$128+ Cheap flights from Illinois to Caribbean
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 11/15. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
Dec 4 — Dec 111
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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from Illinois to Caribbean
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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 November 4, 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 November 4, 2026.
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 11/232:52 pm -
1 stop22h 08m
Mon 11/303:43 am -
1 stop23h 16m
Deal found 10/30![Frontier logo]()
$245
This Kiwi.com deal was found by Cheapflights users on 10/31. 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.
Thu 12/105:24 pm -
1 stop6h 49m
Sat 12/197:28 am -
1 stop13h 40m
Deal found 10/31![Frontier logo]()
$247
This Kiwi.com deal was found by Cheapflights users on 10/31. 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 12/69:34 pm -
1 stop11h 51m
Mon 12/212:29 am -
1 stop11h 31m
Deal found 10/31![Frontier logo]()
$248
This Kiwi.com deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” 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 12/135:24 pm -
1 stop6h 49m
Fri 12/186:00 am -
1 stop12h 59m
Deal found 11/3![Frontier logo]()
$249
This Cheapflightsfares deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” 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 11/1310:19 am -
1 stop12h 40m
Fri 11/207:12 pm -
Nonstop5h 09m
Deal found 11/1![Frontier logo]()
$250
This Cheapflightsfares deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” 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 11/167:55 am -
1 stop29h 24m
Mon 11/237:58 pm -
1 stop13h 49m
Deal found 11/2![Frontier logo]()
$251
This Cheapflightsfares deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” 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 11/134:42 pm -
1 stop21h 35m
Sun 11/226:00 am -
1 stop11h 57m
Deal found 11/1![Frontier logo]()
$252
This Kiwi.com deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” 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 11/126:00 am -
1 stop15h 28m
Thu 11/266:31 pm -
1 stop15h 15m
Deal found 11/1![Frontier logo]()
$253
This Frontier deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/226:20 am -
1 stop13h 29m
Tue 12/13:43 am -
1 stop10h 01m
Deal found 11/3![Frontier logo]()
$254
This eDestinos deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” 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 11/56:00 am -
1 stop15h 28m
Mon 11/97:26 pm -
1 stop23h 41m
Deal found 11/1![Frontier logo]()
$255
This Cheapflightsfares deal was found by Cheapflights users on 10/31. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/115:35 am -
1 stop15h 54m
Fri 12/1810:26 pm -
Nonstop5h 07m
Deal found 10/31![Frontier logo]()
$256
This Cheapflightsfares deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” 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.
Sat 12/55:24 pm -
1 stop17h 46m
Sun 12/131:27 pm -
1 stop8h 57m
Deal found 11/3![Frontier logo]()
$359
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 November 4, 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 November 4, 2026.
This United Airlines deal was found by Cheapflights users on 10/31. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/2710:30 am -
1 stop8h 54m
Wed 2/108:25 am -
Nonstop5h 24m
Deal found 10/31![United Airlines logo]()
$262
This JetBlue deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” 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 11/187:00 am -
1 stop7h 09m
Fri 12/46:38 am -
1 stop8h 52m
Deal found 11/2![JetBlue logo]()
$284
This Delta deal was found by Cheapflights users on 10/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/295:30 am -
1 stop6h 58m
Fri 12/44:55 pm -
2 stops25h 22m
Deal found 10/30![Delta logo]()
$405
This Copa Airlines deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” 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 2/202:13 pm -
1 stop20h 02m
Sat 2/272:28 pm -
1 stop10h 43m
Deal found 11/2![Copa Airlines logo]()
$500
This United Airlines deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/302:16 pm -
Nonstop4h 44m
Mon 2/83:46 pm -
1 stop9h 13m
Deal found 11/1![United Airlines logo]()
$262
This United Airlines deal was found by Cheapflights users on 10/30. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/92:16 pm -
Nonstop4h 44m
Tue 12/154:55 pm -
Nonstop5h 31m
Deal found 10/30![United Airlines logo]()
$294
This Mytrip deal was found by Cheapflights users on 10/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/57:25 am -
3 stops32h 55m
Tue 12/811:30 am -
2 stops11h 30m
Deal found 10/30![Multiple Airlines logo]()
$647
This United Airlines deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” 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 11/119:21 am -
1 stop10h 03m
Fri 11/138:25 am -
Nonstop5h 22m
Deal found 11/2![United Airlines logo]()
$302
This United Airlines deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” 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 12/210:35 am -
1 stop9h 47m
Sat 12/58:25 am -
Nonstop5h 24m
Deal found 11/3![United Airlines logo]()
$322
This JetBlue deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” 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 12/137:00 am -
1 stop6h 58m
Tue 12/222:50 pm -
1 stop10h 43m
Deal found 11/3![JetBlue logo]()
$439
This Delta deal was found by Cheapflights users on 10/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/81:55 pm -
2 stops20h 33m
Tue 11/174:55 pm -
1 stop8h 59m
Deal found 10/30![Delta logo]()
$445
This JetBlue deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” 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.
