$121+ Cheap flights from O'Hare Intl (ORD) 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 11/13. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
Nov 24 — Dec 11
Round-trip
1 adult, Economy
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Find cheap flights from O'Hare Intl to Caribbean with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Cheapest flights from O'Hare Intl to CaribbeanExplore the most affordable flight options available from O'Hare Intl to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 25, 2026.
Explore the most affordable flight options available from O'Hare Intl to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 25, 2026.
This Mytrip deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 12/13:55 pm -
2 stops26h 42m
Wed 12/95:01 am -
1 stop11h 29m
Deal found 10/21![Frontier logo]()
$236
This Cheapflightsfares deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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
Sun 11/2210:54 pm -
1 stop27h 49m
Deal found 10/22![Frontier logo]()
$237
This Kiwi.com deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 10/254:41 pm -
1 stop16h 38m
Thu 11/122:51 pm -
1 stop9h 52m
Deal found 10/20![Frontier logo]()
$238
This FlightHub deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 11/74:00 pm -
1 stop8h 46m
Tue 11/107:23 am -
1 stop11h 44m
Deal found 10/21![Frontier logo]()
$239
This Kiwi.com deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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 10/3010:26 am -
1 stop13h 33m
Fri 11/132:51 pm -
1 stop9h 52m
Deal found 10/23![Frontier logo]()
$240
This Justfly.com deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 12/1310:37 pm -
1 stop12h 52m
Fri 12/184:30 pm -
1 stop28h 38m
Deal found 10/22![Frontier logo]()
$241
This Kiwi.com deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 11/147:35 pm -
2 stops36h 40m
Sat 11/217:31 am -
1 stop18h 03m
Deal found 10/20![Frontier logo]()
$242
This Cheapflightsfares deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 12/136:00 am -
1 stop12h 04m
Deal found 10/21![Frontier logo]()
$243
This Mytrip deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 11/197:31 am -
2 stops14h 26m
Sun 11/2211:13 am -
1 stop15h 30m
Deal found 10/21![Frontier logo]()
$244
This Cheapflightsfares deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 11/97:55 am -
1 stop29h 24m
Tue 11/107:26 pm -
1 stop23h 41m
Deal found 10/25![Frontier logo]()
$245
This Cheapflightsfares deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 10/309:51 am -
1 stop22h 24m
Wed 11/47:23 am -
1 stop27h 23m
Deal found 10/21![Frontier logo]()
$246
This American Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 10/297:29 pm -
1 stop12h 53m
Thu 11/57:19 pm -
1 stop14h 41m
Deal found 10/21![American Airlines logo]()
$344
Best flights from O'Hare Intl to CaribbeanDiscover carefully curated flight deals from O'Hare Intl to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 25, 2026.
Discover carefully curated flight deals from O'Hare Intl to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated October 25, 2026.
This JetBlue deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 12/92:59 pm -
1 stop9h 00m
Tue 12/156:10 pm -
1 stop7h 23m
Deal found 10/22![JetBlue logo]()
$266
This United Airlines deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” 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 11/131:30 pm -
1 stop6h 52m
Wed 11/184:55 pm -
Nonstop5h 31m
Deal found 10/24![United Airlines logo]()
$282
This Delta deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 12/91:35 pm -
1 stop8h 23m
Tue 12/157:00 am -
1 stop12h 19m
Deal found 10/20![Delta logo]()
$290
This Arajet deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” 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
Thu 1/287:30 pm -
Nonstop5h 10m
Deal found 10/24![Arajet logo]()
$376
This Copa Airlines deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 2/132:13 pm -
1 stop9h 51m
Thu 2/2512:05 pm -
1 stop14h 06m
Deal found 10/25![Copa Airlines logo]()
$466
This Mytrip deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 12/38:17 am -
2 stops11h 58m
Sun 12/64:45 pm -
3 stops24h 19m
Deal found 10/20![Multiple Airlines logo]()
$597
This United Airlines deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” 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 1/162:26 pm -
1 stop8h 10m
Wed 1/204:55 pm -
Nonstop5h 31m
Deal found 10/24![United Airlines logo]()
$299
This United Airlines deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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 11/910:32 am -
1 stop9h 50m
Thu 11/128:25 am -
Nonstop5h 22m
Deal found 10/23![United Airlines logo]()
$302
This United Airlines deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” 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 11/142:16 pm -
Nonstop4h 44m
Sat 11/214:55 pm -
Nonstop5h 31m
Deal found 10/24![United Airlines logo]()
$329
This JetBlue deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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 11/287:00 am -
1 stop7h 18m
Sat 12/52:37 pm -
1 stop10h 56m
Deal found 10/23![JetBlue logo]()
$403
This Delta deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 11/155:30 am -
1 stop8h 00m
Thu 11/194:55 pm -
2 stops16h 54m
Deal found 10/20![Delta logo]()
$405
This Arajet deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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.
