$188+ 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 9/6. Fares are subject to change and may not be available on all flights or dates of travel.
SGF — SJU
Sep 24 — Oct 11
Round-trip
1 adult, Economy
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Find cheap flights from Springfield to Caribbean Islands with Cheapflights
1. Tell us where you want to go
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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Springfield to Caribbean Islands
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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 August 25, 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 August 25, 2026.
This Delta deal was found by Cheapflights users on 8/24. 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.
Sun 9/206:08 am -
1 stop9h 41m
Sat 9/262:50 pm -
1 stop7h 26m
Deal found 8/24![Delta logo]()
$356
This American Airlines deal was found by Cheapflights users on 8/21. 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 -
2 stops17h 21m
Sat 9/263:35 pm -
1 stop18h 33m
Deal found 8/21![American Airlines logo]()
$366
This American Airlines deal was found by Cheapflights users on 8/24. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/283:15 pm -
2 stops17h 31m
Mon 11/24:59 pm -
1 stop17h 26m
Deal found 8/24![American Airlines logo]()
$371
This American Airlines deal was found by Cheapflights users on 8/24. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/126:35 pm -
2 stops13h 07m
Thu 11/194:42 pm -
1 stop7h 10m
Deal found 8/24![American Airlines logo]()
$406
This American Airlines deal was found by Cheapflights users on 8/25. 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.
Thu 11/57:59 pm -
2 stops17h 29m
Sun 11/86:09 pm -
2 stops18h 47m
Deal found 8/25![American Airlines logo]()
$422
This United Airlines deal was found by Cheapflights users on 8/25. 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.
Thu 11/56:40 pm -
1 stop18h 08m
Sun 11/83:45 pm -
1 stop7h 14m
Deal found 8/25![United Airlines logo]()
$434
This American Airlines deal was found by Cheapflights users on 8/25. 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.
Thu 9/245:35 pm -
2 stops18h 16m
Sun 10/41:41 pm -
2 stops21h 21m
Deal found 8/25![American Airlines logo]()
$434
This American Airlines deal was found by Cheapflights users on 8/21. 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 9/267:51 pm -
2 stops17h 35m
Wed 9/301:07 pm -
2 stops21h 01m
Deal found 8/21![American Airlines logo]()
$440
This United Airlines deal was found by Cheapflights users on 8/24. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/246:00 am -
1 stop7h 44m
Tue 10/271:05 am -
2 stops14h 28m
Deal found 8/24![United Airlines logo]()
$446
This American Airlines deal was found by Cheapflights users on 8/21. 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 12/95:40 pm -
2 stops14h 02m
Mon 12/143:53 pm -
2 stops9h 59m
Deal found 8/21![American Airlines logo]()
$451
This American Airlines deal was found by Cheapflights users on 8/25. 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.
Thu 9/245:35 pm -
2 stops18h 16m
Thu 10/11:41 pm -
2 stops23h 48m
Deal found 8/25![American Airlines logo]()
$453
This American Airlines deal was found by Cheapflights users on 8/22. 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 9/112:25 pm -
2 stops17h 59m
Thu 9/244:19 pm -
1 stop17h 49m
Deal found 8/22![American Airlines logo]()
$461
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 August 25, 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 August 25, 2026.
This Delta deal was found by Cheapflights users on 8/21. 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 9/206:08 am -
1 stop9h 41m
Sat 9/2612:56 pm -
1 stop9h 20m
Deal found 8/21![Delta logo]()
$356
This United Airlines deal was found by Cheapflights users on 8/25. 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.