Fri 1/87:00 am -
1 stop6h 48m
Tue 1/125:20 pm -
1 stop8h 27m
Deal found 11/2![JetBlue logo]()
$461
This United Airlines deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” 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 11/178:52 am -
Nonstop4h 48m
Fri 11/204:55 pm -
Nonstop5h 31m
Deal found 11/3![United Airlines logo]()
$348
This Copa Airlines deal was found by Cheapflights users on 10/30. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/182:13 pm -
1 stop20h 05m
Wed 11/2512:17 pm -
1 stop12h 54m
Deal found 10/30![Copa Airlines logo]()
$510
This Delta deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” 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 1/307:10 am -
1 stop7h 40m
Tue 2/24:58 pm -
1 stop7h 22m
Deal found 11/2![Delta logo]()
$480
This JetBlue deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” 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.
Mon 1/47:00 am -
1 stop7h 18m
Sat 1/93:00 pm -
1 stop10h 47m
Deal found 11/2![JetBlue logo]()
$474
This United Airlines deal was found by Cheapflights users on 10/31. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/302:16 pm -
Nonstop4h 44m
Mon 12/74:55 pm -
Nonstop5h 31m
Deal found 10/31![United Airlines logo]()
$368
This Delta deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/295:30 am -
1 stop10h 27m
Tue 12/86:12 pm -
2 stops17h 47m
Deal found 11/1![Delta logo]()
$503
This Copa Airlines deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” 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.
Fri 2/122:13 pm -
1 stop22h 15m
Thu 2/1812:18 pm -
1 stop12h 53m
Deal found 11/3![Copa Airlines logo]()
$557
This JetBlue deal was found by Cheapflights users on 10/31. 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.
Tue 1/57:00 am -
1 stop7h 19m
Fri 1/292:44 pm -
1 stop11h 03m
Deal found 10/31![JetBlue logo]()
$491
This Copa Airlines deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” 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 4/273:13 pm -
1 stop19h 57m
Mon 5/312:19 pm -
1 stop25h 15m
Deal found 11/2![Copa Airlines logo]()
$557
This United Airlines deal was found by Cheapflights users on 10/31. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/15:55 am -
1 stop9h 33m
Tue 12/224:25 pm -
Nonstop5h 16m
Deal found 10/31![United Airlines logo]()
$390
This Delta deal was found by Cheapflights users on 10/30. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/87:00 am -
2 stops8h 44m
Thu 1/146:09 pm -
1 stop6h 48m
Deal found 10/30![Delta logo]()
$522
This JetBlue deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” 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 12/55:46 pm -
1 stop8h 10m
Mon 12/76:01 am -
1 stop9h 29m
Deal found 11/1![JetBlue logo]()
$510
This Copa Airlines deal was found by Cheapflights users on 10/30. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/67:35 am -
1 stop26h 07m
Fri 3/58:40 am -
1 stop17h 04m
Deal found 10/30![Copa Airlines logo]()
$568
This Delta deal was found by Cheapflights users on 10/31. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 1/51:45 pm -
2 stops12h 13m
Fri 1/299:35 pm -
2 stops16h 27m
Deal found 10/31![Delta logo]()
$525
This United Airlines deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/232:16 pm -
Nonstop4h 44m
Tue 1/265:50 pm -
1 stop7h 54m
Deal found 11/1![United Airlines logo]()
$402
This JetBlue deal was found by Cheapflights users on 10/31. 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 1/177:50 pm -
1 stop12h 48m
Sat 1/232:41 pm -
1 stop10h 06m
Deal found 10/31![JetBlue logo]()
$515
This Copa Airlines deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” 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.