Sun 11/84:20 am -
Nonstop4h 45m
Thu 11/127:30 pm -
Nonstop5h 10m
Deal found 10/20![Arajet logo]()
$406
This Copa Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 2/212:13 pm -
1 stop20h 02m
Sat 2/272:28 pm -
1 stop10h 43m
Deal found 10/21![Copa Airlines logo]()
$470
This United Airlines deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” 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 1/172:16 pm -
Nonstop4h 44m
Fri 1/228:25 am -
Nonstop5h 24m
Deal found 10/24![United Airlines logo]()
$357
This JetBlue deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” 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 1/67:00 am -
1 stop6h 28m
Mon 1/113:00 pm -
1 stop10h 42m
Deal found 10/24![JetBlue logo]()
$457
This Delta deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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.
Mon 1/259:30 am -
2 stops27h 25m
Tue 2/23:25 pm -
2 stops22h 11m
Deal found 10/20![Delta logo]()
$474
This Copa Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 2/132:13 pm -
1 stop9h 51m
Mon 2/2212:42 pm -
1 stop26h 04m
Deal found 10/21![Copa Airlines logo]()
$480
This United Airlines deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” 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 11/182:16 pm -
Nonstop4h 44m
Mon 11/234:55 pm -
Nonstop5h 31m
Deal found 10/24![United Airlines logo]()
$377
This JetBlue deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 11/131:00 pm -
1 stop12h 05m
Fri 11/205:01 am -
1 stop10h 31m
Deal found 10/20![JetBlue logo]()
$469
This Copa Airlines deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 11/282:13 pm -
1 stop9h 55m
Sat 12/512:09 pm -
1 stop26h 37m
Deal found 10/20![Copa Airlines logo]()
$495
This Arajet deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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 1/911:10 am -
Nonstop4h 45m
Sat 3/207:00 am -
Nonstop5h 10m
Deal found 10/23![Arajet logo]()
$545
This Delta deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 1/176:00 am -
1 stop11h 20m
Sat 1/307:30 am -
2 stops13h 02m
Deal found 10/20![Delta logo]()
$525
This United Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 11/145:30 am -
1 stop8h 34m
Tue 11/175:10 pm -
1 stop8h 51m
Deal found 10/21![United Airlines logo]()
$400
This Copa Airlines deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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
Sun 2/2112:18 pm -
1 stop12h 53m
Deal found 10/25![Copa Airlines logo]()
$500
This JetBlue deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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 12/147:00 am -
1 stop6h 58m
Thu 12/172:50 pm -
1 stop10h 43m
Deal found 10/23![JetBlue logo]()
$503
This Mytrip deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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.
Fri 12/43:45 pm -
3 stops25h 45m
Fri 12/114:20 pm -
1 stop29h 32m
Deal found 10/20![Multiple Airlines logo]()
$694
This United Airlines deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 11/31:30 pm -
1 stop6h 52m
Fri 11/64:55 pm -
Nonstop5h 31m
Deal found 10/20![United Airlines logo]()
$402
This Delta deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” 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 11/141:30 pm -
2 stops10h 44m
Mon 11/168:55 pm -
2 stops16h 53m
Deal found 10/24![Delta logo]()
$545
This JetBlue deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/217:45 pm -
1 stop12h 53m
Sat 1/2310:38 am -
1 stop9h 17m
Deal found 10/24![JetBlue logo]()
$521
This United deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 1/162:26 pm -
2 stops17h 28m
Thu 1/2112:01 pm -
1 stop25h 48m
Deal found 10/24![Multiple Airlines logo]()
$708
Last-minute flights from O'Hare Intl to CaribbeanDiscover last-minute flight deals from O'Hare Intl to Caribbean. Data last updated October 25, 2026 and is based on user searches.
