$152+ 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 9/7. Fares are subject to change and may not be available on all flights or dates of travel.
SGF — SJU
Jun 3 — Jun 101
Round-trip
1 adult, Economy
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Find cheap flights from Springfield to Caribbean Islands with Cheapflights
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Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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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 May 4, 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 May 4, 2026.
This American Airlines deal was found by Cheapflights users on 4/30. 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 8/247:15 am
SGF
- SJU
1 stop14h 52m
American Airlines
Fri 8/283:44 pm
SJU
- SGF
1 stop18h 16m
American Airlines
Deal found 4/30![American Airlines logo]()
$326
This American Airlines deal was found by Cheapflights users on 5/2. 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 10/116:32 pm
SGF
- MBJ
2 stops18h 08m
American Airlines
Fri 10/165:00 pm
MBJ
- SGF
2 stops19h 20m
American Airlines
Deal found 5/2![American Airlines logo]()
$357
This American Airlines deal was found by Cheapflights users on 4/30. 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 10/197:42 pm
SGF
- SJU
1 stop17h 03m
American Airlines
Tue 10/278:35 am
SJU
- SGF
1 stop10h 14m
American Airlines
Deal found 4/30![American Airlines logo]()
$362
This American Airlines deal was found by Cheapflights users on 5/2. 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 9/266:32 pm
SGF
- SJU
2 stops15h 38m
American Airlines
Fri 10/23:42 pm
SJU
- SGF
1 stop18h 28m
American Airlines
Deal found 5/2![American Airlines logo]()
$406
This American Airlines deal was found by Cheapflights users on 5/1. 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 8/156:16 am
SGF
- SJU
1 stop16h 59m
American Airlines
Sat 8/223:44 pm
SJU
- SGF
1 stop18h 16m
American Airlines
Deal found 5/1![American Airlines logo]()
$438
This Kiwi.com deal was found by Cheapflights users on 4/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/85:37 pm
SGF
- SJU
2 stops26h 11m
Multiple Airlines
Sat 8/155:22 pm
SJU
- SGF
1 stop26h 52m
Multiple Airlines
Deal found 4/30![Multiple Airlines logo]()
$443
This Faresmojo deal was found by Cheapflights users on 4/30. 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 Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/2912:07 pm
SGF
- SJU
1 stop9h 10m
JetBlue
Tue 6/22:48 pm
SJU
- SGF
1 stop8h 31m
JetBlue
Deal found 4/30![JetBlue logo]()
$446
This Delta deal was found by Cheapflights users on 4/29. 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.
Sun 9/206:00 am
SGF
- SJU
1 stop9h 31m
Delta
Sat 9/262:26 pm
SJU
- SGF
1 stop9h 03m
Delta
Deal found 4/29![Delta logo]()
$455
This American Airlines deal was found by Cheapflights users on 5/4. 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 8/177:55 pm
SGF
- PUJ
1 stop17h 16m
American Airlines
Fri 8/214:18 pm
PUJ
- SGF
2 stops18h 45m
American Airlines
Deal found 5/4![American Airlines logo]()
$461
This American Airlines deal was found by Cheapflights users on 4/30. 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 12/66:34 pm
SGF
- PLS
1 stop16h 33m
American Airlines
Fri 12/113:26 pm
PLS
- SGF
2 stops19h 20m
American Airlines
Deal found 4/30![American Airlines logo]()
$466
This United Airlines deal was found by Cheapflights users on 5/3. 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.
Thu 5/76:25 am
SGF
- MBJ
1 stop7h 05m
United Airlines
Sat 5/92:40 pm
MBJ
- SGF
1 stop7h 52m
United Airlines
Deal found 5/3![United Airlines logo]()
$467
This American Airlines deal was found by Cheapflights users on 5/1. 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 8/164:52 pm
SGF
- PLS
1 stop18h 34m
American Airlines
Fri 8/211:27 pm
PLS
- SGF
1 stop8h 25m
American Airlines
Deal found 5/1![American Airlines logo]()
$471
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 May 4, 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 May 4, 2026.
