 pm-9:00 pm

1 stop8h 00m

$446

DallasSan Juan

DAL - SJU

DALSJU

Dallas Love Field

Fri 5/8

8:10 am-11:40 pm

1 stop14h 30m

San Juan Luis Munoz Marin Intl

Wed 5/13

5:35 am-2:00 pm

1 stop9h 25m

$446

DallasSaint Thomas Island

DAL - STT

DALSTT

Dallas Love Field

Wed 3/25

6:15 am-2:20 pm

1 stop7h 05m

Saint Thomas Island Cyril E King

Tue 3/31

1:50 pm-9:10 pm

1 stop8h 20m

$446

DallasSaint Thomas Island

DAL - STT

DALSTT

Dallas Love Field

Tue 3/17

6:15 am-2:20 pm

1 stop7h 05m

Saint Thomas Island Cyril E King

Tue 3/24

1:50 pm-9:10 pm

1 stop8h 20m

$457

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/21

Showing 1-10 of 60 results
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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, April is the cheapest month in which you can book a flight from Dallas Love Field Airport to Caribbean (average of $238). Flying from Dallas Love Field Airport to Caribbean in December is currently the most expensive (average of $557). 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.

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 February 22, 2026.
See what other customers who have flown with Southwest and Delta 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.

Food

7.0

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Food

7.0

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

Food

7.0

Overall

8.0

Comfort

8.0

Crew

8.6

Boarding

8.1

Entertainment

7.5

Reviews

1 / 20
2.0
Mediocre

Thomas,Dec 2025

SEA - DEN

Plane two hours late in leaving 1:00 pm west coat time got home next day at 2:45am most car rental places are closed and don’t open till 5am

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.
  • How long is the flight from Dallas Love Field Airport to Caribbean?

    For as low as $364, Southwest can have you in Caribbean from Dallas Love Field Airport in 12h 15m. The distance between Dallas Love Field Airport and Caribbean is about 2151 mi. Both multi-stop and nonstop flights can be found to your destination and back.

  • What are the most popular routes 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, April is the cheapest month in which you can book a flight from Dallas Love Field Airport to Caribbean (average of $238). Flying from Dallas Love Field Airport to Caribbean in December is currently the most expensive (average of $557). 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

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Alternative routes for Love Field to Caribbean

See prices for flight routes from nearby airports that may be better suited for you.

Top 2 airlines flying from Love Field to Caribbean

Discover the top 2 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 February 22, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$275Average$597FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$378Average$713FlexibilityNo cancel feeOn-time63%

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