Tue 1/268:00 am -
2 stops11h 26m
Sat 1/307:45 am -
1 stop10h 18m
Deal found 8/25![United Airlines logo]()
$356
This American Airlines deal was found by Cheapflights users on 8/20. 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 10/156:22 pm -
2 stops14h 24m
Wed 10/216:20 am -
2 stops9h 24m
Deal found 8/20![American Airlines logo]()
$366
This American Airlines deal was found by Cheapflights users on 8/20. 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 -
2 stops17h 21m
Sat 9/263:35 pm -
1 stop18h 33m
Deal found 8/20![American Airlines logo]()
$366
This American Airlines deal was found by Cheapflights users on 8/24. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/283:15 pm -
2 stops17h 31m
Mon 11/24:59 pm -
1 stop17h 26m
Deal found 8/24![American Airlines logo]()
$371
This Delta deal was found by Cheapflights users on 8/24. 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.
Wed 1/66:00 am -
1 stop8h 25m
Thu 1/142:20 pm -
1 stop9h 12m
Deal found 8/24![Delta logo]()
$413
This United Airlines deal was found by Cheapflights users on 8/25. 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.
Thu 11/56:40 pm -
1 stop18h 08m
Sun 11/83:45 pm -
1 stop7h 14m
Deal found 8/25![United Airlines logo]()
$434
This United Airlines deal was found by Cheapflights users on 8/24. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/246:00 am -
1 stop7h 44m
Tue 10/271:05 am -
2 stops14h 28m
Deal found 8/24![United Airlines logo]()
$446
This American Airlines deal was found by Cheapflights users on 8/21. 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 1/56:34 pm -
1 stop16h 09m
Tue 1/124:16 pm -
2 stops19h 43m
Deal found 8/21![American Airlines logo]()
$418
This American Airlines deal was found by Cheapflights users on 8/25. 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.
Thu 11/57:59 pm -
2 stops17h 29m
Sun 11/86:09 pm -
2 stops18h 47m
Deal found 8/25![American Airlines logo]()
$422
This United deal was found by Cheapflights users on 8/22. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/96:25 am -
2 stops26h 49m
Sun 9/135:40 pm -
2 stops23h 31m
Deal found 8/22![Multiple Airlines logo]()
$1,133
This American Airlines deal was found by Cheapflights users on 8/24. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/67:58 pm -
2 stops17h 15m
Wed 1/131:16 pm -
1 stop9h 58m
Deal found 8/24![American Airlines logo]()
$423
This United Airlines deal was found by Cheapflights users on 8/22. 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 2/16:15 pm -
1 stop18h 31m
Fri 2/52:48 pm -
1 stop7h 35m
Deal found 8/22![United Airlines logo]()
$541
This Delta deal was found by Cheapflights users on 8/24. 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.
Sat 10/176:00 am -
1 stop7h 40m
Sat 10/241:10 pm -
1 stop9h 09m
Deal found 8/24![Delta logo]()
$630
This American Airlines deal was found by Cheapflights users on 8/25. 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.
Thu 9/245:35 pm -
2 stops18h 16m
Thu 10/11:41 pm -
2 stops23h 48m
Deal found 8/25![American Airlines logo]()
$453
This United Airlines deal was found by Cheapflights users on 8/22. 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 12/66:15 pm -
2 stops18h 33m
Wed 12/92:40 pm -
1 stop8h 18m
Deal found 8/22![United Airlines logo]()
$642
This Delta deal was found by Cheapflights users on 8/23. 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 10/316:00 am -
1 stop6h 30m
Sat 11/72:10 pm -
1 stop9h 09m
Deal found 8/23![Delta logo]()
$745
This American Airlines deal was found by Cheapflights users on 8/21. 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 1/68:26 am -
1 stop7h 44m
Tue 1/123:17 pm -
1 stop8h 20m
Deal found 8/21![American Airlines logo]()
$509
This Delta deal was found by Cheapflights users on 8/21. 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 10/166:00 am -
1 stop5h 40m
Tue 10/202:05 pm -
1 stop9h 14m
Deal found 8/21![Delta logo]()
$750
This American Airlines deal was found by Cheapflights users on 8/22. 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 11/182:55 pm -
2 stops19h 17m
Sat 11/213:15 pm -
1 stop8h 39m
Deal found 8/22![American Airlines logo]()
$523
This United Airlines deal was found by Cheapflights users on 8/23. 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 1/96:35 am -
1 stop7h 39m
Sat 1/164:25 pm -
1 stop20h 09m
Deal found 8/23![United Airlines logo]()
$730
This Delta deal was found by Cheapflights users on 8/21. 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 9/266:06 am -
1 stop5h 34m
Wed 9/302:05 pm -
1 stop9h 03m
Deal found 8/21![Delta logo]()
$759
This American Airlines deal was found by Cheapflights users on 8/24. 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 American Airlines is selected, and click “Compare selected ” under the list of providers to see comparable flight deals.
