$109+ Cheap flights from Caribbean to O'Hare Intl (ORD)
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 9/8. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — ORD
Jul 12 — Jul 191
Round-trip
1 adult, Economy
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Find cheap flights from Caribbean to O'Hare Intl with Cheapflights
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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 June 12, 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 June 12, 2026.
This Frontier deal was found by Cheapflights users on 6/7. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/47:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Mon 8/1012:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 6/7![Frontier logo]()
$222
This Expedia deal was found by Cheapflights users on 6/8. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/127:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Mon 8/1712:29 am
ORD
- SJU
Nonstop4h 57m
Frontier
Deal found 6/8![Frontier logo]()
$223
This Kiwi.com deal was found by Cheapflights users on 6/9. 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.
Wed 8/196:00 am
SJU
- ORD
1 stop31h 25m
Frontier
Sun 8/2312:29 am
ORD
- SJU
Nonstop4h 57m
Frontier
Deal found 6/9![Frontier logo]()
$227
This Frontier deal was found by Cheapflights users on 6/9. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/127:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Tue 8/1812:29 am
ORD
- SJU
Nonstop4h 57m
Frontier
Deal found 6/9![Frontier logo]()
$228
This Frontier deal was found by Cheapflights users on 6/8. 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 8/266:11 pm
SJU
- ORD
Nonstop5h 15m
Frontier
Fri 8/2812:29 am
ORD
- SJU
Nonstop4h 57m
Frontier
Deal found 6/8![Frontier logo]()
$230
This American Airlines deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” 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 8/201:38 pm
SJU
- ORD
1 stop11h 57m
American Airlines
Sun 8/235:20 pm
ORD
- SJU
Nonstop4h 55m
American Airlines
Deal found 6/12![American Airlines logo]()
$232
This Frontier deal was found by Cheapflights users on 6/9. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/137:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Fri 8/2112:29 am
ORD
- SJU
Nonstop4h 57m
Frontier
Deal found 6/9![Frontier logo]()
$233
This Frontier deal was found by Cheapflights users on 6/7. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/297:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Mon 8/1712:29 am
ORD
- SJU
Nonstop4h 57m
Frontier
Deal found 6/7![Frontier logo]()
$235
This American Airlines deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” 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 8/275:10 pm
SJU
- ORD
1 stop8h 25m
American Airlines
Sun 8/305:05 am
ORD
- SJU
1 stop8h 48m
American Airlines
Deal found 6/12![American Airlines logo]()
$236
This American Airlines deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” 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 8/261:38 pm
SJU
- ORD
1 stop11h 57m
American Airlines
Wed 9/25:20 pm
ORD
- SJU
Nonstop4h 55m
American Airlines
Deal found 6/12![American Airlines logo]()
$237
This Kiwi.com deal was found by Cheapflights users on 6/7. 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.
Thu 7/306:00 am
SJU
- ORD
1 stop31h 15m
Frontier
Mon 8/1712:29 am
ORD
- SJU
Nonstop4h 57m
Frontier
Deal found 6/7![Frontier logo]()
$239
This Frontier deal was found by Cheapflights users on 6/9. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/196:11 pm
SJU
- ORD
Nonstop5h 15m
Frontier
Tue 8/2512:29 am
ORD
- SJU
Nonstop4h 57m
Frontier
Deal found 6/9![Frontier logo]()
$240
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 June 12, 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 June 12, 2026.
This United Airlines deal was found by Cheapflights users on 6/9. 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.
Wed 9/93:56 pm
SJU
- ORD
Nonstop5h 09m
United Airlines
Tue 9/221:30 pm
ORD
- SJU
1 stop9h 20m
United Airlines
Deal found 6/9![United Airlines logo]()
$272
This Arajet deal was found by Cheapflights users on 6/8. 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.
