$119+ Cheap flights from Caribbean to O'Hare Intl (ORD)
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 11/21. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — ORD
Nov 24 — Dec 11
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Caribbean to O'Hare Intl 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 Caribbean to O'Hare Intl
Cheapest
Best
Last-minute
One-way
Cheapest flights from Caribbean to O'Hare IntlExplore the most affordable flight options available from Caribbean to O'Hare Intl. 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 Caribbean to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on October 25, 2026.
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/33:55 am -
1 stop15h 12m
Thu 11/1210:19 am -
1 stop12h 40m
Deal found 10/24![Frontier logo]()
$227
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/2010:54 pm -
1 stop27h 49m
Wed 11/252:52 pm -
1 stop22h 08m
Deal found 10/20![Frontier logo]()
$228
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.
Thu 11/193:55 pm -
1 stop10h 18m
Thu 11/265:12 pm -
1 stop7h 12m
Deal found 10/23![Frontier logo]()
$230
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/217:58 pm -
1 stop13h 49m
Thu 11/265:12 pm -
1 stop7h 12m
Deal found 10/23![Frontier logo]()
$232
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 12/12:49 am -
2 stops20h 46m
Sat 12/54:00 pm -
1 stop7h 07m
Deal found 10/21![Frontier logo]()
$233
This Travelocity 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/247:31 am -
1 stop18h 03m
Thu 11/265:12 pm -
1 stop7h 12m
Deal found 10/24![Frontier logo]()
$234
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.
Thu 11/57:23 am -
1 stop27h 23m
Mon 11/97:55 am -
1 stop29h 24m
Deal found 10/22![Frontier logo]()
$236
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2912:59 am -
1 stop22h 44m
Mon 12/76:07 am -
1 stop12h 30m
Deal found 10/20![Frontier logo]()
$237
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/42:36 pm -
1 stop25h 54m
Fri 12/119:34 pm -
1 stop25h 45m
Deal found 10/24![Frontier logo]()
$238
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/217:31 am -
1 stop18h 03m
Wed 11/252:52 pm -
2 stops33h 19m
Deal found 10/21![Frontier logo]()
$240
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.
Wed 12/211:48 am -
2 stops11h 47m
Mon 12/76:07 am -
1 stop12h 30m
Deal found 10/20![Frontier logo]()
$241
This flugladen.de 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 flugladen.de is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/202:20 pm -
1 stop30h 32m
Sun 11/2910:15 am -
1 stop25h 35m
Deal found 10/24![Air Canada logo]()
$335
Best flights from Caribbean to O'Hare IntlDiscover carefully curated flight deals from Caribbean to O'Hare Intl 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 Caribbean to O'Hare Intl 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.
Fri 12/253:50 pm -
1 stop9h 43m
Fri 1/17:00 am -
1 stop7h 10m
Deal found 10/22![JetBlue logo]()
$351
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.
Mon 11/98:05 am -
1 stop8h 33m
Fri 11/132:16 pm -
Nonstop4h 44m
Deal found 10/24![United Airlines logo]()
$367
This Trip.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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/81:10 pm -
1 stop29h 33m
Tue 12/1510:05 am -
1 stop25h 05m
Deal found 10/24![Air Canada logo]()
$381
This Arajet 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/147:30 pm -
Nonstop5h 10m
Fri 1/295:45 am -
Nonstop4h 45m
Deal found 10/21![Arajet logo]()
$387
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.
Sat 11/213:53 pm -
1 stop10h 01m
Sat 11/285:30 am -
1 stop8h 00m
Deal found 10/20![Delta logo]()
$416
This Copa 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/2412:18 pm -
1 stop12h 53m
Thu 12/312:17 pm -
1 stop20h 02m
Deal found 10/24![Copa Airlines logo]()
$438
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/104:18 pm -
Nonstop4h 40m
Mon 2/159:45 am -
Nonstop4h 07m
Deal found 10/23![American Airlines logo]()
$439
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.
