$104+ Cheap flights from O'Hare Intl (ORD) to Caribbean Islands
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 9/6. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
Oct 2 — Oct 91
Round-trip
1 adult, Economy
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Find cheap flights from O'Hare Intl to Caribbean Islands with Cheapflights
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Cheapest flights from O'Hare Intl to Caribbean IslandsExplore the most affordable flight options available from O'Hare Intl to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 2, 2026.
Explore the most affordable flight options available from O'Hare Intl to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 2, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/30. 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.
Sat 9/512:44 am -
Nonstop5h 00m
Wed 9/98:45 am -
1 stop31h 00m
Deal found 8/30![Frontier logo]()
$213
This CheapOair deal was found by Cheapflights users on 8/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/212:44 am -
Nonstop5h 00m
Tue 9/87:14 pm -
Nonstop5h 13m
Deal found 8/29![Frontier logo]()
$216
This American Airlines deal was found by Cheapflights users on 8/31. 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 10/58:13 am -
Nonstop4h 50m
Wed 10/142:53 pm -
Nonstop5h 36m
Deal found 8/31![American Airlines logo]()
$217
This American Airlines deal was found by Cheapflights users on 8/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/178:13 am -
Nonstop4h 50m
Wed 10/212:53 pm -
Nonstop5h 36m
Deal found 8/28![American Airlines logo]()
$218
This CheapOair deal was found by Cheapflights users on 8/28. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/3112:44 am -
Nonstop5h 00m
Thu 9/37:14 pm -
Nonstop5h 13m
Deal found 8/28![Frontier logo]()
$219
This American Airlines deal was found by Cheapflights users on 8/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/166:40 pm -
1 stop15h 40m
Wed 10/212:53 pm -
Nonstop5h 36m
Deal found 8/28![American Airlines logo]()
$222
This Super.com deal was found by Cheapflights users on 8/28. 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.
Sun 8/3012:44 am -
Nonstop5h 00m
Sat 9/57:14 pm -
Nonstop5h 13m
Deal found 8/28![Frontier logo]()
$223
This Kiwi.com deal was found by Cheapflights users on 8/30. 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 8/3112:44 am -
Nonstop5h 00m
Wed 9/98:45 am -
1 stop31h 00m
Deal found 8/30![Frontier logo]()
$224
This American Airlines deal was found by Cheapflights users on 8/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/226:00 am -
1 stop6h 57m
Tue 9/292:58 pm -
1 stop10h 35m
Deal found 8/28![American Airlines logo]()
$226
This American Airlines deal was found by Cheapflights users on 9/2. 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.
Wed 9/306:00 am -
1 stop13h 47m
Tue 10/62:53 pm -
Nonstop5h 36m
Deal found 9/2![American Airlines logo]()
$227
This Super.com deal was found by Cheapflights users on 8/29. 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 9/112:44 am -
Nonstop5h 00m
Sat 9/57:14 pm -
Nonstop5h 13m
Deal found 8/29![Frontier logo]()
$228
This Vliegwinkel deal was found by Cheapflights users on 8/30. 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 Vliegwinkel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/113:45 pm -
1 stop18h 00m
Thu 9/1712:25 pm -
1 stop20h 35m
Deal found 8/30![Air Canada logo]()
$301
Best flights from O'Hare Intl to Caribbean IslandsDiscover carefully curated flight deals from O'Hare Intl to Caribbean Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 2, 2026.
Discover carefully curated flight deals from O'Hare Intl to Caribbean Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 2, 2026.
This United Airlines deal was found by Cheapflights users on 9/1. 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.