This American Airlines deal was found by Cheapflights users on 5/2. 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 10/116:32 pm
SGF
- MBJ
2 stops18h 08m
American Airlines
Fri 10/165:00 pm
MBJ
- SGF
2 stops19h 20m
American Airlines
Deal found 5/2![American Airlines logo]()
$357
This Kiwi.com deal was found by Cheapflights users on 4/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/85:37 pm
SGF
- SJU
2 stops26h 11m
Multiple Airlines
Sat 8/155:22 pm
SJU
- SGF
1 stop26h 52m
Multiple Airlines
Deal found 4/30![Multiple Airlines logo]()
$443
This Delta deal was found by Cheapflights users on 4/29. 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.
Sun 9/206:00 am
SGF
- SJU
1 stop9h 31m
Delta
Sat 9/262:26 pm
SJU
- SGF
1 stop9h 03m
Delta
Deal found 4/29![Delta logo]()
$455
This United Airlines deal was found by Cheapflights users on 5/1. 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 8/246:35 pm
SGF
- PUJ
2 stops17h 05m
United Airlines
Thu 8/273:35 pm
PUJ
- SGF
2 stops31h 23m
United Airlines
Deal found 5/1![United Airlines logo]()
$638
This American Airlines deal was found by Cheapflights users on 5/1. 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 10/197:42 pm
SGF
- SJU
1 stop17h 03m
American Airlines
Tue 10/278:35 am
SJU
- SGF
1 stop10h 14m
American Airlines
Deal found 5/1![American Airlines logo]()
$366
This American Airlines deal was found by Cheapflights users on 5/4. 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 8/176:43 pm
SGF
- PUJ
2 stops19h 36m
American Airlines
Fri 8/211:44 pm
PUJ
- SGF
2 stops20h 16m
American Airlines
Deal found 5/4![American Airlines logo]()
$461
This Kiwi.com deal was found by Cheapflights users on 4/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/2310:46 am
SGF
- SJU
1 stop12h 51m
Multiple Airlines
Tue 6/306:00 am
SJU
- SGF
2 stops31h 00m
Multiple Airlines
Deal found 4/29![Multiple Airlines logo]()
$541
This American Airlines deal was found by Cheapflights users on 5/1. 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 10/27:48 pm
SGF
- SJU
1 stop18h 14m
American Airlines
Thu 10/83:50 pm
SJU
- SGF
1 stop6h 55m
American Airlines
Deal found 5/1![American Airlines logo]()
$466
This Delta deal was found by Cheapflights users on 5/3. 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 9/76:00 am
SGF
- PLS
1 stop5h 45m
Delta
Tue 9/152:10 pm
PLS
- SGF
1 stop9h 19m
Delta
Deal found 5/3![Delta logo]()
$609
This American Airlines deal was found by Cheapflights users on 5/1. 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 8/164:52 pm
SGF
- PLS
1 stop18h 34m
American Airlines
Fri 8/211:27 pm
PLS
- SGF
1 stop8h 25m
American Airlines
Deal found 5/1![American Airlines logo]()
$471
This United Airlines deal was found by Cheapflights users on 5/2. 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 8/246:35 pm
SGF
- NAS
2 stops17h 58m
United Airlines
Thu 8/272:35 pm
NAS
- SGF
2 stops32h 23m
United Airlines
Deal found 5/2![United Airlines logo]()
$696
This American Airlines deal was found by Cheapflights users on 5/4. 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 10/176:45 pm
SGF
- PUJ
2 stops16h 50m
American Airlines
Sat 10/245:10 pm
PUJ
- SGF
2 stops18h 21m
American Airlines
Deal found 5/4![American Airlines logo]()
$496
This Kiwi.com deal was found by Cheapflights users on 5/1. 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 6/66:23 pm
SGF
- STT
1 stop18h 53m
Multiple Airlines
Sat 6/131:52 pm
STT
- SGF
2 stops30h 28m
Multiple Airlines
Deal found 5/1![Multiple Airlines logo]()
$690
This Delta deal was found by Cheapflights users on 5/1. 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.