Sun 12/64:45 pm -
3 stops24h 19m
Sun 12/138:50 pm -
1 stop14h 20m
Deal found 10/21![Multiple Airlines logo]()
$543
This Kissandfly.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 Kissandfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/172:10 pm -
Nonstop6h 01m
Wed 12/238:40 am -
Nonstop5h 17m
Deal found 10/25![Lufthansa logo]()
$574
This Avianca 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/2111:45 am -
1 stop10h 45m
Mon 2/2210:30 pm -
1 stop15h 30m
Deal found 10/22![Avianca logo]()
$617
This Flysmarter 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 Flysmarter is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/54:16 pm -
Nonstop5h 50m
Sat 12/129:11 pm -
1 stop15h 20m
Deal found 10/21![British Airways logo]()
$618
This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/202:20 pm -
2 stops18h 40m
Sun 11/299:21 pm -
1 stop18h 59m
Deal found 10/25![Air Canada logo]()
$381
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.
Mon 12/74:55 pm -
Nonstop5h 31m
Sat 12/122:16 pm -
Nonstop4h 44m
Deal found 10/20![United Airlines logo]()
$384
This Arajet 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/247:30 pm -
Nonstop5h 10m
Sat 1/211:10 am -
Nonstop4h 45m
Deal found 10/22![Arajet logo]()
$398
This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/236:20 pm -
1 stop16h 03m
Sun 11/294:30 pm -
1 stop23h 50m
Deal found 10/21![Air Canada logo]()
$398
This Arajet 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/147:30 pm -
Nonstop5h 10m
Sun 1/314:20 am -
Nonstop4h 45m
Deal found 10/22![Arajet logo]()
$398
This Copa 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/1212:20 pm -
1 stop13h 51m
Sat 2/202:13 pm -
1 stop19h 12m
Deal found 10/24![Copa Airlines logo]()
$448
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/65:33 pm -
2 stops15h 52m
Mon 11/96:00 am -
1 stop8h 31m
Deal found 10/22![American Airlines logo]()
$456
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.
Fri 11/64:05 pm -
1 stop9h 52m
Mon 11/95:30 am -
1 stop7h 10m
Deal found 10/24![Delta logo]()
$460
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.
Sun 12/202:55 pm -
Nonstop5h 15m
Fri 1/19:43 pm -
1 stop16h 21m
Deal found 10/23![United Airlines logo]()
$419
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 2/102:46 pm -
1 stop10h 56m
Wed 2/172:50 pm -
1 stop8h 07m
Deal found 10/24![JetBlue logo]()
$508
This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/71:50 pm -
1 stop20h 33m
Sat 11/141:55 pm -
1 stop22h 30m
Deal found 10/20![Air Canada logo]()
$424
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 12/2212:56 pm -
1 stop20h 36m
Tue 12/299:43 pm -
1 stop16h 21m
Deal found 10/22![United Airlines logo]()
$425
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.
Thu 1/217:30 pm -
1 stop16h 32m
Thu 1/2812:55 pm -
1 stop22h 13m
Deal found 10/22![United Airlines logo]()
$425
This Copa 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/2312:45 pm -
1 stop13h 26m
Mon 11/302:13 pm -
1 stop19h 29m
Deal found 10/24![Copa Airlines logo]()
$515
This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/31:50 pm -
1 stop20h 18m
Thu 1/283:45 pm -
1 stop20h 25m
Deal found 10/22![Air Canada logo]()
$441
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.
Fri 11/134:15 am -
1 stop9h 45m
Sun 11/222:59 pm -
1 stop8h 00m
Deal found 10/22![JetBlue logo]()
$548
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.
Mon 1/257:05 pm -
1 stop19h 41m
Mon 2/17:35 am -
1 stop27h 31m
Deal found 10/21![Copa Airlines logo]()
$515
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.
