$148+ Cheap flights from Springfield (SGF) 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 8/19. Fares are subject to change and may not be available on all flights or dates of travel.
SGF — SJU
Jul 30 — Aug 61
Round-trip
1 adult, Economy
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Find cheap flights from Springfield to Caribbean Islands with Cheapflights
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Cheapest flights from Springfield to Caribbean IslandsExplore the most affordable flight options available from Springfield to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 30, 2026.
Explore the most affordable flight options available from Springfield to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on June 30, 2026.
This American Airlines deal was found by Cheapflights users on 6/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/256:25 am
SGF
- SJU
2 stops14h 30m
American Airlines
Fri 8/283:44 pm
SJU
- SGF
1 stop18h 16m
American Airlines
Deal found 6/26![American Airlines logo]()
$326
This United Airlines deal was found by Cheapflights users on 6/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/186:25 am
SGF
- SJU
1 stop8h 17m
United Airlines
Tue 8/257:00 am
SJU
- SGF
1 stop8h 16m
United Airlines
Deal found 6/28![United Airlines logo]()
$354
This American Airlines deal was found by Cheapflights users on 6/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/207:36 pm
SGF
- SJU
2 stops17h 18m
American Airlines
Sat 9/263:35 pm
SJU
- SGF
1 stop18h 33m
American Airlines
Deal found 6/28![American Airlines logo]()
$366
This American Airlines deal was found by Cheapflights users on 6/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/137:51 pm
SGF
- MBJ
2 stops17h 37m
American Airlines
Thu 8/205:08 pm
MBJ
- SGF
2 stops17h 49m
American Airlines
Deal found 6/28![American Airlines logo]()
$377
This American Airlines deal was found by Cheapflights users on 6/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/247:36 pm
SGF
- MBJ
2 stops17h 17m
American Airlines
Thu 10/112:05 pm
MBJ
- SGF
1 stop21h 03m
American Airlines
Deal found 6/29![American Airlines logo]()
$383
This American Airlines deal was found by Cheapflights users on 6/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/57:58 pm
SGF
- STT
2 stops17h 27m
American Airlines
Sat 12/126:17 pm
STT
- SGF
2 stops18h 21m
American Airlines
Deal found 6/30![American Airlines logo]()
$414
This American Airlines deal was found by Cheapflights users on 6/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/316:00 am
SGF
- SJU
1 stop7h 54m
American Airlines
Wed 9/96:27 am
SJU
- SGF
2 stops15h 15m
American Airlines
Deal found 6/29![American Airlines logo]()
$426
This Delta deal was found by Cheapflights users on 6/28. 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.
Fri 8/216:06 am
SGF
- SJU
1 stop6h 36m
Delta
Thu 8/272:59 pm
SJU
- SGF
1 stop8h 22m
Delta
Deal found 6/28![Delta logo]()
$433
This American Airlines deal was found by Cheapflights users on 6/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/83:15 pm
SGF
- STT
2 stops20h 43m
American Airlines
Sat 10/171:19 pm
STT
- SGF
2 stops20h 42m
American Airlines
Deal found 6/28![American Airlines logo]()
$433
This American Airlines deal was found by Cheapflights users on 6/25. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/164:23 pm
SGF
- STT
2 stops17h 45m
American Airlines
Thu 2/252:16 pm
STT
- SGF
1 stop10h 14m
American Airlines
Deal found 6/25![American Airlines logo]()
$438
This American Airlines deal was found by Cheapflights users on 6/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/216:00 am
SGF
- SJU
2 stops11h 33m
American Airlines
Thu 8/277:30 am
SJU
- SGF
1 stop14h 12m
American Airlines
Deal found 6/28![American Airlines logo]()
$463
This American Airlines deal was found by Cheapflights users on 6/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/96:22 pm
SGF
- STT
2 stops19h 33m
American Airlines
Sat 10/171:19 pm
STT
- SGF
2 stops20h 42m
American Airlines
Deal found 6/28![American Airlines logo]()
$468
Best flights from Springfield to Caribbean IslandsDiscover carefully curated flight deals from Springfield to Caribbean Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 30, 2026.
Discover carefully curated flight deals from Springfield to Caribbean Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated June 30, 2026.