Thu 10/227:30 pm
PUJ
- ORD
Nonstop5h 10m
Arajet
Fri 10/236:45 am
ORD
- PUJ
Nonstop4h 45m
Arajet
Deal found 6/8![Arajet logo]()
$311
This JetBlue deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 11/123:59 pm
MBJ
- ORD
1 stop8h 45m
JetBlue
Mon 11/167:00 am
ORD
- MBJ
1 stop6h 54m
JetBlue
Deal found 6/11![JetBlue logo]()
$334
This Delta deal was found by Cheapflights users on 6/7. 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 8/232:59 pm
SJU
- ORD
1 stop6h 56m
Delta
Sun 9/66:40 am
ORD
- SJU
1 stop8h 58m
Delta
Deal found 6/7![Delta logo]()
$361
This Expedia deal was found by Cheapflights users on 6/7. 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 7/226:30 pm
NAS
- ORD
2 stops21h 25m
Multiple Airlines
Wed 7/297:00 am
ORD
- NAS
1 stop9h 22m
Multiple Airlines
Deal found 6/7![Multiple Airlines logo]()
$384
This American Airlines deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” 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 8/133:23 pm
MBJ
- ORD
1 stop16h 07m
American Airlines
Mon 8/175:00 am
ORD
- MBJ
1 stop9h 23m
American Airlines
Deal found 6/12![American Airlines logo]()
$394
This Frontier deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 7/1112:19 pm
BQN
- ORD
1 stop11h 51m
Frontier
Sat 7/255:13 pm
ORD
- BQN
1 stop7h 57m
Frontier
Deal found 6/11![Frontier logo]()
$436
This Air Canada deal was found by Cheapflights users on 6/7. 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 7/166:30 pm
NAS
- ORD
2 stops16h 46m
Air Canada
Tue 7/218:40 pm
ORD
- NAS
2 stops15h 55m
Air Canada
Deal found 6/7![Air Canada logo]()
$452
This Copa Airlines deal was found by Cheapflights users on 6/10. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/252:56 pm
KIN
- ORD
1 stop13h 04m
Copa Airlines
Fri 7/311:20 am
ORD
- KIN
1 stop12h 34m
Copa Airlines
Deal found 6/10![Copa Airlines logo]()
$480
This United Airlines deal was found by Cheapflights users on 6/8. 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.
Fri 9/113:56 pm
SJU
- ORD
Nonstop5h 09m
United Airlines
Tue 9/158:55 am
ORD
- SJU
Nonstop4h 49m
United Airlines
Deal found 6/8![United Airlines logo]()
$298
This Arajet deal was found by Cheapflights users on 6/8. 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.
Sun 11/16:10 pm
PUJ
- ORD
Nonstop5h 10m
Arajet
Sun 11/13:20 am
ORD
- PUJ
Nonstop4h 45m
Arajet
Deal found 6/8![Arajet logo]()
$330
This JetBlue deal was found by Cheapflights users on 6/10. 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.
Wed 7/1512:20 pm
NAS
- ORD
1 stop12h 24m
JetBlue
Sun 7/197:00 am
ORD
- NAS
1 stop9h 22m
JetBlue
Deal found 6/10![JetBlue logo]()
$344
This United Airlines deal was found by Cheapflights users on 6/7. 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.
Sat 7/44:33 pm
MBJ
- ORD
1 stop16h 32m
United Airlines
Sat 7/1111:15 am
ORD
- MBJ
1 stop27h 55m
United Airlines
Deal found 6/7![United Airlines logo]()
$321
This JetBlue deal was found by Cheapflights users on 6/8. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/1612:20 pm
NAS
- ORD
1 stop12h 24m
JetBlue
Tue 7/217:00 am
ORD
- NAS
1 stop9h 22m
JetBlue
Deal found 6/8![JetBlue logo]()
$353
This United Airlines deal was found by Cheapflights users on 6/8. 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.
Fri 7/174:12 pm
MBJ
- ORD
1 stop7h 19m
United Airlines
Sun 7/196:29 am
ORD
- MBJ
1 stop8h 57m
United Airlines
Deal found 6/8![United Airlines logo]()
$326
This Delta deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” 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 8/134:59 pm
MBJ
- ORD
2 stops14h 57m
Delta
Mon 8/175:30 am
ORD
- MBJ
1 stop6h 14m
Delta
Deal found 6/12![Delta logo]()
$412
This American Airlines deal was found by Cheapflights users on 6/10. 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.