Fri 12/257:30 pm -
1 stop30h 09m
Fri 1/12:22 pm -
1 stop20h 46m
Deal found 10/20![United Airlines logo]()
$429
This Gotogate 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/214:35 pm -
1 stop7h 45m
Mon 2/223:45 pm -
2 stops22h 45m
Deal found 10/22![Multiple Airlines logo]()
$632
Last-minute flights from Caribbean to O'Hare IntlDiscover last-minute flight deals from Caribbean to O'Hare Intl. Data last updated October 25, 2026 and is based on user searches.
Discover last-minute flight deals from Caribbean to O'Hare Intl. Data last updated October 25, 2026 and is based on user searches.
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/2912:59 am -
1 stop22h 44m
Mon 12/76:07 am -
1 stop12h 30m
Deal found 10/20![Frontier logo]()
$237
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/33:55 am -
1 stop15h 12m
Thu 11/1210:19 am -
1 stop12h 40m
Deal found 10/24![Frontier logo]()
$227
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.
Thu 11/57:23 am -
1 stop27h 23m
Mon 11/97:55 am -
1 stop29h 24m
Deal found 10/22![Frontier logo]()
$236
This Booking.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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/77:00 am -
Nonstop5h 10m
Sat 11/1411:10 am -
Nonstop4h 45m
Deal found 10/20![Arajet logo]()
$359
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.
Fri 11/134:52 pm -
2 stops21h 59m
Sun 11/156:00 am -
1 stop15h 28m
Deal found 10/21![Frontier logo]()
$243
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.
Thu 11/193:55 pm -
1 stop10h 18m
Thu 11/265:12 pm -
1 stop7h 12m
Deal found 10/23![Frontier logo]()
$230
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/2010:54 pm -
1 stop27h 49m
Wed 11/252:52 pm -
1 stop22h 08m
Deal found 10/20![Frontier logo]()
$228
This flugladen.de 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 flugladen.de is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/202:20 pm -
1 stop30h 32m
Sun 11/2910:15 am -
1 stop25h 35m
Deal found 10/24![Air Canada logo]()
$335
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/217:58 pm -
1 stop13h 49m
Thu 11/265:12 pm -
1 stop7h 12m
Deal found 10/23![Frontier logo]()
$232
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/217:31 am -
1 stop18h 03m
Wed 11/252:52 pm -
2 stops33h 19m
Deal found 10/21![Frontier logo]()
$240
This Travelocity 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/247:31 am -
1 stop18h 03m
Thu 11/265:12 pm -
1 stop7h 12m
Deal found 10/24![Frontier logo]()
$234
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.
Tue 11/247:31 am -
1 stop18h 03m
Fri 11/275:26 pm -
1 stop7h 07m
Deal found 10/22![Frontier logo]()
$242
One-way flights from Caribbean to O'Hare IntlSearch for one-way flight options from Caribbean to O'Hare Intl. Find affordable one-way fares based on user searches. Data last updated October 25, 2026.
Search for one-way flight options from Caribbean to O'Hare Intl. Find affordable one-way fares based on user searches. Data last updated October 25, 2026.
This OneTravel 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 OneTravel is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/216:00 am -
1 stop11h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![Frontier logo]()
$119
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 11/2010:21 pm -
1 stop28h 22m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/23![Frontier logo]()
$120
This Cheapflightsfares 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/245:35 pm -
1 stop25h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![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.
Mon 11/26:15 am -
1 stop18h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![Frontier logo]()
$122
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.
Wed 12/93:28 am -
2 stops14h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Frontier logo]()
$123
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.
Sat 12/197:28 am -
1 stop13h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![Frontier logo]()
$124
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.
Fri 12/119:52 pm -
2 stops26h 08m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Frontier logo]()
$125
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.
Tue 11/247:31 am -
1 stop18h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Frontier logo]()
$126
This Kiwi.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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/279:14 pm -
2 stops16h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/24![Frontier logo]()
$127
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/226:00 am -
1 stop12h 59m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/22![Frontier logo]()
$128
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.
