$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 9/30. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — ORD
Oct 5 — Oct 121
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
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
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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 5, 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 5, 2026.
This CheapOair deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/27:14 pm -
Nonstop5h 13m
Sat 9/512:44 am -
Nonstop5h 00m
Deal found 8/31![Frontier logo]()
$171
This FlightHub deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/27:14 pm -
Nonstop5h 13m
Sun 9/612:44 am -
Nonstop5h 00m
Deal found 8/31![Frontier logo]()
$172
This eDestinos deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/37:14 pm -
Nonstop5h 13m
Sat 9/512:44 am -
Nonstop5h 00m
Deal found 8/31![Frontier logo]()
$205
This FlightHub deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub 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 9/2![Frontier logo]()
$211
This Expedia deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/47:14 pm -
Nonstop5h 13m
Sun 9/612:44 am -
Nonstop5h 00m
Deal found 8/31![Frontier logo]()
$212
This Booking.com deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/17:14 pm -
Nonstop5h 13m
Fri 9/412:44 am -
Nonstop5h 00m
Deal found 8/31![Frontier logo]()
$213
This Frontier deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/237:12 pm -
Nonstop5h 21m
Thu 11/2611:53 pm -
Nonstop4h 39m
Deal found 9/3![Frontier logo]()
$216
This JetBlue deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/161:00 pm -
1 stop10h 10m
Sat 10/246:10 am -
1 stop9h 15m
Deal found 9/2![JetBlue logo]()
$217
This American Airlines deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/53:52 pm -
Nonstop5h 38m
Mon 11/97:50 pm -
1 stop12h 55m
Deal found 9/2![American Airlines logo]()
$222
This Kiwi.com deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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 11/247:12 pm -
Nonstop5h 21m
Thu 11/2611:53 pm -
Nonstop4h 39m
Deal found 9/3![Frontier logo]()
$223
This Expedia deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/127:30 pm -
Nonstop5h 10m
Sun 11/153:20 am -
Nonstop4h 45m
Deal found 9/1![Arajet logo]()
$286
This Expedia deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/215:47 am -
Nonstop5h 10m
Sat 11/2810:27 am -
Nonstop4h 45m
Deal found 9/2![Arajet logo]()
$310
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 5, 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 5, 2026.
This United Airlines deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” 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 11/63:46 pm -
1 stop9h 40m
Fri 11/132:16 pm -
Nonstop4h 44m
Deal found 9/4![United Airlines logo]()
$312
This Air Canada deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” 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 10/36:30 pm -
1 stop15h 30m
Sat 10/108:40 pm -
1 stop19h 50m
Deal found 9/4![Air Canada logo]()
$376
This FlightHub deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/13:42 pm -
1 stop26h 41m
Sun 10/187:44 pm -
1 stop18h 49m
Deal found 9/2![Frontier logo]()
$384
This Delta deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” 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 12/182:05 pm -
1 stop7h 10m
Fri 1/17:00 am -
2 stops12h 41m
Deal found 9/4![Delta logo]()
$407
This Priceline deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” 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 9/196:30 pm -
2 stops16h 45m
Sun 9/276:00 am -
1 stop9h 00m
Deal found 9/4![Multiple Airlines logo]()
$414
This JetBlue deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/272:56 pm -
1 stop10h 01m
Sat 10/317:00 am -
1 stop5h 51m
Deal found 9/2![JetBlue logo]()
$442
This Copa Airlines deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/412:10 pm -
1 stop14h 01m
Mon 11/92:13 pm -
1 stop9h 55m
Deal found 9/1![Copa Airlines logo]()
$526
This American Airlines deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” 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 1/123:07 pm -
1 stop10h 33m
Tue 1/198:22 am -
Nonstop4h 52m
Deal found 9/4![American Airlines logo]()
$576
This United Airlines deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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 10/231:00 am -
1 stop7h 42m
Fri 10/302:16 pm -
Nonstop4h 44m
Deal found 9/3![United Airlines logo]()
$312
This United Airlines deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” 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 10/121:00 am -
1 stop9h 00m
Mon 10/195:00 am -
1 stop7h 45m
Deal found 9/4![United Airlines logo]()
$316
This Air Canada deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/236:20 pm -
2 stops17h 47m
Sun 11/295:58 pm -
2 stops22h 22m
Deal found 8/31![Air Canada logo]()
$390
This Priceline deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/163:48 pm -
1 stop19h 44m
Fri 10/237:44 pm -
1 stop18h 49m
Deal found 9/1![Frontier logo]()
$392
This United Airlines deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” 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 11/165:50 pm -
1 stop8h 12m
Sun 11/221:30 pm -
1 stop6h 52m
Deal found 9/4![United Airlines logo]()
$331
This Delta deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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 12/244:45 pm -
1 stop8h 18m
Fri 1/16:25 am -
1 stop7h 55m
Deal found 9/3![Delta logo]()
$427
This Travelocity deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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.
