$88+ 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 7/15. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
Jul 8 — Jul 151
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 June 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 June 8, 2026.
This Kiwi.com deal was found by Cheapflights users on 6/3. 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.
Sun 8/1612:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Mon 8/246:11 pm
SJU
- ORD
Nonstop5h 15m
Frontier
Deal found 6/3![Frontier logo]()
$239
This Frontier deal was found by Cheapflights users on 6/3. 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 8/2312:29 am
ORD
- SJU
Nonstop4h 57m
Frontier
Sat 8/296:11 pm
SJU
- ORD
Nonstop5h 15m
Frontier
Deal found 6/3![Frontier logo]()
$240
This American Airlines deal was found by Cheapflights users on 6/3. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/198:20 am
ORD
- SJU
1 stop13h 04m
American Airlines
Mon 8/313:28 pm
SJU
- ORD
1 stop10h 07m
American Airlines
Deal found 6/3![American Airlines logo]()
$241
This American Airlines deal was found by Cheapflights users on 6/4. 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.
Sat 8/224:59 pm
ORD
- SJU
Nonstop4h 55m
American Airlines
Tue 8/256:00 am
SJU
- ORD
1 stop10h 05m
American Airlines
Deal found 6/4![American Airlines logo]()
$242
This 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/49:26 am
ORD
- SJU
1 stop7h 10m
Frontier
Tue 10/136:05 am
SJU
- ORD
1 stop8h 11m
Frontier
Deal found 6/7![Frontier logo]()
$244
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/155:59 pm
ORD
- SJU
1 stop14h 44m
American Airlines
Sat 8/297:00 am
SJU
- ORD
1 stop13h 46m
American Airlines
Deal found 6/7![American Airlines logo]()
$246
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/1712:29 am
ORD
- SJU
Nonstop4h 57m
Frontier
Wed 9/26:11 pm
SJU
- ORD
Nonstop5h 15m
Frontier
Deal found 6/7![Frontier logo]()
$249
This Frontier deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2012:29 am
ORD
- SJU
Nonstop4h 57m
Frontier
Wed 8/266:11 pm
SJU
- ORD
Nonstop5h 15m
Frontier
Deal found 6/6![Frontier logo]()
$250
This American Airlines deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/195:00 am
ORD
- SJU
1 stop8h 54m
American Airlines
Sat 8/225:47 pm
SJU
- ORD
1 stop14h 47m
American Airlines
Deal found 6/6![American Airlines logo]()
$251
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/154:59 pm
ORD
- SJU
Nonstop4h 55m
American Airlines
Sat 8/227:20 pm
SJU
- ORD
1 stop13h 14m
American Airlines
Deal found 6/7![American Airlines logo]()
$252
This Kiwi.com deal was found by Cheapflights users on 6/5. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/312:29 am
ORD
- SJU
Nonstop4h 57m
Frontier
Tue 9/86:11 pm
SJU
- ORD
Nonstop5h 15m
Frontier
Deal found 6/5![Frontier logo]()
$253
This JetBlue deal was found by Cheapflights users on 6/3. 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.
Tue 9/87:00 am
ORD
- NAS
1 stop9h 14m
JetBlue
Tue 9/2212:18 pm
NAS
- ORD
1 stop12h 26m
JetBlue
Deal found 6/3![JetBlue logo]()
$284
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 June 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 June 8, 2026.
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.
Sat 8/158:05 am
ORD
- SJU
1 stop7h 33m
Delta
Sat 8/297:00 am
SJU
- ORD
1 stop10h 51m
Delta
Deal found 6/7![Delta logo]()
$256
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.
Thu 9/175:00 am
ORD
- SJU
1 stop7h 45m
United Airlines
Mon 9/214:55 pm
SJU
- ORD
1 stop7h 45m
United Airlines
Deal found 6/7![United Airlines logo]()
$276
This JetBlue deal was found by Cheapflights users on 6/3. 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.
Tue 9/87:00 am
ORD
- NAS
1 stop5h 48m
JetBlue
Wed 9/163:00 pm
NAS
- ORD
1 stop9h 44m
JetBlue
Deal found 6/3![JetBlue logo]()
$284
This Arajet deal was found by Cheapflights users on 6/4. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/46:45 am
ORD
- PUJ
Nonstop4h 45m
Arajet
Sun 9/136:00 pm
PUJ
- ORD
Nonstop5h 10m
Arajet
Deal found 6/4![Arajet logo]()
$412
This Expedia deal was found by Cheapflights users on 6/4. 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.