Sun 9/278:55 am -
Nonstop4h 49m
Tue 9/293:56 pm -
Nonstop5h 09m
Deal found 9/1![United Airlines logo]()
$324
This Arajet deal was found by Cheapflights users on 8/28. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/236:45 am -
Nonstop4h 45m
Sat 10/315:47 am -
Nonstop5h 10m
Deal found 8/28![Arajet logo]()
$365
This SmartFares deal was found by Cheapflights users on 8/28. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/168:40 pm -
1 stop19h 20m
Thu 10/226:00 pm -
1 stop16h 00m
Deal found 8/28![Air Canada logo]()
$390
This Arajet deal was found by Cheapflights users on 9/1. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/312:12 pm -
1 stop8h 28m
Fri 10/91:40 am -
1 stop10h 32m
Deal found 9/1![Multiple Airlines logo]()
$394
This Delta deal was found by Cheapflights users on 8/31. 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 10/275:27 am -
1 stop7h 03m
Mon 11/23:55 pm -
1 stop10h 02m
Deal found 8/31![Delta logo]()
$410
This Copa Airlines deal was found by Cheapflights users on 9/1. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/42:13 pm -
1 stop23h 59m
Sun 11/88:55 am -
1 stop17h 16m
Deal found 9/1![Copa Airlines logo]()
$476
This American Airlines deal was found by Cheapflights users on 9/1. 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.
Fri 11/136:49 pm -
1 stop16h 35m
Tue 11/175:33 pm -
1 stop16h 27m
Deal found 9/1![American Airlines logo]()
$583
This JetBlue deal was found by Cheapflights users on 8/31. 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.
Mon 11/28:24 pm -
1 stop14h 26m
Thu 11/53:40 pm -
1 stop10h 17m
Deal found 8/31![JetBlue logo]()
$619
This Arajet deal was found by Cheapflights users on 8/30. 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.
Fri 1/225:45 am -
Nonstop4h 45m
Sat 2/65:47 am -
Nonstop5h 10m
Deal found 8/30![Arajet logo]()
$385
This United Airlines deal was found by Cheapflights users on 8/31. 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 9/158:55 am -
Nonstop4h 49m
Wed 9/161:00 am -
1 stop7h 41m
Deal found 8/31![United Airlines logo]()
$388
This Air Canada deal was found by Cheapflights users on 8/31. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/215:35 pm -
1 stop22h 25m
Sun 10/253:45 pm -
1 stop18h 38m
Deal found 8/31![Air Canada logo]()
$409
This Delta deal was found by Cheapflights users on 8/30. 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.
Thu 1/287:35 pm -
2 stops19h 07m
Wed 2/34:55 pm -
1 stop17h 39m
Deal found 8/30![Delta logo]()
$415
This United Airlines deal was found by Cheapflights users on 9/1. 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.
Fri 11/278:50 am -
1 stop6h 38m
Fri 12/42:55 pm -
Nonstop5h 15m
Deal found 9/1![United Airlines logo]()
$400
This Copa Airlines deal was found by Cheapflights users on 8/29. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/313:13 pm -
1 stop9h 55m
Sat 11/712:10 pm -
1 stop14h 01m
Deal found 8/29![Copa Airlines logo]()
$476
This United Airlines deal was found by Cheapflights users on 8/31. 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.
Sat 10/317:38 am -
Nonstop4h 37m
Sat 11/73:25 pm -
1 stop11h 20m
Deal found 8/31![United Airlines logo]()
$406
This Copa Airlines deal was found by Cheapflights users on 8/31. 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.
Tue 1/197:35 am -
1 stop27h 33m
Fri 1/298:52 am -
1 stop17h 15m
Deal found 8/31![Copa Airlines logo]()
$476
This United Airlines deal was found by Cheapflights users on 8/30. 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.
Mon 12/79:17 am -
Nonstop4h 40m
Sun 12/133:25 pm -
1 stop11h 18m
Deal found 8/30![United Airlines logo]()
$406
This Delta deal was found by Cheapflights users on 8/28. 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.
Wed 2/35:30 am -
1 stop6h 45m
Wed 3/37:30 am -
2 stops18h 20m
Deal found 8/28![Delta logo]()
$495
This Copa Airlines deal was found by Cheapflights users on 8/29. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/288:35 am -
1 stop16h 36m
Wed 11/412:45 pm -
1 stop26h 01m
Deal found 8/29![Copa Airlines logo]()
$476
This American Airlines deal was found by Cheapflights users on 9/1. 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.