Wed 8/192:12 pm
MBJ
- ORD
Nonstop4h 43m
American Airlines
Thu 8/275:00 am
ORD
- MBJ
1 stop9h 23m
American Airlines
Deal found 6/10![American Airlines logo]()
$416
This Arajet deal was found by Cheapflights users on 6/10. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/137:30 pm
PUJ
- ORD
Nonstop5h 10m
Arajet
Sat 8/2212:12 pm
ORD
- PUJ
Nonstop4h 45m
Arajet
Deal found 6/10![Arajet logo]()
$387
This United Airlines deal was found by Cheapflights users on 6/10. 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.
Fri 9/113:56 pm
SJU
- ORD
Nonstop5h 09m
United Airlines
Sun 9/138:55 am
ORD
- SJU
Nonstop4h 49m
United Airlines
Deal found 6/10![United Airlines logo]()
$327
This American Airlines deal was found by Cheapflights users on 6/9. 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 6/2412:48 pm
MBJ
- ORD
1 stop10h 44m
American Airlines
Tue 6/309:31 am
ORD
- MBJ
Nonstop4h 00m
American Airlines
Deal found 6/9![American Airlines logo]()
$422
This JetBlue deal was found by Cheapflights users on 6/9. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/262:30 pm
BQN
- ORD
1 stop10h 14m
JetBlue
Thu 8/272:35 pm
ORD
- BQN
1 stop8h 58m
JetBlue
Deal found 6/9![JetBlue logo]()
$385
This Priceline deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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 7/115:01 am
BQN
- ORD
2 stops12h 15m
Multiple Airlines
Sat 7/255:13 pm
ORD
- BQN
1 stop7h 57m
Multiple Airlines
Deal found 6/11![Multiple Airlines logo]()
$477
This Delta deal was found by Cheapflights users on 6/10. 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.
Wed 9/237:16 pm
STI
- ORD
2 stops20h 16m
Delta
Wed 9/307:01 am
ORD
- STI
2 stops9h 45m
Delta
Deal found 6/10![Delta logo]()
$448
This United Airlines deal was found by Cheapflights users on 6/10. 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.
Thu 8/134:12 pm
MBJ
- ORD
1 stop7h 28m
United Airlines
Mon 8/178:45 am
ORD
- MBJ
1 stop6h 25m
United Airlines
Deal found 6/10![United Airlines logo]()
$347
This American Airlines deal was found by Cheapflights users on 6/9. 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 10/712:40 pm
GCM
- ORD
1 stop11h 13m
American Airlines
Tue 10/135:22 am
ORD
- GCM
1 stop5h 38m
American Airlines
Deal found 6/9![American Airlines logo]()
$439
This Air Canada deal was found by Cheapflights users on 6/12. Clicking the “Pick Dates” 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 7/106:30 pm
NAS
- ORD
2 stops16h 46m
Air Canada
Wed 7/159:50 am
ORD
- NAS
1 stop6h 40m
Air Canada
Deal found 6/12![Air Canada logo]()
$533
This Priceline deal was found by Cheapflights users on 6/9. 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.
Thu 7/912:04 pm
BQN
- ORD
1 stop12h 06m
Multiple Airlines
Wed 7/156:00 am
ORD
- BQN
2 stops17h 33m
Multiple Airlines
Deal found 6/9![Multiple Airlines logo]()
$491
This Delta deal was found by Cheapflights users on 6/7. 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.
Mon 8/177:00 am
SJU
- ORD
1 stop6h 40m
Delta
Tue 9/87:10 am
ORD
- SJU
1 stop8h 25m
Delta
Deal found 6/7![Delta logo]()
$451
This Cheapflightsfares deal was found by Cheapflights users on 6/7. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/215:01 am
BQN
- ORD
1 stop9h 38m
JetBlue
Fri 7/312:35 pm
ORD
- BQN
1 stop8h 58m
JetBlue
Deal found 6/7![JetBlue logo]()
$410
This Copa Airlines deal was found by Cheapflights users on 6/8. 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.