Sat 10/243:45 pm
ORD
- GCM
1 stop19h 15m
Air Canada
Sat 10/3112:10 pm
GCM
- ORD
1 stop21h 50m
Air Canada
Deal found 6/4![Air Canada logo]()
$415
This Copa Airlines deal was found by Cheapflights users on 6/6. 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.
Sat 7/183:21 pm
ORD
- MBJ
1 stop19h 54m
Copa Airlines
Sat 7/2512:22 pm
MBJ
- ORD
1 stop15h 38m
Copa Airlines
Deal found 6/6![Copa Airlines logo]()
$468
This Avianca 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/311:20 pm
ORD
- CUR
1 stop10h 00m
Avianca
Wed 8/1211:35 am
CUR
- ORD
1 stop10h 45m
Avianca
Deal found 6/8![Avianca logo]()
$566
This American Airlines deal was found by Cheapflights users on 6/3. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/45:59 pm
ORD
- SDQ
1 stop14h 28m
American Airlines
Sun 7/122:20 pm
SDQ
- ORD
2 stops11h 09m
American Airlines
Deal found 6/3![American Airlines logo]()
$576
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/17:00 am
ORD
- NAS
1 stop5h 48m
JetBlue
Wed 9/212:20 pm
NAS
- ORD
1 stop12h 24m
JetBlue
Deal found 6/7![JetBlue logo]()
$334
This United Airlines deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/218:55 am
ORD
- SJU
Nonstop4h 49m
United Airlines
Thu 9/243:56 pm
SJU
- ORD
Nonstop5h 09m
United Airlines
Deal found 6/6![United Airlines logo]()
$357
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/37:00 am
ORD
- MBJ
1 stop6h 54m
JetBlue
Wed 11/113:59 pm
MBJ
- ORD
1 stop8h 45m
JetBlue
Deal found 6/7![JetBlue logo]()
$374
This Arajet 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/112:12 pm
ORD
- PUJ
Nonstop4h 45m
Arajet
Sat 8/87:02 am
PUJ
- ORD
Nonstop5h 10m
Arajet
Deal found 6/7![Arajet logo]()
$422
This United Airlines deal was found by Cheapflights users on 6/3. 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.
Wed 9/28:55 am
ORD
- SJU
Nonstop4h 49m
United Airlines
Mon 9/143:56 pm
SJU
- ORD
Nonstop5h 09m
United Airlines
Deal found 6/3![United Airlines logo]()
$397
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/267:00 am
ORD
- SDQ
1 stop7h 16m
JetBlue
Wed 10/281:28 pm
SDQ
- ORD
1 stop11h 16m
JetBlue
Deal found 6/7![JetBlue logo]()
$378
This Orbitz deal was found by Cheapflights users on 6/3. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/42:00 pm
ORD
- PLS
1 stop21h 25m
Air Canada
Sun 11/81:30 pm
PLS
- ORD
1 stop26h 26m
Air Canada
Deal found 6/3![Air Canada logo]()
$468
This Copa Airlines deal was found by Cheapflights users on 6/4. 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 7/41:20 am
ORD
- MBJ
1 stop9h 55m
Copa Airlines
Thu 7/912:22 pm
MBJ
- ORD
1 stop15h 38m
Copa Airlines
Deal found 6/4![Copa Airlines logo]()
$483
This United Airlines deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/32:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Sat 7/113:56 pm
SJU
- ORD
Nonstop5h 19m
United Airlines
Deal found 6/6![United Airlines logo]()
$407
This Delta deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/55:30 am
ORD
- SDQ
1 stop6h 58m
Delta
Wed 8/122:53 pm
SDQ
- ORD
2 stops18h 03m
Delta
Deal found 6/6![Delta logo]()
$517
This Air Canada deal was found by Cheapflights users on 6/4. 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.