Thu 1/712:27 am -
1 stop16h 02m
Wed 1/133:40 pm -
1 stop10h 27m
Deal found 11/3![Copa Airlines logo]()
$575
This United Airlines deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” 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 12/42:16 pm -
Nonstop4h 44m
Thu 12/178:25 am -
Nonstop5h 24m
Deal found 11/3![United Airlines logo]()
$412
Last-minute flights from Illinois to CaribbeanDiscover last-minute flight deals from Illinois to Caribbean. Data last updated November 4, 2026 and is based on user searches.
Discover last-minute flight deals from Illinois to Caribbean. Data last updated November 4, 2026 and is based on user searches.
This eDestinos deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” 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 11/56:00 am -
1 stop15h 28m
Mon 11/97:26 pm -
1 stop23h 41m
Deal found 11/1![Frontier logo]()
$255
This Kiwi.com deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” 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 11/126:00 am -
1 stop15h 28m
Mon 11/237:58 pm -
1 stop13h 49m
Deal found 11/1![Frontier logo]()
$253
This Cheapflightsfares deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” 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 11/1310:19 am -
1 stop12h 40m
Fri 11/207:12 pm -
Nonstop5h 09m
Deal found 11/1![Frontier logo]()
$250
This Cheapflightsfares deal was found by Cheapflights users on 10/30. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/156:00 am -
1 stop15h 28m
Sun 11/2210:54 pm -
1 stop27h 49m
Deal found 10/30![Frontier logo]()
$252
This Cheapflightsfares deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” 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 11/167:55 am -
1 stop29h 24m
Mon 11/237:58 pm -
1 stop13h 49m
Deal found 11/2![Frontier logo]()
$251
This Frontier deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/226:20 am -
1 stop13h 29m
Thu 11/266:31 pm -
1 stop15h 15m
Deal found 11/2![Frontier logo]()
$254
This Kiwi.com deal was found by Cheapflights users on 10/30. 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 11/232:52 pm -
1 stop22h 08m
Mon 11/303:43 am -
1 stop23h 16m
Deal found 10/30![Frontier logo]()
$245
This Cheapflightsfares deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” 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.
Sat 12/55:24 pm -
1 stop17h 46m
Sun 12/131:27 pm -
1 stop8h 57m
Deal found 11/3![Frontier logo]()
$359
This Kiwi.com deal was found by Cheapflights users on 10/31. 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 12/610:29 pm -
1 stop13h 00m
Sun 12/202:29 am -
1 stop11h 31m
Deal found 10/31![Frontier logo]()
$248
This Kiwi.com deal was found by Cheapflights users on 10/31. 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.
Thu 12/105:24 pm -
1 stop6h 49m
Sat 12/197:28 am -
1 stop13h 40m
Deal found 10/31![Frontier logo]()
$247
This Kiwi.com deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” 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 12/135:24 pm -
1 stop6h 49m
Fri 12/186:00 am -
1 stop12h 59m
Deal found 11/3![Frontier logo]()
$249
This Cheapflightsfares deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” 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 12/145:24 pm -
1 stop6h 49m
Fri 12/1810:26 pm -
Nonstop5h 07m
Deal found 11/1![Frontier logo]()
$256
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 November 4, 2026.
Search for one-way flight options from Illinois to Caribbean. Find affordable one-way fares based on user searches. Data last updated November 4, 2026.
This Mytrip deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” 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.
Sun 11/157:55 am -
1 stop27h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Frontier logo]()
$128
This American Airlines deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/175:01 pm -
Nonstop4h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![American Airlines logo]()
$129
This Super.com deal was found by Cheapflights users on 10/30. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/1312:17 am -
Nonstop4h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/30![Frontier logo]()
$130
This Super.com deal was found by Cheapflights users on 10/30. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/12:59 pm -
1 stop9h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/30![JetBlue logo]()
$131
This Cheapflightsfares deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/1010:31 pm -
Nonstop4h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![Frontier logo]()
$132
This JetBlue deal was found by Cheapflights users on 11/3. Clicking the “Pick Dates” 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.
