$104+ Cheap flights from Illinois to Caribbean
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 9/30. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
Aug 30 — Sep 61
Round-trip
1 adult, Economy
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Find cheap flights from Illinois to Caribbean 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 Illinois to CaribbeanExplore the most affordable flight options available from Illinois to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 31, 2026.
Explore the most affordable flight options available from Illinois to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on July 31, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/258:05 am
ORD
- SJU
1 stop31h 06m
Frontier
Tue 9/16:35 am
SJU
- ORD
1 stop31h 15m
Frontier
Deal found 7/30![Frontier logo]()
$224
This deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/86:05 am
ORD
- SJU
1 stop10h 31m
Frontier
Thu 10/152:58 am
SJU
- ORD
1 stop11h 18m
Frontier
Deal found 7/30![Frontier logo]()
$225
This FlightHub deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/2312:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Sat 8/297:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 7/29![Frontier logo]()
$226
This Super.com deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2212:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Wed 8/267:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 7/29![Frontier logo]()
$227
This Frontier deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2812:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Tue 9/17:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 7/30![Frontier logo]()
$228
This Frontier deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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.
Mon 8/3112:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Wed 9/27:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 7/31![Frontier logo]()
$229
This Kiwi.com deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/268:05 am
ORD
- SJU
1 stop31h 06m
Frontier
Sat 8/297:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 7/29![Frontier logo]()
$231
This Kiwi.com deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/318:05 am
ORD
- SJU
1 stop31h 06m
Frontier
Thu 9/247:00 am
SJU
- ORD
1 stop8h 45m
Frontier
Deal found 7/30![Frontier logo]()
$232
This Kiwi.com deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” 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 8/1712:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Mon 8/246:35 am
SJU
- ORD
1 stop31h 15m
Frontier
Deal found 7/27![Frontier logo]()
$233
This Kiwi.com deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/18:05 am
ORD
- SJU
1 stop31h 06m
Frontier
Sun 11/16:12 pm
SJU
- ORD
1 stop23h 12m
Frontier
Deal found 7/30![Frontier logo]()
$234
This FlightHub deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/3112:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Fri 9/47:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 7/29![Frontier logo]()
$235
This Southwest deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/812:45 pm
MDW
- SJU
2 stops8h 20m
Southwest
Wed 9/95:15 am
SJU
- MDW
1 stop7h 50m
Southwest
Deal found 7/29![Southwest logo]()
$269
Best flights from Illinois to CaribbeanDiscover carefully curated flight deals from Illinois to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 31, 2026.
Discover carefully curated flight deals from Illinois to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated July 31, 2026.
This Southwest deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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.
Tue 9/17:30 am
MDW
- SJU
1 stop10h 30m
Southwest
Wed 9/25:15 am
SJU
- MDW
1 stop7h 50m
Southwest
Deal found 7/31![Southwest logo]()
$271
This JetBlue deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/132:35 pm
ORD
- SJU
1 stop7h 45m
JetBlue
Fri 9/45:05 am
SJU
- ORD
1 stop9h 34m
JetBlue
Deal found 7/31![JetBlue logo]()
$300
This Delta deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” 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 9/2210:25 am