Sun 11/223:55 pm
ORD
- PLS
1 stop20h 05m
Air Canada
Thu 11/261:30 pm
PLS
- ORD
1 stop20h 30m
Air Canada
Deal found 6/4![Air Canada logo]()
$482
This Copa Airlines deal was found by Cheapflights users on 6/4. 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 10/93:20 pm
ORD
- MBJ
1 stop19h 57m
Copa Airlines
Sun 10/1812:22 pm
MBJ
- ORD
1 stop25h 37m
Copa Airlines
Deal found 6/4![Copa Airlines logo]()
$483
This Arajet deal was found by Cheapflights users on 6/6. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/246:45 am
ORD
- PUJ
Nonstop4h 45m
Arajet
Sat 8/17:02 am
PUJ
- ORD
Nonstop5h 10m
Arajet
Deal found 6/6![Arajet logo]()
$484
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.
Thu 8/135:30 am
ORD
- SDQ
1 stop6h 58m
Delta
Thu 8/202:53 pm
SDQ
- ORD
2 stops18h 03m
Delta
Deal found 6/7![Delta logo]()
$517
This Avianca deal was found by Cheapflights users on 6/3. 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/1911:20 pm
ORD
- CUR
1 stop10h 00m
Avianca
Sat 9/2611:35 am
CUR
- ORD
1 stop10h 45m
Avianca
Deal found 6/3![Avianca logo]()
$570
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/317:00 am
ORD
- MBJ
1 stop6h 48m
JetBlue
Fri 11/133:59 pm
MBJ
- ORD
1 stop8h 45m
JetBlue
Deal found 6/7![JetBlue logo]()
$433
This Air Canada deal was found by Cheapflights users on 6/5. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/13:55 pm
ORD
- PLS
1 stop20h 05m
Air Canada
Sun 12/61:30 pm
PLS
- ORD
1 stop20h 30m
Air Canada
Deal found 6/5![Air Canada logo]()
$482
This Copa Airlines deal was found by Cheapflights users on 6/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/251:20 am
ORD
- MBJ
1 stop9h 55m
Copa Airlines
Fri 7/3112:22 pm
MBJ
- ORD
1 stop15h 38m
Copa Airlines
Deal found 6/5![Copa Airlines logo]()
$483
This Arajet 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/246:45 am
ORD
- PUJ
Nonstop4h 45m
Arajet
Sun 7/266:00 pm
PUJ
- ORD
Nonstop5h 10m
Arajet
Deal found 6/7![Arajet logo]()
$484
This United Airlines deal was found by Cheapflights users on 6/4. 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 9/278:55 am
ORD
- SJU
Nonstop4h 49m
United Airlines
Fri 10/23:56 pm
SJU
- ORD
Nonstop5h 09m
United Airlines
Deal found 6/4![United Airlines logo]()
$457
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.
Wed 8/55:30 am
ORD
- SDQ
1 stop6h 58m
Delta
Mon 8/102:53 pm
SDQ
- ORD
2 stops18h 03m
Delta
Deal found 6/7![Delta logo]()
$517
This American Airlines deal was found by Cheapflights users on 6/5. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/116:26 pm
ORD
- GCM
1 stop16h 34m
American Airlines
Sun 10/1812:40 pm
GCM
- ORD
1 stop11h 13m
American Airlines
Deal found 6/5![American Airlines logo]()
$651
Last-minute flights from O'Hare Intl to CaribbeanDiscover last-minute flight deals from O'Hare Intl to Caribbean. Data last updated June 8, 2026 and is based on user searches.
Discover last-minute flight deals from O'Hare Intl to Caribbean. Data last updated June 8, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 6/6. 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.
Tue 6/911:40 am
ORD
- SJU
1 stop10h 20m
American Airlines
Tue 6/166:21 am
SJU
- ORD
1 stop14h 05m
American Airlines
Deal found 6/6![American Airlines logo]()
$306
This Frontier deal was found by Cheapflights users on 6/4. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/412:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Wed 7/87:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 6/4![Frontier logo]()
$311
This Frontier deal was found by Cheapflights users on 6/3. 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 7/512:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Wed 7/87:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 6/3![Frontier logo]()
$295
This Kiwi.com deal was found by Cheapflights users on 6/4. 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.
Sun 7/512:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Thu 7/96:00 am
SJU
- ORD
1 stop31h 15m
Frontier
Deal found 6/4![Frontier logo]()
$312
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.