Thu 5/286:05 am
SGF
- AUA
1 stop7h 05m
Delta
Thu 6/41:15 pm
AUA
- SGF
1 stop10h 04m
Delta
Deal found 5/1![Delta logo]()
$721
This American Airlines deal was found by Cheapflights users on 5/2. 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 7/176:34 pm
SGF
- PUJ
2 stops17h 14m
American Airlines
Tue 7/285:56 pm
PUJ
- SGF
2 stops17h 58m
American Airlines
Deal found 5/2![American Airlines logo]()
$496
This United Airlines deal was found by Cheapflights users on 4/29. 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.
Fri 8/76:00 am
SGF
- SJU
2 stops14h 24m
United Airlines
Sat 8/81:00 am
SJU
- SGF
2 stops18h 06m
United Airlines
Deal found 4/29![United Airlines logo]()
$776
This American Airlines deal was found by Cheapflights users on 5/1. 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 6/156:43 pm
SGF
- MBJ
2 stops16h 36m
American Airlines
Fri 6/265:17 pm
MBJ
- SGF
2 stops18h 59m
American Airlines
Deal found 5/1![American Airlines logo]()
$520
This United Airlines deal was found by Cheapflights users on 5/4. 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 5/196:25 am
SGF
- STT
1 stop8h 18m
United Airlines
Sat 5/234:00 pm
STT
- SGF
1 stop25h 10m
United Airlines
Deal found 5/4![United Airlines logo]()
$776
This American Airlines deal was found by Cheapflights users on 5/3. 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 7/17:53 pm
SGF
- STT
2 stops19h 07m
American Airlines
Tue 7/74:50 pm
STT
- SGF
2 stops19h 04m
American Airlines
Deal found 5/3![American Airlines logo]()
$524
This United Airlines deal was found by Cheapflights users on 5/3. 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 8/246:35 pm
SGF
- AUA
2 stops19h 45m
United Airlines
Fri 8/284:30 pm
AUA
- SGF
2 stops19h 13m
United Airlines
Deal found 5/3![United Airlines logo]()
$776
This American Airlines deal was found by Cheapflights users on 5/1. 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 5/276:12 pm
SGF
- MBJ
2 stops17h 33m
American Airlines
Mon 6/15:17 pm
MBJ
- SGF
2 stops19h 35m
American Airlines
Deal found 5/1![American Airlines logo]()
$525
This United Airlines deal was found by Cheapflights users on 4/29. 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.
Sun 8/236:35 pm
SGF
- NAS
2 stops39h 53m
United Airlines
Thu 8/272:35 pm
NAS
- SGF
2 stops32h 23m
United Airlines
Deal found 4/29![United Airlines logo]()
$791
This American Airlines deal was found by Cheapflights users on 5/2. 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 7/137:53 pm
SGF
- PLS
2 stops17h 22m
American Airlines
Sat 7/1811:30 am
PLS
- SGF
1 stop12h 10m
American Airlines
Deal found 5/2![American Airlines logo]()
$527
This United Airlines deal was found by Cheapflights users on 4/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/46:15 am
SGF
- AUA
1 stop8h 05m
United Airlines
Wed 7/81:50 pm
AUA
- SGF
1 stop10h 37m
United Airlines
Deal found 4/30![United Airlines logo]()
$801
This United Airlines deal was found by Cheapflights users on 5/1. 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 5/306:35 pm
SGF
- STT
2 stops16h 45m
United Airlines
Sat 6/66:05 pm
STT
- SGF
2 stops21h 27m
United Airlines
Deal found 5/1![United Airlines logo]()
$818
This American Airlines deal was found by Cheapflights users on 5/2. 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 6/56:12 pm
SGF
- PLS
1 stop14h 55m
American Airlines
Wed 6/102:55 pm
PLS
- SGF
2 stops20h 35m
American Airlines
Deal found 5/2![American Airlines logo]()
$562
This American Airlines deal was found by Cheapflights users on 5/3. 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 9/83:01 pm
SGF
- PLS
2 stops20h 04m
American Airlines
Tue 9/152:00 pm
PLS
- SGF
2 stops20h 10m
American Airlines
Deal found 5/3![American Airlines logo]()
$570
This United Airlines deal was found by Cheapflights users on 5/1. 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 5/236:35 pm
SGF
- STT
2 stops16h 45m
United Airlines
Sat 5/306:05 pm
STT
- SGF
2 stops21h 27m
United Airlines
Deal found 5/1![United Airlines logo]()
$862
This American Airlines deal was found by Cheapflights users on 4/30. 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 7/136:12 pm
SGF
- PLS
1 stop17h 21m
American Airlines
Fri 7/173:15 pm
PLS
- SGF
2 stops18h 36m
American Airlines
Deal found 4/30![American Airlines logo]()
$571
This United Airlines deal was found by Cheapflights users on 4/29. 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.
