$110+ 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 11/16. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
Oct 19 — Oct 261
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 September 19, 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 September 19, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 10/296:00 am -
1 stop16h 25m
Mon 11/26:15 am -
1 stop18h 28m
Deal found 9/17![Frontier logo]()
$217
This CheapOair deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 10/206:21 am -
1 stop8h 45m
Thu 10/293:59 pm -
1 stop8h 48m
Deal found 9/18![Frontier logo]()
$217
This CheapOair deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/77:11 am -
1 stop7h 06m
Sat 10/177:15 am -
1 stop16h 24m
Deal found 9/17![Frontier logo]()
$218
This Frontier deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 10/256:00 am -
1 stop18h 17m
Sat 10/316:26 pm -
1 stop16h 20m
Deal found 9/17![Frontier logo]()
$219
This Cheapflightsfares deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 10/164:41 pm -
1 stop22h 45m
Fri 10/232:51 pm -
1 stop8h 48m
Deal found 9/17![Frontier logo]()
$220
This Cheapflightsfares deal was found by Cheapflights users on 9/16. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/76:25 am -
1 stop7h 54m
Tue 11/173:59 pm -
1 stop9h 48m
Deal found 9/16![Frontier logo]()
$220
This Super.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/67:11 am -
1 stop7h 06m
Thu 10/157:00 am -
1 stop9h 30m
Deal found 9/15![Frontier logo]()
$221
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/304:42 pm -
1 stop22h 34m
Thu 11/57:00 am -
1 stop10h 37m
Deal found 9/16![Frontier logo]()
$222
This Frontier deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/76:25 am -
1 stop7h 54m
Wed 10/283:59 pm -
1 stop8h 48m
Deal found 9/16![Frontier logo]()
$222
This FlightHub deal was found by Cheapflights users on 9/16. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/104:41 pm -
1 stop16h 38m
Thu 10/157:00 am -
1 stop9h 30m
Deal found 9/16![Frontier logo]()
$223
This Kiwi.com deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 11/210:26 am -
1 stop12h 33m
Fri 11/66:15 am -
1 stop18h 28m
Deal found 9/17![Frontier logo]()
$224
This CheapOair deal was found by Cheapflights users on 9/16. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/266:15 am -
1 stop8h 51m
Wed 11/43:59 pm -
1 stop9h 48m
Deal found 9/16![Frontier logo]()
$224
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 September 19, 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 September 19, 2026.
This JetBlue deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 11/181:00 pm -
1 stop10h 13m
Fri 12/43:30 pm -
1 stop10h 03m
Deal found 9/17![JetBlue logo]()
$241
This United Airlines deal was found by Cheapflights users on 9/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/295:00 am -
1 stop7h 11m
Thu 11/58:25 am -
Nonstop5h 22m
Deal found 9/15![United Airlines logo]()
$242
This Southwest deal was found by Cheapflights users on 9/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/161:20 pm -
1 stop7h 05m
Mon 11/232:20 pm -
1 stop10h 25m
Deal found 9/15![Southwest logo]()
$285
This Arajet deal was found by Cheapflights users on 9/15. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/710:27 am -
Nonstop4h 45m
Thu 11/127:30 pm -
Nonstop5h 10m
Deal found 9/15![Arajet logo]()
$365
This Air Canada deal was found by Cheapflights users on 9/15. 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.
Fri 10/303:45 pm -
2 stops19h 25m
Fri 11/61:10 pm -
1 stop7h 48m
Deal found 9/15![Air Canada logo]()
$379
This Delta deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 11/36:30 am -
1 stop6h 30m
Tue 11/106:12 pm -
2 stops14h 34m
Deal found 9/17![Delta logo]()
$467
This Copa Airlines deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 10/163:20 pm -
1 stop19h 57m
Sat 10/2412:22 pm -
1 stop12h 35m
Deal found 9/18![Copa Airlines logo]()
$470
This United Airlines deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 10/2710:32 am -
1 stop9h 50m
Fri 10/303:55 pm -
Nonstop5h 31m
Deal found 9/18![United Airlines logo]()
$242
This United Airlines deal was found by Cheapflights users on 9/15. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/65:00 am -
1 stop7h 45m
Tue 10/277:25 am -
Nonstop5h 22m
Deal found 9/15![United Airlines logo]()
$242
This United Airlines deal was found by Cheapflights users on 9/16. 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 1/219:15 am -
1 stop10h 09m
Fri 1/298:05 am -
1 stop8h 06m
Deal found 9/16![United Airlines logo]()
$250
This American Airlines deal was found by Cheapflights users on 9/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/146:49 pm -
1 stop15h 34m
Sat 11/214:25 pm -
Nonstop4h 40m
Deal found 9/16![American Airlines logo]()
$627
This JetBlue deal was found by Cheapflights users on 9/14. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/252:35 pm -
1 stop8h 24m
Sun 12/66:01 am -
1 stop9h 29m
Deal found 9/14![JetBlue logo]()
$318
This Southwest deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 10/61:40 pm -
2 stops8h 30m
Thu 10/158:50 pm -
1 stop12h 55m
Deal found 9/18![Southwest logo]()
$321
This Mytrip deal was found by Cheapflights users on 9/13. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/197:05 am -
3 stops25h 35m
Mon 11/2311:45 am -
3 stops29h 07m
Deal found 9/13![Multiple Airlines logo]()
$682
This United Airlines deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 10/282:16 pm -
Nonstop4h 44m
Sun 11/18:25 am -
Nonstop5h 22m
Deal found 9/18![United Airlines logo]()
$273