Thu 8/63:08 pm
PUJ
- ORD
1 stop10h 54m
Copa Airlines
Thu 8/208:02 am
ORD
- PUJ
1 stop8h 34m
Copa Airlines
Deal found 6/8![Copa Airlines logo]()
$560
Last-minute flights from Caribbean to O'Hare IntlDiscover last-minute flight deals from Caribbean to O'Hare Intl. Data last updated June 12, 2026 and is based on user searches.
Discover last-minute flight deals from Caribbean to O'Hare Intl. Data last updated June 12, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 6/10. 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.
Thu 6/114:12 pm
MBJ
- ORD
1 stop21h 03m
United Airlines
Sun 6/146:30 am
ORD
- MBJ
1 stop8h 40m
United Airlines
Deal found 6/10![United Airlines logo]()
$322
This United Airlines deal was found by Cheapflights users on 6/9. 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 6/124:12 pm
MBJ
- ORD
1 stop7h 14m
United Airlines
Sun 6/146:30 am
ORD
- MBJ
1 stop8h 40m
United Airlines
Deal found 6/9![United Airlines logo]()
$326
This American Airlines deal was found by Cheapflights users on 6/8. 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.
Thu 6/181:47 pm
SJU
- ORD
1 stop11h 47m
American Airlines
Sat 6/208:29 am
ORD
- SJU
1 stop13h 31m
American Airlines
Deal found 6/8![American Airlines logo]()
$291
This American Airlines deal was found by Cheapflights users on 6/8. 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.
Thu 6/181:47 pm
SJU
- ORD
1 stop11h 47m
American Airlines
Sat 7/185:50 pm
ORD
- SJU
Nonstop4h 58m
American Airlines
Deal found 6/8![American Airlines logo]()
$337
This American Airlines deal was found by Cheapflights users on 6/9. 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.
Thu 6/181:47 pm
SJU
- ORD
1 stop11h 47m
American Airlines
Sun 7/55:50 pm
ORD
- SJU
Nonstop4h 58m
American Airlines
Deal found 6/9![American Airlines logo]()
$362
This American Airlines deal was found by Cheapflights users on 6/10. 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.
Thu 6/181:47 pm
SJU
- ORD
1 stop11h 47m
American Airlines
Fri 7/31:17 pm
ORD
- SJU
1 stop8h 42m
American Airlines
Deal found 6/10![American Airlines logo]()
$381
This American Airlines deal was found by Cheapflights users on 6/8. 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.
Thu 6/181:47 pm
SJU
- ORD
1 stop11h 47m
American Airlines
Wed 6/241:38 pm
ORD
- SJU
1 stop8h 22m
American Airlines
Deal found 6/8![American Airlines logo]()
$393
This United Airlines deal was found by Cheapflights users on 6/10. 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.
Fri 6/193:56 pm
SJU
- ORD
Nonstop5h 19m
United Airlines
Sat 6/202:21 pm
ORD
- SJU
1 stop8h 29m
United Airlines
Deal found 6/10![United Airlines logo]()
$367
This United Airlines deal was found by Cheapflights users on 6/7. 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.
Sat 7/44:33 pm
MBJ
- ORD
1 stop16h 32m
United Airlines
Sat 7/1111:15 am
ORD
- MBJ
1 stop27h 55m
United Airlines
Deal found 6/7![United Airlines logo]()
$321
This Cheapflightsfares deal was found by Cheapflights users on 6/10. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/115:01 am
BQN
- ORD
1 stop9h 38m
JetBlue
Sat 7/252:35 pm
ORD
- BQN
1 stop8h 58m
JetBlue
Deal found 6/10![JetBlue logo]()
$385
This Expedia deal was found by Cheapflights users on 6/10. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/235:01 am
SDQ
- ORD
1 stop9h 38m
JetBlue
Thu 7/302:35 pm
ORD
- SDQ
1 stop8h 24m
JetBlue
Deal found 6/10![JetBlue logo]()
$394
This eDestinos deal was found by Cheapflights users on 6/11. Clicking the “Pick Dates” 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.