Fri 12/43:50 pm -
Nonstop5h 39m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![American Airlines logo]()
$129
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/203:00 pm -
1 stop10h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 10/21![JetBlue logo]()
$196
Find flight deals from Caribbean to O'Hare Intl
Keep the following information in mind while searching for Caribbean to O'Hare Intl flight deals. Data was last updated October 25, 2026.
Round-trip from | $227 (Cheapflightsfares) |
|---|---|
One-way from | $119 (OneTravel) |
Popular in | June |
Cheapest in | February |
Average price | $405 |
Good round-trip deal | $318 or less |
Good one-way deal | $189 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Caribbean to O'Hare Intl 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 Caribbean to Chicago O'Hare Intl Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
Quickest round-trip
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - ORD Chicago O'Hare Intl
SJUORD
San Juan Luis Munoz Marin Intl
Wed 2/3
8:25 am-11:49 am
Nonstop5h 24m
Chicago O'Hare Intl
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$129
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - ORD Chicago O'Hare Intl
SJUORD
San Juan Luis Munoz Marin Intl
Sun 2/7
9:14 pm-2:19 pm
1 stop19h 05m
Chicago O'Hare Intl
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$132
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - ORD Chicago O'Hare Intl
SJUORD
San Juan Luis Munoz Marin Intl
Fri 1/22
2:05 am-10:02 am
1 stop9h 57m
Chicago O'Hare Intl
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$145
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - ORD Chicago O'Hare Intl
SJUORD
San Juan Luis Munoz Marin Intl
Sat 2/6
6:10 pm-11:47 pm
1 stop7h 37m
Chicago O'Hare Intl
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$167
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - ORD Chicago O'Hare Intl
SJUORD
San Juan Luis Munoz Marin Intl
Thu 12/10
8:25 am-11:49 am
Nonstop5h 24m
Chicago O'Hare Intl
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$179
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - ORD Chicago O'Hare Intl
SJUORD
San Juan Luis Munoz Marin Intl
Tue 2/2
8:25 am-11:49 am
Nonstop5h 24m
Chicago O'Hare Intl
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$179
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - ORD Chicago O'Hare Intl
SJUORD
San Juan Luis Munoz Marin Intl
Thu 12/24
2:05 am-9:59 am
1 stop9h 54m
Chicago O'Hare Intl
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$183
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - ORD Chicago O'Hare Intl
SJUORD
San Juan Luis Munoz Marin Intl
Fri 12/25
2:05 am-9:00 am
1 stop8h 55m
Chicago O'Hare Intl
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$183
Punta CanaChicago
PUJ Punta Cana - ORD Chicago O'Hare Intl
PUJORD
Punta Cana
Wed 1/20
3:00 pm-11:42 pm
1 stop10h 42m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:30 am
Nonstop0h 00m
$196
Santo DomingoChicago
SDQ Santo Domingo Las Americas - ORD Chicago O'Hare Intl
SDQORD
Santo Domingo Las Americas
Fri 12/11
12:15 pm-3:02 pm
1 stop28h 47m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:30 am
Nonstop0h 00m
$205
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Caribbean to O'Hare Intl
Have a flexible travel schedule? Discover the best time to fly to O'Hare Intl from Caribbean with our price prediction graph.
SJU-ORD
GCM-ORD
PUJ-ORD
MBJ-ORD
SXM-ORD
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 Caribbean to Chicago O'Hare Intl Airport
0CB-ORD
SJU-ORD
GCM-ORD
PUJ-ORD
MBJ-ORD
What is the cheapest month to book a flight from Caribbean to Chicago O'Hare Intl Airport?
Currently, February is the cheapest month in which you can book a flight from Caribbean to Chicago O'Hare Intl Airport (average of $246). Flying from Caribbean to Chicago O'Hare Intl Airport in June is currently the most expensive (average of $460). 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 CB to ORD?