Tue 6/236:00 am
SGF
- SJU
2 stops14h 24m
United Airlines
Tue 6/307:20 am
SJU
- SGF
2 stops17h 22m
United Airlines
Deal found 4/29![United Airlines logo]()
$871
Last-minute flights from Springfield to Caribbean IslandsDiscover last-minute flight deals from Springfield to Caribbean Islands. Data last updated May 4, 2026 and is based on user searches.
Discover last-minute flight deals from Springfield to Caribbean Islands. Data last updated May 4, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 4/29. 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.
Tue 5/56:00 am
SGF
- SJU
1 stop7h 42m
American Airlines
Tue 5/127:25 am
SJU
- SGF
1 stop14h 44m
American Airlines
Deal found 4/29![American Airlines logo]()
$490
This Delta deal was found by Cheapflights users on 4/30. 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 5/53:59 pm
SGF
- SJU
1 stop6h 14m
Delta
Tue 5/127:30 am
SJU
- SGF
1 stop11h 36m
Delta
Deal found 4/30![Delta logo]()
$510
This United Airlines deal was found by Cheapflights users on 5/3. 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.
Thu 5/76:22 pm
SGF
- MBJ
2 stops19h 08m
United Airlines
Sat 5/92:40 pm
MBJ
- SGF
1 stop7h 52m
United Airlines
Deal found 5/3![United Airlines logo]()
$467
This American Airlines deal was found by Cheapflights users on 5/2. 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 5/106:00 am
SGF
- SJU
2 stops11h 10m
American Airlines
Tue 5/1210:03 am
SJU
- SGF
2 stops12h 06m
American Airlines
Deal found 5/2![American Airlines logo]()
$522
This United Airlines deal was found by Cheapflights users on 5/1. 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 5/116:25 am
SGF
- SJU
1 stop8h 17m
United Airlines
Sat 5/231:00 am
SJU
- SGF
2 stops10h 42m
United Airlines
Deal found 5/1![United Airlines logo]()
$486
This American Airlines deal was found by Cheapflights users on 5/1. 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 5/129:54 am
SGF
- SJU
2 stops9h 57m
American Airlines
Thu 5/141:31 pm
SJU
- SGF
2 stops11h 25m
American Airlines
Deal found 5/1![American Airlines logo]()
$550
This American Airlines deal was found by Cheapflights users on 5/1. 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 5/256:12 pm
SGF
- MBJ
2 stops17h 33m
American Airlines
Sat 5/305:17 pm
MBJ
- SGF
2 stops17h 40m
American Airlines
Deal found 5/1![American Airlines logo]()
$520
This American Airlines deal was found by Cheapflights users on 5/1. 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 5/276:12 pm
SGF
- MBJ
2 stops17h 33m
American Airlines
Mon 6/15:17 pm
MBJ
- SGF
2 stops19h 35m
American Airlines
Deal found 5/1![American Airlines logo]()
$525
This Faresmojo deal was found by Cheapflights users on 4/30. 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 Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/2912:07 pm
SGF
- SJU
1 stop9h 10m
JetBlue
Tue 6/22:48 pm
SJU
- SGF
1 stop8h 31m
JetBlue
Deal found 4/30![JetBlue logo]()
$446
This American Airlines deal was found by Cheapflights users on 4/30. 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 6/26:12 pm
SGF
- PUJ
2 stops17h 40m
American Airlines
Tue 6/94:51 pm
PUJ
- SGF
2 stops18h 13m
American Airlines
Deal found 4/30![American Airlines logo]()
$496
This American Airlines deal was found by Cheapflights users on 5/4. 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 6/37:59 pm
SGF
- PLS
2 stops17h 13m
American Airlines
Thu 6/113:12 pm
PLS
- SGF
2 stops19h 52m
American Airlines
Deal found 5/4![American Airlines logo]()
$506
This American Airlines deal was found by Cheapflights users on 5/2. 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 6/56:12 pm
SGF
- PLS
1 stop14h 55m
American Airlines
Wed 6/103:12 pm
PLS
- SGF
1 stop7h 29m
American Airlines
Deal found 5/2![American Airlines logo]()
$557
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 May 4, 2026.