Thu 10/158:55 pm -
2 stops15h 28m
Tue 10/204:39 pm -
2 stops15h 48m
Deal found 9/1![American Airlines logo]()
$588
This United Airlines deal was found by Cheapflights users on 8/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/158:55 am -
Nonstop4h 49m
Tue 9/293:56 pm -
Nonstop5h 09m
Deal found 8/29![United Airlines logo]()
$417
This Justfly.com deal was found by Cheapflights users on 9/2. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/157:05 am -
1 stop30h 15m
Sat 11/214:20 pm -
2 stops25h 18m
Deal found 9/2![Air Canada logo]()
$559
This Delta deal was found by Cheapflights users on 8/28. 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.
Wed 11/111:30 pm -
2 stops10h 44m
Mon 11/167:02 am -
2 stops14h 03m
Deal found 8/28![Delta logo]()
$510
This Copa Airlines deal was found by Cheapflights users on 8/30. 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.
Tue 1/52:13 pm -
1 stop19h 29m
Tue 1/1212:42 pm -
1 stop13h 25m
Deal found 8/30![Copa Airlines logo]()
$484
This United Airlines deal was found by Cheapflights users on 9/1. 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.
Mon 11/232:16 pm -
Nonstop4h 44m
Thu 11/262:05 am -
1 stop10h 43m
Deal found 9/1![United Airlines logo]()
$418
This Delta deal was found by Cheapflights users on 8/29. 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 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 8/29![Delta logo]()
$523
This United Airlines deal was found by Cheapflights users on 8/29. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/32:16 pm -
Nonstop4h 44m
Mon 11/98:25 am -
Nonstop5h 22m
Deal found 8/29![United Airlines logo]()
$427
This American Airlines deal was found by Cheapflights users on 8/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/125:05 am -
1 stop7h 18m
Mon 10/194:39 pm -
1 stop16h 08m
Deal found 8/28![American Airlines logo]()
$702
This Copa Airlines deal was found by Cheapflights users on 9/1. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/253:13 pm -
1 stop22h 27m
Thu 10/293:51 pm -
1 stop10h 14m
Deal found 9/1![Copa Airlines logo]()
$535
This United Airlines deal was found by Cheapflights users on 8/30. 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.
Sat 11/72:16 pm -
Nonstop4h 44m
Fri 11/132:05 am -
1 stop10h 43m
Deal found 8/30![United Airlines logo]()
$432
Last-minute flights from O'Hare Intl to Caribbean IslandsDiscover last-minute flight deals from O'Hare Intl to Caribbean Islands. Data last updated September 2, 2026 and is based on user searches.
Discover last-minute flight deals from O'Hare Intl to Caribbean Islands. Data last updated September 2, 2026 and is based on user searches.
This Super.com deal was found by Cheapflights users on 8/31. 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.
Tue 9/112:44 am -
Nonstop5h 00m
Sat 9/57:14 pm -
Nonstop5h 13m
Deal found 8/31![Frontier logo]()
$224
This CheapOair deal was found by Cheapflights users on 8/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/212:44 am -
Nonstop5h 00m
Tue 9/87:14 pm -
Nonstop5h 13m
Deal found 8/29![Frontier logo]()
$216
This Kiwi.com deal was found by Cheapflights users on 8/30. 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.