Sat 7/257:02 am
PUJ
- ORD
Nonstop5h 10m
Arajet
Sat 8/1512:12 pm
ORD
- PUJ
Nonstop4h 45m
Arajet
Deal found 6/11![Arajet logo]()
$390
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 June 12, 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 June 12, 2026.
This Frontier deal was found by Cheapflights users on 6/10. 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.
Tue 9/86:11 pm
SJU
- ORD
Nonstop5h 15m
Frontier
Deal found 6/10![Frontier logo]()
$109
This American Airlines deal was found by Cheapflights users on 6/8. 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.
Tue 8/2512:55 am
SJU
- ORD
Nonstop5h 05m
American Airlines
Deal found 6/8![American Airlines logo]()
$114
This Delta deal was found by Cheapflights users on 6/8. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/262:59 pm
SJU
- ORD
1 stop6h 56m
Delta
Deal found 6/8![Delta logo]()
$118
This Delta deal was found by Cheapflights users on 6/7. 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.
Tue 9/15:49 pm
SJU
- ORD
1 stop7h 08m
Delta
Deal found 6/7![Delta logo]()
$123
This Delta deal was found by Cheapflights users on 6/9. 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.
Mon 8/312:59 pm
SJU
- ORD
1 stop6h 56m
Delta
Deal found 6/9![Delta logo]()
$128
This Expedia deal was found by Cheapflights users on 6/9. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/316:11 pm
SJU
- ORD
Nonstop5h 15m
Frontier
Deal found 6/9![Frontier logo]()
$129
This Super.com deal was found by Cheapflights users on 6/9. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/37:14 pm
SJU
- ORD
Nonstop5h 15m
Frontier
Deal found 6/9![Frontier logo]()
$130
This United Airlines deal was found by Cheapflights users on 6/8. 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.
Thu 9/33:56 pm
SJU
- ORD
Nonstop5h 09m
United Airlines
Deal found 6/8![United Airlines logo]()
$134
This American Airlines deal was found by Cheapflights users on 6/9. 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.
Thu 6/181:47 pm
SJU
- ORD
1 stop11h 47m
American Airlines
Deal found 6/9![American Airlines logo]()
$138
This Frontier deal was found by Cheapflights users on 6/7. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/147:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 6/7![Frontier logo]()
$140
This Faresmojo deal was found by Cheapflights users on 6/8. 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 Faresmojo is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/24:44 pm
SDQ
- ORD
1 stop8h 00m
JetBlue
Deal found 6/8![JetBlue logo]()
$177
This United Airlines deal was found by Cheapflights users on 6/9. 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 12/42:48 pm
MBJ
- ORD
Nonstop4h 28m
United Airlines
Deal found 6/9![United Airlines logo]()
$183
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 June 12, 2026.
Round-trip from | $222 (Frontier) |
|---|---|
One-way from | $109 (Frontier) |
Popular in | June |
Cheapest in | February |
Average price | $424 |
Good round-trip deal | $213 or less |
Good one-way deal | $196 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 2,558,603 searches. Data last updated June 12, 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 - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Wed 9/9
3:56 pm-8:05 pm
Nonstop5h 09m
Chicago O'Hare Intl
Tue 9/22
1:30 pm-11:50 pm
1 stop9h 20m
$272
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Fri 9/11
3:56 pm-8:05 pm
Nonstop5h 09m
Chicago O'Hare Intl
Tue 9/15
8:55 am-2:44 pm
Nonstop4h 49m
$298
Quickest round-trip
Punta CanaChicago
PUJ - ORD
PUJORD
Punta Cana
Thu 10/22
7:30 pm-11:40 pm
Nonstop5h 10m
Chicago O'Hare Intl
Fri 10/23
6:45 am-12:30 pm
Nonstop4h 45m
$311
Montego BayChicago
MBJ - ORD
MBJORD
Montego Bay Sangster Intl
Sat 7/4
4:33 pm-9:05 am
1 stop16h 32m
Chicago O'Hare Intl
Sat 7/11
11:15 am-3:10 pm
1 stop27h 55m