This American Airlines deal was found by Cheapflights users on 6/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/253:01 pm
SGF
- SJU
1 stop7h 58m
American Airlines
Fri 8/283:44 pm
SJU
- SGF
1 stop18h 16m
American Airlines
Deal found 6/26![American Airlines logo]()
$326
This United Airlines deal was found by Cheapflights users on 6/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/316:25 am
SGF
- SJU
1 stop8h 17m
United Airlines
Wed 9/97:00 am
SJU
- SGF
1 stop10h 11m
United Airlines
Deal found 6/29![United Airlines logo]()
$511
This Kiwi.com deal was found by Cheapflights users on 6/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/256:19 pm
SGF
- SJU
2 stops28h 39m
Multiple Airlines
Fri 7/313:10 am
SJU
- SGF
1 stop15h 19m
Multiple Airlines
Deal found 6/27![Multiple Airlines logo]()
$581
This Delta deal was found by Cheapflights users on 6/28. 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.
Mon 10/266:06 am
SGF
- PUJ
1 stop6h 18m
Delta
Sat 10/312:49 pm
PUJ
- SGF
1 stop7h 30m
Delta
Deal found 6/28![Delta logo]()
$590
This American Airlines deal was found by Cheapflights users on 6/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/246:49 pm
SGF
- MBJ
2 stops18h 04m
American Airlines
Thu 10/15:16 pm
MBJ
- SGF
2 stops15h 52m
American Airlines
Deal found 6/29![American Airlines logo]()
$377
This American Airlines deal was found by Cheapflights users on 6/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/138:04 pm
SGF
- MBJ
1 stop17h 08m
American Airlines
Thu 8/2012:47 pm
MBJ
- SGF
1 stop23h 56m
American Airlines
Deal found 6/28![American Airlines logo]()
$379
This American Airlines deal was found by Cheapflights users on 6/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/207:36 pm
SGF
- SJU
1 stop18h 09m
American Airlines
Sat 9/263:35 pm
SJU
- SGF
1 stop18h 33m
American Airlines
Deal found 6/30![American Airlines logo]()
$406
This American Airlines deal was found by Cheapflights users on 6/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/57:58 pm
SGF
- STT
2 stops17h 27m
American Airlines
Sat 12/126:17 pm
STT
- SGF
2 stops18h 21m
American Airlines
Deal found 6/30![American Airlines logo]()
$414
This United Airlines deal was found by Cheapflights users on 6/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/26:15 pm
SGF
- MBJ
1 stop18h 33m
United Airlines
Thu 11/52:54 pm
MBJ
- SGF
1 stop7h 29m
United Airlines
Deal found 6/27![United Airlines logo]()
$560
This Delta deal was found by Cheapflights users on 6/28. 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.
Wed 10/286:06 am
SGF
- PUJ
1 stop7h 25m
Delta
Fri 10/303:56 pm
PUJ
- SGF
1 stop7h 23m
Delta
Deal found 6/28![Delta logo]()
$590
This American Airlines deal was found by Cheapflights users on 6/25. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/164:23 pm
SGF
- STT
2 stops17h 45m
American Airlines
Thu 2/256:36 pm
STT
- SGF
2 stops17h 28m
American Airlines
Deal found 6/25![American Airlines logo]()
$438
This United Airlines deal was found by Cheapflights users on 6/26. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/186:15 am
SGF
- NAS
1 stop8h 41m
United Airlines
Sat 7/254:58 pm
NAS
- SGF
2 stops18h 46m
United Airlines
Deal found 6/26![United Airlines logo]()
$590
This United Airlines deal was found by Cheapflights users on 6/26. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/86:35 am
SGF
- NAS
1 stop5h 58m
United Airlines
Thu 12/102:35 pm
NAS
- SGF
1 stop7h 53m
United Airlines
Deal found 6/26![United Airlines logo]()
$600
This American Airlines deal was found by Cheapflights users on 6/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/96:22 pm
SGF
- STT
2 stops19h 33m
American Airlines
Sat 10/171:19 pm
STT
- SGF
2 stops20h 42m
American Airlines
Deal found 6/28![American Airlines logo]()
$468
This United Airlines deal was found by Cheapflights users on 6/26. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/266:15 am
SGF
- MBJ
1 stop7h 15m
United Airlines
Sun 8/22:40 pm
MBJ
- SGF
1 stop28h 03m
United Airlines
Deal found 6/26![United Airlines logo]()
$636
This American Airlines deal was found by Cheapflights users on 6/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/173:01 pm
SGF
- SJU
1 stop7h 58m
American Airlines
Mon 8/247:30 am