Sat 9/512:44 am -
Nonstop5h 00m
Wed 9/98:45 am -
1 stop31h 00m
Deal found 8/30![Frontier logo]()
$213
This Vliegwinkel deal was found by Cheapflights users on 8/30. 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 Vliegwinkel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/113:45 pm -
1 stop18h 00m
Thu 9/1712:25 pm -
1 stop20h 35m
Deal found 8/30![Air Canada logo]()
$301
This Air Canada deal was found by Cheapflights users on 8/29. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/118:40 pm -
1 stop13h 05m
Thu 9/2412:25 pm -
1 stop20h 35m
Deal found 8/29![Air Canada logo]()
$361
This American Airlines deal was found by Cheapflights users on 8/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/226:00 am -
1 stop6h 57m
Tue 9/292:58 pm -
1 stop10h 35m
Deal found 8/28![American Airlines logo]()
$226
This American Airlines deal was found by Cheapflights users on 8/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/306:00 am -
1 stop13h 47m
Tue 10/62:53 pm -
Nonstop5h 36m
Deal found 8/28![American Airlines logo]()
$227
This American Airlines deal was found by Cheapflights users on 8/31. 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 10/58:13 am -
Nonstop4h 50m
Wed 10/142:53 pm -
Nonstop5h 36m
Deal found 8/31![American Airlines logo]()
$217
This American Airlines deal was found by Cheapflights users on 8/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/166:40 pm -
1 stop15h 40m
Wed 10/212:53 pm -
Nonstop5h 36m
Deal found 8/28![American Airlines logo]()
$222
This American Airlines deal was found by Cheapflights users on 8/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/178:13 am -
Nonstop4h 50m
Wed 10/212:53 pm -
Nonstop5h 36m
Deal found 8/28![American Airlines logo]()
$218
This Arajet deal was found by Cheapflights users on 9/1. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2412:12 pm -
1 stop8h 28m
Fri 10/301:40 am -
1 stop9h 17m
Deal found 9/1![Multiple Airlines logo]()
$354
This Arajet deal was found by Cheapflights users on 9/1. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/3111:27 am -
1 stop9h 13m
Fri 11/61:40 am -
1 stop9h 17m
Deal found 9/1![Multiple Airlines logo]()
$343
One-way flights from O'Hare Intl to Caribbean IslandsSearch for one-way flight options from O'Hare Intl to Caribbean Islands. Find affordable one-way fares based on user searches. Data last updated September 2, 2026.
Search for one-way flight options from O'Hare Intl to Caribbean Islands. Find affordable one-way fares based on user searches. Data last updated September 2, 2026.
This Super.com deal was found by Cheapflights users on 8/31. 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.
Sun 9/612:44 am -
Nonstop5h 00m
Deal found 8/31![Frontier logo]()
$104
This Kiwi.com deal was found by Cheapflights users on 9/2. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/512:44 am -
Nonstop5h 00m
Deal found 9/2![Frontier logo]()
$106
This American Airlines deal was found by Cheapflights users on 8/31. 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 10/58:13 am -
Nonstop4h 50m
Deal found 8/31![American Airlines logo]()
$109
This American Airlines deal was found by Cheapflights users on 8/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/27:00 pm -
1 stop13h 24m
Deal found 8/28![American Airlines logo]()
$113
This American Airlines deal was found by Cheapflights users on 9/1. 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.
Thu 10/15:29 pm -
1 stop16h 31m
Deal found 9/1![American Airlines logo]()
$114
This American Airlines deal was found by Cheapflights users on 8/28. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/276:59 am -
1 stop12h 48m
Deal found 8/28![American Airlines logo]()
$116
This American Airlines deal was found by Cheapflights users on 8/31. 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.
Wed 9/308:59 am -
2 stops10h 48m
Deal found 8/31![American Airlines logo]()
$118
This American Airlines deal was found by Cheapflights users on 9/1. 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.
Wed 9/238:50 am -
2 stops10h 57m
Deal found 9/1![American Airlines logo]()
$121
This Frontier deal was found by Cheapflights users on 8/31. 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 9/712:44 am -
Nonstop5h 00m
Deal found 8/31![Frontier logo]()
$124
This United Airlines deal was found by Cheapflights users on 8/28. 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.
Mon 11/232:16 pm -
Nonstop4h 44m
Deal found 8/28![United Airlines logo]()
$125
This Expedia deal was found by Cheapflights users on 8/31. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/309:55 am -
1 stop25h 30m
Deal found 8/31![Air Canada logo]()
$131
This Air Canada deal was found by Cheapflights users on 8/31. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 9/273:45 pm -
1 stop19h 40m
Deal found 8/31![Air Canada logo]()
$136
Find flight deals from O'Hare Intl to Caribbean Islands
Keep the following information in mind while searching for O'Hare Intl to Caribbean Islands flight deals. Data was last updated September 2, 2026.