Wed 10/2112:30 pm -
1 stop24h 53m
Sat 10/243:40 pm -
1 stop20h 45m
Deal found 9/3![Air Canada logo]()
$395
This United Airlines deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/221:25 pm -
1 stop8h 35m
Sat 9/261:55 pm -
1 stop8h 55m
Deal found 9/1![United Airlines logo]()
$346
This Delta deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/256:06 pm -
1 stop7h 44m
Mon 2/16:00 am -
1 stop8h 10m
Deal found 8/31![Delta logo]()
$427
This Air Canada deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” 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 11/232:05 pm -
1 stop22h 02m
Sat 11/285:58 pm -
2 stops18h 17m
Deal found 9/4![Air Canada logo]()
$397
This Delta deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 1/146:06 pm -
1 stop7h 44m
Sun 1/317:10 am -
1 stop6h 20m
Deal found 8/31![Delta logo]()
$427
This Copa Airlines deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” 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 1/228:52 am -
1 stop17h 15m
Fri 1/292:13 pm -
1 stop23h 55m
Deal found 9/4![Copa Airlines logo]()
$526
This Flysmarter deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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 10/243:05 pm -
1 stop19h 18m
Sun 11/15:58 pm -
2 stops20h 27m
Deal found 9/3![Air Canada logo]()
$408
This Copa Airlines deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/3112:12 pm -
1 stop13h 59m
Sat 11/72:13 pm -
1 stop9h 55m
Deal found 8/31![Copa Airlines logo]()
$526
This American Airlines deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” 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 11/42:01 pm -
1 stop10h 29m
Tue 11/109:06 pm -
1 stop16h 32m
Deal found 9/4![American Airlines logo]()
$580
This United Airlines deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/291:00 am -
1 stop9h 00m
Sun 10/48:55 am -
Nonstop4h 49m
Deal found 9/2![United Airlines logo]()
$402
This Copa Airlines deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” 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 9/4![Copa Airlines logo]()
$526
This American Airlines deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” 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 11/34:53 pm -
1 stop17h 07m
Mon 11/96:41 am -
1 stop6h 57m
Deal found 9/4![American Airlines logo]()
$580
This Kiwi.com deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/234:45 pm -
2 stops18h 47m
Wed 10/2812:20 pm -
1 stop25h 15m
Deal found 8/31![Multiple Airlines logo]()
$641
This United Airlines deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/232:54 pm -
Nonstop4h 26m
Sun 11/298:40 am -
Nonstop4h 08m
Deal found 8/31![United Airlines logo]()
$411
This Copa Airlines deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 1/2012:06 pm -
1 stop26h 40m
Wed 1/277:35 am -
1 stop16h 29m
Deal found 9/2![Copa Airlines logo]()
$526
This American Airlines deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” 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 11/53:15 pm -
2 stops10h 46m
Mon 11/96:41 am -
1 stop6h 57m
Deal found 9/4![American Airlines logo]()
$580
Last-minute flights from Caribbean to O'Hare IntlDiscover last-minute flight deals from Caribbean to O'Hare Intl. Data last updated September 5, 2026 and is based on user searches.