Search for one-way flight options from Springfield to Caribbean Islands. Find affordable one-way fares based on user searches. Data last updated May 4, 2026.
This Delta deal was found by Cheapflights users on 4/29. 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 9/76:00 am
SGF
- MBJ
1 stop9h 34m
Delta
Deal found 4/29![Delta logo]()
$152
This American Airlines deal was found by Cheapflights users on 4/30. 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 9/77:55 pm
SGF
- MBJ
2 stops17h 55m
American Airlines
Deal found 4/30![American Airlines logo]()
$158
This American Airlines deal was found by Cheapflights users on 5/1. 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 6/207:53 pm
SGF
- STT
2 stops19h 04m
American Airlines
Deal found 5/1![American Airlines logo]()
$214
This United Airlines deal was found by Cheapflights users on 5/2. 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.
Wed 5/136:25 am
SGF
- STT
1 stop8h 18m
United Airlines
Deal found 5/2![United Airlines logo]()
$218
This American Airlines deal was found by Cheapflights users on 5/2. 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 5/133:36 pm
SGF
- STT
2 stops18h 59m
American Airlines
Deal found 5/2![American Airlines logo]()
$233
This Delta deal was found by Cheapflights users on 5/1. 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 5/106:05 am
SGF
- STT
1 stop8h 12m
Delta
Deal found 5/1![Delta logo]()
$243
This American Airlines deal was found by Cheapflights users on 5/2. 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 5/241:27 pm
SGF
- SJU
1 stop8h 18m
American Airlines
Deal found 5/2![American Airlines logo]()
$268
This American Airlines deal was found by Cheapflights users on 5/1. 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 6/136:43 pm
SGF
- STT
2 stops15h 20m
American Airlines
Deal found 5/1![American Airlines logo]()
$282
This Delta deal was found by Cheapflights users on 5/1. 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 6/206:00 am
SGF
- STT
1 stop9h 40m
Delta
Deal found 5/1![Delta logo]()
$322
This American Airlines deal was found by Cheapflights users on 5/1. 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 5/105:47 pm
SGF
- STT
2 stops16h 00m
American Airlines
Deal found 5/1![American Airlines logo]()
$348
This Kiwi.com deal was found by Cheapflights users on 4/30. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/206:23 pm
SGF
- SJU
3 stops41h 43m
Multiple Airlines
Deal found 4/30![Multiple Airlines logo]()
$353
This Kiwi.com deal was found by Cheapflights users on 5/1. 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.
Sun 5/1010:24 am
SGF
- STT
3 stops26h 52m
Multiple Airlines
Deal found 5/1![Multiple Airlines logo]()
$722
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 May 4, 2026.