This Arajet deal was found by Cheapflights users on 9/14. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/3111:27 am -
Nonstop4h 45m
Sun 11/86:10 pm -
Nonstop5h 10m
Deal found 9/14![Arajet logo]()
$395
This Southwest deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 10/287:40 am -
2 stops11h 55m
Sun 11/16:05 am -
2 stops10h 20m
Deal found 9/18![Southwest logo]()
$373
This Southwest deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 10/912:50 pm -
1 stop6h 10m
Tue 10/138:15 am -
1 stop7h 30m
Deal found 9/18![Southwest logo]()
$373
This United Airlines deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 11/1812:59 pm -
1 stop9h 37m
Sat 11/214:55 pm -
Nonstop5h 31m
Deal found 9/18![United Airlines logo]()
$314
This JetBlue deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 10/307:00 am -
1 stop6h 25m
Wed 11/44:31 pm -
1 stop9h 26m
Deal found 9/18![JetBlue logo]()
$425
This Copa Airlines deal was found by Cheapflights users on 9/16. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/132:13 pm -
1 stop20h 57m
Mon 11/1612:45 pm -
1 stop26h 01m
Deal found 9/16![Copa Airlines logo]()
$478
This Southwest deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 10/1512:45 pm -
1 stop10h 25m
Thu 10/228:50 pm -
1 stop12h 55m
Deal found 9/17![Southwest logo]()
$373
This United Airlines deal was found by Cheapflights users on 9/16. 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.
Wed 10/148:55 am -
Nonstop4h 49m
Wed 10/213:56 pm -
Nonstop5h 09m
Deal found 9/16![United Airlines logo]()
$319
This Air Canada deal was found by Cheapflights users on 9/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/43:45 pm -
2 stops22h 45m
Mon 1/115:25 pm -
1 stop17h 43m
Deal found 9/13![Air Canada logo]()
$523
This Delta deal was found by Cheapflights users on 9/13. 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.
Wed 9/306:00 am -
1 stop11h 07m
Wed 10/72:57 pm -
1 stop10h 00m
Deal found 9/13![Delta logo]()
$524
This Copa Airlines deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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.
Mon 3/87:08 am -
1 stop26h 28m
Mon 3/152:37 pm -
1 stop23h 57m
Deal found 9/17![Copa Airlines logo]()
$488
This Southwest deal was found by Cheapflights users on 9/15. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/162:50 pm -
2 stops8h 20m
Mon 10/196:00 am -
2 stops10h 00m
Deal found 9/15![Southwest logo]()
$383
This Delta deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 11/46:04 am -
1 stop6h 28m
Wed 11/187:02 am -
2 stops11h 37m
Deal found 9/18![Delta logo]()
$525
This Copa Airlines deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 10/278:35 am -
1 stop26h 10m
Tue 11/312:10 pm -
1 stop14h 01m
Deal found 9/17![Copa Airlines logo]()
$490
This United Airlines deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 10/295:55 am -
1 stop6h 45m
Sat 10/313:55 pm -
Nonstop5h 31m
Deal found 9/18![United Airlines logo]()
$342
Last-minute flights from Illinois to CaribbeanDiscover last-minute flight deals from Illinois to Caribbean. Data last updated September 19, 2026 and is based on user searches.
Discover last-minute flight deals from Illinois to Caribbean. Data last updated September 19, 2026 and is based on user searches.
This deal was found by Cheapflights users on 9/15. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/266:20 am -
1 stop8h 46m
Tue 9/298:45 am -
1 stop7h 35m
Deal found 9/15![Frontier logo]()
$225
This Super.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/67:11 am -
1 stop7h 06m
Thu 10/157:00 am -
1 stop9h 30m
Deal found 9/15![Frontier logo]()
$221
This FlightHub deal was found by Cheapflights users on 9/16. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/77:11 am -
1 stop7h 06m
Sat 10/177:15 am -
1 stop16h 24m
Deal found 9/16![Frontier logo]()
$218
This Cheapflightsfares deal was found by Cheapflights users on 9/16. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/76:25 am -
1 stop7h 54m
Tue 11/173:59 pm -
1 stop9h 48m
Deal found 9/16![Frontier logo]()
$220
This Frontier deal was found by Cheapflights users on 9/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/76:25 am -
1 stop7h 54m
Tue 10/273:59 pm -
1 stop8h 48m
Deal found 9/16![Frontier logo]()
$222
This FlightHub deal was found by Cheapflights users on 9/16. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/104:41 pm -
1 stop16h 38m
Thu 10/157:00 am -
1 stop9h 30m
Deal found 9/16![Frontier logo]()
$223
This Cheapflightsfares deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 10/164:41 pm -
1 stop22h 45m
Fri 10/232:51 pm -
1 stop8h 48m
Deal found 9/17![Frontier logo]()
$220
This CheapOair deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 10/206:21 am -
1 stop8h 45m
Thu 10/293:59 pm -
1 stop8h 48m
Deal found 9/18![Frontier logo]()
$217
This Frontier deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 10/256:00 am -
1 stop18h 17m
Sat 10/316:26 pm -
1 stop16h 20m
Deal found 9/17![Frontier logo]()
$219
This CheapOair deal was found by Cheapflights users on 9/16. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/266:15 am -
1 stop8h 51m
Wed 11/43:59 pm -
1 stop9h 48m
Deal found 9/16![Frontier logo]()
$224
This Kiwi.com deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 10/296:00 am -
1 stop16h 25m
Mon 11/26:15 am -
1 stop18h 28m
Deal found 9/17![Frontier logo]()
$217
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/304:42 pm -
1 stop22h 34m
Thu 11/57:00 am -
1 stop10h 37m
Deal found 9/16![Frontier logo]()
$222
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 September 19, 2026.