Tue 1/125:39 pm -
1 stop17h 04m
Tue 1/191:16 pm -
1 stop22h 43m
Deal found 8/24![American Airlines logo]()
$531
This United Airlines deal was found by Cheapflights users on 8/20. 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 10/266:40 pm -
2 stops17h 40m
Thu 10/295:06 pm -
2 stops22h 27m
Deal found 8/20![United Airlines logo]()
$736
This United Airlines deal was found by Cheapflights users on 8/23. 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 10/3111:12 am -
2 stops29h 16m
Sat 11/73:25 pm -
2 stops21h 11m
Deal found 8/23![United Airlines logo]()
$753
This American Airlines deal was found by Cheapflights users on 8/20. 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 11/13:46 pm -
2 stops20h 24m
Sun 11/87:00 am -
2 stops18h 52m
Deal found 8/20![American Airlines logo]()
$566
This Delta deal was found by Cheapflights users on 8/22. 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 9/66:06 am -
1 stop6h 28m
Thu 9/102:52 pm -
1 stop8h 16m
Deal found 8/22![Delta logo]()
$850
This American Airlines deal was found by Cheapflights users on 8/21. 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 9/265:35 pm -
1 stop19h 44m
Wed 9/301:07 pm -
2 stops21h 01m
Deal found 8/21![American Airlines logo]()
$569
This United Airlines deal was found by Cheapflights users on 8/23. 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 10/276:40 pm -
2 stops41h 40m
Fri 10/305:06 pm -
2 stops18h 30m
Deal found 8/23![United Airlines logo]()
$777
This Delta deal was found by Cheapflights users on 8/23. 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 10/76:00 am -
1 stop5h 40m
Wed 10/142:05 pm -
1 stop9h 14m
Deal found 8/23![Delta logo]()
$917
Last-minute flights from Springfield to Caribbean IslandsDiscover last-minute flight deals from Springfield to Caribbean Islands. Data last updated August 25, 2026 and is based on user searches.
Discover last-minute flight deals from Springfield to Caribbean Islands. Data last updated August 25, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 8/22. 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 9/96:00 am -
2 stops13h 47m
Wed 9/166:00 am -
2 stops16h 37m
Deal found 8/22![American Airlines logo]()
$466
This American Airlines deal was found by Cheapflights users on 8/21. 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 9/105:35 pm -
2 stops19h 18m
Wed 9/162:09 pm -
2 stops18h 59m
Deal found 8/21![American Airlines logo]()
$476
This American Airlines deal was found by Cheapflights users on 8/22. 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 9/112:25 pm -
2 stops17h 59m
Thu 9/244:19 pm -
1 stop17h 49m
Deal found 8/22![American Airlines logo]()
$461
This American Airlines deal was found by Cheapflights users on 8/21. 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 9/136:29 pm -
2 stops15h 31m
Sun 9/206:00 am -
2 stops12h 56m
Deal found 8/21![American Airlines logo]()
$536
This American Airlines deal was found by Cheapflights users on 8/23. 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 9/157:51 pm -
2 stops18h 48m
Mon 9/214:40 pm -
2 stops18h 28m
Deal found 8/23![American Airlines logo]()
$557
This Delta deal was found by Cheapflights users on 8/21. 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 9/186:08 am -
1 stop9h 41m
Fri 9/257:00 am -
1 stop8h 34m
Deal found 8/21![Delta logo]()
$578
This Delta deal was found by Cheapflights users on 8/24. 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.
