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$146+ 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 2/23. Fares are subject to change and may not be available on all flights or dates of travel.
DAL — SJU
Feb 5 — Feb 121
Thu 2/5
Thu 2/12
1 adult, Economy
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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 January 6, 2026.

Round-trip from

$292
(Delta)

One-way from

$146
(Southwest)

Popular in

December

Cheapest in

April

Average price

$341
From Dallas Love Field to Caribbean
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One-way flight from Dallas Love Field to Caribbean
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Highest demand for flights based on searches. 11% potential increase in price ($48 potential increase over avg. RT price).
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Cheapest flight prices on average. 2% potential price decrease ($10 potential savings vs. average RT price).
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Average for round-trip flights in January 2026
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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 January 6, 2026.

This Delta deal was found by Cheapflights users on 1/6. 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.
Wed 2/182:27 pmDAL - SJU
1 stop7h 31mDelta
Wed 3/46:15 amSJU - DAL
1 stop9h 23mDelta
Deal found 1/6$292
This Southwest deal was found by Cheapflights users on 1/6. 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 3/34:00 pmDAL - SJU
1 stop6h 35mSouthwest
Wed 3/46:10 amSJU - DAL
1 stop12h 45mSouthwest
Deal found 1/6$312
This Southwest deal was found by Cheapflights users on 1/6. 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 2/184:00 pmDAL - SJU
1 stop6h 35mSouthwest
Wed 2/255:40 amSJU - DAL
1 stop11h 15mSouthwest
Deal found 1/6$317
This Southwest deal was found by Cheapflights users on 1/5. 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 2/71:15 pmDAL - SJU
1 stop8h 55mSouthwest
Sat 2/146:05 amSJU - DAL
1 stop13h 50mSouthwest
Deal found 1/5$342
This Delta deal was found by Cheapflights users on 1/6. 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.
Tue 2/1710:45 amDAL - SJU
1 stop8h 27mDelta
Wed 3/47:30 amSJU - DAL
1 stop8h 08mDelta
Deal found 1/6$348
This Southwest deal was found by Cheapflights users on 1/5. 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 1/266:55 amDAL - SJU
1 stop6h 00mSouthwest
Thu 1/295:40 amSJU - DAL
1 stop9h 00mSouthwest
Deal found 1/5$352
This Southwest deal was found by Cheapflights users on 1/5. 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 1/2611:00 amDAL - SJU
1 stop6h 05mSouthwest
Fri 1/3010:20 amSJU - DAL
2 stops9h 10mSouthwest
Deal found 1/5$354
This Southwest deal was found by Cheapflights users on 1/5. 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 3/179:10 amDAL - SJU
1 stop12h 50mSouthwest
Wed 3/255:15 amSJU - DAL
1 stop12h 05mSouthwest
Deal found 1/5$356
This Southwest deal was found by Cheapflights users on 1/4. 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 2/212:40 pmDAL - SJU
1 stop6h 15mSouthwest
Sat 2/76:00 amSJU - DAL
2 stops10h 30mSouthwest
Deal found 1/4$357
This Southwest deal was found by Cheapflights users on 1/5. 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 3/42:35 pmDAL - SJU
2 stops8h 00mSouthwest
Wed 3/116:40 amSJU - DAL
1 stop7h 35mSouthwest
Deal found 1/5$364
This Delta deal was found by Cheapflights users on 1/6. 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 2/1910:45 amDAL - SJU
1 stop11h 13mDelta
Wed 3/47:30 amSJU - DAL
1 stop8h 08mDelta
Deal found 1/6$373
This Southwest deal was found by Cheapflights users on 1/6. 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 2/511:10 amDAL - SJU
1 stop8h 40mSouthwest
Fri 2/67:00 amSJU - DAL
2 stops9h 10mSouthwest
Deal found 1/6$374

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 January 6, 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 2/9