Search for one-way flight options from Illinois to Caribbean. Find affordable one-way fares based on user searches. Data last updated September 19, 2026.
This Trip.com deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/1610:15 am -
1 stop24h 55m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Air Canada logo]()
$110
This Cheapflightsfares deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 10/156:00 am -
1 stop18h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Frontier logo]()
$110
This Super.com deal was found by Cheapflights users on 9/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/136:21 am -
1 stop8h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Frontier logo]()
$110
This Frontier deal was found by Cheapflights users on 9/15. 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.
Sun 10/116:24 am -
1 stop8h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Frontier logo]()
$111
This Frontier deal was found by Cheapflights users on 9/15. 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.
Sat 10/318:00 am -
1 stop13h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Frontier logo]()
$113
This CheapOair deal was found by Cheapflights users on 9/14. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/76:25 am -
1 stop7h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Frontier logo]()
$113
This Kiwi.com deal was found by Cheapflights users on 9/15. 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.
Fri 10/164:41 pm -
1 stop16h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Frontier logo]()
$115
This Travelocity deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 1/1512:17 am -
Nonstop4h 46m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Frontier logo]()
$116
This Priceline deal was found by Cheapflights users on 9/15. 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.
Sun 11/228:42 pm -
1 stop27h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Frontier logo]()
$117
This Kiwi.com deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 11/156:00 am -
1 stop15h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Frontier logo]()
$118
This JetBlue deal was found by Cheapflights users on 9/17. Clicking the “Pick Dates” 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 11/171:00 pm -
1 stop10h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![JetBlue logo]()
$119
This Kiwi.com deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” 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 12/152:04 pm -
1 stop9h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Frontier logo]()
$119
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 September 19, 2026.
Round-trip from | $217 (Kiwi.com) |
|---|---|
One-way from | $110 (Trip.com) |
Popular in | December |
Cheapest in | August |
Average price | $340 |
Good round-trip deal | $315 or less |
Good one-way deal | $159 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 September 19, 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
Sun 2/21
9:30 am-9:00 pm
1 stop9h 30m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$120
ChicagoSan Juan
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Tue 2/9
3:00 pm-11:50 pm
1 stop6h 50m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$120
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Tue 11/10
1:05 pm-11:15 pm
1 stop8h 10m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$120
ChicagoSan Juan
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Wed 11/11
12:59 pm-12:36 am
1 stop9h 37m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$123
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Wed 11/11
4:25 pm-12:50 am
1 stop6h 25m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$123
ChicagoGeorge Town
ORD Chicago O'Hare Intl - GCM George Town Owen Roberts Intl
ORDGCM
Chicago O'Hare Intl
Wed 11/18
4:30 pm-12:10 pm
1 stop18h 40m
George Town Owen Roberts Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$124
ChicagoSan Juan
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Sat 1/16
12:40 pm-12:36 am
1 stop9h 56m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$125
ChicagoGeorge Town
ORD Chicago O'Hare Intl - GCM George Town Owen Roberts Intl
ORDGCM
Chicago O'Hare Intl
Sun 10/18
8:45 am-11:25 am
2 stops26h 40m
George Town Owen Roberts Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$132
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Sat 10/3
6:25 am-4:06 pm
1 stop8h 41m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$136
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Thu 10/22
4:15 pm-1:25 am
2 stops8h 10m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$143
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-GCM
ORD-SDQ
ORD-PUJ
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-GCM
ORD-SDQ
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 $431). 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 September 19, 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 31% 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 September 19, 2026.
The most flights from USIL to 0CB are scheduled on a Monday (3 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (1 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 September 12, 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 September 19, 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 September 19, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$91 | Average$520 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$118 | Average$615 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$118 | Average$461 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$223 | Average$376 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$231 | Average$554 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$235 | Average$586 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$262 | Average$589 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$276 | Average$674 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$286 | Average$641 | FlexibilityNo cancel fee | On-time71% |