$103+ Cheap flights from O'Hare Intl (ORD) to Caribbean
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 8/19. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
Sep 7 — Sep 141
Round-trip
1 adult, Economy
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Find cheap flights from O'Hare Intl to Caribbean with Cheapflights
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Cheapest flights from O'Hare Intl to CaribbeanExplore the most affordable flight options available from O'Hare Intl to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 8, 2026.
Explore the most affordable flight options available from O'Hare Intl to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 8, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/3. 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.
Thu 9/177:11 am -
1 stop29h 23m
Thu 9/247:00 am -
1 stop8h 45m
Deal found 8/3![Frontier logo]()
$222
This Kiwi.com deal was found by Cheapflights users on 8/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/512:44 am -
Nonstop5h 00m
Wed 9/168:45 am -
1 stop31h 00m
Deal found 8/7![Frontier logo]()
$223
This Kiwi.com deal was found by Cheapflights users on 8/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/112:44 am -
Nonstop5h 00m
Wed 9/98:45 am -
1 stop31h 00m
Deal found 8/4![Frontier logo]()
$224
This Super.com deal was found by Cheapflights users on 8/6. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2712:44 am -
Nonstop5h 00m
Fri 9/47:14 pm -
Nonstop5h 13m
Deal found 8/6![Frontier logo]()
$225
This Super.com deal was found by Cheapflights users on 8/4. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2712:44 am -
Nonstop5h 00m
Sat 8/297:14 pm -
Nonstop5h 13m
Deal found 8/4![Frontier logo]()
$226
This Expedia deal was found by Cheapflights users on 8/3. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2912:44 am -
Nonstop5h 00m
Sat 9/57:14 pm -
Nonstop5h 13m
Deal found 8/3![Frontier logo]()
$228
This Orbitz deal was found by Cheapflights users on 8/5. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2212:44 am -
Nonstop5h 00m
Sat 8/295:00 pm -
1 stop7h 44m
Deal found 8/5![Multiple Airlines logo]()
$229
This Kiwi.com deal was found by Cheapflights users on 8/3. 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.
Mon 8/1712:44 am -
Nonstop5h 00m
Mon 9/1411:23 am -
2 stops25h 28m
Deal found 8/3![Frontier logo]()
$230
This Super.com deal was found by Cheapflights users on 8/3. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/1612:44 am -
Nonstop5h 00m
Sat 8/227:14 pm -
Nonstop5h 13m
Deal found 8/3![Frontier logo]()
$231
This Frontier deal was found by Cheapflights users on 8/3. 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 8/1712:44 am -
Nonstop5h 00m
Sat 8/227:14 pm -
Nonstop5h 13m
Deal found 8/3![Frontier logo]()
$233
This CheapOair deal was found by Cheapflights users on 8/7. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/3012:44 am -
Nonstop5h 00m
Sat 9/122:32 pm -
1 stop9h 36m
Deal found 8/7![Multiple Airlines logo]()
$234
This FlightHub deal was found by Cheapflights users on 8/4. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/2412:44 am -
Nonstop5h 00m
Fri 8/287:14 pm -
Nonstop5h 13m
Deal found 8/4![Frontier logo]()
$235
Best flights from O'Hare Intl to CaribbeanDiscover carefully curated flight deals from O'Hare Intl to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 8, 2026.
Discover carefully curated flight deals from O'Hare Intl to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 8, 2026.
This United Airlines deal was found by Cheapflights users on 8/4. 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.
