Caribbean

$140+ 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 2/8. Fares are subject to change and may not be available on all flights or dates of travel.
DAL — SJU
Dec 13 — Dec 201
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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 November 13, 2025.

This Southwest deal was found by Cheapflights users on 11/12. 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.
Wed 12/101:00 pmDAL - SJU
1 stop9h 35mSouthwest
Fri 12/126:40 amSJU - DAL
1 stop13h 50mSouthwest
Deal found 11/12$236
This Southwest deal was found by Cheapflights users on 11/13. 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.
Sun 12/712:55 pmDAL - SJU
1 stop7h 05mSouthwest
Thu 12/112:05 pmSJU - DAL
1 stop9h 05mSouthwest
Deal found 11/13$276
This Southwest deal was found by Cheapflights users on 11/11. 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 12/28:30 amDAL - SJU
1 stop8h 05mSouthwest
Wed 12/102:05 pmSJU - DAL
1 stop9h 05mSouthwest
Deal found 11/11$311
This Southwest deal was found by Cheapflights users on 11/12. 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.
Sun 12/712:55 pmDAL - SJU
1 stop7h 05mSouthwest
Sat 12/138:20 amSJU - DAL
2 stops8h 45mSouthwest
Deal found 11/12$341
This Southwest deal was found by Cheapflights users on 11/12. 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 12/511:45 amDAL - SJU
2 stops9h 35mSouthwest
Fri 12/126:10 amSJU - DAL
1 stop13h 30mSouthwest
Deal found 11/12$358
This Southwest deal was found by Cheapflights users on 11/12. 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.
Wed 12/32:35 pmDAL - SJU
2 stops8h 00mSouthwest
Sat 12/66:15 amSJU - DAL
2 stops10h 15mSouthwest
Deal found 11/12$383
This Southwest deal was found by Cheapflights users on 11/10. 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 12/21:25 pmDAL - SJU
1 stop6h 05mSouthwest
Tue 1/135:40 amSJU - DAL
1 stop11h 15mSouthwest
Deal found 11/10$392
This Southwest deal was found by Cheapflights users on 11/11. 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.
Thu 11/277:50 amDAL - SJU
1 stop7h 35mSouthwest
Wed 12/103:55 pmSJU - DAL
1 stop8h 15mSouthwest
Deal found 11/11$393
This Southwest deal was found by Cheapflights users on 11/13. 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.
Mon 12/158:40 pmDAL - PLS
2 stops16h 05mSouthwest
Sat 12/2012:20 pmPLS - DAL
2 stops9h 30mSouthwest
Deal found 11/13$501
This Southwest deal was found by Cheapflights users on 11/12. 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.
Wed 12/38:45 pmDAL - GCM
2 stops14h 50mSouthwest
Wed 12/101:30 pmGCM - DAL
2 stops10h 20mSouthwest
Deal found 11/12$563
This Southwest deal was found by Cheapflights users on 11/11. 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 12/98:30 pmDAL - NAS
2 stops14h 45mSouthwest
Tue 12/161:10 pmNAS - DAL
1 stop7h 55mSouthwest
Deal found 11/11$582
This Southwest deal was found by Cheapflights users on 11/12. 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 12/136:05 amDAL - GCM
1 stop5h 55mSouthwest
Sat 12/201:25 pmGCM - DAL
1 stop9h 55mSouthwest
Deal found 11/12$582

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 November 13, 2025.

Round-trip from

$236
(Southwest)

One-way from

$140
(Southwest)

Popular in

November

Cheapest in

October

Average price

$426
From Dallas Love Field to Caribbean
One-way flight from Dallas Love Field to Caribbean
Highest demand for flights based on searches. 5% potential increase in price ($20 potential increase over avg. RT price).
Cheapest flight prices on average. 1% potential price decrease ($6 potential savings vs. average RT price).
Average for round-trip flights in November 2025

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 November 13, 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