Tue 7/712:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Thu 7/306:00 am
SJU
- ORD
1 stop31h 15m
Frontier
Deal found 6/7![Frontier logo]()
$309
This Kiwi.com deal was found by Cheapflights users on 6/3. 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 7/912:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Fri 8/76:00 am
SJU
- ORD
1 stop31h 15m
Frontier
Deal found 6/3![Frontier logo]()
$291
This Expedia deal was found by Cheapflights users on 6/4. 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.
Fri 7/107:00 am
ORD
- NAS
1 stop9h 22m
JetBlue
Fri 7/173:02 pm
NAS
- ORD
1 stop9h 42m
JetBlue
Deal found 6/4![JetBlue logo]()
$284
This deal was found by Cheapflights users on 6/4. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/147:00 am
ORD
- NAS
1 stop5h 50m
JetBlue
Wed 7/226:27 pm
NAS
- ORD
1 stop6h 17m
JetBlue
Deal found 6/4![JetBlue logo]()
$313
This Justfly.com deal was found by Cheapflights users on 6/3. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/177:00 am
ORD
- NAS
1 stop9h 22m
JetBlue
Fri 7/246:27 pm
NAS
- ORD
1 stop6h 17m
JetBlue
Deal found 6/3![JetBlue logo]()
$303
This Kiwi.com deal was found by Cheapflights users on 6/4. 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.
Sat 7/1812:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Thu 7/306:00 am
SJU
- ORD
1 stop31h 15m
Frontier
Deal found 6/4![Frontier logo]()
$293
This Kiwi.com deal was found by Cheapflights users on 6/4. 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.
Sat 7/1812:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Fri 7/316:00 am
SJU
- ORD
1 stop31h 15m
Frontier
Deal found 6/4![Frontier logo]()
$299
This Delta deal was found by Cheapflights users on 6/5. 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.
Tue 7/286:35 am
ORD
- SJU
1 stop9h 04m
Delta
Tue 8/187:00 am
SJU
- ORD
1 stop10h 51m
Delta
Deal found 6/5![Delta logo]()
$296
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 June 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 June 8, 2026.
This Expedia deal was found by Cheapflights users on 6/4. 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 7/157:00 am
ORD
- NAS
1 stop9h 22m
JetBlue
Deal found 6/4![JetBlue logo]()
$88
This JetBlue deal was found by Cheapflights users on 6/4. 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.
Wed 7/297:00 am
ORD
- NAS
1 stop9h 22m
JetBlue
Deal found 6/4![JetBlue logo]()
$93
This American Airlines deal was found by Cheapflights users on 6/6. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/227:00 am
ORD
- NAS
Nonstop3h 29m
American Airlines
Deal found 6/6![American Airlines logo]()
$99
This Expedia deal was found by Cheapflights users on 6/4. 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 7/227:00 am
ORD
- NAS
1 stop9h 22m
JetBlue
Deal found 6/4![JetBlue logo]()
$107
This Frontier deal was found by Cheapflights users on 6/4. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/112:29 am
ORD
- SJU
Nonstop4h 57m
Frontier
Deal found 6/4![Frontier logo]()
$109
This Justfly.com deal was found by Cheapflights users on 6/4. 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 Justfly.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/267:00 am
ORD
- NAS
1 stop5h 50m
JetBlue
Deal found 6/4![JetBlue logo]()
$112
This JetBlue 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/17:00 am
ORD
- NAS
1 stop5h 48m
JetBlue
Deal found 6/7![JetBlue logo]()
$113
This American Airlines deal was found by Cheapflights users on 6/4. 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 8/255:20 pm
ORD
- SJU
Nonstop4h 55m
American Airlines
Deal found 6/4![American Airlines logo]()
$114
This Delta deal was found by Cheapflights users on 6/3. 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.
Wed 9/21:50 pm
ORD
- SJU
1 stop7h 39m
Delta
Deal found 6/3![Delta logo]()
$118
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/25:20 pm
ORD
- SJU
Nonstop4h 55m
American Airlines
Deal found 6/7![American Airlines logo]()
$119
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/226:59 pm
ORD
- SJU
1 stop13h 44m
American Airlines
Deal found 6/7![American Airlines logo]()
$120
This American Airlines deal was found by Cheapflights users on 6/3. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/306:59 am
ORD
- SJU
1 stop10h 26m
American Airlines
Deal found 6/3![American Airlines logo]()
$121
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 June 8, 2026.