Round-trip from | $326 (American Airlines) |
|---|---|
One-way from | $152 (Delta) |
Popular in | June |
Cheapest in | April |
Average price | $419 |
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 May 4, 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
SpringfieldMontego Bay
SGF - MBJ
SGFMBJ
Springfield-Branson
Sun 10/11
6:32 pm-12:40 pm
2 stops18h 08m
Montego Bay Sangster Intl
Fri 10/16
5:00 pm-12:20 pm
2 stops19h 20m
$357
SpringfieldSan Juan
SGF - SJU
SGFSJU
Springfield-Branson
Mon 10/19
7:42 pm-1:45 pm
1 stop17h 03m
San Juan Luis Munoz Marin Intl
Tue 10/27
8:35 am-5:49 pm
1 stop10h 14m
$366
SpringfieldSan Juan
SGF - SJU
SGFSJU
Springfield-Branson
Sat 8/8
5:37 pm-8:48 pm
2 stops26h 11m
San Juan Luis Munoz Marin Intl
Sat 8/15
5:22 pm-7:14 pm
1 stop26h 52m
$443
SpringfieldSan Juan
SGF - SJU
SGFSJU
Springfield-Branson
Sun 9/20
6:00 am-4:31 pm
1 stop9h 31m
San Juan Luis Munoz Marin Intl
Sat 9/26
2:26 pm-10:29 pm
1 stop9h 03m
$455
SpringfieldPunta Cana
SGF - PUJ
SGFPUJ
Springfield-Branson
Mon 8/17
6:43 pm-3:19 pm
2 stops19h 36m
Punta Cana
Fri 8/21
1:44 pm-9:00 am
2 stops20h 16m
$461
SpringfieldSan Juan
SGF - SJU
SGFSJU
Springfield-Branson
Fri 10/2
7:48 pm-3:02 pm
1 stop18h 14m
San Juan Luis Munoz Marin Intl
Thu 10/8
3:50 pm-9:45 pm
1 stop6h 55m
$466
SpringfieldProvidenciales
SGF - PLS
SGFPLS
Springfield-Branson
Sun 8/16
4:52 pm-12:26 pm
1 stop18h 34m
Providenciales
Fri 8/21
1:27 pm-8:52 pm
1 stop8h 25m
$471
SpringfieldPunta Cana
SGF - PUJ
SGFPUJ
Springfield-Branson
Sat 10/17
6:45 pm-12:35 pm
2 stops16h 50m
Punta Cana
Sat 10/24
5:10 pm-10:31 am
2 stops18h 21m
$496
SpringfieldPunta Cana
SGF - PUJ
SGFPUJ
Springfield-Branson
Fri 7/17
6:34 pm-12:48 pm
2 stops17h 14m
Punta Cana
Tue 7/28
5:56 pm-10:54 am
2 stops17h 58m
$496
SpringfieldMontego Bay
SGF - MBJ
SGFMBJ
Springfield-Branson
Mon 6/15
6:43 pm-11:19 am
2 stops16h 36m
Montego Bay Sangster Intl
Fri 6/26
5:17 pm-12:16 pm
2 stops18h 59m
$520
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-MBJ
SGF-STT
SGF-SJU
SGF-PUJ
SGF-PLS
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-MBJ
SGF-STT
SGF-SJU
SGF-PUJ
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 May 4, 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.
Boarding
8.1
Overall
7.9
Food
7.2
Entertainment
7.8
Comfort
7.9
Crew
8.5
Reviews
1 / 20
4.0
OkayJoel,May 2026
ATL - JAX
Boarding
8.1
Overall
7.9
Food
7.2
Entertainment
7.8
Comfort
7.9
Crew
8.5
Reviews
1 / 20
4.0
OkayJoel,May 2026
ATL - JAX
Boarding
8.1
Overall
7.9
Food
7.2
Entertainment
7.8
Comfort
7.9
Crew
8.5
Reviews
1 / 20
4.0
OkayJoel,May 2026
ATL - JAX
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 May 4, 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 May 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$128 | Average$614 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$257 | Average$430 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$266 | Average$589 | FlexibilityNo cancel fee | On-time71% |