$95+ Cheap flights from Caribbean Islands to Illinois
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 3/23. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — ORD
Mar 18 — Mar 251
1 adult, Economy
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Find cheap flights from Caribbean Islands to Illinois with Cheapflights
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Cheapest flights from Caribbean Islands to IllinoisExplore the most affordable flight options available from Caribbean Islands to Illinois. 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 Illinois. 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 2/16. 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 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 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
Mon 3/1610:55 am
ORD
- SJU
1 stop12h 03m
Spirit Airlines
Deal found 2/12![Spirit Airlines logo]()
$177
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 3/612:32 pm
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Tue 3/1012:22 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Deal found 2/12![Spirit Airlines logo]()
$178
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.
Fri 2/275:25 pm
SJU
- STL
1 stop9h 02m
Frontier
Mon 3/23:49 pm
STL
- SJU
1 stop9h 04m
Frontier
Deal found 2/12![Frontier logo]()
$202
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 5/83:18 pm
SJU
- MDW
1 stop8h 01m
Frontier
Mon 5/116:00 am
MDW
- SJU
1 stop7h 08m
Frontier
Deal found 2/14![Frontier logo]()
$202
This Trip.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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/266:00 am
SJU
- MDW
1 stop9h 56m
Frontier
Mon 3/29:22 pm
MDW
- SJU
1 stop10h 32m
Frontier
Deal found 2/12![Frontier logo]()
$207
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 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.
Wed 3/411:52 am
SJU
- MDW
1 stop28h 04m
Multiple Airlines
Mon 3/96:00 am
MDW
- SJU
1 stop18h 21m
Multiple Airlines
Deal found 2/12![Multiple Airlines logo]()
$219
Best flights from Caribbean Islands to IllinoisDiscover carefully curated flight deals from Caribbean Islands to Illinois 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 Illinois that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 16, 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.
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.
Thu 4/163:19 pm
SJU
- STL
1 stop9h 00m
Frontier
Sun 4/194:55 pm
STL
- SJU
1 stop8h 06m
Frontier
Deal found 2/15![Frontier logo]()
$202
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 Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/42:30 pm
SJU
- ORD
Nonstop5h 05m
Southwest
Mon 6/810:30 am
ORD
- SJU
Nonstop4h 50m
Southwest
Deal found 2/14![Southwest logo]()
$237
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 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.
Mon 4/201:59 am
SJU
- ORD
2 stops17h 55m
Multiple Airlines
Sat 4/2512:18 pm
ORD
- SJU
Nonstop4h 36m
Multiple Airlines
Deal found 2/15![Multiple Airlines logo]()
$242
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/166:15 am
SJU
- MDW
1 stop11h 14m
Delta
Wed 4/2212:53 pm
MDW
- SJU
1 stop6h 31m
Delta
Deal found 2/13![Delta logo]()
$246
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 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 3/611:52 am
SJU
- ORD
1 stop8h 26m
Spirit Airlines
Tue 3/1012:22 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Deal found 2/12![Spirit Airlines logo]()
$191
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.
Thu 5/73:18 pm
SJU
- MDW
1 stop8h 01m
Frontier
Sun 5/106:00 am
MDW
- SJU
1 stop7h 08m
Frontier
Deal found 2/14![Frontier logo]()
$202
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 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 Southwest 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/2211:25 am
SJU
- MDW
2 stops9h 05m
Southwest
Mon 4/275:35 am
MDW
- SJU
1 stop6h 35m
Southwest
Deal found 2/14![Southwest logo]()
$246
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.
Wed 5/132:20 pm
SJU
- ORD
1 stop10h 39m
Delta
Sun 5/178:10 am
ORD
- SJU
1 stop10h 56m
Delta
Deal found 2/15![Delta logo]()
$246
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.