Sun 2/15

11:10 am-9:50 pm

1 stop8h 40m

San Juan Luis Munoz Marin Intl

Wed 2/18

6:10 am-2:45 pm

2 stops10h 35m

$304

DallasSan Juan

DAL - SJU

DALSJU

Dallas Love Field

Sun 12/7

12:55 pm-10:00 pm

1 stop7h 05m

San Juan Luis Munoz Marin Intl

Sat 12/13

5:40 am-10:50 am

1 stop7h 10m

$341

DallasSan Juan

DAL - SJU

DALSJU

Dallas Love Field

Thu 2/5

9:35 am-12:05 am

1 stop12h 30m

San Juan Luis Munoz Marin Intl

Mon 2/9

6:10 am-6:45 pm

1 stop14h 35m

$344

DallasSan Juan

DAL - SJU

DALSJU

Dallas Love Field

Fri 1/23

4:00 pm-12:35 am

1 stop6h 35m

San Juan Luis Munoz Marin Intl

Tue 1/27

6:00 am-2:55 pm

1 stop10h 55m

$344

DallasSan Juan

DAL - SJU

DALSJU

Dallas Love Field

Sat 12/6

2:50 pm-12:30 am

2 stops7h 40m

San Juan Luis Munoz Marin Intl

Tue 12/9

6:40 am-6:15 pm

1 stop13h 35m

$358

DallasSan Juan

DAL - SJU

DALSJU

Dallas Love Field

Fri 1/30

2:35 pm-12:35 am

2 stops8h 00m

San Juan Luis Munoz Marin Intl

Sat 2/7

6:00 am-2:30 pm

2 stops10h 30m

$369

DallasSan Juan

DAL - SJU

DALSJU

Dallas Love Field

Fri 2/6

4:45 pm-12:40 am

1 stop5h 55m

San Juan Luis Munoz Marin Intl

Mon 2/9

7:00 am-12:15 pm

1 stop7h 15m

$369

DallasSan Juan

DAL - SJU

DALSJU

Dallas Love Field

Sat 2/21

2:50 pm-12:40 am

2 stops7h 50m

San Juan Luis Munoz Marin Intl

Sat 2/28

7:35 am-4:15 pm

2 stops10h 40m

$369

DallasSan Juan

DAL - SJU

DALSJU

Dallas Love Field

Sat 1/17

8:35 am-11:00 pm

1 stop12h 25m

San Juan Luis Munoz Marin Intl

Wed 1/21

6:10 am-4:55 pm

1 stop12h 45m

$372

DallasSan Juan

DAL - SJU

DALSJU

Dallas Love Field

Thu 1/22

9:00 am-11:10 pm

1 stop12h 10m

San Juan Luis Munoz Marin Intl

Sun 1/25

6:10 am-6:45 pm

1 stop14h 35m

$379

Flights are sorted by cheapest round-trip flights first.

Deals found on 11/10

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, January is the cheapest month in which you can book a flight from Dallas Love Field Airport to Caribbean (average of $198). Flying from Dallas Love Field Airport to Caribbean in December is currently the most expensive (average of $585). 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 November 13, 2025.

It’s typically best to fly out from Dallas Love Field Airport to Caribbean in the evening. Doing so could potentially save you 29% on the flight price compared to flying in the morning, which is usually more expensive.

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 November 13, 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.

Crew

8.6

Overall

8.0

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Crew

8.6

Overall

8.0

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Crew

8.6

Overall

8.0

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

Crew

8.6

Overall

8.0

Entertainment

7.5

Boarding

8.1

Comfort

8.0

Food

7.0

Reviews

1 / 20
2.0
Mediocre

Mike,Aug 2025

OKC - AUS

AC was not adequate, even on a night flight. WiFi subpar even for the airlines

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 $304, Southwest can have you in Caribbean from Dallas Love Field Airport in 8h 40m. 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, January is the cheapest month in which you can book a flight from Dallas Love Field Airport to Caribbean (average of $198). Flying from Dallas Love Field Airport to Caribbean in December is currently the most expensive (average of $585). 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 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 November 13, 2025.
AirlineCheapestAverageFlexibilityOn-time
Spirit AirlinesCheapest$156Average$260FlexibilityNo cancel feeOn-time65%
DeltaCheapest$258Average$404FlexibilityNo cancel feeOn-timeN/A
SouthwestCheapest$285Average$688FlexibilityNo cancel feeOn-time63%

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