$115+ 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 10/11. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — ORD
Oct 10 — Oct 171
Round-trip
1 adult, Economy
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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
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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
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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 September 10, 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 September 10, 2026.
This FlightHub deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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.
Thu 10/296:15 am -
1 stop17h 28m
Mon 11/24:42 pm -
1 stop21h 35m
Deal found 9/9![Frontier logo]()
$213
This Expedia deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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.
Mon 11/237:12 pm -
Nonstop5h 21m
Fri 11/2711:53 pm -
Nonstop4h 39m
Deal found 9/6![Frontier logo]()
$216
This United Airlines deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 10/233:56 pm -
Nonstop5h 09m
Tue 10/278:52 am -
Nonstop4h 48m
Deal found 9/6![United Airlines logo]()
$217
This Orbitz deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/912:59 am -
1 stop22h 40m
Sat 10/174:41 pm -
1 stop16h 38m
Deal found 9/10![Frontier logo]()
$219
This eDestinos deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/298:45 am -
1 stop7h 35m
Tue 10/67:11 am -
1 stop7h 06m
Deal found 9/8![Frontier logo]()
$221
This United Airlines deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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 10/234:55 pm -
1 stop7h 37m
Mon 10/268:52 am -
Nonstop4h 48m
Deal found 9/5![United Airlines logo]()
$222
This American Airlines deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 10/2312:41 pm -
1 stop12h 27m
Sun 10/258:55 pm -
1 stop13h 25m
Deal found 9/6![American Airlines logo]()
$226
This American Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 10/232:53 pm -
Nonstop5h 36m
Wed 10/286:00 am -
1 stop8h 23m
Deal found 9/10![American Airlines logo]()
$227
This eDestinos deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/68:45 am -
1 stop7h 35m
Tue 10/136:00 am -
1 stop9h 06m
Deal found 9/9![Frontier logo]()
$229
This Delta deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 10/232:59 pm -
1 stop9h 58m
Wed 10/281:50 pm -
1 stop8h 54m
Deal found 9/10![Delta logo]()
$230
This Booking.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 10/315:47 am -
Nonstop5h 10m
Sat 11/711:10 am -
Nonstop4h 45m
Deal found 9/9![Arajet logo]()
$289
This Booking.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 11/75:47 am -
Nonstop5h 10m
Fri 11/135:45 am -
Nonstop4h 45m
Deal found 9/9![Arajet logo]()
$304
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 September 10, 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 September 10, 2026.
This United Airlines deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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 10/231:25 pm -
1 stop10h 03m
Sat 10/248:55 am -
Nonstop4h 49m
Deal found 9/5![United Airlines logo]()
$216
This Trip.com deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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.
Fri 9/256:30 pm -
1 stop26h 18m
Sun 9/278:40 pm -
1 stop19h 50m
Deal found 9/7![Air Canada logo]()
$328
This American Airlines deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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 10/2112:18 pm -
1 stop9h 12m
Sat 10/246:59 pm -
1 stop16h 19m
Deal found 9/7![American Airlines logo]()
$366
This Justfly.com deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 9/203:42 pm -
1 stop17h 38m
Sun 10/47:28 pm -
1 stop18h 59m
Deal found 9/6![Frontier logo]()
$394
This Delta deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 11/116:12 pm -
2 stops14h 34m
Mon 11/167:05 am -
2 stops8h 52m
Deal found 9/9![Delta logo]()
$397
This WorldTicket deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure WorldTicket is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/76:10 pm -
Nonstop5h 10m
Sat 2/2010:27 am -
Nonstop4h 45m
Deal found 9/9![WorldTicket logo]()
$452
This United Airlines deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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 9/221:25 pm -
1 stop9h 50m
Tue 10/68:55 am -
Nonstop4h 49m
Deal found 9/8![United Airlines logo]()
$242
This Cheapflightsfares deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/73:25 pm -
1 stop10h 30m
Sun 11/152:42 pm -
