$95+ Cheap flights from Caribbean Islands to Indiana
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 4/13. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — IND
Mar 18 — Mar 251
1 adult, Economy
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Find cheap flights from Caribbean Islands to Indiana 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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Cheapest flights from Caribbean Islands to IndianaExplore the most affordable flight options available from Caribbean Islands to Indiana. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 16, 2026.
Explore the most affordable flight options available from Caribbean Islands to Indiana. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 16, 2026.
This Expedia deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” 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.
Thu 2/2612:32 pm
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Tue 3/312:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Deal found 2/15![Spirit Airlines logo]()
$164
This eDestinos deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” 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.
Thu 2/2612:32 pm
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Mon 3/212:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Deal found 2/15![Spirit Airlines logo]()
$166
This Orbitz deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” 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.
Fri 2/274:31 pm
SJU
- ORD
1 stop9h 16m
Spirit Airlines
Wed 3/412:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Deal found 2/15![Spirit Airlines logo]()
$171
This eDestinos deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” 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.
Fri 2/274:31 pm
SJU
- ORD
1 stop9h 16m
Spirit Airlines
Mon 3/27:00 am
ORD
- SJU
1 stop6h 31m
Spirit Airlines
Deal found 2/15![Spirit Airlines logo]()
$172
This eDestinos deal was found by Cheapflights users on 2/14. Clicking the “Pick Dates” 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.
Thu 2/194:36 pm
SJU
- ORD
1 stop9h 11m
Spirit Airlines
Mon 2/235:15 am
ORD
- SJU
1 stop8h 16m
Spirit Airlines
Deal found 2/14![Spirit Airlines logo]()
$174
This Expedia deal was found by Cheapflights users on 2/16. Clicking the “Pick Dates” 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.
Sat 2/2112:32 pm
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Tue 2/2412:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Deal found 2/16![Spirit Airlines logo]()
$176
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 4/131:29 am
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Tue 4/2112:18 pm
ORD
- SJU
Nonstop4h 36m
Spirit Airlines
Deal found 2/12![Spirit Airlines logo]()
$178
This Frontier deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” 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.
Fri 4/176:00 am
SJU
- IND
1 stop8h 55m
Frontier
Tue 4/2112:07 pm
IND
- SJU
1 stop10h 41m
Frontier
Deal found 2/15![Frontier logo]()
$192
This Priceline deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” 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.
Fri 5/13:18 pm
SJU
- MDW
1 stop8h 01m
Frontier
Sun 5/36:00 am
MDW
- SJU
1 stop7h 08m
Frontier
Deal found 2/15![Frontier logo]()
$202
This eDestinos deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” 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.
Thu 2/264:36 pm
SJU
- IND
1 stop7h 12m
Spirit Airlines
Mon 3/26:00 am
IND
- SJU
1 stop9h 39m
Spirit Airlines
Deal found 2/15![Spirit Airlines logo]()
$204
This Mytrip deal was found by Cheapflights users on 2/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/33:53 am
SJU
- IND
1 stop9h 35m
Frontier
Mon 3/95:40 pm
IND
- SJU
1 stop8h 18m
Frontier
Deal found 2/14![Frontier logo]()
$206
This eDestinos deal was found by Cheapflights users on 2/14. Clicking the “Pick Dates” 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.
Thu 4/307:30 pm
PUJ
- ORD
Nonstop5h 10m
Arajet
Mon 5/44:30 am
ORD
- PUJ
Nonstop4h 45m
Arajet
Deal found 2/14![Arajet logo]()
$208
Best flights from Caribbean Islands to IndianaDiscover carefully curated flight deals from Caribbean Islands to Indiana that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 16, 2026.
Discover carefully curated flight deals from Caribbean Islands to Indiana that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 16, 2026.
This eDestinos deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” 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.
Fri 2/274:31 pm
SJU
- ORD
1 stop9h 16m
Spirit Airlines
Mon 3/27:00 am
ORD
- SJU
1 stop6h 31m
Spirit Airlines
Deal found 2/15![Spirit Airlines logo]()
$172
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.
