$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 1/27. Fares are subject to change and may not be available on all flights or dates of travel.
DAL — SJU
Nov 29 — Dec 61
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 October 30, 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 October 30, 2025.
This Southwest deal was found by Cheapflights users on 10/28. 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 12/71:55 pmDAL - SJU
1 stop9h 30mSouthwest
Wed 12/106:40 amSJU - DAL
1 stop13h 35mSouthwest
Deal found 10/28![Southwest logo]()
$273
This Southwest deal was found by Cheapflights users on 10/29. 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 12/29:55 amDAL - SJU
1 stop10h 10mSouthwest
Thu 12/42:05 pmSJU - DAL
1 stop9h 05mSouthwest
Deal found 10/29![Southwest logo]()
$324
This Southwest deal was found by Cheapflights users on 10/28. 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 12/11:45 pmDAL - SJU
1 stop7h 30mSouthwest
Fri 12/126:40 amSJU - DAL
1 stop13h 50mSouthwest
Deal found 10/28![Southwest logo]()
$344
This Southwest deal was found by Cheapflights users on 10/27. 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 12/112:15 pmDAL - SJU
2 stops9h 00mSouthwest
Sun 12/77:40 amSJU - DAL
1 stop12h 05mSouthwest
Deal found 10/27![Southwest logo]()
$364
This Southwest deal was found by Cheapflights users on 10/28. 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
Thu 12/42:05 pmSJU - DAL
1 stop9h 05mSouthwest
Deal found 10/28![Southwest logo]()
$369
This Southwest deal was found by Cheapflights users on 10/28. 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 12/137:45 amDAL - SJU
1 stop13h 15mSouthwest
Tue 12/162:05 pmSJU - DAL
1 stop9h 05mSouthwest
Deal found 10/28![Southwest logo]()
$374
This Southwest deal was found by Cheapflights users on 10/28. 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
Sun 12/77:40 amSJU - DAL
1 stop12h 05mSouthwest
Deal found 10/28![Southwest logo]()
$389
This Southwest deal was found by Cheapflights users on 10/28. 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 10/28![Southwest logo]()
$394
This Southwest deal was found by Cheapflights users on 10/28. 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 12/134:05 pmDAL - GCM
2 stops19h 30mSouthwest
Tue 12/161:30 pmGCM - DAL
2 stops10h 25mSouthwest
Deal found 10/28![Southwest logo]()
$503
This Southwest deal was found by Cheapflights users on 10/29. 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 12/64:50 pmDAL - PLS
2 stops19h 55mSouthwest
Wed 12/102:40 pmPLS - DAL
1 stop8h 30mSouthwest
Deal found 10/29![Southwest logo]()
$515
This Delta deal was found by Cheapflights users on 10/29. 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 11/196:40 pmDAL - NAS
1 stop16h 14mDelta
Mon 11/241:19 pmNAS - DAL
1 stop11h 33mDelta
Deal found 10/29![Delta logo]()
$525
This Southwest deal was found by Cheapflights users on 10/29. 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 11/198:45 pmDAL - NAS
2 stops14h 30mSouthwest
Sat 11/223:00 pmNAS - DAL
1 stop8h 55mSouthwest
Deal found 10/29![Southwest logo]()
$529
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 October 30, 2025.
Round-trip from | $273 (Southwest) |
|---|---|
One-way from | $140 (Southwest) |
Popular in | November |
Cheapest in | April |
Average price | $324 |
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 October 30, 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 12/7
1:55 pm-1:25 am
1 stop9h 30m
San Juan Luis Munoz Marin Intl
Wed 12/10
6:40 am-6:15 pm
1 stop13h 35m
$273
DallasSan Juan
DAL - SJU
DALSJU
Dallas Love Field
Sat 1/31
11:10 am-9:30 pm
2 stops8h 20m
San Juan Luis Munoz Marin Intl
Wed 2/11
5:40 am-1:00 pm
2 stops9h 20m
$304
DallasSan Juan
DAL - SJU
DALSJU
Dallas Love Field
Sun 1/25
11:10 am-9:50 pm
1 stop8h 40m
San Juan Luis Munoz Marin Intl
Sun 2/1
7:00 am-12:15 pm
1 stop7h 15m
$319
DallasSan Juan
DAL - SJU
DALSJU
Dallas Love Field
Mon 12/1
1:45 pm-11:15 pm
1 stop7h 30m
San Juan Luis Munoz Marin Intl
Fri 12/12
6:40 am-6:30 pm
1 stop13h 50m
$344
DallasSan Juan
DAL - SJU
DALSJU
Dallas Love Field
Mon 12/1
12:15 pm-11:15 pm
2 stops9h 00m
San Juan Luis Munoz Marin Intl
Sun 12/7
7:40 am-5:45 pm
1 stop12h 05m
$364
DallasSan Juan
DAL - SJU
DALSJU
Dallas Love Field
Sat 2/7
11:10 am-9:30 pm
2 stops8h 20m
San Juan Luis Munoz Marin Intl
Mon 2/9
7:00 am-4:05 pm
1 stop11h 05m
$369
DallasSan Juan
DAL - SJU
DALSJU
Dallas Love Field
Tue 3/3
8:55 am-7:05 pm
1 stop8h 10m
San Juan Luis Munoz Marin Intl
Fri 3/6
6:30 am-12:05 pm
1 stop7h 35m
$372
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
Sun 2/1
7:00 am-12:15 pm
1 stop7h 15m
$384
DallasSan Juan
DAL - SJU
DALSJU
Dallas Love Field
Fri 12/5
11:45 am-11:20 pm
2 stops9h 35m
San Juan Luis Munoz Marin Intl
Sun 12/7
7:40 am-5:45 pm
1 stop12h 05m
$389
DallasSan Juan
DAL - SJU
DALSJU
Dallas Love Field
Mon 4/27
3:15 pm-11:55 pm
2 stops7h 40m
San Juan Luis Munoz Marin Intl
Mon 5/4
5:05 am-11:25 am
1 stop7h 20m
$415
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 $600). 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 October 30, 2025.
It’s typically best to fly out from Dallas Love Field Airport to Caribbean at noon. Doing so could potentially save you 38% 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 October 30, 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.
Overall
8.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Comfort
8.0
Food
7.0
Reviews
1 / 20
2.0
MediocreMike,Aug 2025
OKC - AUS
Overall
8.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Comfort
8.0
Food
7.0
Reviews
1 / 20
2.0
MediocreMike,Aug 2025
OKC - AUS
Overall
8.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
Comfort
8.0
Food
7.0
Reviews
1 / 20
2.0
MediocreMike,Aug 2025
OKC - AUS
Overall
8.0
Boarding
8.1
Entertainment
7.5
Crew
8.6
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 October 30, 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$281 | Average$689 | FlexibilityNo cancel fee | On-time63% |