SJU
- SGF
1 stop14h 12m
American Airlines
Deal found 6/28![American Airlines logo]()
$483
This United Airlines deal was found by Cheapflights users on 6/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/276:15 pm
SGF
- PUJ
1 stop19h 42m
United Airlines
Fri 10/304:10 pm
PUJ
- SGF
3 stops19h 24m
United Airlines
Deal found 6/28![United Airlines logo]()
$673
This American Airlines deal was found by Cheapflights users on 6/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/176:40 pm
SGF
- PUJ
2 stops17h 16m
American Airlines
Sat 10/243:35 pm
PUJ
- SGF
1 stop18h 26m
American Airlines
Deal found 6/28![American Airlines logo]()
$535
This United Airlines deal was found by Cheapflights users on 6/25. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/286:25 pm
SGF
- PUJ
2 stops20h 05m
United Airlines
Thu 10/13:35 pm
PUJ
- SGF
2 stops20h 10m
United Airlines
Deal found 6/25![United Airlines logo]()
$717
This American Airlines deal was found by Cheapflights users on 6/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/277:53 pm
SGF
- STT
2 stops16h 55m
American Airlines
Thu 8/61:48 pm
STT
- SGF
2 stops21h 16m
American Airlines
Deal found 6/28![American Airlines logo]()
$539
This business-class.com deal was found by Cheapflights users on 6/28. 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 business-class.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/36:12 pm
SGF
- MBJ
1 stop17h 13m
Multiple Airlines
Fri 4/304:42 pm
MBJ
- SGF
2 stops17h 42m
Multiple Airlines
Deal found 6/28![Multiple Airlines logo]()
$1,177
This American Airlines deal was found by Cheapflights users on 6/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/76:35 am
SGF
- SJU
2 stops12h 44m
American Airlines
Fri 12/113:38 pm
SJU
- SGF
2 stops10h 14m
American Airlines
Deal found 6/28![American Airlines logo]()
$551
This American Airlines deal was found by Cheapflights users on 6/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/137:51 pm
SGF
- AUA
2 stops18h 19m
American Airlines
Tue 9/222:30 pm
AUA
- SGF
2 stops22h 59m
American Airlines
Deal found 6/30![American Airlines logo]()
$564
This United Airlines deal was found by Cheapflights users on 6/28. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/276:15 am
SGF
- STT
1 stop8h 28m
United Airlines
Thu 8/61:22 pm
STT
- SGF
1 stop27h 58m
United Airlines
Deal found 6/28![United Airlines logo]()
$861
This American Airlines deal was found by Cheapflights users on 6/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/266:12 pm
SGF
- PLS
1 stop17h 21m
American Airlines
Sun 8/23:15 pm
PLS
- SGF
1 stop7h 19m
American Airlines
Deal found 6/26![American Airlines logo]()
$568
This United Airlines deal was found by Cheapflights users on 6/27. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/256:34 pm
SGF
- SJU
2 stops25h 50m
United Airlines
Tue 8/117:00 am
SJU
- SGF
1 stop8h 16m
United Airlines
Deal found 6/27![United Airlines logo]()
$879
This American Airlines deal was found by Cheapflights users on 6/27. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/54:23 pm
SGF
- PUJ
2 stops17h 31m
American Airlines
Sat 12/125:30 pm
PUJ
- SGF
2 stops18h 35m
American Airlines
Deal found 6/27![American Airlines logo]()
$569
This American Airlines deal was found by Cheapflights users on 6/25. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/113:01 pm
SGF
- SJU
1 stop7h 58m
American Airlines
Thu 8/1312:55 am
SJU
- SGF
1 stop10h 09m
American Airlines
Deal found 6/25![American Airlines logo]()
$571
This American Airlines deal was found by Cheapflights users on 6/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/146:25 am
SGF
- PLS
1 stop6h 53m
American Airlines
Fri 8/211:27 pm
PLS
- SGF
1 stop8h 15m
American Airlines
Deal found 6/29![American Airlines logo]()
$603
This American Airlines deal was found by Cheapflights users on 6/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/126:00 am
SGF
- SJU
2 stops14h 55m
American Airlines
Sat 8/1512:55 am
SJU
- SGF
1 stop10h 09m
American Airlines
Deal found 6/28![American Airlines logo]()
$613
Last-minute flights from Springfield to Caribbean IslandsDiscover last-minute flight deals from Springfield to Caribbean Islands. Data last updated June 30, 2026 and is based on user searches.