Mon 5/186:00 am
SJU
- IND
1 stop8h 55m
Frontier
Wed 5/2012:07 pm
IND
- SJU
1 stop13h 54m
Frontier
Deal found 2/12![Frontier logo]()
$192
This Expedia deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” 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 3/1011:07 am
SJU
- ORD
1 stop13h 31m
Multiple Airlines
Mon 5/1112:18 pm
ORD
- SJU
Nonstop4h 36m
Multiple Airlines
Deal found 2/15![Multiple Airlines logo]()
$196
This eDestinos deal was found by Cheapflights users on 2/14. Clicking the “Pick Dates” 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.
Thu 4/307:30 pm
PUJ
- ORD
Nonstop5h 10m
Arajet
Mon 5/44:30 am
ORD
- PUJ
Nonstop4h 45m
Arajet
Deal found 2/14![Arajet logo]()
$208
This American Airlines deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” 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 5/71:15 pm
MBJ
- ORD
Nonstop4h 40m
American Airlines
Mon 5/118:05 am
ORD
- MBJ
Nonstop4h 08m
American Airlines
Deal found 2/13![American Airlines logo]()
$241
This Southwest deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/72:55 pm
MBJ
- ORD
2 stops18h 50m
Southwest
Mon 5/116:00 am
ORD
- MBJ
1 stop7h 25m
Southwest
Deal found 2/13![Southwest logo]()
$261
This Delta deal was found by Cheapflights users on 2/14. Clicking the “Pick Dates” 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 4/237:15 am
SJU
- IND
1 stop9h 03m
Delta
Sat 4/251:47 pm
IND
- SJU
1 stop6h 37m
Delta
Deal found 2/14![Delta logo]()
$266
This United Airlines deal was found by Cheapflights users on 2/16. Clicking the “Pick Dates” 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 4/301:50 pm
PUJ
- ORD
Nonstop5h 09m
United Airlines
Sun 5/310:45 pm
ORD
- PUJ
1 stop15h 45m
United Airlines
Deal found 2/16![United Airlines logo]()
$286
This Air Canada deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” 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.
Wed 4/11:15 pm
NAS
- ORD
1 stop22h 38m
Air Canada
Tue 4/77:55 am
ORD
- NAS
1 stop11h 10m
Air Canada
Deal found 2/13![Air Canada logo]()
$347
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.
Fri 5/812:30 pm
SJU
- ORD
Nonstop5h 08m
Spirit Airlines
Mon 5/1112:18 pm
ORD
- SJU
Nonstop4h 36m
Spirit Airlines
Deal found 2/12![Spirit Airlines logo]()
$178
This Frontier deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” 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.
Fri 4/176:00 am
SJU
- IND
1 stop8h 55m
Frontier
Tue 4/2112:07 pm
IND
- SJU
1 stop10h 41m
Frontier
Deal found 2/15![Frontier logo]()
$192
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.
Thu 4/1612:30 pm
SJU
- ORD
Nonstop5h 08m
Spirit Airlines
Wed 4/2212:18 pm
ORD
- SJU
Nonstop4h 36m
Spirit Airlines
Deal found 2/12![Spirit Airlines logo]()
$178
This CheapOair deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” 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.
Fri 5/1510:53 am
SJU
- ORD
1 stop8h 12m
Multiple Airlines
Tue 5/1912:18 pm
ORD
- SJU
Nonstop4h 36m
Multiple Airlines
Deal found 2/13![Multiple Airlines logo]()
$201
This Frontier deal was found by Cheapflights users on 2/16. Clicking the “Pick Dates” 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.
Fri 5/13:18 pm
SJU
- MDW
1 stop8h 01m
Frontier
Sun 5/106:00 am
MDW
- SJU
1 stop7h 08m
Frontier
Deal found 2/16![Frontier logo]()
$202
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.
Thu 2/264:36 pm
SJU
- ORD
1 stop9h 11m
Spirit Airlines
Mon 3/28:16 pm
ORD
- SJU
1 stop17h 15m
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.
