$128+ Cheap flights from Love Field (DAL) to Caribbean Islands
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 8/30. Fares are subject to change and may not be available on all flights or dates of travel.
DAL — SJU
Jun 28 — Jul 51
Round-trip
1 adult, Economy
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Find cheap flights from Love Field to Caribbean Islands with Cheapflights
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Cheapest flights from Love Field to Caribbean IslandsExplore the most affordable flight options available from Love Field to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 29, 2026.
Explore the most affordable flight options available from Love Field to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 29, 2026.
This Southwest deal was found by Cheapflights users on 5/29. 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.
Thu 9/106:25 am
DAL
- SJU
2 stops9h 30m
Southwest
Tue 9/1510:30 am
SJU
- DAL
2 stops8h 00m
Southwest
Deal found 5/29![Southwest logo]()
$243
This Southwest deal was found by Cheapflights users on 5/29. 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 9/211:35 am
DAL
- SJU
1 stop9h 25m
Southwest
Sun 9/66:00 am
SJU
- DAL
1 stop11h 55m
Southwest
Deal found 5/29![Southwest logo]()
$246
This Southwest deal was found by Cheapflights users on 5/28. 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 8/203:45 pm
DAL
- SJU
1 stop6h 20m
Southwest
Wed 8/2610:30 am
SJU
- DAL
2 stops8h 00m
Southwest
Deal found 5/28![Southwest logo]()
$252
This Southwest deal was found by Cheapflights users on 5/29. 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.
Thu 9/311:40 am
DAL
- SJU
2 stops9h 35m
Southwest
Sun 9/66:00 am
SJU
- DAL
1 stop8h 15m
Southwest
Deal found 5/29![Southwest logo]()
$270
This Southwest deal was found by Cheapflights users on 5/29. 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.
Thu 8/203:45 pm
DAL
- SJU
1 stop6h 20m
Southwest
Sun 8/239:25 pm
SJU
- DAL
1 stop12h 55m
Southwest
Deal found 5/29![Southwest logo]()
$272
This Southwest deal was found by Cheapflights users on 5/29. 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.
Fri 8/288:45 am
DAL
- SJU
1 stop7h 10m
Southwest
Mon 8/316:00 am
SJU
- DAL
1 stop6h 15m
Southwest
Deal found 5/29![Southwest logo]()
$286
This Southwest deal was found by Cheapflights users on 5/28. 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.
Tue 9/110:50 am
DAL
- SJU
1 stop7h 10m
Southwest
Sun 9/66:00 am
SJU
- DAL
1 stop8h 15m
Southwest
Deal found 5/28![Southwest logo]()
$310
This Southwest deal was found by Cheapflights users on 5/28. 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 9/311:40 am
DAL
- SJU
2 stops9h 35m
Southwest
Tue 9/86:00 am
SJU
- DAL
1 stop12h 20m
Southwest
Deal found 5/28![Southwest logo]()
$324
This Southwest deal was found by Cheapflights users on 5/29. 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.
Sun 9/67:10 pm
DAL
- NAS
2 stops16h 05m
Southwest
Wed 9/91:10 pm
NAS
- DAL
1 stop5h 15m
Southwest
Deal found 5/29![Southwest logo]()
$387
This Delta deal was found by Cheapflights users on 5/26. 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 8/306:33 pm
DAL
- SXM
1 stop18h 20m
Delta
Wed 9/163:20 pm
SXM
- DAL
1 stop8h 18m
Delta
Deal found 5/26![Delta logo]()
$413
This Southwest deal was found by Cheapflights users on 5/29. 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.
Mon 9/146:00 am
DAL
- NAS
1 stop5h 15m
Southwest
Fri 9/181:10 pm
NAS
- DAL
1 stop10h 00m
Southwest
Deal found 5/29![Southwest logo]()
$431
This Southwest deal was found by Cheapflights users on 5/26. 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 9/26:05 am
DAL
- NAS
1 stop5h 10m
Southwest
Wed 9/91:10 pm
NAS
- DAL
1 stop8h 20m
Southwest
Deal found 5/26![Southwest logo]()
$445
Best flights from Love Field to Caribbean IslandsDiscover carefully curated flight deals from Love Field to Caribbean Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 29, 2026.