Discover last-minute flight deals from Springfield to Caribbean Islands. Data last updated June 30, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 6/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/27:10 am
SGF
- SJU
1 stop15h 38m
American Airlines
Sun 7/55:45 am
SJU
- SGF
1 stop15h 46m
American Airlines
Deal found 6/29![American Airlines logo]()
$693
This American Airlines deal was found by Cheapflights users on 6/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/710:43 am
SGF
- SJU
1 stop12h 07m
American Airlines
Mon 7/1312:59 am
SJU
- SGF
1 stop10h 04m
American Airlines
Deal found 6/30![American Airlines logo]()
$545
This Kiwi.com deal was found by Cheapflights users on 6/28. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/116:19 pm
SGF
- PUJ
2 stops15h 21m
Multiple Airlines
Sun 7/198:11 pm
PUJ
- SGF
1 stop12h 50m
Multiple Airlines
Deal found 6/28![Multiple Airlines logo]()
$705
This American Airlines deal was found by Cheapflights users on 6/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/187:20 am
SGF
- NAS
1 stop5h 50m
American Airlines
Sat 7/256:05 pm
NAS
- SGF
1 stop15h 46m
American Airlines
Deal found 6/26![American Airlines logo]()
$586
This United Airlines deal was found by Cheapflights users on 6/26. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/186:15 am
SGF
- NAS
1 stop8h 41m
United Airlines
Sat 7/254:58 pm
NAS
- SGF
2 stops18h 46m
United Airlines
Deal found 6/26![United Airlines logo]()
$590
This Kiwi.com deal was found by Cheapflights users on 6/27. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/256:19 pm
SGF
- SJU
2 stops28h 39m
Multiple Airlines
Fri 7/313:10 am
SJU
- SGF
1 stop15h 19m
Multiple Airlines
Deal found 6/27![Multiple Airlines logo]()
$581
This American Airlines deal was found by Cheapflights users on 6/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/266:12 pm
SGF
- MBJ
2 stops17h 35m
American Airlines
Sun 8/25:14 pm
MBJ
- SGF
2 stops19h 02m
American Airlines
Deal found 6/26![American Airlines logo]()
$542
This American Airlines deal was found by Cheapflights users on 6/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/266:12 pm
SGF
- PLS
1 stop17h 21m
American Airlines
Sun 8/23:15 pm
PLS
- SGF
1 stop7h 19m
American Airlines
Deal found 6/26![American Airlines logo]()
$568
This American Airlines deal was found by Cheapflights users on 6/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/267:53 pm
SGF
- AUA
2 stops19h 16m
American Airlines
Sun 8/25:12 pm
AUA
- SGF
2 stops18h 00m
American Airlines
Deal found 6/26![American Airlines logo]()
$635
This United Airlines deal was found by Cheapflights users on 6/26. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/266:15 am
SGF
- MBJ
1 stop7h 15m
United Airlines
Sun 8/22:40 pm
MBJ
- SGF
1 stop28h 03m
United Airlines
Deal found 6/26![United Airlines logo]()
$636
This American Airlines deal was found by Cheapflights users on 6/25. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/276:12 pm
SGF
- STT
1 stop15h 51m
American Airlines
Thu 8/64:42 pm
STT
- SGF
2 stops18h 22m
American Airlines
Deal found 6/25![American Airlines logo]()
$539
This American Airlines deal was found by Cheapflights users on 6/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/291:23 pm
SGF
- SJU
1 stop8h 36m
American Airlines
Fri 8/712:55 am
SJU
- SGF
1 stop10h 09m
American Airlines
Deal found 6/28![American Airlines logo]()
$733
One-way flights from Springfield to Caribbean IslandsSearch for one-way flight options from Springfield to Caribbean Islands. Find affordable one-way fares based on user searches. Data last updated June 30, 2026.
