$87+ Cheap flights from Indiana 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 3/3. Fares are subject to change and may not be available on all flights or dates of travel.
IND — SJU
Mar 14 — Mar 211
1 adult, Economy
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Find cheap flights from Indiana 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
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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 Indiana to Caribbean Islands
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Cheapest flights from Indiana to Caribbean IslandsExplore the most affordable flight options available from Indiana to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 12, 2026.
Explore the most affordable flight options available from Indiana to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 12, 2026.
This Spirit deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/2012:18 pm
ORD
- SJU
Nonstop4h 36m
Spirit Airlines
Thu 4/2312:30 pm
SJU
- ORD
Nonstop5h 08m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$179
This Cheapflightsfares deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/15:15 am
ORD
- SJU
1 stop8h 16m
Spirit Airlines
Thu 3/511:52 am
SJU
- ORD
1 stop8h 26m
Spirit Airlines
Deal found 2/11![Spirit Airlines logo]()
$181
This CheapOair deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/2212:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Thu 2/2611:52 am
SJU
- ORD
1 stop8h 26m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$182
This CheapOair deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/2312:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Fri 2/274:31 pm
SJU
- ORD
1 stop9h 16m
Spirit Airlines
Deal found 2/12![Spirit Airlines logo]()
$183
This Kiwi.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 5/91:27 pm
ORD
- SJU
1 stop22h 06m
Frontier
Fri 5/156:00 am
SJU
- ORD
1 stop17h 57m
Frontier
Deal found 2/10![Frontier logo]()
$184
This Kiwi.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 2/2412:17 pm
ORD
- SJU
Nonstop4h 32m
Multiple Airlines
Mon 3/93:22 pm
SJU
- ORD
1 stop8h 17m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$185
This Cheapflightsfares deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/212:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Thu 3/511:52 am
SJU
- ORD
1 stop8h 26m
Spirit Airlines
Deal found 2/12![Spirit Airlines logo]()
$186
This Kiwi.com deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” 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 2/2312:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Thu 3/511:52 am
SJU
- ORD
1 stop8h 26m
Spirit Airlines
Deal found 2/12![Spirit Airlines logo]()
$187
This Kiwi.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 4/710:55 am
ORD
- SJU
1 stop12h 03m
Spirit Airlines
Thu 4/91:29 am
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$188
This Kiwi.com deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 2/236:00 am
MDW
- SJU
1 stop30h 22m
Multiple Airlines
Thu 2/266:27 pm
SJU
- MDW
1 stop26h 11m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$188
This Priceline deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/1310:55 am
ORD
- SJU
1 stop12h 03m
Multiple Airlines
Fri 4/173:42 pm
SJU
- ORD
1 stop9h 16m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$189
This Kiwi.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 4/712:29 pm
ORD
- SJU
Nonstop4h 31m
Spirit Airlines
Mon 4/131:29 am
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$190
Best flights from Indiana to Caribbean IslandsDiscover carefully curated flight deals from Indiana to Caribbean Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 12, 2026.