$321
Montego BayChicago
MBJ - ORD
MBJORD
Montego Bay Sangster Intl
Fri 7/17
4:12 pm-11:31 pm
1 stop7h 19m
Chicago O'Hare Intl
Sun 7/19
6:29 am-3:26 pm
1 stop8h 57m
$326
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Fri 9/11
3:56 pm-8:05 pm
Nonstop5h 09m
Chicago O'Hare Intl
Sun 9/13
8:55 am-2:44 pm
Nonstop4h 49m
$327
Punta CanaChicago
PUJ - ORD
PUJORD
Punta Cana
Sun 11/1
6:10 pm-9:20 pm
Nonstop5h 10m
Chicago O'Hare Intl
Sun 11/1
3:20 am-10:05 am
Nonstop4h 45m
$330
Montego BayChicago
MBJ - ORD
MBJORD
Montego Bay Sangster Intl
Thu 11/12
3:59 pm-11:44 pm
1 stop8h 45m
Chicago O'Hare Intl
Mon 11/16
7:00 am-2:54 pm
1 stop6h 54m
$334
NassauChicago
NAS - ORD
NASORD
Nassau Intl
Wed 7/15
12:20 pm-11:44 pm
1 stop12h 24m
Chicago O'Hare Intl
Sun 7/19
7:00 am-5:22 pm
1 stop9h 22m
$344
Montego BayChicago
MBJ - ORD
MBJORD
Montego Bay Sangster Intl
Thu 8/13
4:12 pm-11:40 pm
1 stop7h 28m
Chicago O'Hare Intl
Mon 8/17
8:45 am-3:10 pm
1 stop6h 25m
$347
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
MBJ-ORD
BQN-ORD
PUJ-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
MBJ-ORD
BQN-ORD
PUJ-ORD
What is the cheapest month to book a flight from Caribbean to Chicago O'Hare Intl Airport?
Currently, May is the cheapest month in which you can book a flight from Caribbean to Chicago O'Hare Intl Airport (average of $64). Flying from Caribbean to Chicago O'Hare Intl Airport in July is currently the most expensive (average of $745). 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 June 12, 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 37% 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 June 12, 2026.
The most flights from 0CB to ORD are scheduled on a Monday (8 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (8 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 June 8, 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. Tuesday mornings 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 June 12, 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.
Entertainment
7.1
Food
6.6
Overall
7.4
Comfort
7.3
Boarding
7.7
Crew
8.1
Reviews
1 / 20
4.0
OkayDynasty,May 2026
LAX - EWR
Entertainment
7.1
Food
6.6
Overall
7.4
Comfort
7.3
Boarding
7.7
Crew
8.1
Reviews
1 / 20
4.0
OkayDynasty,May 2026
LAX - EWR
Entertainment
7.1
Food
6.6
Overall
7.4
Comfort
7.3
Boarding
7.7
Crew
8.1
Reviews
1 / 20
4.0
OkayDynasty,May 2026
LAX - EWR
Entertainment
7.1
Food
6.6
Overall
7.4
Comfort
7.3
Boarding
7.7
Crew
8.1
Reviews
1 / 20
4.0
OkayDynasty,May 2026
LAX - EWR
Entertainment
7.1
Food
6.6
Overall
7.4
Comfort
7.3
Boarding
7.7
Crew
8.1
Reviews
1 / 20
4.0
OkayDynasty,May 2026
LAX - EWR
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
Schaumburg
Naperville
Lake Geneva
Gurnee
Delavan
Oakbrook Terrace
Downers Grove
Des Plaines
Hoffman Estates
Oak Brook
South Holland
Libertyville
Warrenville
Rockford
Great Lakes
Northbrook
Waukegan
Elk Grove Village
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 June 12, 2026.
Caribbean and O'Hare Intl flights
Browse other Caribbean and O'Hare Intl flight options. Last updated on June 12, 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 7 airlines flying from Caribbean to O'Hare Intl
Discover the top 7 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 2,558,603 searches. Data last updated June 12, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$112 | Average$395 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$119 | Average$250 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$131 | Average$201 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$195 | Average$404 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$257 | Average$531 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$265 | Average$482 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$292 | Average$457 | FlexibilityNo cancel fee | On-time63% |