Fri 3/139:58 pm
SJU
- ORD
1 stop11h 27m
Multiple Airlines
Tue 3/1710:55 am
ORD
- SJU
1 stop12h 03m
Multiple Airlines
Deal found 2/12![Multiple Airlines logo]()
$208
This Priceline deal was found by Cheapflights users on 2/16. Clicking the “Pick Dates” 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.
Thu 5/143:18 pm
SJU
- MDW
1 stop8h 01m
Frontier
Sun 5/179:14 am
MDW
- SJU
1 stop15h 47m
Frontier
Deal found 2/16![Frontier logo]()
$202
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.
Thu 4/237:15 am
SJU
- IND
1 stop9h 03m
Delta
Sun 4/266:00 am
IND
- SJU
1 stop7h 14m
Delta
Deal found 2/12![Delta logo]()
$266
This Frontier deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” 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.
Fri 5/83:18 pm
SJU
- MDW
1 stop8h 01m
Frontier
Mon 5/116:00 am
MDW
- SJU
1 stop7h 08m
Frontier
Deal found 2/13![Frontier logo]()
$202
This eDestinos deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” 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.
Fri 2/274:31 pm
SJU
- ORD
1 stop9h 16m
Spirit Airlines
Wed 3/410:44 am
ORD
- SJU
1 stop10h 25m
Spirit Airlines
Deal found 2/15![Spirit Airlines logo]()
$202
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 3/301:27 pm
MBJ
- ORD
1 stop20h 43m
American Airlines
Mon 4/68:05 am
ORD
- MBJ
Nonstop4h 06m
American Airlines
Deal found 2/12![American Airlines logo]()
$287
This United Airlines deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” 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 3/113:25 pm
PUJ
- ORD
Nonstop5h 13m
United Airlines
Wed 3/188:47 am
ORD
- PUJ
Nonstop4h 32m
United Airlines
Deal found 2/13![United Airlines logo]()
$290
This CheapOair deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” 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 3/1011:07 am
SJU
- MDW
1 stop8h 06m
Frontier
Mon 5/116:00 am
MDW
- SJU
1 stop7h 08m
Frontier
Deal found 2/15![Frontier logo]()
$202
This Kiwi.com deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” 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 2/264:36 pm
SJU
- IND
1 stop18h 24m
Multiple Airlines
Mon 3/26:10 pm
IND
- SJU
2 stops20h 21m
Multiple Airlines
Deal found 2/15![Multiple Airlines logo]()
$250
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.
Fri 3/64:25 pm
PUJ
- ORD
Nonstop5h 13m
United Airlines
Tue 3/101:06 pm
ORD
- PUJ
1 stop26h 19m
United Airlines
Deal found 2/12![United Airlines logo]()
$291
This Priceline deal was found by Cheapflights users on 2/14. Clicking the “Pick Dates” 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.
Fri 2/273:53 am
SJU
- MDW
1 stop13h 02m
Frontier
Sat 4/189:14 am
MDW
- SJU
1 stop12h 34m
Frontier
Deal found 2/14![Frontier logo]()
$202
This American Airlines deal was found by Cheapflights users on 2/14. Clicking the “Pick Dates” 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 4/3012:06 pm
PUJ
- ORD
Nonstop5h 19m
American Airlines
Mon 5/48:46 pm
ORD
- PUJ
1 stop17h 04m
American Airlines
Deal found 2/14![American Airlines logo]()
$300
This Delta deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” 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 6/24:55 pm
MBJ
- ORD
2 stops15h 03m
Delta
Wed 8/267:10 am
ORD
- MBJ
1 stop5h 54m
Delta
Deal found 2/15![Delta logo]()
$307
This United Airlines deal was found by Cheapflights users on 2/16. Clicking the “Pick Dates” 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 4/234:40 pm
PUJ
- ORD
1 stop15h 46m
United Airlines
Sun 4/268:45 am
ORD
- PUJ
Nonstop4h 42m
United Airlines
Deal found 2/16![United Airlines logo]()
$292
This Air Canada deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” 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.