Discover carefully curated flight deals from Love Field to Caribbean Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 29, 2026.
This Southwest deal was found by Cheapflights users on 5/29. 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.
Sun 9/67:10 pm
DAL
- NAS
2 stops16h 05m
Southwest
Wed 9/91:10 pm
NAS
- DAL
1 stop5h 15m
Southwest
Deal found 5/29![Southwest logo]()
$387
This Delta deal was found by Cheapflights users on 5/26. 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 8/306:33 pm
DAL
- SXM
1 stop18h 20m
Delta
Thu 9/173:20 pm
SXM
- DAL
1 stop8h 18m
Delta
Deal found 5/26![Delta logo]()
$413
This Delta deal was found by Cheapflights users on 5/26. 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 8/306:33 pm
DAL
- SXM
1 stop18h 20m
Delta
Wed 9/163:20 pm
SXM
- DAL
1 stop8h 18m
Delta
Deal found 5/26![Delta logo]()
$413
This Southwest deal was found by Cheapflights users on 5/24. 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 8/2711:40 am
DAL
- SJU
2 stops9h 30m
Southwest
Mon 8/3111:35 am
SJU
- DAL
2 stops9h 15m
Southwest
Deal found 5/24![Southwest logo]()
$426
This Delta deal was found by Cheapflights users on 5/26. 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 8/306:33 pm
DAL
- SXM
1 stop18h 20m
Delta
Fri 9/183:20 pm
SXM
- DAL
1 stop8h 18m
Delta
Deal found 5/26![Delta logo]()
$413
This Southwest deal was found by Cheapflights users on 5/24. 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 9/248:05 pm
DAL
- SJU
1 stop12h 05m
Southwest
Sun 9/275:30 am
SJU
- DAL
1 stop11h 45m
Southwest
Deal found 5/24![Southwest logo]()
$426
This Southwest deal was found by Cheapflights users on 5/28. 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 9/311:40 am
DAL
- SJU
2 stops9h 35m
Southwest
Mon 9/76:30 am
SJU
- DAL
2 stops9h 10m
Southwest
Deal found 5/28![Southwest logo]()
$445
This Delta deal was found by Cheapflights users on 5/26. 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 8/306:33 pm
DAL
- SXM
1 stop18h 20m
Delta
Sat 9/193:20 pm
SXM
- DAL
1 stop8h 18m
Delta
Deal found 5/26![Delta logo]()
$448
This Southwest deal was found by Cheapflights users on 5/26. 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 10/2911:00 am
DAL
- SJU
2 stops8h 55m
Southwest
Tue 11/36:45 am
SJU
- DAL
2 stops10h 20m
Southwest
Deal found 5/26![Southwest logo]()
$476
This Delta deal was found by Cheapflights users on 5/26. 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 8/306:00 am
DAL
- KIN
1 stop14h 13m
Delta
Sat 9/199:00 am
KIN
- DAL
1 stop13h 38m
Delta
Deal found 5/26![Delta logo]()
$494
This Southwest deal was found by Cheapflights users on 5/29. 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 8/266:05 am
DAL
- NAS
1 stop5h 10m
Southwest
Sat 8/291:25 pm
NAS
- DAL
1 stop8h 15m
Southwest
Deal found 5/29![Southwest logo]()
$482
This Delta deal was found by Cheapflights users on 5/26. 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 9/110:30 am
DAL
- KIN
1 stop9h 43m
Delta
Tue 9/159:00 am
KIN
- DAL
1 stop9h 02m
Delta
Deal found 5/26![Delta logo]()
$494
This Delta deal was found by Cheapflights users on 5/26. 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 8/306:00 am
DAL
- KIN
1 stop14h 13m
Delta
Tue 9/159:00 am
KIN
- DAL
1 stop9h 02m
Delta
Deal found 5/26![Delta logo]()
$494
This Southwest deal was found by Cheapflights users on 5/28. 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 6/285:10 pm
DAL
- SJU
1 stop6h 15m
Southwest
Fri 7/37:00 am
SJU
- DAL
1 stop11h 55m
Southwest
Deal found 5/28![Southwest logo]()
$496
This Delta deal was found by Cheapflights users on 5/26. 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 9/16:00 am
DAL
- KIN
1 stop14h 13m
Delta
Sat 9/199:00 am
KIN
- DAL
1 stop9h 02m
Delta
Deal found 5/26![Delta logo]()
$494
This Southwest deal was found by Cheapflights users on 5/27. 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.