Search for one-way flight options from Springfield to Caribbean Islands. Find affordable one-way fares based on user searches. Data last updated June 30, 2026.
This Delta deal was found by Cheapflights users on 6/29. 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 8/1911:38 am
SGF
- SJU
1 stop9h 51m
Delta
Deal found 6/29![Delta logo]()
$148
This American Airlines deal was found by Cheapflights users on 6/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/55:06 pm
SGF
- MBJ
2 stops18h 28m
American Airlines
Deal found 6/28![American Airlines logo]()
$162
This American Airlines deal was found by Cheapflights users on 6/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/67:51 pm
SGF
- MBJ
2 stops15h 51m
American Airlines
Deal found 6/28![American Airlines logo]()
$168
This American Airlines deal was found by Cheapflights users on 6/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/196:25 am
SGF
- SJU
2 stops14h 30m
American Airlines
Deal found 6/28![American Airlines logo]()
$171
This American Airlines deal was found by Cheapflights users on 6/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/246:49 pm
SGF
- MBJ
1 stop21h 27m
American Airlines
Deal found 6/29![American Airlines logo]()
$175
This Delta deal was found by Cheapflights users on 6/28. 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.
Mon 12/76:00 am
SGF
- SJU
1 stop9h 25m
Delta
Deal found 6/28![Delta logo]()
$204
This American Airlines deal was found by Cheapflights users on 6/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/85:58 pm
SGF
- SJU
1 stop9h 21m
American Airlines
Deal found 6/28![American Airlines logo]()
$207
This Delta deal was found by Cheapflights users on 6/30. 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 9/16:06 am
SGF
- MBJ
1 stop5h 38m
Delta
Deal found 6/30![Delta logo]()
$232
This American Airlines deal was found by Cheapflights users on 6/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/16:44 pm
SGF
- MBJ
2 stops19h 02m
American Airlines
Deal found 6/28![American Airlines logo]()
$243
This Kiwi.com deal was found by Cheapflights users on 6/26. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/108:42 am
SGF
- SJU
3 stops54h 29m
Multiple Airlines
Deal found 6/26![Multiple Airlines logo]()
$252
This American Airlines deal was found by Cheapflights users on 6/30. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/316:25 am
SGF
- SJU
2 stops14h 30m
American Airlines
Deal found 6/30![American Airlines logo]()
$260
This American Airlines deal was found by Cheapflights users on 6/26. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/103:01 pm
SGF
- SJU
1 stop7h 58m
American Airlines
Deal found 6/26![American Airlines logo]()
$266
Find flight deals from Springfield to Caribbean Islands
Keep the following information in mind while searching for Springfield to Caribbean Islands flight deals. Data was last updated June 30, 2026.
Round-trip from | $326 (American Airlines) |
|---|---|
One-way from | $148 (Delta) |
Popular in | June |
Cheapest in | April |
Average price | $976 |
Cheapflights Fare Finder
Customize your flight search to find flights from Springfield 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 June 30, 2026.