Sat 9/198:55 am -
Nonstop4h 49m
Sat 9/261:25 pm -
1 stop10h 04m
Deal found 8/4![United Airlines logo]()
$252
This Air Canada deal was found by Cheapflights users on 8/7. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/115:35 pm -
1 stop16h 10m
Thu 9/1712:25 pm -
1 stop20h 35m
Deal found 8/7![Air Canada logo]()
$351
This Arajet deal was found by Cheapflights users on 8/8. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/186:45 am -
Nonstop4h 45m
Sun 9/206:00 pm -
Nonstop5h 10m
Deal found 8/8![Arajet logo]()
$395
This Orbitz deal was found by Cheapflights users on 8/7. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/176:21 pm -
2 stops39h 24m
Wed 9/237:00 am -
2 stops36h 48m
Deal found 8/7![Multiple Airlines logo]()
$465
This Delta deal was found by Cheapflights users on 8/4. 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.
Wed 2/35:30 am -
1 stop9h 50m
Wed 2/107:30 am -
1 stop11h 07m
Deal found 8/4![Delta logo]()
$466
This JetBlue deal was found by Cheapflights users on 8/5. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/117:40 am -
1 stop8h 25m
Tue 1/262:59 pm -
1 stop10h 45m
Deal found 8/5![JetBlue logo]()
$495
This Copa Airlines deal was found by Cheapflights users on 8/6. 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.
Wed 11/182:13 pm -
1 stop20h 05m
Wed 11/2512:17 pm -
1 stop12h 54m
Deal found 8/6![Copa Airlines logo]()
$498
This United Airlines deal was found by Cheapflights users on 8/3. 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.
Tue 9/18:50 am -
1 stop10h 48m
Sat 9/121:00 am -
1 stop9h 13m
Deal found 8/3![United Airlines logo]()
$256
This American Airlines deal was found by Cheapflights users on 8/6. 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 10/98:55 pm -
2 stops15h 28m
Mon 10/124:39 pm -
2 stops15h 48m
Deal found 8/6![American Airlines logo]()
$670
This Air Canada deal was found by Cheapflights users on 8/7. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/263:45 pm -
2 stops22h 00m
Tue 12/14:45 pm -
2 stops20h 22m
Deal found 8/7![Air Canada logo]()
$355
This United Airlines deal was found by Cheapflights users on 8/4. 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 9/910:40 am -
1 stop8h 58m
Wed 9/163:56 pm -
Nonstop5h 09m
Deal found 8/4![United Airlines logo]()
$342
This Arajet deal was found by Cheapflights users on 8/8. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/512:12 pm -
Nonstop4h 45m
Sat 9/127:02 am -
Nonstop5h 10m
Deal found 8/8![Arajet logo]()
$415
This Air Canada deal was found by Cheapflights users on 8/6. 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.
Sat 10/319:05 pm -
1 stop15h 05m
Sat 11/71:10 pm -
1 stop21h 13m
Deal found 8/6![Air Canada logo]()
$399
This United Airlines deal was found by Cheapflights users on 8/5. 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.
Tue 10/276:04 am -
1 stop9h 24m
Sat 10/311:55 pm -
Nonstop5h 15m
Deal found 8/5![United Airlines logo]()
$380
This Expedia deal was found by Cheapflights users on 8/7. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/27:05 am -
2 stops30h 40m
Sat 11/76:15 pm -
1 stop28h 05m
Deal found 8/7![Multiple Airlines logo]()
$473
This Arajet deal was found by Cheapflights users on 8/3. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2212:12 pm -
Nonstop4h 45m
Sat 8/297:02 am -
Nonstop5h 10m
Deal found 8/3![Arajet logo]()
$455
This United Airlines deal was found by Cheapflights users on 8/5. 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.
Sat 10/318:50 am -
1 stop6h 38m
Tue 11/32:55 pm -
Nonstop5h 15m
Deal found 8/5![United Airlines logo]()
$380
This Delta deal was found by Cheapflights users on 8/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/256:40 am -
1 stop8h 55m
Fri 10/24:50 pm -
2 stops15h 07m
Deal found 8/7![Delta logo]()
$513
This Copa Airlines deal was found by Cheapflights users on 8/4. 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.