Discover carefully curated flight deals from Indiana to Caribbean Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 12, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/212:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Thu 3/512:32 pm
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Deal found 2/12![Spirit Airlines logo]()
$187
This Kiwi.com deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” 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 5/1112:18 pm
ORD
- SJU
Nonstop4h 36m
Multiple Airlines
Sat 5/168:41 am
SJU
- ORD
1 stop16h 18m
Multiple Airlines
Deal found 2/12![Multiple Airlines logo]()
$193
This Priceline deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/115:30 am
CVG
- SJU
1 stop19h 21m
Frontier
Fri 4/173:08 am
SJU
- CVG
1 stop10h 36m
Frontier
Deal found 2/12![Frontier logo]()
$212
This Delta deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” 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 4/2112:53 pm
MDW
- SJU
1 stop6h 31m
Delta
Wed 4/292:34 pm
SJU
- MDW
1 stop8h 54m
Delta
Deal found 2/12![Delta logo]()
$246
This United Airlines deal was found by Cheapflights users on 2/8. Clicking the “Pick Dates” 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 3/16:10 pm
IND
- SJU
2 stops11h 01m
United Airlines
Wed 3/48:30 am
SJU
- IND
1 stop7h 28m
United Airlines
Deal found 2/8![United Airlines logo]()
$256
This American Airlines deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” 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 3/3011:02 am
IND
- SJU
1 stop11h 56m
American Airlines
Tue 4/77:00 pm
SJU
- IND
1 stop16h 26m
American Airlines
Deal found 2/12![American Airlines logo]()
$266
This Southwest deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/21:25 pm
MDW
- SJU
1 stop8h 40m
Southwest
Thu 3/56:30 am
SJU
- MDW
1 stop9h 05m
Southwest
Deal found 2/10![Southwest logo]()
$266
This Air Canada deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/188:40 pm
ORD
- MBJ
1 stop14h 40m
Air Canada
Tue 6/2312:30 pm
MBJ
- ORD
2 stops19h 05m
Air Canada
Deal found 2/10![Air Canada logo]()
$381
This Orbitz deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/288:15 am
ORD
- SJU
1 stop16h 38m
Multiple Airlines
Wed 3/412:32 pm
SJU
- ORD
Nonstop5h 16m
Multiple Airlines
Deal found 2/12![Multiple Airlines logo]()
$197
This Priceline deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/314:33 pm
MDW
- SJU
1 stop8h 30m
Frontier
Fri 4/106:00 am
SJU
- MDW
1 stop9h 01m
Frontier
Deal found 2/12![Frontier logo]()
$223
This Delta deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” 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 4/2010:43 am
MDW
- SJU
1 stop8h 41m
Delta
Wed 4/292:34 pm
SJU
- MDW
1 stop8h 54m
Delta
Deal found 2/12![Delta logo]()
$246
This Kiwi.com deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” 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 3/16:15 am
MDW
- SJU
1 stop17h 54m
Multiple Airlines
Wed 3/46:27 pm
SJU
- MDW
2 stops21h 59m
Multiple Airlines
Deal found 2/12![Multiple Airlines logo]()
$230
This eDestinos deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/288:50 pm
CVG
- SJU
1 stop28h 19m
Frontier
Sat 3/73:53 am
SJU
- CVG
1 stop27h 30m
Frontier
Deal found 2/12![Frontier logo]()
$230
This United Airlines deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” 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 4/208:49 am
ORD
- SJU
Nonstop4h 55m
United Airlines
Fri 4/247:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
Deal found 2/12![United Airlines logo]()
$260
This CheapOair deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/88:16 pm
ORD
- STT
2 stops16h 15m
Spirit Airlines
Tue 3/174:35 pm
STT
- ORD
2 stops25h 21m
Spirit Airlines
Deal found 2/12![Spirit Airlines logo]()
$277
This Delta deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 4/266:00 am
IND
- SJU
1 stop10h 23m
Delta
Wed 5/65:34 pm
SJU
- IND
1 stop7h 07m
Delta
Deal found 2/9![Delta logo]()
$256
This Expedia deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/1011:19 am
MDW
- SJU
1 stop13h 44m
Frontier
Fri 3/136:30 am
SJU
- MDW
1 stop18h 21m
Frontier
Deal found 2/12![Frontier logo]()
$239
This United Airlines deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 4/211:50 pm
IND
- SJU
2 stops10h 00m
United Airlines
Wed 4/294:55 pm
SJU
- IND
1 stop7h 02m
United Airlines
Deal found 2/11![United Airlines logo]()
$266