Use the filters below to find and compare flights from Springfield to Caribbean Islands that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
SpringfieldSan Juan
SGF - SJU
SGFSJU
Springfield-Branson
Tue 8/25
3:01 pm-11:59 pm
1 stop7h 58m
San Juan Luis Munoz Marin Intl
Fri 8/28
3:44 pm-9:00 am
1 stop18h 16m
$326
SpringfieldMontego Bay
SGF - MBJ
SGFMBJ
Springfield-Branson
Thu 9/24
6:49 pm-12:53 pm
2 stops18h 04m
Montego Bay Sangster Intl
Thu 10/1
5:16 pm-9:08 am
2 stops15h 52m
$377
SpringfieldMontego Bay
SGF - MBJ
SGFMBJ
Springfield-Branson
Thu 8/13
8:04 pm-1:12 pm
1 stop17h 08m
Montego Bay Sangster Intl
Thu 8/20
12:47 pm-12:43 pm
1 stop23h 56m
$379
SpringfieldSan Juan
SGF - SJU
SGFSJU
Springfield-Branson
Sun 9/20
7:36 pm-2:45 pm
1 stop18h 09m
San Juan Luis Munoz Marin Intl
Sat 9/26
3:35 pm-9:08 am
1 stop18h 33m
$406
SpringfieldSaint Thomas Island
SGF - STT
SGFSTT
Springfield-Branson
Sat 12/5
7:58 pm-3:25 pm
2 stops17h 27m
Saint Thomas Island Cyril E King
Sat 12/12
6:17 pm-10:38 am
2 stops18h 21m
$414
SpringfieldSaint Thomas Island
SGF - STT
SGFSTT
Springfield-Branson
Wed 12/16
4:23 pm-12:08 pm
2 stops17h 45m
Saint Thomas Island Cyril E King
Thu 2/25
6:36 pm-10:04 am
2 stops17h 28m
$438
SpringfieldSaint Thomas Island
SGF - STT
SGFSTT
Springfield-Branson
Fri 10/9
6:22 pm-2:55 pm
2 stops19h 33m
Saint Thomas Island Cyril E King
Sat 10/17
1:19 pm-9:01 am
2 stops20h 42m
$468
SpringfieldSan Juan
SGF - SJU
SGFSJU
Springfield-Branson
Mon 8/17
3:01 pm-11:59 pm
1 stop7h 58m
San Juan Luis Munoz Marin Intl
Mon 8/24
7:30 am-8:42 pm
1 stop14h 12m
$483
SpringfieldSan Juan
SGF - SJU
SGFSJU
Springfield-Branson
Mon 8/31
6:25 am-3:42 pm
1 stop8h 17m
San Juan Luis Munoz Marin Intl
Wed 9/9
7:00 am-4:11 pm
1 stop10h 11m
$511
SpringfieldPunta Cana
SGF - PUJ
SGFPUJ
Springfield-Branson
Sat 10/17
6:40 pm-12:56 pm
2 stops17h 16m
Punta Cana
Sat 10/24
3:35 pm-9:01 am
1 stop18h 26m
$535
Showing 1-10 of 41 resultsSorted by cheapest first
Best time to book a flight from Springfield to Caribbean Islands
Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands from Springfield with our price prediction graph.
SGF-SJU
SGF-MBJ
SGF-STT
SGF-PLS
SGF-NAS
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 Springfield to Caribbean Islands
SGF-zzEPX
SGF-SJU
SGF-MBJ
SGF-STT
SGF-PLS
What is the cheapest month to book a flight from Springfield to Caribbean Islands?
Currently, August is the cheapest month in which you can book a flight from Springfield to Caribbean Islands (average of $209). Flying from Springfield to Caribbean Islands in March is currently the most expensive (average of $599). 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 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 June 30, 2026.
See what other customers who have flown with Delta and American Airlines from Springfield to Caribbean Islands have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.8
Food
7.2
Boarding
8.1
Overall
7.8
Comfort
7.8
Crew
8.5
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Entertainment
7.8
Food
7.2
Boarding
8.1
Overall
7.8
Comfort
7.8
Crew
8.5
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Entertainment
7.8
Food
7.2
Boarding
8.1
Overall
7.8
Comfort
7.8
Crew
8.5
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Related info for your journey
Find useful and relevant information for your journey from Springfield 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 Springfield 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.
Search flights from Springfield to Caribbean Islands by cabin class
Find flights from Springfield to Caribbean Islands, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Springfield and Caribbean Islands flights
Browse other Springfield and Caribbean Islands flight options. Last updated on June 30, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Springfield to Caribbean Islands flights
Consider these flights traveling from Springfield to Caribbean Islands.
Top 3 airlines flying from Springfield to Caribbean Islands
Discover the top 3 airlines that operate flights from Springfield 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 June 30, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$128 | Average$586 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$257 | Average$430 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$268 | Average$591 | FlexibilityNo cancel fee | On-time71% |