Discover last-minute flight deals from Caribbean to O'Hare Intl. Data last updated September 5, 2026 and is based on user searches.
This eDestinos deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/37:14 pm -
Nonstop5h 13m
Sat 9/512:44 am -
Nonstop5h 00m
Deal found 8/31![Frontier logo]()
$205
This Expedia deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/47:14 pm -
Nonstop5h 13m
Sun 9/612:44 am -
Nonstop5h 00m
Deal found 8/31![Frontier logo]()
$212
This CheapOair deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/47:14 pm -
Nonstop5h 13m
Sat 9/512:44 am -
Nonstop5h 00m
Deal found 9/1![Frontier logo]()
$229
This Trip.com deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” 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.
Thu 9/102:20 pm -
1 stop20h 55m
Thu 9/175:35 pm -
1 stop22h 55m
Deal found 9/3![Air Canada logo]()
$320
This American Airlines deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/2510:16 am -
1 stop15h 17m
Tue 9/299:53 am -
2 stops9h 54m
Deal found 9/2![American Airlines logo]()
$226
This American Airlines deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/253:41 pm -
1 stop7h 50m
Mon 9/285:00 am -
1 stop7h 57m
Deal found 8/31![American Airlines logo]()
$230
This United Airlines deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/263:56 pm -
Nonstop5h 09m
Thu 10/292:16 pm -
Nonstop4h 44m
Deal found 8/31![United Airlines logo]()
$232
This JetBlue deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/161:00 pm -
1 stop10h 10m
Sat 10/246:10 am -
1 stop9h 15m
Deal found 9/2![JetBlue logo]()
$217
This United Airlines deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” 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
Sat 10/248:55 am -
Nonstop4h 49m
Deal found 9/4![United Airlines logo]()
$222
This American Airlines deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/212:53 pm -
Nonstop5h 36m
Wed 10/288:55 pm -
1 stop13h 25m
Deal found 9/2![American Airlines logo]()
$227
This American Airlines deal was found by Cheapflights users on 8/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/233:51 pm -
1 stop9h 17m
Sat 10/248:13 am -
Nonstop4h 50m
Deal found 8/30![American Airlines logo]()
$220
This Booking.com deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/247:02 am -
Nonstop5h 10m
Sat 10/3111:27 am -
Nonstop4h 45m
Deal found 9/1![Arajet logo]()
$313
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 5, 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 5, 2026.
This American Airlines deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/306:00 am -
2 stops11h 00m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/1![American Airlines logo]()
$115
This American Airlines deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/262:58 pm -
1 stop10h 35m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/1![American Airlines logo]()
$116
This Trip.com deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/217:00 pm -
Nonstop5h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Frontier logo]()
$118
This United Airlines deal was found by Cheapflights users on 9/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/13:56 pm -
Nonstop5h 09m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/2![United Airlines logo]()
$119
This JetBlue deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/22:32 pm -
1 stop9h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![JetBlue logo]()
$120
This Orbitz deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/193:55 am -
Nonstop5h 21m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/1![Frontier logo]()
$122
This American Airlines deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” 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 stop13h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![American Airlines logo]()
$123
This United Airlines deal was found by Cheapflights users on 9/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 12/218:25 am -
Nonstop5h 24m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/1![United Airlines logo]()
$124
This Expedia deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/237:00 pm -
Nonstop5h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![Frontier logo]()
$125
This Kiwi.com deal was found by Cheapflights users on 8/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/17:00 am -
1 stop8h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 8/31![Frontier logo]()
$126
This Frontier deal was found by Cheapflights users on 9/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/17:00 am -
1 stop10h 37m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/3![Frontier logo]()
$128
This United Airlines deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” 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 9/4![United Airlines logo]()
$129
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 5, 2026.