ORD
- SJU
1 stop12h 24m
Delta
Tue 9/297:30 am
SJU
- ORD
1 stop10h 29m
Delta
Deal found 7/27![Delta logo]()
$316
This Kiwi.com deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/1512:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Mon 8/318:57 pm
SJU
- ORD
2 stops24h 11m
Frontier
Deal found 7/26![Frontier logo]()
$338
This United Airlines deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” 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 9/228:55 am
ORD
- SJU
Nonstop4h 49m
United Airlines
Tue 9/293:56 pm
SJU
- ORD
Nonstop5h 09m
United Airlines
Deal found 7/27![United Airlines logo]()
$355
This Arajet deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2412:12 pm
ORD
- PUJ
Nonstop4h 45m
Arajet
Sun 11/16:10 pm
PUJ
- ORD
Nonstop5h 10m
Arajet
Deal found 7/30![Arajet logo]()
$375
This FlightHub deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/168:40 pm
ORD
- GCM
1 stop14h 45m
Multiple Airlines
Wed 9/237:00 am
GCM
- ORD
2 stops26h 00m
Multiple Airlines
Deal found 7/28![Multiple Airlines logo]()
$470
This Copa Airlines deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/123:20 pm
ORD
- MBJ
1 stop19h 57m
Copa Airlines
Sun 9/2012:22 pm
MBJ
- ORD
1 stop12h 40m
Copa Airlines
Deal found 7/31![Copa Airlines logo]()
$489
This Southwest deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/3111:15 am
MDW
- SJU
1 stop7h 50m
Southwest
Sat 9/55:05 am
SJU
- MDW
1 stop6h 55m
Southwest
Deal found 7/29![Southwest logo]()
$275
This American Airlines deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/195:05 am
ORD
- STT
1 stop6h 53m
American Airlines
Mon 10/263:46 pm
STT
- ORD
1 stop9h 52m
American Airlines
Deal found 7/31![American Airlines logo]()
$580
This JetBlue deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/127:00 am
ORD
- SJU
1 stop8h 05m
JetBlue
Sat 9/55:00 pm
SJU
- ORD
1 stop7h 44m
JetBlue
Deal found 7/31![JetBlue logo]()
$300
This Delta deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” 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 9/301:29 pm
ORD
- SJU
1 stop9h 20m
Delta
Mon 10/51:16 pm
SJU
- ORD
1 stop9h 21m
Delta
Deal found 7/27![Delta logo]()
$331
This Southwest deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” 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.
Fri 8/2811:15 am
MDW
- SJU
1 stop7h 50m
Southwest
Fri 9/46:30 am
SJU
- MDW
1 stop10h 05m
Southwest
Deal found 7/27![Southwest logo]()
$316
This United Airlines deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” 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 9/910:40 am
ORD
- SJU
1 stop8h 58m
United Airlines
Wed 9/163:56 pm
SJU
- ORD
Nonstop5h 09m
United Airlines
Deal found 7/26![United Airlines logo]()
$360
This Southwest deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” 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.
Sun 8/238:05 am
MDW
- SJU
1 stop8h 00m
Southwest
Sun 8/309:25 pm
SJU
- MDW
1 stop13h 35m
Southwest
Deal found 7/26![Southwest logo]()
$316
This United Airlines deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” 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 9/118:55 am
ORD
- SJU
Nonstop4h 49m
United Airlines
Fri 9/183:56 pm
SJU
- ORD
Nonstop5h 09m
United Airlines
Deal found 7/28![United Airlines logo]()
$378
This Delta deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” 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 9/2210:25 am
ORD
- SJU
1 stop12h 24m
Delta
Sat 9/267:30 am
SJU
- ORD
1 stop10h 33m
Delta
Deal found 7/26![Delta logo]()
$381
This Southwest deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” 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.
Sun 9/278:05 pm
MDW
- SJU
1 stop12h 05m
Southwest
Thu 10/110:50 pm
SJU
- MDW
1 stop10h 55m
Southwest
Deal found 7/27![Southwest logo]()
$316
This Arajet deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2212:12 pm
ORD
- PUJ
Nonstop4h 45m
Arajet
Sat 8/297:02 am
PUJ
- ORD
Nonstop5h 10m
Arajet
Deal found 7/30![Arajet logo]()
$425
This Southwest deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” 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.