Sun 9/206:08 am -
1 stop9h 41m
Sat 9/262:50 pm -
1 stop7h 26m
Deal found 8/24![Delta logo]()
$356
This American Airlines deal was found by Cheapflights users on 8/21. 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 -
2 stops17h 21m
Sat 9/263:35 pm -
1 stop18h 33m
Deal found 8/21![American Airlines logo]()
$366
This American Airlines deal was found by Cheapflights users on 8/23. 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 9/215:35 pm -
2 stops17h 32m
Mon 9/281:07 pm -
2 stops21h 01m
Deal found 8/23![American Airlines logo]()
$568
This American Airlines deal was found by Cheapflights users on 8/25. 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.
Thu 9/245:35 pm -
2 stops18h 16m
Sun 10/41:41 pm -
2 stops21h 21m
Deal found 8/25![American Airlines logo]()
$434
This American Airlines deal was found by Cheapflights users on 8/25. 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.
Thu 9/245:35 pm -
2 stops18h 16m
Thu 10/11:41 pm -
2 stops23h 48m
Deal found 8/25![American Airlines logo]()
$453
This American Airlines deal was found by Cheapflights users on 8/21. 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 9/267:51 pm -
2 stops17h 35m
Wed 9/301:07 pm -
2 stops21h 01m
Deal found 8/21![American Airlines logo]()
$440
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 August 25, 2026.
Search for one-way flight options from Springfield to Caribbean Islands. Find affordable one-way fares based on user searches. Data last updated August 25, 2026.
This American Airlines deal was found by Cheapflights users on 8/21. 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 -
2 stops15h 51m
Deal found 8/21![American Airlines logo]()
$188
This American Airlines deal was found by Cheapflights users on 8/21. 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 9/76:44 pm -
2 stops19h 05m
Deal found 8/21![American Airlines logo]()
$247
This American Airlines deal was found by Cheapflights users on 8/22. 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 8/316:44 pm -
2 stops18h 44m
Deal found 8/22![American Airlines logo]()
$283
This American Airlines deal was found by Cheapflights users on 8/25. 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.
Sat 9/56:44 pm -
1 stop21h 24m
Deal found 8/25![American Airlines logo]()
$335
This American Airlines deal was found by Cheapflights users on 8/21. 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 12/157:14 am -
2 stops13h 25m
Deal found 8/21![American Airlines logo]()
$362
This American Airlines deal was found by Cheapflights users on 8/24. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/234:14 pm -
2 stops16h 58m
Deal found 8/24![American Airlines logo]()
$368
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 August 25, 2026.