This CheapOair deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/148:24 pm
ORD
- SJU
1 stop17h 18m
Multiple Airlines
Mon 5/1812:30 pm
SJU
- ORD
Nonstop5h 08m
Multiple Airlines
Deal found 2/12![Multiple Airlines logo]()
$246
This Delta deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 5/132:59 pm
ORD
- SJU
1 stop6h 18m
Delta
Sun 5/2412:50 pm
SJU
- ORD
1 stop12h 09m
Delta
Deal found 2/10![Delta logo]()
$256
This United Airlines deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 4/267:15 am
IND
- SJU
1 stop7h 29m
United Airlines
Thu 4/307:20 am
SJU
- IND
2 stops10h 32m
United Airlines
Deal found 2/10![United Airlines logo]()
$266
This Frontier deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/239:14 am
MDW
- SJU
1 stop12h 34m
Frontier
Sat 4/253:18 pm
SJU
- MDW
1 stop8h 01m
Frontier
Deal found 2/12![Frontier logo]()
$244
This Delta deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 5/179:44 am
ORD
- SJU
1 stop11h 33m
Delta
Sat 5/237:00 am
SJU
- ORD
1 stop11h 35m
Delta
Deal found 2/10![Delta logo]()
$256
This United Airlines deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 2/248:35 am
CVG
- SJU
2 stops11h 51m
United Airlines
Wed 2/257:40 am
SJU
- CVG
1 stop8h 56m
United Airlines
Deal found 2/10![United Airlines logo]()
$271
This Expedia deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/278:49 pm
CVG
- SJU
1 stop21h 54m
Frontier
Fri 3/63:19 pm
SJU
- CVG
1 stop10h 22m
Frontier
Deal found 2/12![Frontier logo]()
$254
This Delta deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 5/58:15 am
ORD
- SJU
1 stop7h 08m
Delta
Fri 5/1512:50 pm
SJU
- ORD
1 stop12h 09m
Delta
Deal found 2/10![Delta logo]()
$256
This CheapOair deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/78:16 pm
ORD
- STT
1 stop17h 18m
Spirit Airlines
Sat 3/142:36 pm
STT
- ORD
1 stop27h 20m
Spirit Airlines
Deal found 2/12![Spirit Airlines logo]()
$344
This CheapOair deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/253:12 pm
IND
- SJU
1 stop6h 57m
Multiple Airlines
Tue 3/33:53 am
SJU
- IND
1 stop9h 35m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$291
This United Airlines deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” 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 2/196:25 am
CVG
- SJU
1 stop9h 11m
United Airlines
Mon 2/237:40 am
SJU
- CVG
1 stop8h 56m
United Airlines
Deal found 2/12![United Airlines logo]()
$276
This Delta deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 4/218:15 am
ORD
- SJU
1 stop7h 08m
Delta
Thu 4/306:15 am
SJU
- ORD
1 stop7h 59m
Delta
Deal found 2/10![Delta logo]()
$256
Last-minute flights from Indiana to Caribbean IslandsDiscover last-minute flight deals from Indiana to Caribbean Islands. Data last updated February 12, 2026 and is based on user searches.
Discover last-minute flight deals from Indiana to Caribbean Islands. Data last updated February 12, 2026 and is based on user searches.
This CheapOair deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/2212:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Thu 2/2611:52 am
SJU
- ORD
1 stop8h 26m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$182
This CheapOair deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/2312:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Fri 2/274:31 pm
SJU
- ORD
1 stop9h 16m
Spirit Airlines
Deal found 2/12![Spirit Airlines logo]()
$183
This Kiwi.com deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 2/2312:17 pm
ORD
- SJU
Nonstop4h 32m
Multiple Airlines
Wed 2/254:06 pm
SJU
- ORD
2 stops32h 59m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$187
This Kiwi.com deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” 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 2/236:00 am
MDW
- SJU
1 stop30h 22m
Multiple Airlines
Thu 2/266:27 pm
SJU
- MDW
1 stop26h 11m
Multiple Airlines
Deal found 2/9![Multiple Airlines logo]()
$188
This Kiwi.com deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” 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 2/2312:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Thu 3/512:32 pm
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Deal found 2/12![Spirit Airlines logo]()
$189
This Kiwi.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 2/236:00 am
MDW
- SJU
1 stop30h 22m
Multiple Airlines
Wed 2/254:06 pm
SJU
- MDW
1 stop26h 10m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$191
This Kiwi.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 2/2412:17 pm