Fri 10/234:15 pm
MDW
- SJU
2 stops8h 05m
Southwest
Wed 11/46:15 am
SJU
- MDW
1 stop8h 45m
Southwest
Deal found 7/28![Southwest logo]()
$316
This United Airlines deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” 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 10/228:55 am
ORD
- SJU
Nonstop4h 49m
United Airlines
Mon 10/267:25 am
SJU
- ORD
Nonstop5h 24m
United Airlines
Deal found 7/26![United Airlines logo]()
$401
This Arajet deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/1012:12 pm
ORD
- PUJ
Nonstop4h 45m
Arajet
Thu 10/157:30 pm
PUJ
- ORD
Nonstop5h 10m
Arajet
Deal found 7/29![Arajet logo]()
$452
This Southwest deal was found by Cheapflights users on 7/26. Clicking the “Pick Dates” 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 9/99:40 am
MDW
- SJU
1 stop7h 30m
Southwest
Wed 9/161:45 pm
SJU
- MDW
1 stop8h 15m
Southwest
Deal found 7/26![Southwest logo]()
$316
This Copa Airlines deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/88:01 am
ORD
- MBJ
1 stop27h 16m
Copa Airlines
Tue 9/1512:22 pm
MBJ
- ORD
1 stop12h 40m
Copa Airlines
Deal found 7/27![Copa Airlines logo]()
$510
This JetBlue deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/297:00 am
ORD
- NAS
1 stop9h 22m
JetBlue
Tue 9/13:02 pm
NAS
- ORD
1 stop9h 42m
JetBlue
Deal found 7/27![JetBlue logo]()
$470
This Gotogate deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/143:45 pm
ORD
- GCM
2 stops42h 40m
Multiple Airlines
Mon 9/2112:25 pm
GCM
- ORD
1 stop20h 35m
Multiple Airlines
Deal found 7/31![Multiple Airlines logo]()
$523
This Delta deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/245:27 am
ORD
- MBJ
1 stop7h 33m
Delta
Wed 10/2812:59 pm
MBJ
- ORD
1 stop8h 44m
Delta
Deal found 7/28![Delta logo]()
$442
This United Airlines deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/279:17 am
ORD
- PUJ
Nonstop4h 40m
United Airlines
Sat 10/311:55 pm
PUJ
- ORD
Nonstop5h 15m
United Airlines
Deal found 7/28![United Airlines logo]()
$417
This Southwest deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/143:25 pm
MDW
- SJU
1 stop7h 20m
Southwest
Sat 10/245:00 am
SJU
- MDW
2 stops9h 55m
Southwest
Deal found 7/30![Southwest logo]()
$326
This JetBlue deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/266:00 am
ORD
- NAS
1 stop9h 04m
JetBlue
Wed 8/266:27 pm
NAS
- ORD
1 stop6h 17m
JetBlue
Deal found 7/27![JetBlue logo]()
$483
Last-minute flights from Illinois to CaribbeanDiscover last-minute flight deals from Illinois to Caribbean. Data last updated July 31, 2026 and is based on user searches.
Discover last-minute flight deals from Illinois to Caribbean. Data last updated July 31, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” 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 8/1712:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Tue 8/256:35 am
SJU
- ORD
1 stop31h 15m
Frontier
Deal found 7/27![Frontier logo]()
$230
This Kiwi.com deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” 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 8/1712:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Mon 8/246:35 am
SJU
- ORD
1 stop31h 15m
Frontier
Deal found 7/27![Frontier logo]()
$233
This Super.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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.
Fri 8/2112:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Sat 8/297:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 7/31![Frontier logo]()
$225
This Super.com deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2212:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Wed 8/267:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 7/29![Frontier logo]()
$227
This FlightHub deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/2312:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Sat 8/297:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 7/29![Frontier logo]()
$226
This Kiwi.com deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/258:05 am
ORD
- SJU
1 stop31h 06m
Frontier
Tue 9/16:35 am
SJU
- ORD
1 stop31h 15m
Frontier
Deal found 7/30![Frontier logo]()
$224
This Kiwi.com deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/268:05 am
ORD
- SJU
1 stop31h 06m
Frontier
Sat 8/297:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 7/29![Frontier logo]()
$231
This Frontier deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2812:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Tue 9/17:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 7/30![Frontier logo]()
$228
This Frontier deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2812:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Wed 9/27:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 7/29![Frontier logo]()
$229
This FlightHub deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2912:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Sun 9/67:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 7/29![Frontier logo]()
$235
This Kiwi.com deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 8/3012:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Mon 9/217:00 am
SJU
- ORD
1 stop8h 45m
Frontier
Deal found 7/31![Frontier logo]()
$234
This Kiwi.com deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/318:05 am
ORD
- SJU
1 stop31h 06m
Frontier
Thu 9/247:00 am
SJU
- ORD
1 stop8h 45m
Frontier
Deal found 7/30![Frontier logo]()
$232
One-way flights from Illinois to CaribbeanSearch for one-way flight options from Illinois to Caribbean. Find affordable one-way fares based on user searches. Data last updated July 31, 2026.