Round-trip from | $211 (FlightHub) |
|---|---|
One-way from | $115 (American Airlines) |
Popular in | June |
Cheapest in | February |
Average price | $276 |
Good round-trip deal | $346 or less |
Good one-way deal | $216 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 5, 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
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - ORD Chicago O'Hare Intl
SJUORD
San Juan Luis Munoz Marin Intl
Fri 9/18
1:00 am-7:41 am
1 stop7h 41m
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
Mon 10/26
7:25 am-11:47 am
Nonstop5h 22m
Chicago O'Hare Intl
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$148
Quickest round-trip
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
$154
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - ORD Chicago O'Hare Intl
SJUORD
San Juan Luis Munoz Marin Intl
Sat 10/31
7:25 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 10/3
1:00 am-7:42 am
1 stop7h 42m
Chicago O'Hare Intl
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$158
Santo DomingoChicago
SDQ Santo Domingo Las Americas - ORD Chicago O'Hare Intl
SDQORD
Santo Domingo Las Americas
Thu 9/24
3:30 pm-11:40 pm
1 stop9h 10m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:30 am
Nonstop0h 00m
$199
Santo DomingoChicago
SDQ Santo Domingo Las Americas - ORD Chicago O'Hare Intl
SDQORD
Santo Domingo Las Americas
Fri 9/25
1:40 am-11:12 am
1 stop10h 32m
Chicago O'Hare Intl
Wed 12/31
12:00 am-1:30 am
Nonstop0h 00m
$199
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - ORD Chicago O'Hare Intl
SJUORD
San Juan Luis Munoz Marin Intl
Wed 9/16
2:59 pm-11:59 pm
1 stop10h 00m
Chicago O'Hare Intl
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$208
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - ORD Chicago O'Hare Intl
SJUORD
San Juan Luis Munoz Marin Intl
Sat 10/3
3:56 pm-8:05 pm
Nonstop5h 09m
Chicago O'Hare Intl
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$214
San JuanChicago
SJU San Juan Luis Munoz Marin Intl - ORD Chicago O'Hare Intl
SJUORD
San Juan Luis Munoz Marin Intl
Thu 10/1
3:56 pm-8:05 pm
Nonstop5h 09m
Chicago O'Hare Intl
Wed 12/31
12:00 am-2:00 am
Nonstop0h 00m
$214
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
SDQ-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 5, 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 5, 2026.
The most flights from 0CB to ORD are scheduled on a Wednesday (6 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (4 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 August 29, 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 5, 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.
Food
6.7
Entertainment
7.1
Comfort
7.3
Overall
7.4
Boarding
7.7
Crew
8.1
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Food
6.7
Entertainment
7.1
Comfort
7.3
Overall
7.4
Boarding
7.7
Crew
8.1
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Food
6.7
Entertainment
7.1
Comfort
7.3
Overall
7.4
Boarding
7.7
Crew
8.1
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Food
6.7
Entertainment
7.1
Comfort
7.3
Overall
7.4
Boarding
7.7
Crew
8.1
Reviews
1 / 20
4.0
OkayChris,Aug 2026
MIA - ORD
Food
6.7
Entertainment
7.1
Comfort
7.3
Overall
7.4
Boarding
7.7
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
Glenview
Lake Geneva
Schaumburg
Oakbrook Terrace
Delavan
Oak Brook
Libertyville
Des Plaines
Orland Park
Hoffman Estates
Aurora
Beloit
Rockford
South Holland
Elgin
Racine
Skokie
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
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 September 5, 2026.
Caribbean and O'Hare Intl flights
Browse other Caribbean and O'Hare Intl flight options. Last updated on September 5, 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 5, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$112 | Average$418 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$128 | Average$282 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$131 | Average$405 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$227 | Average$570 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$237 | Average$476 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$267 | Average$472 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$292 | Average$427 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$616 | Average$616 | FlexibilityNo cancel fee | On-time71% |