Tue 12/152:59 pm -
1 stop9h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/3![JetBlue logo]()
$133
This eDestinos deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” 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.
Sun 11/86:00 am -
1 stop15h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![Frontier logo]()
$135
This Cheapflightsfares deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” 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 11/134:42 pm -
1 stop16h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Frontier logo]()
$136
This Cheapflightsfares deal was found by Cheapflights users on 11/2. Clicking the “Pick Dates” 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 12/318:59 am -
1 stop13h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/2![Frontier logo]()
$137
This Frontier deal was found by Cheapflights users on 11/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/226:20 am -
1 stop13h 29m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/4![Frontier logo]()
$138
This American Airlines deal was found by Cheapflights users on 11/1. Clicking the “Pick Dates” 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 11/307:50 pm -
1 stop14h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 11/1![American Airlines logo]()
$139
This Mytrip deal was found by Cheapflights users on 10/30. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/810:00 am -
2 stops13h 07m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/30![Frontier logo]()
$140
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 November 4, 2026.
Round-trip from | $245 (Kiwi.com) |
|---|---|
One-way from | $128 (Mytrip) |
Popular in | December |
Cheapest in | August |
Average price | $492 |
Good round-trip deal | $406 or less |
Good one-way deal | $196 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 7,457,451 searches. Data last updated November 4, 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
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Tue 12/15
2:59 pm-2:05 am
1 stop9h 06m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$133
ChicagoSan Juan
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Mon 12/14
2:59 pm-1:59 am
1 stop9h 00m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$133
Quickest round-trip
ChicagoSan Juan
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Mon 11/9
2:16 pm-9:00 pm
Nonstop4h 44m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$149
ChicagoSan Juan
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Fri 11/13
2:16 pm-9:00 pm
Nonstop4h 44m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$149
ChicagoSanto Domingo
ORD Chicago O'Hare Intl - SDQ Santo Domingo Las Americas
ORDSDQ
Chicago O'Hare Intl
Thu 11/12
7:50 pm-2:55 pm
1 stop17h 05m
Santo Domingo Las Americas
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$155
ChicagoGeorge Town
ORD Chicago O'Hare Intl - GCM George Town Owen Roberts Intl
ORDGCM
Chicago O'Hare Intl
Sun 12/13
7:05 am-12:10 pm
2 stops28h 05m
George Town Owen Roberts Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$160
ChicagoSanto Domingo
ORD Chicago O'Hare Intl - SDQ Santo Domingo Las Americas
ORDSDQ
Chicago O'Hare Intl
Thu 11/12
1:00 pm-3:05 am
1 stop12h 05m
Santo Domingo Las Americas
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$169
ChicagoPunta Cana
ORD Chicago O'Hare Intl - PUJ Punta Cana
ORDPUJ
Chicago O'Hare Intl
Sat 1/2
7:00 am-4:22 pm
1 stop7h 22m
Punta Cana
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$178
ChicagoPunta Cana
ORD Chicago O'Hare Intl - PUJ Punta Cana
ORDPUJ
Chicago O'Hare Intl
Tue 1/5
7:00 am-3:48 pm
1 stop6h 48m
Punta Cana
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$179
ChicagoPunta Cana
ORD Chicago O'Hare Intl - PUJ Punta Cana
ORDPUJ
Chicago O'Hare Intl
Tue 12/1
5:55 am-5:28 pm
1 stop9h 33m
Punta Cana
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$183
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
ORD-SDQ
ORD-GCM
ORD-NAS
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
ORD-SDQ
ORD-GCM
ORD-NAS
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 $433). Flying from Illinois to Caribbean in December is currently the most expensive (average of $648). 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 November 4, 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 36% 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 November 4, 2026.
The most flights from USIL to 0CB are scheduled on a Monday (8 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (6 on average).
How far ahead should I book a flight from Illinois to Caribbean?
Booking 19 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 October 31, 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 November 4, 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 7,457,451 searches. Data last updated November 4, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$91 | Average$550 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$118 | Average$469 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$118 | Average$615 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$229 | Average$379 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$235 | Average$449 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$262 | Average$624 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$276 | Average$650 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$285 | Average$664 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$318 | Average$486 | FlexibilityNo cancel fee | On-timeN/A |