Find hourly flight availability from Caribbean to O'Hare Intl. 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 Caribbean to Chicago O'Hare Intl Airport in the evening. If you’re flexible enough to do this you can expect to save up to 39% on your trip compared to booking a flight in the afternoon.
Weekly flight availability from Caribbean to Chicago O'Hare Intl Airport
Explore weekly flight availability from Caribbean to O'Hare Intl. 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 0CB to ORD 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 Caribbean to Chicago delayed?
About 9% of weekly flights between Caribbean and Chicago have experienced delays in the past year, with the average delay time being 187 minutes.
What is the most punctual flight time for Caribbean to Chicago flights?
Historically, flights departing in the morning 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?
Thursday 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 Caribbean to Chicago flights?
Over the last year, United Airlines have had the lowest number of delays on this route, with just 4% of flights being delayed.
How far ahead should I book a flight from Caribbean to Chicago O'Hare Intl Airport?
The best time to book flights from Caribbean to Chicago O'Hare Intl Airport is 81 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
What is the cheapest day to fly from Caribbean to Chicago O'Hare Intl Airport?
Use this chart to determine the cheapest time to fly round-trip from Caribbean to O'Hare Intl. Price data was last updated on October 24, 2026.
Travelers seeking maximum savings on their Caribbean to Chicago O'Hare Intl Airport flight should consider departing on Friday evenings when fares are most often at their lowest. Saturday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing O'Hare Intl
Get insights into the airlines that provide service to O'Hare Intl. 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 O'Hare Intl. Reviews last updated October 25, 2026.
Get a feel of what it's like to fly with United Airlines,JetBlue, andAmerican Airlines from Caribbean to Chicago O'Hare Intl Airport by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
6.7
Entertainment
7.1
Overall
7.3
Boarding
7.7
Comfort
7.3
Crew
8.1
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Food
6.7
Entertainment
7.1
Overall
7.3
Boarding
7.7
Comfort
7.3
Crew
8.1
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Food
6.7
Entertainment
7.1
Overall
7.3
Boarding
7.7
Comfort
7.3
Crew
8.1
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Food
6.7
Entertainment
7.1
Overall
7.3
Boarding
7.7
Comfort
7.3
Crew
8.1
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Food
6.7
Entertainment
7.1
Overall
7.3
Boarding
7.7
Comfort
7.3
Crew
8.1
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Related info for your journey
Find useful and relevant information for your journey from Caribbean to O'Hare Intl. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago O'Hare Intl Airport?
Book flights to Chicago O'Hare Intl Airport if you plan to visit one of these locationsBenton Harbor
Rosemont
Naperville
Lake Geneva
Des Plaines
Glenview
Schaumburg
Oak Brook
Aurora
Oakbrook Terrace
Delavan
Libertyville
Rockford
Hoffman Estates
Beloit
Gurnee
Orland Park
South Holland
Elgin
Racine
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.
Alternative routes
Complete your trip
Flights by cabin class
O'Hare Intl flight routes
Other flight options
Popular flights
Top destinations
Alternative routes for Caribbean to O'Hare Intl
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to O'Hare Intl by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Caribbean to O'Hare Intl by cabin class
Find flights from Caribbean to O'Hare Intl, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Other flights to O'Hare Intl
Explore flights to O'Hare Intl departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on October 25, 2026.
Caribbean and O'Hare Intl flights
Browse other Caribbean and O'Hare Intl flight options. Last updated on October 25, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Caribbean to O'Hare Intl flights
Consider these flights traveling from Caribbean to O'Hare Intl.
Top 6 airlines flying from Caribbean to O'Hare Intl
Discover the top 6 airlines that operate flights from Caribbean to O'Hare Intl. 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$116 | Average$265 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$136 | Average$321 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$226 | Average$539 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$253 | Average$507 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$266 | Average$476 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$616 | Average$616 | FlexibilityNo cancel fee | On-time71% |