1 stop9h 21m
Deal found 9/9![JetBlue logo]()
$510
This Copa Airlines deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 11/512:10 pm -
1 stop14h 01m
Mon 11/92:13 pm -
1 stop9h 55m
Deal found 9/6![Copa Airlines logo]()
$526
This United Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 9/253:56 pm -
Nonstop5h 09m
Mon 9/285:00 am -
1 stop7h 45m
Deal found 9/9![United Airlines logo]()
$262
This Priceline deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 10/2311:20 am -
2 stops13h 10m
Sun 10/257:44 pm -
2 stops37h 08m
Deal found 9/6![Multiple Airlines logo]()
$614
This Air Canada deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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 12/35:25 pm -
2 stops19h 42m
Sat 12/124:30 pm -
2 stops19h 55m
Deal found 9/8![Air Canada logo]()
$355
This United Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 11/252:05 am -
1 stop8h 57m
Wed 12/210:35 am -
1 stop9h 47m
Deal found 9/10![United Airlines logo]()
$306
This American Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 11/113:56 pm -
Nonstop4h 50m
Mon 11/166:00 am -
1 stop10h 09m
Deal found 9/9![American Airlines logo]()
$396
This Delta deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 11/116:12 pm -
2 stops14h 34m
Tue 11/177:05 am -
2 stops8h 52m
Deal found 9/9![Delta logo]()
$397
This Air Canada deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 9/242:20 pm -
1 stop20h 55m
Sun 9/279:55 am -
1 stop6h 35m
Deal found 9/6![Air Canada logo]()
$371
This United Airlines deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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 10/161:25 pm -
1 stop10h 03m
Mon 10/198:55 am -
Nonstop4h 49m
Deal found 9/7![United Airlines logo]()
$312
This Priceline deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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.
Sat 10/1711:17 am -
1 stop21h 14m
Sat 11/79:51 am -
1 stop23h 01m
Deal found 9/8![Frontier logo]()
$434
This United Airlines deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 10/313:55 pm -
Nonstop5h 31m
Sat 11/71:30 pm -
1 stop6h 52m
Deal found 9/6![United Airlines logo]()
$312
This Air Canada deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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 -
1 stop21h 47m
Sat 12/123:45 pm -
1 stop20h 40m
Deal found 9/8![Air Canada logo]()
$380
This Delta deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 12/243:40 pm -
1 stop9h 23m
Sat 1/26:25 am -
1 stop7h 55m
Deal found 9/6![Delta logo]()
$427
This Frontier deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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.
Fri 10/2310:52 am -
1 stop9h 10m
Sun 10/256:58 pm -
1 stop13h 59m
Deal found 9/8![Frontier logo]()
$436
This United Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 10/24:55 pm -
1 stop7h 37m
Sun 10/45:00 am -
1 stop7h 45m
Deal found 9/9![United Airlines logo]()
$316
This Trip.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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.
Fri 11/61:10 pm -
1 stop25h 03m
Tue 11/104:30 pm -
1 stop18h 40m
Deal found 9/9![Air Canada logo]()
$391
This Copa Airlines deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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 10/1712:42 pm -
1 stop13h 15m
Sat 10/248:01 am -
1 stop17h 24m
Deal found 9/8![Copa Airlines logo]()
$526
This Kiwi.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 11/1011:57 am -
2 stops26h 54m
Fri 11/139:51 am -
1 stop23h 26m
Deal found 9/9![Frontier logo]()
$454
This United Airlines deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” 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 9/243:56 pm -
Nonstop5h 09m
Tue 9/298:55 am -
Nonstop4h 49m
Deal found 9/7![United Airlines logo]()
$327
This Air Canada deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 11/122:05 pm -
1 stop25h 47m
Mon 11/234:30 pm -
1 stop18h 00m
Deal found 9/6![Air Canada logo]()
$397
This Copa Airlines deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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 11/168:55 am -
1 stop17h 16m
Mon 11/232:13 pm -
1 stop20h 57m
Deal found 9/5![Copa Airlines logo]()
$544
This Trip.com deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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 9/2611:12 am -
1 stop12h 47m
Sat 10/108:46 am -
1 stop24h 11m
Deal found 9/5![Frontier logo]()
$467
Last-minute flights from Caribbean to O'Hare IntlDiscover last-minute flight deals from Caribbean to O'Hare Intl. Data last updated September 10, 2026 and is based on user searches.