ORD
- SJU
Nonstop4h 32m
Multiple Airlines
Mon 3/93:22 pm
SJU
- ORD
1 stop8h 17m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$185
This Priceline deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/258:30 am
ORD
- SJU
1 stop14h 13m
Frontier
Tue 3/33:53 am
SJU
- ORD
1 stop13h 59m
Frontier
Deal found 2/10![Frontier logo]()
$188
This Cheapflightsfares deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/15:15 am
ORD
- SJU
1 stop8h 16m
Spirit Airlines
Thu 3/511:52 am
SJU
- ORD
1 stop8h 26m
Spirit Airlines
Deal found 2/11![Spirit Airlines logo]()
$181
This Cheapflightsfares deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/212:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Thu 3/511:52 am
SJU
- ORD
1 stop8h 26m
Spirit Airlines
Deal found 2/12![Spirit Airlines logo]()
$186
This Kiwi.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 3/22:13 pm
ORD
- SJU
1 stop10h 12m
Multiple Airlines
Thu 3/511:52 am
SJU
- ORD
1 stop8h 26m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$191
This Kiwi.com deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” 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 3/312:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Fri 3/612:32 pm
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Deal found 2/11![Spirit Airlines logo]()
$190
One-way flights from Indiana to Caribbean IslandsSearch for one-way flight options from Indiana to Caribbean Islands. Find affordable one-way fares based on user searches. Data last updated February 12, 2026.
Search for one-way flight options from Indiana to Caribbean Islands. Find affordable one-way fares based on user searches. Data last updated February 12, 2026.
This Priceline deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/33:20 pm
CVG
- SJU
1 stop8h 23m
Frontier
Deal found 2/10![Frontier logo]()
$87
This Super.com deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/1610:55 am
ORD
- SJU
1 stop12h 03m
Spirit Airlines
Deal found 2/12![Spirit Airlines logo]()
$92
This Kiwi.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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 2/236:00 am
MDW
- SJU
1 stop31h 06m
Frontier
Deal found 2/10![Frontier logo]()
$92
This Cheapflightsfares deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/36:00 am
IND
- SJU
1 stop7h 04m
Spirit Airlines
Deal found 2/11![Spirit Airlines logo]()
$93
This Super.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/247:00 am
ORD
- SJU
1 stop6h 31m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$93
This Cheapflightsfares deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/237:00 am
ORD
- SJU
1 stop6h 31m
Spirit Airlines
Deal found 2/11![Spirit Airlines logo]()
$94
This CheapOair deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/125:15 am
ORD
- AUA
1 stop8h 18m
Spirit Airlines
Deal found 2/11![Spirit Airlines logo]()
$94
This Kiwi.com deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” 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.
Thu 5/712:22 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$95
This Trip.com deal was found by Cheapflights users on 2/11. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/96:00 am
MDW
- SJU
1 stop18h 21m
Frontier
Deal found 2/11![Frontier logo]()
$95
This Frontier deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/19:57 pm
IND
- SJU
1 stop11h 12m
Frontier
Deal found 2/9![Frontier logo]()
$96
This Cheapflightsfares deal was found by Cheapflights users on 2/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/99:18 am
ORD
- SJU
1 stop7h 40m
Spirit Airlines
Deal found 2/9![Spirit Airlines logo]()
$96
This Travelocity deal was found by Cheapflights users on 2/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/245:45 am
CVG
- SJU
1 stop17h 00m
Frontier
Deal found 2/10![Frontier logo]()
$96
Find flight deals from Indiana to Caribbean Islands
Keep the following information in mind while searching for Indiana to Caribbean Islands flight deals. Data was last updated February 12, 2026.
Round-trip from | $179 (Spirit) |
|---|---|
One-way from | $87 (Priceline) |
Popular in | December |
Cheapest in | September |
Average price | $419 |
Cheapflights Fare Finder
Customize your flight search to find flights from Indiana 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 February 12, 2026.
Use the filters below to find and compare flights from Indiana to Caribbean Islands that are best for you.