Round-trip from | $213 (Kiwi.com) |
|---|---|
One-way from | $104 (Super.com) |
Popular in | December |
Cheapest in | August |
Average price | $382 |
Cheapflights Fare Finder
Customize your flight search to find flights from O'Hare Intl to Caribbean Islands 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 2, 2026.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Caribbean Islands 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 9/27
8:55 am-2:44 pm
Nonstop4h 49m
San Juan Luis Munoz Marin Intl
Tue 9/29
3:56 pm-8:05 pm
Nonstop5h 09m
$324
Quickest round-trip
ChicagoPunta Cana
ORD Chicago O'Hare Intl - PUJ Punta Cana
ORDPUJ
Chicago O'Hare Intl
Fri 10/23
6:45 am-12:30 pm
Nonstop4h 45m
Punta Cana
Sat 10/31
5:47 am-9:57 am
Nonstop5h 10m
$365
ChicagoPunta Cana
ORD Chicago O'Hare Intl - PUJ Punta Cana
ORDPUJ
Chicago O'Hare Intl
Fri 1/22
5:45 am-12:30 pm
Nonstop4h 45m
Punta Cana
Sat 2/6
5:47 am-8:57 am
Nonstop5h 10m
$385
ChicagoSan Juan
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Tue 9/15
8:55 am-2:44 pm
Nonstop4h 49m
San Juan Luis Munoz Marin Intl
Wed 9/16
1:00 am-7:41 am
1 stop7h 41m
$388
ChicagoSimpson Bay
ORD Chicago O'Hare Intl - SXM Simpson Bay Princess Juliana
ORDSXM
Chicago O'Hare Intl
Fri 10/16
8:40 pm-5:00 pm
1 stop19h 20m
Simpson Bay Princess Juliana
Thu 10/22
6:00 pm-9:00 am
1 stop16h 00m
$390
ChicagoSanto Domingo
ORD Chicago O'Hare Intl - SDQ Santo Domingo Las Americas
ORDSDQ
Chicago O'Hare Intl
Sat 10/3
12:12 pm-9:40 pm
1 stop8h 28m
Santo Domingo Las Americas
Fri 10/9
1:40 am-11:12 am
1 stop10h 32m
$394
ChicagoPunta Cana
ORD Chicago O'Hare Intl - PUJ Punta Cana
ORDPUJ
Chicago O'Hare Intl
Fri 11/27
8:50 am-5:28 pm
1 stop6h 38m
Punta Cana
Fri 12/4
2:55 pm-6:10 pm
Nonstop5h 15m
$400
ChicagoPunta Cana
ORD Chicago O'Hare Intl - PUJ Punta Cana
ORDPUJ
Chicago O'Hare Intl
Sat 10/31
7:38 am-1:15 pm
Nonstop4h 37m
Punta Cana
Sat 11/7
3:25 pm-12:45 am
1 stop11h 20m
$406
ChicagoPunta Cana
ORD Chicago O'Hare Intl - PUJ Punta Cana
ORDPUJ
Chicago O'Hare Intl
Mon 12/7
9:17 am-3:57 pm
Nonstop4h 40m
Punta Cana
Sun 12/13
3:25 pm-12:43 am
1 stop11h 18m
$406
ChicagoSimpson Bay
ORD Chicago O'Hare Intl - SXM Simpson Bay Princess Juliana
ORDSXM
Chicago O'Hare Intl
Wed 10/21
5:35 pm-5:00 pm
1 stop22h 25m
Simpson Bay Princess Juliana
Sun 10/25
3:45 pm-9:23 am
1 stop18h 38m
$409
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from O'Hare Intl to Caribbean Islands
Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands from O'Hare Intl with our price prediction graph.