Wed 9/163:20 pm -
1 stop19h 57m
Sun 9/2012:22 pm -
1 stop12h 40m
Deal found 8/4![Copa Airlines logo]()
$525
This Justfly.com deal was found by Cheapflights users on 8/6. 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.
Wed 10/2812:50 pm -
1 stop24h 55m
Sat 11/712:35 pm -
1 stop9h 45m
Deal found 8/6![Multiple Airlines logo]()
$485
This JetBlue deal was found by Cheapflights users on 8/3. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/48:20 pm -
1 stop13h 15m
Thu 9/105:57 pm -
1 stop6h 11m
Deal found 8/3![JetBlue logo]()
$541
This United Airlines deal was found by Cheapflights users on 8/4. 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.
Sun 9/205:00 am -
1 stop9h 30m
Fri 9/253:35 pm -
1 stop8h 57m
Deal found 8/4![United Airlines logo]()
$390
This Copa Airlines deal was found by Cheapflights users on 8/4. 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.
Sat 8/293:21 pm -
1 stop26h 10m
Fri 9/43:39 pm -
1 stop10h 23m
Deal found 8/4![Copa Airlines logo]()
$534
This United Airlines deal was found by Cheapflights users on 8/3. 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 9/119:35 pm -
1 stop15h 52m
Wed 9/163:35 pm -
1 stop9h 05m
Deal found 8/3![United Airlines logo]()
$390
This Delta deal was found by Cheapflights users on 8/7. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/235:30 am -
1 stop10h 04m
Sat 8/291:09 pm -
1 stop10h 48m
Deal found 8/7![Delta logo]()
$574
This JetBlue deal was found by Cheapflights users on 8/7. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/37:00 am -
1 stop9h 22m
Tue 9/83:02 pm -
1 stop9h 42m
Deal found 8/7![JetBlue logo]()
$577
This Copa Airlines deal was found by Cheapflights users on 8/6. 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.
Fri 10/168:01 am -
1 stop9h 19m
Wed 10/211:22 pm -
1 stop12h 35m
Deal found 8/6![Copa Airlines logo]()
$534
This Expedia deal was found by Cheapflights users on 8/7. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/106:21 pm -
2 stops41h 09m
Sat 10/1712:25 pm -
2 stops19h 26m
Deal found 8/7![Air Canada logo]()
$535
This United Airlines deal was found by Cheapflights users on 8/7. 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.
Sun 9/135:00 am -
1 stop9h 30m
Wed 9/163:35 pm -
1 stop9h 05m
Deal found 8/7![United Airlines logo]()
$390
This Delta deal was found by Cheapflights users on 8/5. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 1/175:30 am -
1 stop7h 35m
Tue 1/261:50 pm -
1 stop9h 20m
Deal found 8/5![Delta logo]()
$580
Last-minute flights from O'Hare Intl to CaribbeanDiscover last-minute flight deals from O'Hare Intl to Caribbean. Data last updated August 8, 2026 and is based on user searches.
Discover last-minute flight deals from O'Hare Intl to Caribbean. Data last updated August 8, 2026 and is based on user searches.
This Super.com deal was found by Cheapflights users on 8/3. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/1612:44 am -
Nonstop5h 00m
Sat 8/227:14 pm -
Nonstop5h 13m
Deal found 8/3![Frontier logo]()
$231
This Kiwi.com deal was found by Cheapflights users on 8/3. 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.