Discover last-minute flight deals from Caribbean to O'Hare Intl. Data last updated September 10, 2026 and is based on user searches.
This Trip.com deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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.
Fri 9/256:30 pm -
1 stop26h 18m
Sun 9/278:40 pm -
1 stop19h 50m
Deal found 9/10![Air Canada logo]()
$328
This eDestinos deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/298:45 am -
1 stop7h 35m
Tue 10/67:11 am -
1 stop7h 06m
Deal found 9/8![Frontier logo]()
$221
This eDestinos deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/68:45 am -
1 stop7h 35m
Tue 10/136:00 am -
1 stop9h 06m
Deal found 9/9![Frontier logo]()
$229
This Orbitz deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/912:59 am -
1 stop22h 40m
Sat 10/174:41 pm -
1 stop16h 38m
Deal found 9/10![Frontier logo]()
$219
This CheapOair deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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.
Fri 10/166:15 am -
1 stop17h 24m
Mon 10/194:41 pm -
1 stop16h 38m
Deal found 9/10![Frontier logo]()
$217
This American Airlines deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 10/166:00 am -
1 stop14h 16m
Mon 10/198:55 pm -
1 stop14h 14m
Deal found 9/6![American Airlines logo]()
$226
This United Airlines deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 10/231:25 pm -
1 stop10h 03m
Tue 10/272:16 pm -
Nonstop4h 44m
Deal found 9/6![United Airlines logo]()
$222
This American Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 10/232:53 pm -
Nonstop5h 36m
Wed 10/286:00 am -
1 stop8h 23m
Deal found 9/10![American Airlines logo]()
$227
This Delta deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 10/235:59 pm -
1 stop6h 58m
Wed 10/281:50 pm -
1 stop8h 54m
Deal found 9/10![Delta logo]()
$230
This American Airlines deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” 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 10/2312:41 pm -
1 stop12h 27m
Sun 10/258:55 pm -
1 stop13h 25m
Deal found 9/8![American Airlines logo]()
$232
This FlightHub deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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.
Thu 10/296:15 am -
1 stop17h 28m
Mon 11/24:42 pm -
1 stop21h 35m
Deal found 9/9![Frontier logo]()
$213
This Booking.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 10/315:47 am -
Nonstop5h 10m
Sat 11/711:10 am -
Nonstop4h 45m
Deal found 9/9![Arajet logo]()
$289
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 September 10, 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 September 10, 2026.
This JetBlue deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/114:40 pm -
1 stop7h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![JetBlue logo]()
$115
This American Airlines deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 10/712:41 pm -
1 stop11h 19m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![American Airlines logo]()
$116
This American Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 11/103:52 pm -
Nonstop5h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![American Airlines logo]()
$119
This Delta deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 10/61:15 pm -
1 stop9h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Delta logo]()
$123
This Frontier deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/78:45 am -
1 stop7h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![Frontier logo]()
$126
This Kiwi.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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 10/107:15 am -
1 stop16h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Frontier logo]()
$128
This United Airlines deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 9/163:56 pm -
Nonstop5h 09m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![United Airlines logo]()
$129
This Frontier deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/96:25 pm -
1 stop14h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Frontier logo]()
$132
This United Airlines deal was found by Cheapflights users on 9/10. Clicking the “Pick Dates” 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 9/223:00 pm -
1 stop9h 27m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/10![United Airlines logo]()
$133
This Frontier deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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.
Thu 10/87:00 am -
1 stop9h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/6![Frontier logo]()
$135
This Priceline deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” 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.
Wed 10/1411:17 am -
1 stop21h 14m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Frontier logo]()
$175
This Kiwi.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/57:30 pm -
Nonstop5h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Arajet logo]()
$179
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 September 10, 2026.