Mon 4/279:10 pm
NAS
- ORD
2 stops18h 45m
Air Canada
Tue 5/59:55 am
ORD
- NAS
1 stop6h 35m
Air Canada
Deal found 2/13![Air Canada logo]()
$355
Last-minute flights from Caribbean Islands to IndianaDiscover last-minute flight deals from Caribbean Islands to Indiana. Data last updated February 16, 2026 and is based on user searches.
Discover last-minute flight deals from Caribbean Islands to Indiana. Data last updated February 16, 2026 and is based on user searches.
This eDestinos deal was found by Cheapflights users on 2/14. Clicking the “Pick Dates” 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.
Thu 2/194:36 pm
SJU
- ORD
1 stop9h 11m
Spirit Airlines
Mon 2/235:15 am
ORD
- SJU
1 stop8h 16m
Spirit Airlines
Deal found 2/14![Spirit Airlines logo]()
$174
This Trip.com deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” 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.
Wed 2/253:53 am
SJU
- MDW
1 stop12h 33m
Frontier
Mon 3/29:22 pm
MDW
- SJU
1 stop10h 32m
Frontier
Deal found 2/13![Frontier logo]()
$228
This Expedia deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” 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.
Thu 2/2612:32 pm
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Tue 3/312:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Deal found 2/15![Spirit Airlines logo]()
$164
This eDestinos deal was found by Cheapflights users on 2/16. Clicking the “Pick Dates” 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.
Thu 2/2612:32 pm
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Mon 3/212:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Deal found 2/16![Spirit Airlines logo]()
$166
This eDestinos deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” 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.
Thu 2/264:36 pm
SJU
- IND
1 stop7h 12m
Spirit Airlines
Mon 3/26:00 am
IND
- SJU
1 stop9h 39m
Spirit Airlines
Deal found 2/15![Spirit Airlines logo]()
$204
This Orbitz deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” 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.
Thu 2/264:11 pm
SJU
- MDW
1 stop8h 18m
Frontier
Sun 3/17:30 am
MDW
- SJU
1 stop24h 39m
Frontier
Deal found 2/13![Frontier logo]()
$223
This Orbitz deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” 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.
Fri 2/274:31 pm
SJU
- ORD
1 stop9h 16m
Spirit Airlines
Wed 3/412:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Deal found 2/15![Spirit Airlines logo]()
$171
This eDestinos deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” 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.
Fri 2/274:31 pm
SJU
- ORD
1 stop9h 16m
Spirit Airlines
Mon 3/27:00 am
ORD
- SJU
1 stop6h 31m
Spirit Airlines
Deal found 2/15![Spirit Airlines logo]()
$172
This Frontier deal was found by Cheapflights users on 2/14. Clicking the “Pick Dates” 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.
Fri 2/273:53 am
SJU
- MDW
1 stop13h 02m
Frontier
Mon 3/29:22 pm
MDW
- SJU
1 stop10h 32m
Frontier
Deal found 2/14![Frontier logo]()
$202
This Mytrip deal was found by Cheapflights users on 2/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/33:53 am
SJU
- IND
1 stop9h 35m
Frontier
Mon 3/95:40 pm
IND
- SJU
1 stop8h 18m
Frontier
Deal found 2/14![Frontier logo]()
$206
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.
Thu 3/121:29 am
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Tue 3/1710:55 am
ORD
- SJU
1 stop12h 03m
Spirit Airlines
Deal found 2/12![Spirit Airlines logo]()
$177
This Expedia deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” 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 3/243:08 am
SJU
- IND
1 stop29h 04m
Frontier
Mon 3/305:18 pm
IND
- SJU
1 stop8h 40m
Frontier
Deal found 2/13![Frontier logo]()
$216
One-way flights from Caribbean Islands to IndianaSearch for one-way flight options from Caribbean Islands to Indiana. Find affordable one-way fares based on user searches. Data last updated February 16, 2026.