Fri 7/174:10 pm
DAL
- SJU
1 stop6h 30m
Southwest
Tue 7/217:20 pm
SJU
- DAL
1 stop13h 30m
Southwest
Deal found 5/27![Southwest logo]()
$501
This Delta deal was found by Cheapflights users on 5/26. 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 8/306:00 am
DAL
- KIN
1 stop14h 13m
Delta
Mon 9/149:00 am
KIN
- DAL
1 stop9h 02m
Delta
Deal found 5/26![Delta logo]()
$494
This Southwest deal was found by Cheapflights users on 5/28. 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 7/104:30 pm
DAL
- SJU
1 stop7h 05m
Southwest
Tue 7/148:35 pm
SJU
- DAL
1 stop12h 15m
Southwest
Deal found 5/28![Southwest logo]()
$516
This Delta deal was found by Cheapflights users on 5/26. 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 9/110:30 am
DAL
- KIN
1 stop9h 43m
Delta
Fri 9/189:00 am
KIN
- DAL
1 stop9h 02m
Delta
Deal found 5/26![Delta logo]()
$494
This Southwest deal was found by Cheapflights users on 5/25. 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 7/185:30 pm
DAL
- SJU
1 stop6h 50m
Southwest
Fri 7/2410:20 pm
SJU
- DAL
1 stop10h 40m
Southwest
Deal found 5/25![Southwest logo]()
$521
This Delta deal was found by Cheapflights users on 5/24. 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 10/1310:20 am
DAL
- SJU
1 stop10h 39m
Delta
Fri 10/2312:46 pm
SJU
- DAL
1 stop8h 50m
Delta
Deal found 5/24![Delta logo]()
$496
This Southwest deal was found by Cheapflights users on 5/25. 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 9/76:00 am
DAL
- MBJ
1 stop7h 15m
Southwest
Thu 9/1012:15 pm
MBJ
- DAL
1 stop7h 30m
Southwest
Deal found 5/25![Southwest logo]()
$529
This Delta deal was found by Cheapflights users on 5/25. 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 7/46:40 pm
DAL
- AUA
1 stop16h 40m
Delta
Fri 7/173:25 pm
AUA
- DAL
1 stop8h 00m
Delta
Deal found 5/25![Delta logo]()
$505
This Southwest deal was found by Cheapflights users on 5/24. 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 6/106:00 am
DAL
- SJU
1 stop12h 45m
Southwest
Wed 6/176:00 am
SJU
- DAL
2 stops7h 50m
Southwest
Deal found 5/24![Southwest logo]()
$531
This Southwest deal was found by Cheapflights users on 5/28. 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 7/33:30 pm
DAL
- SJU
1 stop7h 55m
Southwest
Mon 7/610:20 pm
SJU
- DAL
1 stop12h 00m
Southwest
Deal found 5/28![Southwest logo]()
$531
This Delta deal was found by Cheapflights users on 5/26. 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.
Fri 7/36:40 pm
DAL
- AUA
1 stop16h 40m
Delta
Thu 7/161:55 pm
AUA
- DAL
2 stops20h 26m
Delta
Deal found 5/26![Delta logo]()
$574
This Southwest deal was found by Cheapflights users on 5/29. 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.
Sun 9/136:00 am
DAL
- NAS
1 stop5h 15m
Southwest
Wed 9/161:10 pm
NAS
- DAL
1 stop5h 15m
Southwest
Deal found 5/29![Southwest logo]()
$532
This Southwest deal was found by Cheapflights users on 5/27. 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.