Mon 8/1712:44 am -
Nonstop5h 00m
Mon 9/1411:23 am -
2 stops25h 28m
Deal found 8/3![Frontier logo]()
$230
This Frontier deal was found by Cheapflights users on 8/3. 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 8/1712:44 am -
Nonstop5h 00m
Sat 8/227:14 pm -
Nonstop5h 13m
Deal found 8/3![Frontier logo]()
$233
This Orbitz deal was found by Cheapflights users on 8/5. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2212:44 am -
Nonstop5h 00m
Sat 8/295:00 pm -
1 stop7h 44m
Deal found 8/5![Multiple Airlines logo]()
$229
This FlightHub deal was found by Cheapflights users on 8/4. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/2412:44 am -
Nonstop5h 00m
Fri 8/287:14 pm -
Nonstop5h 13m
Deal found 8/4![Frontier logo]()
$235
This Super.com deal was found by Cheapflights users on 8/6. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2712:44 am -
Nonstop5h 00m
Fri 9/47:14 pm -
Nonstop5h 13m
Deal found 8/6![Frontier logo]()
$225
This Super.com deal was found by Cheapflights users on 8/4. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2712:44 am -
Nonstop5h 00m
Sat 8/297:14 pm -
Nonstop5h 13m
Deal found 8/4![Frontier logo]()
$226
This Expedia deal was found by Cheapflights users on 8/3. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/2912:44 am -
Nonstop5h 00m
Sat 9/57:14 pm -
Nonstop5h 13m
Deal found 8/3![Frontier logo]()
$228
This CheapOair deal was found by Cheapflights users on 8/7. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/3012:44 am -
Nonstop5h 00m
Sat 9/122:32 pm -
1 stop9h 36m
Deal found 8/7![Multiple Airlines logo]()
$234
This Kiwi.com deal was found by Cheapflights users on 8/4. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/112:44 am -
Nonstop5h 00m
Wed 9/98:45 am -
1 stop31h 00m
Deal found 8/4![Frontier logo]()
$224
This Kiwi.com deal was found by Cheapflights users on 8/7. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/512:44 am -
Nonstop5h 00m
Wed 9/168:45 am -
1 stop31h 00m
Deal found 8/7![Frontier logo]()
$223
This Kiwi.com deal was found by Cheapflights users on 8/3. 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.
Thu 9/177:11 am -
1 stop29h 23m
Thu 9/247:00 am -
1 stop8h 45m
Deal found 8/3![Frontier logo]()
$222
One-way flights from O'Hare Intl to CaribbeanSearch for one-way flight options from O'Hare Intl to Caribbean. Find affordable one-way fares based on user searches. Data last updated August 8, 2026.
Search for one-way flight options from O'Hare Intl to Caribbean. Find affordable one-way fares based on user searches. Data last updated August 8, 2026.
This eDestinos deal was found by Cheapflights users on 8/8. 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.
Wed 8/1912:44 am -
Nonstop5h 00m
Deal found 8/8![Frontier logo]()
$103
This Kiwi.com deal was found by Cheapflights users on 8/3. 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.
Sat 9/267:11 am -
1 stop8h 52m
Deal found 8/3![Frontier logo]()
$105
This Trip.com deal was found by Cheapflights users on 8/7. 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.
Thu 10/157:45 am -
1 stop14h 53m
Deal found 8/7![Frontier logo]()
$107
This Kiwi.com deal was found by Cheapflights users on 8/3. 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.
Sat 9/127:11 am -
1 stop29h 23m
Deal found 8/3![Frontier logo]()
$109
This Kiwi.com deal was found by Cheapflights users on 8/3. 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.
Wed 9/167:11 am -
1 stop29h 23m
Deal found 8/3![Frontier logo]()
$110
This Super.com deal was found by Cheapflights users on 8/4. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/3112:44 am -
Nonstop5h 00m
Deal found 8/4![Frontier logo]()
$112
This Super.com deal was found by Cheapflights users on 8/3. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2712:44 am -
Nonstop5h 00m
Deal found 8/3![Frontier logo]()
$113
This Frontier deal was found by Cheapflights users on 8/3. 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.
Tue 9/112:44 am -
Nonstop5h 00m
Deal found 8/3![Frontier logo]()
$114
This eDestinos deal was found by Cheapflights users on 8/3. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/1412:44 am -
Nonstop5h 00m
Deal found 8/3![Frontier logo]()
$117
This Super.com deal was found by Cheapflights users on 8/3. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2612:44 am -
Nonstop5h 00m
Deal found 8/3![Frontier logo]()
$118
This Frontier deal was found by Cheapflights users on 8/3. 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.