Search for one-way flight options from Caribbean Islands to Indiana. Find affordable one-way fares based on user searches. Data last updated February 16, 2026.
This Super.com deal was found by Cheapflights users on 2/15. Clicking the “Pick Dates” 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 4/133:08 am
SJU
- IND
1 stop8h 03m
Frontier
Deal found 2/15![Frontier logo]()
$95
This Cheapflightsfares deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” 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 3/231:29 am
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Deal found 2/13![Spirit Airlines logo]()
$95
This Frontier deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” 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.
Tue 4/143:08 am
SJU
- IND
1 stop8h 03m
Frontier
Deal found 2/13![Frontier logo]()
$96
This Cheapflightsfares deal was found by Cheapflights users on 2/14. Clicking the “Pick Dates” 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.
Fri 3/64:31 pm
SJU
- ORD
1 stop9h 16m
Spirit Airlines
Deal found 2/14![Spirit Airlines logo]()
$97
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 6/98:10 pm
SJU
- ORD
Nonstop5h 15m
Frontier
Deal found 2/12![Frontier logo]()
$99
This Cheapflightsfares deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” 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.
Thu 4/1611:07 am
SJU
- ORD
1 stop8h 08m
Spirit Airlines
Deal found 2/13![Spirit Airlines logo]()
$100
This Priceline deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” 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 4/153:19 pm
SJU
- MDW
1 stop17h 45m
Frontier
Deal found 2/13![Frontier logo]()
$101
This Priceline deal was found by Cheapflights users on 2/16. Clicking the “Pick Dates” 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.
Fri 5/154:11 pm
SJU
- ORD
1 stop8h 05m
Frontier
Deal found 2/16![Frontier logo]()
$101
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 3/35:25 pm
SJU
- IND
1 stop20h 03m
Frontier
Deal found 2/12![Frontier logo]()
$102
This Kiwi.com deal was found by Cheapflights users on 2/14. Clicking the “Pick Dates” 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 5/308:10 pm
SJU
- ORD
Nonstop5h 15m
Frontier
Deal found 2/14![Frontier logo]()
$102
This Expedia deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” 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.
Sat 2/2812:32 pm
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Deal found 2/13![Spirit Airlines logo]()
$103
This Trip.com deal was found by Cheapflights users on 2/14. Clicking the “Pick Dates” 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.
Thu 2/263:53 am
SJU
- MDW
1 stop12h 33m
Frontier
Deal found 2/14![Frontier logo]()
$104
Find flight deals from Caribbean Islands to Indiana
Keep the following information in mind while searching for Caribbean Islands to Indiana flight deals. Data was last updated February 16, 2026.
Round-trip from | $164 (Expedia) |
|---|---|
One-way from | $95 (Super.com) |
Cheapflights Fare Finder
Customize your flight search to find flights from Caribbean Islands to Indiana 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 16, 2026.
Use the filters below to find and compare flights from Caribbean Islands to Indiana that are best for you.