Search for one-way flight options from Illinois to Caribbean. Find affordable one-way fares based on user searches. Data last updated July 31, 2026.
This Kiwi.com deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” 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 9/307:11 am
ORD
- SJU
1 stop29h 23m
Frontier
Deal found 7/28![Frontier logo]()
$104
This Kiwi.com deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/2512:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 7/30![Frontier logo]()
$106
This Super.com deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” 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.
Fri 8/2812:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 7/28![Frontier logo]()
$108
This Super.com deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” 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.
Fri 8/2112:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 7/27![Frontier logo]()
$109
This Frontier deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” 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 9/112:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 7/27![Frontier logo]()
$114
This Kiwi.com deal was found by Cheapflights users on 7/27. Clicking the “Pick Dates” 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 9/237:11 am
ORD
- SJU
1 stop29h 23m
Frontier
Deal found 7/27![Frontier logo]()
$115
This Kiwi.com deal was found by Cheapflights users on 7/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/97:11 am
ORD
- SJU
1 stop29h 23m
Frontier
Deal found 7/30![Frontier logo]()
$116
This eDestinos deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” 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.
Wed 8/512:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 7/28![Frontier logo]()
$117
This Super.com deal was found by Cheapflights users on 7/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1812:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 7/29![Frontier logo]()
$119
This Expedia deal was found by Cheapflights users on 7/28. Clicking the “Pick Dates” 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 8/252:00 pm
ORD
- NAS
2 stops22h 35m
Air Canada
Deal found 7/28![Air Canada logo]()
$130
This JetBlue deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/276:00 am
ORD
- NAS
1 stop9h 00m
JetBlue
Deal found 7/31![JetBlue logo]()
$132
This Orbitz deal was found by Cheapflights users on 7/31. Clicking the “Pick Dates” 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 10/178:45 am
ORD
- NAS
2 stops31h 45m
Air Canada
Deal found 7/31![Air Canada logo]()
$133
Find flight deals from Illinois to Caribbean
Keep the following information in mind while searching for Illinois to Caribbean flight deals. Data was last updated July 31, 2026.
Round-trip from | $224 (Kiwi.com) |
|---|---|
One-way from | $104 (Kiwi.com) |
Popular in | December |
Cheapest in | August |
Average price | $386 |
Good round-trip deal | $322 or less |
Good one-way deal | $133 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Illinois to Caribbean 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 July 31, 2026.