Round-trip from | $213 (FlightHub) |
|---|---|
One-way from | $115 (JetBlue) |
Popular in | June |
Cheapest in | February |
Average price | $278 |
Good round-trip deal | $322 or less |
Good one-way deal | $217 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 September 10, 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
Thu 9/24
3:56 pm-8:05 pm
Nonstop5h 09m
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
Tue 9/22
1:00 am-9:13 am
1 stop9h 13m
Chicago O'Hare Intl
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$133
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - ORD Chicago O'Hare Intl
SJUORD
San Juan Luis Munoz Marin Intl
Wed 10/7
3:56 pm-8:05 pm
Nonstop5h 09m
Chicago O'Hare Intl
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$154
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - ORD Chicago O'Hare Intl
SJUORD
San Juan Luis Munoz Marin Intl
Tue 11/3
8:25 am-11:47 am
Nonstop5h 22m
Chicago O'Hare Intl
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$154
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - ORD Chicago O'Hare Intl
SJUORD
San Juan Luis Munoz Marin Intl
Sat 10/10
3:56 pm-8:05 pm
Nonstop5h 09m
Chicago O'Hare Intl
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$154
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - ORD Chicago O'Hare Intl
SJUORD
San Juan Luis Munoz Marin Intl
Tue 11/10
4:55 pm-8:26 pm
Nonstop5h 31m
Chicago O'Hare Intl
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$154
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - ORD Chicago O'Hare Intl
SJUORD
San Juan Luis Munoz Marin Intl
Fri 10/2
3:56 pm-8:05 pm
Nonstop5h 09m
Chicago O'Hare Intl
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$155
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - ORD Chicago O'Hare Intl
SJUORD
San Juan Luis Munoz Marin Intl
Sat 9/26
1:00 am-9:00 am
1 stop9h 00m
Chicago O'Hare Intl
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$178
AguadillaChicago
BQN Aguadilla Borinquen - ORD Chicago O'Hare Intl
BQNORD
Aguadilla Borinquen
Sat 10/10
11:17 am-7:31 am
1 stop21h 14m
Chicago O'Hare Intl
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$180
Punta CanaChicago
PUJ Punta Cana - ORD Chicago O'Hare Intl
PUJORD
Punta Cana
Sun 3/7
6:10 pm-9:20 pm
Nonstop5h 10m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:30 am
Nonstop0h 00m
$192
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
PUJ-ORD
NAS-ORD
MBJ-ORD
BQN-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
PUJ-ORD
NAS-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 September 10, 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 41% 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 September 10, 2026.
The most flights from 0CB to ORD are scheduled on a Monday (3 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (3 on average).
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 September 5, 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. Wednesday afternoons 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 September 10, 2026.
Get a feel of what it's like to fly with United Airlines,American Airlines, andJetBlue 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.
Boarding
7.7
Crew
8.1
Comfort
7.3
Food
6.7
Overall
7.4
Entertainment
7.1
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Boarding
7.7
Crew
8.1
Comfort
7.3
Food
6.7
Overall
7.4
Entertainment
7.1
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Boarding
7.7
Crew
8.1
Comfort
7.3
Food
6.7
Overall
7.4
Entertainment
7.1
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Boarding
7.7
Crew
8.1
Comfort
7.3
Food
6.7
Overall
7.4
Entertainment
7.1
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Boarding
7.7
Crew
8.1
Comfort
7.3
Food
6.7
Overall
7.4
Entertainment
7.1
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
Lake Geneva
Naperville
Des Plaines
Glenview
Schaumburg
Oakbrook Terrace
Delavan
Oak Brook
Libertyville
Orland Park
Hoffman Estates
Aurora
Beloit
Rockford
South Holland
Elgin
Racine
Janesville
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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Alternative routes for Caribbean to O'Hare Intl
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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 September 10, 2026.
Caribbean and O'Hare Intl flights
Browse other Caribbean and O'Hare Intl flight options. Last updated on September 10, 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 8 airlines flying from Caribbean to O'Hare Intl
Discover the top 8 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 September 10, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$112 | Average$418 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$118 | Average$264 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$131 | Average$405 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$227 | Average$571 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$237 | Average$477 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$266 | Average$470 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$292 | Average$427 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$616 | Average$616 | FlexibilityNo cancel fee | On-time71% |