Thu 4/1611:43 am
SJU
- STL
1 stop11h 41m
American Airlines
Sun 4/198:03 pm
STL
- SJU
1 stop17h 17m
American Airlines
Deal found 2/12![American Airlines logo]()
$256
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/19:12 pm
SJU
- ORD
2 stops18h 08m
Multiple Airlines
Sun 5/35:16 pm
ORD
- SJU
1 stop6h 37m
Multiple Airlines
Deal found 2/13![Multiple Airlines logo]()
$262
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 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
Sat 3/712:44 pm
ORD
- SJU
1 stop8h 25m
Spirit Airlines
Deal found 2/14![Spirit Airlines logo]()
$253
This American Airlines 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/207:00 pm
SJU
- STL
1 stop16h 16m
American Airlines
Sat 4/256:29 am
STL
- SJU
1 stop14h 36m
American Airlines
Deal found 2/15![American Airlines logo]()
$256
This Delta 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/222:20 pm
SJU
- ORD
1 stop8h 29m
Delta
Mon 6/18:10 am
ORD
- SJU
1 stop10h 56m
Delta
Deal found 2/11![Delta logo]()
$256
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 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 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 Expedia 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 Expedia 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
Multiple Airlines
Mon 5/45:05 am
ORD
- PUJ
1 stop7h 45m
Multiple Airlines
Deal found 2/14![Multiple Airlines logo]()
$281
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 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 Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/29:10 pm
NAS
- ORD
1 stop13h 00m
Air Canada
Thu 4/97:55 am
ORD
- NAS
1 stop11h 10m
Air Canada
Deal found 2/15![Air Canada logo]()
$352
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 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 3/54:11 pm
SJU
- MDW
1 stop8h 18m
Frontier
Mon 3/99:51 pm
MDW
- SJU
1 stop11h 21m
Frontier
Deal found 2/12![Frontier logo]()
$220
Last-minute flights from Caribbean Islands to IllinoisDiscover last-minute flight deals from Caribbean Islands to Illinois. Data last updated February 16, 2026 and is based on user searches.
Discover last-minute flight deals from Caribbean Islands to Illinois. 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 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 Trip.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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/266:00 am
SJU
- MDW
1 stop9h 56m
Frontier
Mon 3/29:22 pm
MDW
- SJU
1 stop10h 32m
Frontier
Deal found 2/12![Frontier logo]()
$207
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
Sun 3/17:30 am
MDW
- SJU
1 stop17h 23m
Frontier
Deal found 2/14![Frontier logo]()
$229
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 2/12. 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.
Fri 2/275:25 pm
SJU
- STL
1 stop9h 02m
Frontier
Mon 3/23:49 pm
STL
- SJU
1 stop9h 04m
Frontier
Deal found 2/12![Frontier logo]()
$202
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 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.
Wed 3/411:52 am
SJU
- MDW
1 stop28h 04m
Multiple Airlines
Mon 3/96:00 am
MDW
- SJU
1 stop18h 21m
Multiple Airlines
Deal found 2/12![Multiple Airlines logo]()
$219
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 3/54:11 pm
SJU
- MDW
1 stop8h 18m
Frontier
Mon 3/99:51 pm
MDW
- SJU
1 stop11h 21m
Frontier
Deal found 2/12![Frontier logo]()
$220
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 3/612:32 pm
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Tue 3/1012:22 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Deal found 2/12![Spirit Airlines logo]()
$178
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
Mon 3/1610:55 am
ORD
- SJU
1 stop12h 03m
Spirit Airlines
Deal found 2/12![Spirit Airlines logo]()
$177
One-way flights from Caribbean Islands to IllinoisSearch for one-way flight options from Caribbean Islands to Illinois. 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 Illinois. Find affordable one-way fares based on user searches. Data last updated February 16, 2026.
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 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 4/1611:07 am
SJU
- ORD
1 stop8h 08m
Spirit Airlines
Deal found 2/12![Spirit Airlines logo]()
$96
This Trip.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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/56:00 am
SJU
- MDW
1 stop9h 56m
Frontier
Deal found 2/12![Frontier logo]()
$97
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 Super.com 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/126:30 am
SJU
- STL
1 stop17h 49m
Frontier
Deal found 2/16![Frontier logo]()
$100
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 4/163:19 pm
SJU
- STL
1 stop9h 00m
Frontier
Deal found 2/16![Frontier logo]()
$101
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.
Wed 3/116:30 am
SJU
- MDW
1 stop12h 43m
Frontier
Deal found 2/12![Frontier logo]()
$101
This Super.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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/106:30 am
SJU
- ORD
1 stop18h 08m
Frontier
Deal found 2/13![Frontier logo]()
$101
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 Illinois
Keep the following information in mind while searching for Caribbean Islands to Illinois flight deals. Data was last updated February 16, 2026.
Round-trip from | $164 (Expedia) |
|---|---|
One-way from | $95 (Cheapflightsfares) |
Cheapflights Fare Finder
Customize your flight search to find flights from Caribbean Islands to Illinois 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 Illinois that are best for you.