Thu 6/256:35 pm
DAL
- SJU
1 stop13h 25m
Southwest
Tue 6/308:35 pm
SJU
- DAL
1 stop12h 15m
Southwest
Deal found 5/27![Southwest logo]()
$546
This Delta deal was found by Cheapflights users on 5/28. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/2812:19 pm
DAL
- KIN
1 stop7h 44m
Delta
Fri 8/79:13 am
KIN
- DAL
1 stop13h 18m
Delta
Deal found 5/28![Delta logo]()
$610
This Delta deal was found by Cheapflights users on 5/29. 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.
Sat 7/411:30 am
DAL
- KIN
1 stop8h 30m
Delta
Fri 7/179:00 am
KIN
- DAL
1 stop13h 25m
Delta
Deal found 5/29![Delta logo]()
$610
Last-minute flights from Love Field to Caribbean IslandsDiscover last-minute flight deals from Love Field to Caribbean Islands. Data last updated May 29, 2026 and is based on user searches.
Discover last-minute flight deals from Love Field to Caribbean Islands. Data last updated May 29, 2026 and is based on user searches.
This Delta deal was found by Cheapflights users on 5/25. 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 6/37:12 am
DAL
- KIN
1 stop12h 48m
Delta
Wed 6/249:00 am
KIN
- DAL
1 stop13h 34m
Delta
Deal found 5/25![Delta logo]()
$494
This Southwest deal was found by Cheapflights users on 5/28. 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 6/43:10 pm
DAL
- SJU
1 stop8h 05m
Southwest
Thu 6/1110:20 pm
SJU
- DAL
1 stop10h 30m
Southwest
Deal found 5/28![Southwest logo]()
$476
This Southwest deal was found by Cheapflights users on 5/28. 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 6/43:10 pm
DAL
- SJU
1 stop8h 05m
Southwest
Tue 6/91:30 pm
SJU
- DAL
1 stop10h 50m
Southwest
Deal found 5/28![Southwest logo]()
$486
This Delta deal was found by Cheapflights users on 5/25. 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 6/86:40 pm
DAL
- SXM
1 stop18h 13m
Delta
Wed 6/173:18 pm
SXM
- DAL
1 stop8h 16m
Delta
Deal found 5/25![Delta logo]()
$473
This Southwest deal was found by Cheapflights users on 5/24. 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 6/86:35 pm
DAL
- SJU
1 stop13h 25m
Southwest
Mon 6/1510:20 pm
SJU
- DAL
1 stop12h 00m
Southwest
Deal found 5/24![Southwest logo]()
$504
This Southwest deal was found by Cheapflights users on 5/28. 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 6/107:45 pm
DAL
- SJU
1 stop12h 15m
Southwest
Wed 6/176:00 am
SJU
- DAL
1 stop9h 10m
Southwest
Deal found 5/28![Southwest logo]()
$498
This Southwest deal was found by Cheapflights users on 5/29. 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.
Fri 6/123:30 pm
DAL
- SJU
1 stop7h 55m
Southwest
Mon 6/158:15 pm
SJU
- DAL
1 stop12h 35m
Southwest
Deal found 5/29![Southwest logo]()
$469
This Southwest deal was found by Cheapflights users on 5/29. 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.
Mon 6/154:30 pm
DAL
- SJU
1 stop6h 55m
Southwest
Thu 7/1610:20 pm
SJU
- DAL
1 stop12h 05m
Southwest
Deal found 5/29![Southwest logo]()
$461
This Southwest deal was found by Cheapflights users on 5/29. 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.
Fri 6/264:30 pm
DAL
- SJU
1 stop6h 55m
Southwest
Tue 7/78:35 pm
SJU
- DAL
1 stop12h 15m
Southwest
Deal found 5/29![Southwest logo]()
$481
This Southwest deal was found by Cheapflights users on 5/28. 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 6/285:10 pm
DAL
- SJU
1 stop6h 15m
Southwest
Fri 7/37:00 am
SJU
- DAL
1 stop11h 55m
Southwest
Deal found 5/28![Southwest logo]()
$496
This Southwest deal was found by Cheapflights users on 5/29. 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.