Round-trip from | $356 (Delta) |
|---|---|
One-way from | $188 (American Airlines) |
Popular in | June |
Cheapest in | April |
Average price | $491 |
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 7,457,451 searches. Data last updated August 25, 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 Springfield-Branson - SJU San Juan Luis Munoz Marin Intl
SGFSJU
Springfield-Branson
Sun 9/20
6:08 am-4:49 pm
1 stop9h 41m
San Juan Luis Munoz Marin Intl
Sat 9/26
12:56 pm-9:16 pm
1 stop9h 20m
$356
SpringfieldSan Juan
SGF Springfield-Branson - SJU San Juan Luis Munoz Marin Intl
SGFSJU
Springfield-Branson
Tue 1/26
8:00 am-9:26 pm
2 stops11h 26m
San Juan Luis Munoz Marin Intl
Sat 1/30
7:45 am-4:03 pm
1 stop10h 18m
$356
SpringfieldSan Juan
SGF Springfield-Branson - SJU San Juan Luis Munoz Marin Intl
SGFSJU
Springfield-Branson
Thu 10/15
6:22 pm-9:46 am
2 stops14h 24m
San Juan Luis Munoz Marin Intl
Wed 10/21
6:20 am-2:44 pm
2 stops9h 24m
$366
SpringfieldSan Juan
SGF Springfield-Branson - SJU San Juan Luis Munoz Marin Intl
SGFSJU
Springfield-Branson
Sun 9/20
7:36 pm-1:57 pm
2 stops17h 21m
San Juan Luis Munoz Marin Intl
Sat 9/26
3:35 pm-9:08 am
1 stop18h 33m
$366
SpringfieldSan Juan
SGF Springfield-Branson - SJU San Juan Luis Munoz Marin Intl
SGFSJU
Springfield-Branson
Wed 10/28
3:15 pm-9:46 am
2 stops17h 31m
San Juan Luis Munoz Marin Intl
Mon 11/2
4:59 pm-8:25 am
1 stop17h 26m
$371
SpringfieldMontego Bay
SGF Springfield-Branson - MBJ Montego Bay Sangster Intl
SGFMBJ
Springfield-Branson
Wed 1/6
6:00 am-3:25 pm
1 stop8h 25m
Montego Bay Sangster Intl
Thu 1/14
2:20 pm-10:32 pm
1 stop9h 12m
$413
SpringfieldMontego Bay
SGF Springfield-Branson - MBJ Montego Bay Sangster Intl
SGFMBJ
Springfield-Branson
Tue 1/5
6:34 pm-11:43 am
1 stop16h 09m
Montego Bay Sangster Intl
Tue 1/12
4:16 pm-10:59 am
2 stops19h 43m
$418
SpringfieldMontego Bay
SGF Springfield-Branson - MBJ Montego Bay Sangster Intl
SGFMBJ
Springfield-Branson
Thu 11/5
7:59 pm-2:28 pm
2 stops17h 29m
Montego Bay Sangster Intl
Sun 11/8
6:09 pm-11:56 am
2 stops18h 47m
$422
SpringfieldMontego Bay
SGF Springfield-Branson - MBJ Montego Bay Sangster Intl
SGFMBJ
Springfield-Branson
Wed 1/6
7:58 pm-2:13 pm
2 stops17h 15m
Montego Bay Sangster Intl
Wed 1/13
1:16 pm-10:14 pm
1 stop9h 58m
$423
SpringfieldMontego Bay
SGF Springfield-Branson - MBJ Montego Bay Sangster Intl
SGFMBJ
Springfield-Branson
Thu 11/5
6:40 pm-1:48 pm
1 stop18h 08m
Montego Bay Sangster Intl
Sun 11/8
3:45 pm-9:59 pm
1 stop7h 14m
$434
Showing 1-10 of 34 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-PUJ
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-PUJ
What is the cheapest month to book a flight from Springfield to Caribbean Islands?
Currently, February is the cheapest month in which you can book a flight from Springfield to Caribbean Islands (average of $507). Flying from Springfield to Caribbean Islands in March is currently the most expensive (average of $1,060). 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 August 25, 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
Comfort
7.8
Food
7.2
Crew
8.5
Entertainment
7.8
Overall
7.8
Reviews
1 / 20
8.0
ExcellentJorge,Aug 2026
TPA - ATL
Boarding
8.1
Comfort
7.8
Food
7.2
Crew
8.5
Entertainment
7.8
Overall
7.8
Reviews
1 / 20
8.0
ExcellentJorge,Aug 2026
TPA - ATL
Boarding
8.1
Comfort
7.8
Food
7.2
Crew
8.5
Entertainment
7.8
Overall
7.8
Reviews
1 / 20
8.0
ExcellentJorge,Aug 2026
TPA - ATL
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 August 25, 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 7,457,451 searches. Data last updated August 25, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$128 | Average$595 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$257 | Average$430 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$268 | Average$609 | FlexibilityNo cancel fee | On-time71% |