Fly from
Indiana
Fly to
Caribbean Islands
Route
Depart
Return
Price
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Mon 3/2
12:17 pm-6:49 pm
Nonstop4h 32m
San Juan Luis Munoz Marin Intl
Thu 3/5
12:32 pm-3:48 pm
Nonstop5h 16m
$187
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Mon 5/11
12:18 pm-5:54 pm
Nonstop4h 36m
San Juan Luis Munoz Marin Intl
Sat 5/16
8:41 am-11:59 pm
1 stop16h 18m
$193
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Sat 2/28
8:15 am-2:53 am
1 stop16h 38m
San Juan Luis Munoz Marin Intl
Wed 3/4
12:32 pm-3:48 pm
Nonstop5h 16m
$197
CincinnatiSan Juan
CVG - SJU
CVGSJU
Cincinnati Cinci./N. Kentucky
Sat 4/11
5:30 am-12:51 am
1 stop19h 21m
San Juan Luis Munoz Marin Intl
Fri 4/17
3:08 am-1:44 pm
1 stop10h 36m
$212
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Tue 3/31
4:33 pm-2:03 am
1 stop8h 30m
San Juan Luis Munoz Marin Intl
Fri 4/10
6:00 am-2:01 pm
1 stop9h 01m
$223
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Sun 3/1
6:15 am-2:09 am
1 stop17h 54m
San Juan Luis Munoz Marin Intl
Wed 3/4
6:27 pm-2:26 pm
2 stops21h 59m
$230
CincinnatiSan Juan
CVG - SJU
CVGSJU
Cincinnati Cinci./N. Kentucky
Sat 2/28
8:50 pm-2:09 am
1 stop28h 19m
San Juan Luis Munoz Marin Intl
Sat 3/7
3:53 am-7:23 am
1 stop27h 30m
$230
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Tue 3/10
11:19 am-2:03 am
1 stop13h 44m
San Juan Luis Munoz Marin Intl
Fri 3/13
6:30 am-11:51 pm
1 stop18h 21m
$239
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Thu 4/23
9:14 am-10:48 pm
1 stop12h 34m
San Juan Luis Munoz Marin Intl
Sat 4/25
3:18 pm-10:19 pm
1 stop8h 01m
$244
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Tue 4/21
12:53 pm-8:24 pm
1 stop6h 31m
San Juan Luis Munoz Marin Intl
Wed 4/29
2:34 pm-10:28 pm
1 stop8h 54m
$246
Showing 1-10 of 60 results
Best time to book a flight from Indiana to Caribbean Islands
Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands from Indiana with our price prediction graph.
CVG-SJU
ORD-SJU
ORD-STT
ORD-NAS
IND-SJU
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 Indiana to Caribbean Islands
USIN-zzEPX
CVG-SJU
ORD-SJU
ORD-STT
ORD-NAS
What is the cheapest month to book a flight from Indiana to Caribbean Islands?
Currently, September is the cheapest month in which you can book a flight from Indiana to Caribbean Islands (average of $142). Flying from Indiana to Caribbean Islands in December is currently the most expensive (average of $259). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from IN to EPX?
Find hourly flight availability from Indiana to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 12, 2026.
When flying from Indiana to Caribbean Islands, the time of day you decide to fly out makes little to no difference towards the overall price you’ll pay on tickets.
Related info for your journey
Find useful and relevant information for your journey from Indiana to Caribbean Islands. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
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Popular flights
Return Flight Options
Top destinations
Alternative routes for Indiana 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 Indiana to Caribbean Islands by cabin class
Find flights from Indiana to Caribbean Islands, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Indiana and Caribbean Islands flights
Browse other Indiana and Caribbean Islands flight options. Last updated on February 12, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Find a return flight route from Caribbean Islands
Find the right flight back to Indiana after your stay in Caribbean Islands
Indiana to Caribbean Islands flights
Consider these flights traveling from Indiana to Caribbean Islands.
Top 6 airlines flying from Indiana to Caribbean Islands
Discover the top 6 airlines that operate flights from Indiana 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 February 12, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$130 | Average$365 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$138 | Average$622 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$191 | Average$411 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$215 | Average$768 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$215 | Average$587 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$248 | Average$654 | FlexibilityNo cancel fee | On-time71% |