Mon 6/295:45 pm
DAL
- SJU
1 stop6h 35m
Southwest
Wed 7/88:35 pm
SJU
- DAL
1 stop12h 15m
Southwest
Deal found 5/29![Southwest logo]()
$411
This Southwest deal was found by Cheapflights users on 5/26. 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 6/304:35 pm
DAL
- SJU
1 stop6h 40m
Southwest
Wed 7/15:30 am
SJU
- DAL
1 stop8h 30m
Southwest
Deal found 5/26![Southwest logo]()
$501
One-way flights from Love Field to Caribbean IslandsSearch for one-way flight options from Love Field to Caribbean Islands. Find affordable one-way fares based on user searches. Data last updated May 29, 2026.
Search for one-way flight options from Love Field to Caribbean Islands. Find affordable one-way fares based on user searches. Data last updated May 29, 2026.
This Delta deal was found by Cheapflights users on 5/26. 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 8/306:33 pm
DAL
- SXM
1 stop18h 20m
Delta
Deal found 5/26![Delta logo]()
$128
This Delta deal was found by Cheapflights users on 5/29. 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.
Mon 7/276:05 am
DAL
- AUA
1 stop7h 05m
Delta
Deal found 5/29![Delta logo]()
$137
This Delta deal was found by Cheapflights users on 5/27. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/216:05 am
DAL
- AUA
1 stop7h 05m
Delta
Deal found 5/27![Delta logo]()
$147
This Southwest deal was found by Cheapflights users on 5/28. 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 8/241:30 pm
DAL
- SJU
2 stops8h 35m
Southwest
Deal found 5/28![Southwest logo]()
$162
This Southwest deal was found by Cheapflights users on 5/29. 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 8/256:05 am
DAL
- PUJ
1 stop6h 15m
Southwest
Deal found 5/29![Southwest logo]()
$180
This Southwest deal was found by Cheapflights users on 5/24. 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 8/203:45 pm
DAL
- SJU
1 stop6h 20m
Southwest
Deal found 5/24![Southwest logo]()
$184
This Southwest deal was found by Cheapflights users on 5/25. 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 7/217:25 am
DAL
- NAS
1 stop4h 50m
Southwest
Deal found 5/25![Southwest logo]()
$187
This Southwest deal was found by Cheapflights users on 5/28. 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 8/149:10 am
DAL
- SJU
1 stop12h 40m
Southwest
Deal found 5/28![Southwest logo]()
$197
This Southwest deal was found by Cheapflights users on 5/27. 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.
Tue 8/411:35 am
DAL
- SJU
1 stop9h 25m
Southwest
Deal found 5/27![Southwest logo]()
$198
This Southwest deal was found by Cheapflights users on 5/28. 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 7/38:50 pm
DAL
- AUA
1 stop14h 30m
Southwest
Deal found 5/28![Southwest logo]()
$212
This Southwest deal was found by Cheapflights users on 5/28. 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 7/47:05 am
DAL
- SJU
1 stop7h 55m
Southwest
Deal found 5/28![Southwest logo]()
$213
This Southwest deal was found by Cheapflights users on 5/27. 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.
Sun 8/237:50 pm
DAL
- NAS
2 stops15h 25m
Southwest
Deal found 5/27![Southwest logo]()
$219
Find flight deals from Love Field to Caribbean Islands
Keep the following information in mind while searching for Love Field to Caribbean Islands flight deals. Data was last updated May 29, 2026.
Round-trip from | $243 (Southwest) |
|---|---|
One-way from | $128 (Delta) |
Popular in | December |
Cheapest in | October |
Average price | $388 |
Cheapflights Fare Finder
Customize your flight search to find flights from Love Field to Caribbean Islands 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 May 29, 2026.