Fly from
Caribbean Islands
Fly to
Illinois
Route
Depart
Return
Price
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
Fri 3/6
11:52 am-6:18 pm
1 stop8h 26m
Chicago O'Hare Intl
Tue 3/10
12:22 pm-5:54 pm
Nonstop4h 32m
$191
San JuanSt. Louis
SJU - STL
SJUSTL
San Juan Luis Munoz Marin Intl
Thu 4/16
3:19 pm-11:19 pm
1 stop9h 00m
Lambert-St Louis
Sun 4/19
4:55 pm-2:01 am
1 stop8h 06m
$202
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 5/7
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
Fri 5/1
3:18 pm-10:19 pm
1 stop8h 01m
Chicago Midway
Sun 5/3
6:00 am-2:08 pm
1 stop7h 08m
$202
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Fri 5/8
3:18 pm-10:19 pm
1 stop8h 01m
Chicago Midway
Mon 5/11
6:00 am-2:08 pm
1 stop7h 08m
$202
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Tue 3/10
11:07 am-6:13 pm
1 stop8h 06m
Chicago Midway
Mon 5/11
6:00 am-2:08 pm
1 stop7h 08m
$202
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Fri 2/27
3:53 am-2:55 pm
1 stop13h 02m
Chicago Midway
Sat 4/18
9:14 am-10:48 pm
1 stop12h 34m
$202
Punta CanaChicago
PUJ - ORD
PUJORD
Punta Cana
Thu 4/30
7:30 pm-11:40 pm
Nonstop5h 10m
Chicago O'Hare Intl
Mon 5/4
4:30 am-10:15 am
Nonstop4h 45m
$208
San JuanChicago
SJU - MDW
SJUMDW
San Juan Luis Munoz Marin Intl
Thu 3/5
4:11 pm-10:29 pm
1 stop8h 18m
Chicago Midway
Mon 3/9
9:51 pm-10:12 am
1 stop11h 21m
$220
Showing 1-10 of 60 results
Best time to book a flight from Caribbean Islands to Illinois
Have a flexible travel schedule? Discover the best time to fly to Illinois from Caribbean Islands with our price prediction graph.
SJU-ORD
SJU-STL
PUJ-ORD
MBJ-ORD
SJU-MDW
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 Illinois
zzEPX-USIL
SJU-ORD
SJU-STL
PUJ-ORD
MBJ-ORD
What is the cheapest month to book a flight from Caribbean Islands to Illinois?
Currently, February is the cheapest month in which you can book a flight from Caribbean Islands to Illinois (average of $111). Flying from Caribbean Islands to Illinois in December is currently the most expensive (average of $157). 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 IL?
Find hourly flight availability from Caribbean Islands to Illinois. 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.
One of the essential ways to save on airfare from Caribbean Islands to Illinois is to remain as flexible as possible. Flights that are in the afternoon tend to be the most expensive. A flight in the evening could potentially save you up to 52% on airfare.
What is the cheapest day to fly from Caribbean Islands to Illinois?
Use this chart to determine the cheapest time to fly round-trip from Caribbean Islands to Illinois. Price data was last updated on February 7, 2026.
Travelers seeking maximum savings on their Caribbean Islands to Illinois flight should consider departing on Friday evenings when fares are most often at their lowest. Monday afternoons flights should be avoided if possible as fares are typically the most expensive at this time.
Weekly flight availability from Caribbean Islands to Illinois
Explore weekly flight availability from Caribbean Islands to Illinois. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated February 16, 2026.
The most flights from zzEPX to USIL are scheduled on a Monday (12 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (9 on average).
Reviews of airlines servicing Illinois
Get insights into the airlines that provide service to Illinois. 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 Illinois. Reviews last updated February 16, 2026.
Peruse reviews from past customers who have flown with Delta, United Airlines, and American Airlines from Caribbean Islands to Illinois to help guide your decision. You can also see how each airline stacks up in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.8
Boarding
8.1
Comfort
7.9
Overall
7.9
Crew
8.5
Food
7.2
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Entertainment
7.8
Boarding
8.1
Comfort
7.9
Overall
7.9
Crew
8.5
Food
7.2
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Entertainment
7.8
Boarding
8.1
Comfort
7.9
Overall
7.9
Crew
8.5
Food
7.2
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Entertainment
7.8
Boarding
8.1
Comfort
7.9
Overall
7.9
Crew
8.5
Food
7.2
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Entertainment
7.8
Boarding
8.1
Comfort
7.9
Overall
7.9
Crew
8.5
Food
7.2
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Entertainment
7.8
Boarding
8.1
Comfort
7.9
Overall
7.9
Crew
8.5
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 Illinois. 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 Illinois
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Illinois by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Caribbean Islands to Illinois by cabin class
Find flights from Caribbean Islands to Illinois, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Caribbean Islands and Illinois flights
Browse other Caribbean Islands and Illinois 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 Illinois
Find the right flight back to Caribbean Islands after your stay in Illinois
Caribbean Islands to Illinois flights
Consider these flights traveling from Caribbean Islands to Illinois.
Top 7 airlines flying from Caribbean Islands to Illinois
Discover the top 7 airlines that operate flights from Caribbean Islands to Illinois. 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$116 | Average$626 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$122 | Average$334 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$131 | Average$201 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$137 | Average$335 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$256 | Average$520 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$258 | Average$544 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$392 | Average$545 | FlexibilityNo cancel fee | On-time63% |