Sat 8/1512:44 am -
Nonstop5h 00m
Deal found 8/3![Frontier logo]()
$119
This Expedia deal was found by Cheapflights users on 8/7. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/73:40 pm -
1 stop20h 45m
Deal found 8/7![Air Canada logo]()
$120
Find flight deals from O'Hare Intl to Caribbean
Keep the following information in mind while searching for O'Hare Intl to Caribbean flight deals. Data was last updated August 8, 2026.
Round-trip from | $222 (Kiwi.com) |
|---|---|
One-way from | $103 (eDestinos) |
Popular in | December |
Cheapest in | August |
Average price | $322 |
Good round-trip deal | $315 or less |
Good one-way deal | $133 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from O'Hare Intl to Caribbean that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 8, 2026.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Caribbean that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoSan Juan
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Sat 9/19
8:55 am-2:44 pm
Nonstop4h 49m
San Juan Luis Munoz Marin Intl
Sat 9/26
1:25 pm-10:29 pm
1 stop10h 04m
$252
ChicagoSan Juan
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Tue 9/1
8:50 am-8:38 pm
1 stop10h 48m
San Juan Luis Munoz Marin Intl
Sat 9/12
1:00 am-9:13 am
1 stop9h 13m
$256
ChicagoSan Juan
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Wed 9/9
10:40 am-8:38 pm
1 stop8h 58m
San Juan Luis Munoz Marin Intl
Wed 9/16
3:56 pm-8:05 pm
Nonstop5h 09m
$342
ChicagoGeorge Town
ORD Chicago O'Hare Intl - GCM George Town Owen Roberts Intl
ORDGCM
Chicago O'Hare Intl
Fri 9/11
5:35 pm-9:45 am
1 stop16h 10m
George Town Owen Roberts Intl
Thu 9/17
12:25 pm-9:00 am
1 stop20h 35m
$351
ChicagoSimpson Bay
ORD Chicago O'Hare Intl - SXM Simpson Bay Princess Juliana
ORDSXM
Chicago O'Hare Intl
Thu 11/26
3:45 pm-3:45 pm
2 stops22h 00m
Simpson Bay Princess Juliana
Tue 12/1
4:45 pm-11:07 am
2 stops20h 22m
$355
ChicagoPunta Cana
ORD Chicago O'Hare Intl - PUJ Punta Cana
ORDPUJ
Chicago O'Hare Intl
Tue 10/27
6:04 am-4:28 pm
1 stop9h 24m
Punta Cana
Sat 10/31
1:55 pm-6:10 pm
Nonstop5h 15m
$380
ChicagoPunta Cana
ORD Chicago O'Hare Intl - PUJ Punta Cana
ORDPUJ
Chicago O'Hare Intl
Sat 10/31
8:50 am-4:28 pm
1 stop6h 38m
Punta Cana
Tue 11/3
2:55 pm-6:10 pm
Nonstop5h 15m
$380
ChicagoPunta Cana
ORD Chicago O'Hare Intl - PUJ Punta Cana
ORDPUJ
Chicago O'Hare Intl
Sun 9/20
5:00 am-3:30 pm
1 stop9h 30m
Punta Cana
Fri 9/25
3:35 pm-11:32 pm
1 stop8h 57m
$390
ChicagoPunta Cana
ORD Chicago O'Hare Intl - PUJ Punta Cana
ORDPUJ
Chicago O'Hare Intl
Fri 9/11
9:35 pm-2:27 pm
1 stop15h 52m
Punta Cana
Wed 9/16
3:35 pm-11:40 pm
1 stop9h 05m
$390
ChicagoPunta Cana
ORD Chicago O'Hare Intl - PUJ Punta Cana
ORDPUJ
Chicago O'Hare Intl
Sun 9/13
5:00 am-3:30 pm
1 stop9h 30m
Punta Cana
Wed 9/16
3:35 pm-11:40 pm
1 stop9h 05m
$390
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from O'Hare Intl to Caribbean
Have a flexible travel schedule? Discover the best time to fly to Caribbean from O'Hare Intl with our price prediction graph.