ORD-SJU
ORD-GCM
ORD-SDQ
ORD-NAS
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 Chicago O'Hare Intl Airport to Caribbean Islands
ORD-zzEPX
ORD-SJU
ORD-GCM
ORD-SDQ
ORD-NAS
What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Caribbean Islands?
Currently, January is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Caribbean Islands (average of $550). Flying from Chicago O'Hare Intl Airport to Caribbean Islands in June is currently the most expensive (average of $708). 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 ORD to EPX?
Find hourly flight availability from O'Hare Intl to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 2, 2026.
One of the essential ways to save on airfare from Chicago O'Hare Intl Airport to Caribbean Islands 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 Chicago O'Hare Intl Airport to Caribbean Islands
Explore weekly flight availability from O'Hare Intl to Caribbean Islands. 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 2, 2026.
The most flights from ORD to zzEPX are scheduled on a Monday (7 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (2 on average).
How far ahead should I book a flight from Chicago O'Hare Intl Airport to Caribbean Islands?
To ensure you get the cheapest price possible for a flight from Chicago O'Hare Intl Airport to Caribbean Islands, you should look to book at least 48 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
What is the cheapest day to fly from Chicago O'Hare Intl Airport to Caribbean Islands?
Use this chart to determine the cheapest time to fly round-trip from O'Hare Intl to Caribbean Islands. Price data was last updated on August 29, 2026.
Travelers seeking maximum savings on their Chicago O'Hare Intl Airport to Caribbean Islands flight should consider departing on Saturday 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.
Reviews of airlines servicing Caribbean Islands
Get insights into the airlines that provide service to Caribbean Islands. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean Islands. Reviews last updated September 2, 2026.
See what other customers who have flown with Delta,United Airlines, andAmerican Airlines from Chicago O'Hare Intl Airport to Caribbean Islands have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
7.2
Overall
7.8
Comfort
7.8
Entertainment
7.8
Boarding
8.1
Crew
8.5
Reviews
1 / 20
8.0
ExcellentJorge,Aug 2026
TPA - ATL
Food
7.2
Overall
7.8
Comfort
7.8
Entertainment
7.8
Boarding
8.1
Crew
8.5
Reviews
1 / 20
8.0
ExcellentJorge,Aug 2026
TPA - ATL
Food
7.2
Overall
7.8
Comfort
7.8
Entertainment
7.8
Boarding
8.1
Crew
8.5
Reviews
1 / 20
8.0
ExcellentJorge,Aug 2026
TPA - ATL
Food
7.2
Overall
7.8
Comfort
7.8
Entertainment
7.8
Boarding
8.1
Crew
8.5
Reviews
1 / 20
8.0
ExcellentJorge,Aug 2026
TPA - ATL
Food
7.2
Overall
7.8
Comfort
7.8
Entertainment
7.8
Boarding
8.1
Crew
8.5
Reviews
1 / 20
8.0
ExcellentJorge,Aug 2026
TPA - ATL
Related info for your journey
Find useful and relevant information for your journey from O'Hare Intl to Caribbean Islands. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for O'Hare Intl to Caribbean Islands
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Complete your trip
Complete your trip to Caribbean Islands by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from O'Hare Intl to Caribbean Islands by cabin class
Find flights from O'Hare Intl to Caribbean Islands, based on your preferred cabin class, be it economy, premium economy, business, or first class.
O'Hare Intl and Caribbean Islands flights
Browse other O'Hare Intl and Caribbean Islands flight options. Last updated on September 2, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
O'Hare Intl to Caribbean Islands flights
Consider these flights traveling from O'Hare Intl to Caribbean Islands.
Top 9 airlines flying from O'Hare Intl to Caribbean Islands
Discover the top 9 airlines that operate flights from O'Hare Intl to Caribbean Islands. 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 2, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$118 | Average$484 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$118 | Average$452 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$144 | Average$553 | 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$264 | Average$590 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$296 | Average$626 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$372 | Average$568 | FlexibilityNo cancel fee | On-time63% |