Use the filters below to find and compare flights from Illinois to Caribbean that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Tue 9/1
7:30 am-7:00 pm
1 stop10h 30m
San Juan Luis Munoz Marin Intl
Wed 9/2
5:15 am-12:05 pm
1 stop7h 50m
$271
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Mon 8/31
11:15 am-8:05 pm
1 stop7h 50m
San Juan Luis Munoz Marin Intl
Sat 9/5
5:05 am-11:00 am
1 stop6h 55m
$275
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Thu 8/13
2:35 pm-11:20 pm
1 stop7h 45m
San Juan Luis Munoz Marin Intl
Fri 9/4
5:05 am-1:39 pm
1 stop9h 34m
$300
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Wed 8/12
7:00 am-4:05 pm
1 stop8h 05m
San Juan Luis Munoz Marin Intl
Sat 9/5
5:00 pm-11:44 pm
1 stop7h 44m
$300
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 9/22
10:25 am-11:49 pm
1 stop12h 24m
San Juan Luis Munoz Marin Intl
Tue 9/29
7:30 am-4:59 pm
1 stop10h 29m
$316
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Fri 8/28
11:15 am-8:05 pm
1 stop7h 50m
San Juan Luis Munoz Marin Intl
Fri 9/4
6:30 am-3:35 pm
1 stop10h 05m
$316
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Sun 8/23
8:05 am-5:05 pm
1 stop8h 00m
San Juan Luis Munoz Marin Intl
Sun 8/30
9:25 pm-10:00 am
1 stop13h 35m
$316
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Sun 9/27
8:05 pm-9:10 am
1 stop12h 05m
San Juan Luis Munoz Marin Intl
Thu 10/1
10:50 pm-8:45 am
1 stop10h 55m
$316
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Fri 10/23
4:15 pm-1:20 am
2 stops8h 05m
San Juan Luis Munoz Marin Intl
Wed 11/4
6:15 am-1:00 pm
1 stop8h 45m
$316
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Wed 9/9
9:40 am-6:10 pm
1 stop7h 30m
San Juan Luis Munoz Marin Intl
Wed 9/16
1:45 pm-9:00 pm
1 stop8h 15m
$316
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Illinois to Caribbean
Have a flexible travel schedule? Discover the best time to fly to Caribbean from Illinois with our price prediction graph.
ORD-SJU
MDW-SJU
ORD-PUJ
ORD-GCM
ORD-MBJ
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 Illinois to Caribbean
USIL-0CB
ORD-SJU
MDW-SJU
ORD-PUJ
ORD-GCM
What is the cheapest month to book a flight from Illinois to Caribbean?
Currently, August is the cheapest month in which you can book a flight from Illinois to Caribbean (average of $444). Flying from Illinois to Caribbean in December is currently the most expensive (average of $611). 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 IL to CB?
Find hourly flight availability from Illinois to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated July 31, 2026.
One of the essential ways to save on airfare from Illinois to Caribbean is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the evening could potentially save you up to 34% on airfare.
Weekly flight availability from Illinois to Caribbean
Explore weekly flight availability from Illinois to Caribbean. 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 July 31, 2026.
The most flights from USIL to 0CB are scheduled on a Thursday (10 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (7 on average).
How far ahead should I book a flight from Illinois to Caribbean?
Booking 48 days in advance of your planned departure date is, on average, the best time to get cheap flights from Illinois to Caribbean. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
What is the cheapest day to fly from Illinois to Caribbean?
Use this chart to determine the cheapest time to fly round-trip from Illinois to Caribbean. Price data was last updated on July 25, 2026.
Travelers seeking maximum savings on their Illinois to Caribbean flight should consider departing on Sunday evenings when fares are most often at their lowest. Thursday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
Related info for your journey
Find useful and relevant information for your journey from Illinois to Caribbean. 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 Illinois to Caribbean
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Caribbean by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Illinois to Caribbean by cabin class
Find flights from Illinois to Caribbean, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Illinois and Caribbean flights
Browse other Illinois and Caribbean flight options. Last updated on July 31, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Find a return flight route from Caribbean
Find the right flight back to Illinois after your stay in Caribbean
Fly to Caribbean countries
Consider these flights traveling to countries located in Caribbean.
Illinois to Caribbean flights
Consider these flights traveling from Illinois to Caribbean.
Top 9 airlines flying from Illinois to Caribbean
Discover the top 9 airlines that operate flights from Illinois to Caribbean. 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 July 31, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$91 | Average$586 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$118 | Average$559 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$119 | Average$440 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$175 | Average$528 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$218 | Average$370 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$228 | Average$486 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$261 | Average$582 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$295 | Average$631 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$346 | Average$691 | FlexibilityNo cancel fee | On-time63% |