6:00 am-2:31 pm

1 stop6h 31m

San Juan Luis Munoz Marin Intl

Thu 2/12

7:30 am-3:08 pm

1 stop9h 38m

$292

DallasSan Juan

DAL - SJU

DALSJU

Dallas Love Field

Tue 3/3

4:00 pm-12:35 am

1 stop6h 35m

San Juan Luis Munoz Marin Intl

Wed 3/4

6:10 am-4:55 pm

1 stop12h 45m

$312

DallasSan Juan

DAL - SJU

DALSJU

Dallas Love Field

Thu 2/19

11:58 am-11:58 pm

1 stop10h 00m

San Juan Luis Munoz Marin Intl

Wed 3/4

6:15 am-1:38 pm

1 stop9h 23m

$317

DallasSan Juan

DAL - SJU

DALSJU

Dallas Love Field

Thu 1/29

4:00 pm-12:35 am

1 stop6h 35m

San Juan Luis Munoz Marin Intl

Thu 2/5

8:00 pm-8:10 am

1 stop14h 10m

$342

DallasSan Juan

DAL - SJU

DALSJU

Dallas Love Field

Mon 1/26

11:00 am-7:05 pm

1 stop6h 05m

San Juan Luis Munoz Marin Intl

Fri 1/30

10:20 am-5:30 pm

2 stops9h 10m

$354

DallasSan Juan

DAL - SJU

DALSJU

Dallas Love Field

Tue 2/10

1:45 pm-12:35 am

2 stops8h 50m

San Juan Luis Munoz Marin Intl

Fri 2/13

6:30 am-3:05 pm

2 stops10h 35m

$377

DallasSan Juan

DAL - SJU

DALSJU

Dallas Love Field

Sat 1/31

9:00 am-5:10 pm

1 stop6h 10m

San Juan Luis Munoz Marin Intl

Tue 2/3

5:40 am-2:55 pm

1 stop11h 15m

$377

DallasSan Juan

DAL - SJU

DALSJU

Dallas Love Field

Thu 2/5

11:10 am-9:50 pm

1 stop8h 40m

San Juan Luis Munoz Marin Intl

Tue 2/10

5:40 am-3:20 pm

1 stop11h 40m

$377

DallasSan Juan

DAL - SJU

DALSJU

Dallas Love Field

Mon 4/13

11:30 am-11:25 pm

1 stop10h 55m

San Juan Luis Munoz Marin Intl

Fri 4/17

5:35 am-5:05 pm

1 stop12h 30m

$386

DallasSan Juan

DAL - SJU

DALSJU

Dallas Love Field

Wed 2/18

2:00 pm-12:35 am

2 stops8h 35m

San Juan Luis Munoz Marin Intl

Mon 2/23

8:00 pm-8:05 am

1 stop14h 05m

$392

Flights are sorted by cheapest round-trip flights first.

Deals found on 1/6

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, February is the cheapest month in which you can book a flight from Dallas Love Field Airport to Caribbean (average of $220). 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 January 6, 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.
Southwest
8.0
Very good
4,247 reviews

Comfort

8.0

Entertainment

7.5

Crew

8.6

Boarding

8.1

Overall

8.0

Food

7.0

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
Southwest
8.0
Very good
4,247 reviews
Southwest
8.0
Very good
4,247 reviews

Comfort

8.0

Entertainment

7.5

Crew

8.6

Boarding

8.1

Overall

8.0

Food

7.0

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
Delta
7.9
Good
8,017 reviews
Southwest
8.0
Very good
4,247 reviews

Comfort

8.0

Entertainment

7.5

Crew

8.6

Boarding

8.1

Overall

8.0

Food

7.0

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 $292, Delta can have you in Caribbean from Dallas Love Field Airport in 6h 31m. 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?

    While some choose either Dallas Love Field - Punta Cana or Dallas Love Field - Nassau 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, February is the cheapest month in which you can book a flight from Dallas Love Field Airport to Caribbean (average of $220). 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.
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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 January 6, 2026.
AirlineCheapestAverageFlexibilityOn-time
DeltaCheapest$258Average$560FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$261Average$719FlexibilityNo cancel feeOn-time63%

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