$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
1 adult, Economy
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Cheapest flights from Love Field to CaribbeanExplore 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.
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![Southwest logo]()
$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![Southwest logo]()
$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![Southwest logo]()
$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![Southwest logo]()
$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![Southwest logo]()
$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![Southwest logo]()
$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![Southwest logo]()
$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![Southwest logo]()
$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![Southwest logo]()
$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![Southwest logo]()
$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![Southwest logo]()
$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![Southwest logo]()
$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 |
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
Showing 1-10 of 60 results
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
MediocreMike,Aug 2025
OKC - AUS
Crew
8.6
Overall
8.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Food
7.0
Reviews
1 / 20
2.0
MediocreMike,Aug 2025
OKC - AUS
Crew
8.6
Overall
8.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Food
7.0
Reviews
1 / 20
2.0
MediocreMike,Aug 2025
OKC - AUS
Crew
8.6
Overall
8.0
Entertainment
7.5
Boarding
8.1
Comfort
8.0
Food
7.0
Reviews
1 / 20
2.0
MediocreMike,Aug 2025
OKC - AUS
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.
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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.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$156 | Average$260 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$258 | Average$404 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$285 | Average$688 | FlexibilityNo cancel fee | On-time63% |