Discover last-minute flight deals from O'Hare Intl to Caribbean. Data last updated October 25, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 10/254:41 pm -
1 stop16h 38m
Thu 11/122:51 pm -
1 stop9h 52m
Deal found 10/20![Frontier logo]()
$238
This American Airlines deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 10/297:29 pm -
1 stop12h 53m
Thu 11/57:19 pm -
1 stop14h 41m
Deal found 10/21![American Airlines logo]()
$344
This Kiwi.com deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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 10/3010:26 am -
1 stop13h 33m
Fri 11/132:51 pm -
1 stop9h 52m
Deal found 10/23![Frontier logo]()
$240
This Cheapflightsfares deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 10/309:51 am -
1 stop22h 24m
Wed 11/47:23 am -
1 stop27h 23m
Deal found 10/21![Frontier logo]()
$246
This FlightHub deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 11/74:00 pm -
1 stop8h 46m
Tue 11/107:23 am -
1 stop11h 44m
Deal found 10/21![Frontier logo]()
$239
This Kiwi.com deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 11/97:50 pm -
2 stops16h 48m
Fri 11/133:55 pm -
1 stop22h 56m
Deal found 10/20![Frontier logo]()
$236
This Cheapflightsfares deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 11/97:55 am -
1 stop29h 24m
Tue 11/107:26 pm -
1 stop23h 41m
Deal found 10/25![Frontier logo]()
$245
This Cheapflightsfares deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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
Sun 11/2210:54 pm -
1 stop27h 49m
Deal found 10/22![Frontier logo]()
$237
This Cheapflightsfares deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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
Sat 11/1412:59 am -
1 stop23h 44m
Deal found 10/21![Frontier logo]()
$243
This Kiwi.com deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 11/147:35 pm -
2 stops36h 40m
Sat 11/217:31 am -
1 stop18h 03m
Deal found 10/20![Frontier logo]()
$242
This Kiwi.com deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 11/167:55 am -
1 stop29h 24m
Thu 11/267:12 pm -
Nonstop5h 09m
Deal found 10/22![Frontier logo]()
$241
This Mytrip deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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 11/197:31 am -
2 stops14h 26m
Sun 11/2211:13 am -
1 stop15h 30m
Deal found 10/21![Frontier logo]()
$244
One-way flights from O'Hare Intl to CaribbeanSearch for one-way flight options from O'Hare Intl to Caribbean. Find affordable one-way fares based on user searches. Data last updated October 25, 2026.
Search for one-way flight options from O'Hare Intl to Caribbean. Find affordable one-way fares based on user searches. Data last updated October 25, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 10/22![Frontier logo]()
$121
This Super.com deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/309:51 am -
1 stop14h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Frontier logo]()
$122
This Super.com deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” 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.
Mon 11/210:19 am -
1 stop12h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Frontier logo]()
$123
This FlightHub deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/309:20 pm -
1 stop25h 58m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Frontier logo]()
$124
This Super.com deal was found by Cheapflights users on 10/24. Clicking the “Pick Dates” 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.
Thu 12/318:22 am -
1 stop13h 52m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![Frontier logo]()
$125
This Kiwi.com deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 1/128:25 am -
2 stops24h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![Frontier logo]()
$126
This Super.com deal was found by Cheapflights users on 10/20. Clicking the “Pick Dates” 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 11/252:52 pm -
1 stop22h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/20![Frontier logo]()
$127
This Cheapflightsfares deal was found by Cheapflights users on 10/23. Clicking the “Pick Dates” 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 1/87:10 am -
1 stop15h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Frontier logo]()
$128
This United Airlines deal was found by Cheapflights users on 10/22. Clicking the “Pick Dates” 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 1/128:52 am -
Nonstop4h 48m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![United Airlines logo]()
$129
This Booking.com deal was found by Cheapflights users on 10/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/14:42 pm -
1 stop20h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Frontier logo]()
$130
This Kiwi.com deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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 11/39:51 am -
1 stop6h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![Frontier logo]()
$131
This Trip.com deal was found by Cheapflights users on 10/25. Clicking the “Pick Dates” 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.
Sat 12/512:50 pm -
1 stop22h 20m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/25![Air Canada logo]()
$154
Find flight deals from O'Hare Intl to Caribbean
Keep the following information in mind while searching for O'Hare Intl to Caribbean flight deals. Data was last updated October 25, 2026.
Round-trip from | $236 (Mytrip) |
|---|---|
One-way from | $121 (Cheapflightsfares) |
Popular in | December |
Cheapest in | August |
Average price | $398 |
Good round-trip deal | $392 or less |
Good one-way deal | $200 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from O'Hare Intl 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 October 25, 2026.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Caribbean that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
ChicagoSan Juan
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Mon 11/16
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
$129
ChicagoSan Juan
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Tue 1/12
8:52 am-3:40 pm
Nonstop4h 48m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$129
ChicagoSan Juan
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Wed 12/9
7:00 am-4:38 pm
1 stop7h 38m
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
ChicagoSan Juan
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Thu 12/10
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
ChicagoSan Juan
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Thu 1/14
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
$145
ChicagoSan Juan
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Fri 10/30
2:16 pm-8:00 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
Sat 10/31
2:16 pm-8:00 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
Wed 11/18
1:00 pm-4:05 am
1 stop13h 05m
Santo Domingo Las Americas
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$160
ChicagoNassau
ORD Chicago O'Hare Intl - NAS Nassau Intl
ORDNAS
Chicago O'Hare Intl
Mon 11/9
7:55 am-1:50 pm
1 stop28h 55m
Nassau Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$162
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from O'Hare Intl to Caribbean
Have a flexible travel schedule? Discover the best time to fly to Caribbean from O'Hare Intl with our price prediction graph.