ORD-SJU
ORD-NAS
ORD-PUJ
ORD-CUR
ORD-GCM
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago O'Hare Intl Airport to Caribbean
ORD-0CB
ORD-SJU
ORD-NAS
ORD-PUJ
ORD-CUR
What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Caribbean?
Currently, August is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Caribbean (average of $440). Flying from Chicago O'Hare Intl Airport to Caribbean in December is currently the most expensive (average of $611). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from ORD to CB?
Find hourly flight availability from O'Hare Intl to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 8, 2026.
A simple way to save on the total cost of your ticket is to fly from Chicago O'Hare Intl Airport to Caribbean in the evening. If you’re flexible enough to do this you can expect to save up to 33% on your trip compared to booking a flight in the morning.
Weekly flight availability from Chicago O'Hare Intl Airport to Caribbean
Explore weekly flight availability from O'Hare Intl to Caribbean. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated August 8, 2026.
The most flights from ORD to 0CB are scheduled on a Wednesday (10 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (1 on average).
How far ahead should I book a flight from Chicago O'Hare Intl Airport to Caribbean?
The price you pay for your flight from Chicago O'Hare Intl Airport to Caribbean may vary depending on when you book. For the best chance of a lower fare, look to book 48 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
What is the cheapest day to fly from Chicago O'Hare Intl Airport to Caribbean?
Use this chart to determine the cheapest time to fly round-trip from O'Hare Intl to Caribbean. Price data was last updated on August 1, 2026.
Travelers seeking maximum savings on their Chicago O'Hare Intl Airport to Caribbean flight should consider departing on Sunday evenings when fares are most often at their lowest. Thursday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
Reviews of airlines servicing Caribbean
Get insights into the airlines that provide service to Caribbean. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean. Reviews last updated August 8, 2026.
See what other customers who have flown with United Airlines,American Airlines, andJetBlue from Chicago O'Hare Intl Airport to Caribbean have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Overall
7.4
Crew
8.1
Entertainment
7.1
Food
6.7
Boarding
7.7
Comfort
7.3
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Overall
7.4
Crew
8.1
Entertainment
7.1
Food
6.7
Boarding
7.7
Comfort
7.3
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Overall
7.4
Crew
8.1
Entertainment
7.1
Food
6.7
Boarding
7.7
Comfort
7.3
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Overall
7.4
Crew
8.1
Entertainment
7.1
Food
6.7
Boarding
7.7
Comfort
7.3
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Overall
7.4
Crew
8.1
Entertainment
7.1
Food
6.7
Boarding
7.7
Comfort
7.3
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Related info for your journey
Find useful and relevant information for your journey from O'Hare Intl to Caribbean. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for O'Hare Intl to Caribbean
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Caribbean by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from O'Hare Intl to Caribbean by cabin class
Find flights from O'Hare Intl to Caribbean, based on your preferred cabin class, be it economy, premium economy, business, or first class.
O'Hare Intl and Caribbean flights
Browse other O'Hare Intl and Caribbean flight options. Last updated on August 8, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
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Top 9 airlines flying from O'Hare Intl to Caribbean
Discover the top 9 airlines that operate flights from O'Hare Intl to Caribbean. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated August 8, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$118 | Average$511 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$119 | Average$441 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$144 | Average$591 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$175 | Average$528 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$218 | Average$369 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$228 | Average$486 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$262 | Average$591 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$302 | Average$614 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$376 | Average$568 | FlexibilityNo cancel fee | On-time63% |