Use the filters below to find and compare flights from Dallas Love Field Airport to Caribbean Islands that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
DallasNassau
DAL - NAS
DALNAS
Dallas Love Field
Sun 9/6
7:10 pm-12:15 pm
2 stops16h 05m
Nassau Intl
Wed 9/9
1:10 pm-5:25 pm
1 stop5h 15m
$387
DallasSimpson Bay
DAL - SXM
DALSXM
Dallas Love Field
Sun 8/30
6:33 pm-1:53 pm
1 stop18h 20m
Simpson Bay Princess Juliana
Thu 9/17
3:20 pm-10:38 pm
1 stop8h 18m
$413
DallasSimpson Bay
DAL - SXM
DALSXM
Dallas Love Field
Sun 8/30
6:33 pm-1:53 pm
1 stop18h 20m
Simpson Bay Princess Juliana
Wed 9/16
3:20 pm-10:38 pm
1 stop8h 18m
$413
DallasSimpson Bay
DAL - SXM
DALSXM
Dallas Love Field
Sun 8/30
6:33 pm-1:53 pm
1 stop18h 20m
Simpson Bay Princess Juliana
Fri 9/18
3:20 pm-10:38 pm
1 stop8h 18m
$413
DallasSan Juan
DAL - SJU
DALSJU
Dallas Love Field
Thu 8/27
11:40 am-10:10 pm
2 stops9h 30m
San Juan Luis Munoz Marin Intl
Mon 8/31
11:35 am-7:50 pm
2 stops9h 15m
$426
DallasSan Juan
DAL - SJU
DALSJU
Dallas Love Field
Thu 9/24
8:05 pm-9:10 am
1 stop12h 05m
San Juan Luis Munoz Marin Intl
Sun 9/27
5:30 am-4:15 pm
1 stop11h 45m
$426
DallasSan Juan
DAL - SJU
DALSJU
Dallas Love Field
Thu 9/3
11:40 am-10:15 pm
2 stops9h 35m
San Juan Luis Munoz Marin Intl
Mon 9/7
6:30 am-2:40 pm
2 stops9h 10m
$445
DallasSimpson Bay
DAL - SXM
DALSXM
Dallas Love Field
Sun 8/30
6:33 pm-1:53 pm
1 stop18h 20m
Simpson Bay Princess Juliana
Sat 9/19
3:20 pm-10:38 pm
1 stop8h 18m
$448
DallasSan Juan
DAL - SJU
DALSJU
Dallas Love Field
Thu 10/29
11:00 am-8:55 pm
2 stops8h 55m
San Juan Luis Munoz Marin Intl
Tue 11/3
6:45 am-3:05 pm
2 stops10h 20m
$476
DallasNassau
DAL - NAS
DALNAS
Dallas Love Field
Wed 8/26
6:05 am-12:15 pm
1 stop5h 10m
Nassau Intl
Sat 8/29
1:25 pm-8:40 pm
1 stop8h 15m
$482
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Love Field to Caribbean Islands
Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands from Love Field with our price prediction graph.
DAL-NAS
DAL-SXM
DAL-SJU
DAL-KIN
DAL-MBJ
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 Islands
DAL-zzEPX
DAL-NAS
DAL-SXM
DAL-SJU
DAL-KIN
No data available for this route at this time. Please check back soon.
Reviews of airlines servicing Caribbean Islands
Get insights into the airlines that provide service to Caribbean Islands. 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 Islands. Reviews last updated May 29, 2026.
Peruse reviews from past customers who have flown with Southwest and Delta from Dallas Love Field Airport to Caribbean Islands to help guide your decision. Reviews also offer insight into each airline's entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.5
Food
7.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Overall
8.0
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
Entertainment
7.5
Food
7.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Overall
8.0
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
Entertainment
7.5
Food
7.0
Comfort
8.0
Crew
8.6
Boarding
8.1
Overall
8.0
Reviews
1 / 20
10.0
ExcellentWalter,May 2026
LAS - BUR
Related info for your journey
Find useful and relevant information for your journey from Love Field to Caribbean Islands. 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 Islands
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Caribbean Islands by adding a car rental and/or hotel reservation to your travel itinerary.
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Find flights from Love Field to Caribbean Islands, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Love Field and Caribbean Islands flights
Browse other Love Field and Caribbean Islands flight options. Last updated on May 29, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Love Field to Caribbean Islands flights
Consider these flights traveling from Love Field to Caribbean Islands.
Top 2 airlines flying from Love Field to Caribbean Islands
Discover the top 2 airlines that operate flights from Love Field to Caribbean Islands. 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 May 29, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$260 | Average$335 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$360 | Average$821 | FlexibilityNo cancel fee | On-time63% |