ORD-SJU
ORD-SDQ
ORD-PUJ
ORD-GCM
ORD-MBJ
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago O'Hare Intl Airport to Caribbean
ORD-0CB
ORD-SJU
ORD-SDQ
ORD-PUJ
ORD-GCM
What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Caribbean?
Currently, August is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Caribbean (average of $422). Flying from Chicago O'Hare Intl Airport to Caribbean in December is currently the most expensive (average of $652). 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 CB?
Find hourly flight availability from O'Hare Intl 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 October 25, 2026.
A simple way to save on the total cost of your ticket is to fly from Chicago O'Hare Intl Airport to Caribbean in the evening. If you’re flexible enough to do this you can expect to save up to 36% on your trip compared to booking a flight in the morning.
Weekly flight availability from Chicago O'Hare Intl Airport to Caribbean
Explore weekly flight availability from O'Hare Intl 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 October 25, 2026.
The most flights from ORD to 0CB are scheduled on a Friday (5 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (2 on average).
How often are flights from Chicago to Caribbean delayed?
About 21% of weekly flights between Chicago and Caribbean have experienced delays in the past year, with the average delay time being 146 minutes.
What is the most punctual flight time for Chicago to Caribbean flights?
Historically, flights departing at night are less likely to be delayed, whereas flights leaving in the evening tend to experience delays more often.
What day of the week experiences the fewest flight delays on this route?
Wednesday tends to have the lowest number of delays on this route, whereas Monday has historically faced a higher average of delays compared to other days of the week.
Which airline has the best punctuality record on Chicago to Caribbean flights?
Over the last year, United Airlines have had the lowest number of delays on this route, with just 20% of flights being delayed.
How far ahead should I book a flight from Chicago O'Hare Intl Airport to Caribbean?
The price you pay for your flight from Chicago O'Hare Intl Airport to Caribbean may vary depending on when you book. For the best chance of a lower fare, look to book 19 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
What is the cheapest day to fly from Chicago O'Hare Intl Airport to Caribbean?
Use this chart to determine the cheapest time to fly round-trip from O'Hare Intl to Caribbean. Price data was last updated on October 24, 2026.
Travelers seeking maximum savings on their Chicago O'Hare Intl Airport 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.
Reviews of airlines servicing Caribbean
Get insights into the airlines that provide service to Caribbean. 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. Reviews last updated October 25, 2026.
See what other customers who have flown with United Airlines,JetBlue, andAmerican Airlines from Chicago O'Hare Intl Airport to Caribbean have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
7.3
Entertainment
7.1
Food
6.7
Crew
8.1
Boarding
7.7
Overall
7.3
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Comfort
7.3
Entertainment
7.1
Food
6.7
Crew
8.1
Boarding
7.7
Overall
7.3
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Comfort
7.3
Entertainment
7.1
Food
6.7
Crew
8.1
Boarding
7.7
Overall
7.3
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Comfort
7.3
Entertainment
7.1
Food
6.7
Crew
8.1
Boarding
7.7
Overall
7.3
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Comfort
7.3
Entertainment
7.1
Food
6.7
Crew
8.1
Boarding
7.7
Overall
7.3
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Related info for your journey
Find useful and relevant information for your journey from O'Hare Intl to Caribbean. 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
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 O'Hare Intl to Caribbean by cabin class
Find flights from O'Hare Intl to Caribbean, based on your preferred cabin class, be it economy, premium economy, business, or first class.
O'Hare Intl and Caribbean flights
Browse other O'Hare Intl and Caribbean flight options. Last updated on October 25, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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Top 9 airlines flying from O'Hare Intl to Caribbean
Discover the top 9 airlines that operate flights from O'Hare Intl 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 October 25, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$118 | Average$538 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$118 | Average$477 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$153 | Average$442 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$229 | Average$379 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$235 | Average$458 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$262 | Average$638 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$284 | Average$635 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$318 | Average$486 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$377 | Average$568 | FlexibilityNo cancel fee | On-time63% |