Fly from
Caribbean Islands
Fly to
Indiana
Route
Depart
Return
Price
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Fri 2/27
4:31 pm-11:47 pm
1 stop9h 16m
Chicago O'Hare Intl
Mon 3/2
7:00 am-3:31 pm
1 stop6h 31m
$172
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Fri 5/8
12:30 pm-4:38 pm
Nonstop5h 08m
Chicago O'Hare Intl
Mon 5/11
12:18 pm-5:54 pm
Nonstop4h 36m
$178
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Thu 4/16
12:30 pm-4:38 pm
Nonstop5h 08m
Chicago O'Hare Intl
Wed 4/22
12:18 pm-5:54 pm
Nonstop4h 36m
$178
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Thu 2/26
4:36 pm-11:47 pm
1 stop9h 11m
Chicago O'Hare Intl
Mon 3/2
8:16 pm-3:31 pm
1 stop17h 15m
$187
San JuanIndianapolis
SJU - IND
SJUIND
San Juan Luis Munoz Marin Intl
Mon 5/18
6:00 am-2:55 pm
1 stop8h 55m
Indianapolis
Wed 5/20
12:07 pm-2:01 am
1 stop13h 54m
$192
San JuanIndianapolis
SJU - IND
SJUIND
San Juan Luis Munoz Marin Intl
Fri 4/17
6:00 am-2:55 pm
1 stop8h 55m
Indianapolis
Tue 4/21
12:07 pm-10:48 pm
1 stop10h 41m
$192
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Tue 3/10
11:07 am-11:38 pm
1 stop13h 31m
Chicago O'Hare Intl
Mon 5/11
12:18 pm-5:54 pm
Nonstop4h 36m
$196
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Fri 5/15
10:53 am-6:05 pm
1 stop8h 12m
Chicago O'Hare Intl
Tue 5/19
12:18 pm-5:54 pm
Nonstop4h 36m
$201
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Fri 5/1
3:18 pm-10:19 pm
1 stop8h 01m
Chicago Midway
Sun 5/10
6:00 am-2:08 pm
1 stop7h 08m
$202
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 5/14
3:18 pm-10:19 pm
1 stop8h 01m
Chicago Midway
Sun 5/17
9:14 am-2:01 am
1 stop15h 47m
$202
Showing 1-10 of 60 results
Best time to book a flight from Caribbean Islands to Indiana
Have a flexible travel schedule? Discover the best time to fly to Indiana from Caribbean Islands with our price prediction graph.
SJU-ORD
SJU-IND
PUJ-ORD
MBJ-ORD
NAS-ORD
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 Caribbean Islands to Indiana
zzEPX-USIN
SJU-ORD
SJU-IND
PUJ-ORD
MBJ-ORD
What is the cheapest month to book a flight from Caribbean Islands to Indiana?
Currently, December is the cheapest month in which you can book a flight from Caribbean Islands to Indiana (average of $109). Flying from Caribbean Islands to Indiana in July is currently the most expensive (average of $264). 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 EPX to IN?
Find hourly flight availability from Caribbean Islands to Indiana. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 16, 2026.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Caribbean Islands to Indiana as you normally would.
Reviews of airlines servicing Indiana
Get insights into the airlines that provide service to Indiana. 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 Indiana. Reviews last updated February 16, 2026.
Read reviews from past customers who have flown Delta, United Airlines, and American Airlines from Caribbean Islands to Indiana. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.5
Boarding
8.1
Comfort
7.9
Entertainment
7.8
Overall
7.9
Food
7.2
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Crew
8.5
Boarding
8.1
Comfort
7.9
Entertainment
7.8
Overall
7.9
Food
7.2
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Crew
8.5
Boarding
8.1
Comfort
7.9
Entertainment
7.8
Overall
7.9
Food
7.2
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Crew
8.5
Boarding
8.1
Comfort
7.9
Entertainment
7.8
Overall
7.9
Food
7.2
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Crew
8.5
Boarding
8.1
Comfort
7.9
Entertainment
7.8
Overall
7.9
Food
7.2
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Related info for your journey
Find useful and relevant information for your journey from Caribbean Islands to Indiana. 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.
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Alternative routes for Caribbean Islands to Indiana
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Indiana by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Caribbean Islands to Indiana by cabin class
Find flights from Caribbean Islands to Indiana, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Caribbean Islands and Indiana flights
Browse other Caribbean Islands and Indiana flight options. Last updated on February 16, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Find a return flight route from Indiana
Find the right flight back to Caribbean Islands after your stay in Indiana
Caribbean Islands to Indiana flights
Consider these flights traveling from Caribbean Islands to Indiana.
Top 6 airlines flying from Caribbean Islands to Indiana
Discover the top 6 airlines that operate flights from Caribbean Islands to Indiana. 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 16, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$118 | Average$467 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$214 | Average$305 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$215 | Average$355 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$235 | Average$516 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$260 | Average$381 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$326 | Average$429 | FlexibilityNo cancel fee | On-time65% |