Round-trip from | $239 (Kiwi.com) |
|---|---|
One-way from | $88 (Expedia) |
Popular in | December |
Cheapest in | January |
Average price | $445 |
Good round-trip deal | $404 or less |
Good one-way deal | $215 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 June 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 - SJU
ORDSJU
Chicago O'Hare Intl
Sat 8/15
8:05 am-4:38 pm
1 stop7h 33m
San Juan Luis Munoz Marin Intl
Sat 8/29
7:00 am-4:51 pm
1 stop10h 51m
$256
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Thu 9/17
5:00 am-1:45 pm
1 stop7h 45m
San Juan Luis Munoz Marin Intl
Mon 9/21
4:55 pm-11:40 pm
1 stop7h 45m
$276
ChicagoNassau
ORD - NAS
ORDNAS
Chicago O'Hare Intl
Tue 9/8
7:00 am-1:48 pm
1 stop5h 48m
Nassau Intl
Wed 9/16
3:00 pm-11:44 pm
1 stop9h 44m
$284
ChicagoNassau
ORD - NAS
ORDNAS
Chicago O'Hare Intl
Tue 9/1
7:00 am-1:48 pm
1 stop5h 48m
Nassau Intl
Wed 9/2
12:20 pm-11:44 pm
1 stop12h 24m
$334
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Mon 9/21
8:55 am-2:44 pm
Nonstop4h 49m
San Juan Luis Munoz Marin Intl
Thu 9/24
3:56 pm-8:05 pm
Nonstop5h 09m
$357
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Tue 11/3
7:00 am-2:54 pm
1 stop6h 54m
Montego Bay Sangster Intl
Wed 11/11
3:59 pm-11:44 pm
1 stop8h 45m
$374
ChicagoSanto Domingo
ORD - SDQ
ORDSDQ
Chicago O'Hare Intl
Mon 10/26
7:00 am-3:16 pm
1 stop7h 16m
Santo Domingo Las Americas
Wed 10/28
1:28 pm-11:44 pm
1 stop11h 16m
$378
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Wed 9/2
8:55 am-2:44 pm
Nonstop4h 49m
San Juan Luis Munoz Marin Intl
Mon 9/14
3:56 pm-8:05 pm
Nonstop5h 09m
$397
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Fri 7/3
2:38 pm-8:34 pm
Nonstop4h 56m
San Juan Luis Munoz Marin Intl
Sat 7/11
3:56 pm-8:15 pm
Nonstop5h 19m
$407
Quickest round-trip
ChicagoPunta Cana
ORD - PUJ
ORDPUJ
Chicago O'Hare Intl
Fri 9/4
6:45 am-12:30 pm
Nonstop4h 45m
Punta Cana
Sun 9/13
6:00 pm-10:10 pm
Nonstop5h 10m
$412
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-NAS
ORD-SJU
ORD-PUJ
ORD-GCM
ORD-MBJ
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-NAS
ORD-SJU
ORD-PUJ
ORD-GCM
What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Caribbean?
Currently, July is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Caribbean (average of $410). Flying from Chicago O'Hare Intl Airport to Caribbean in December is currently the most expensive (average of $655). 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 June 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 31% 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 June 8, 2026.
The most flights from ORD to 0CB are scheduled on a Monday (8 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (6 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 39 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 June 8, 2026.
Travelers seeking maximum savings on their Chicago O'Hare Intl Airport to Caribbean flight should consider departing on Wednesday 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 June 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.
Boarding
7.7
Comfort
7.3
Entertainment
7.1
Food
6.6
Overall
7.4
Crew
8.1
Reviews
1 / 20
4.0
OkayDynasty,May 2026
LAX - EWR
Boarding
7.7
Comfort
7.3
Entertainment
7.1
Food
6.6
Overall
7.4
Crew
8.1
Reviews
1 / 20
4.0
OkayDynasty,May 2026
LAX - EWR
Boarding
7.7
Comfort
7.3
Entertainment
7.1
Food
6.6
Overall
7.4
Crew
8.1
Reviews
1 / 20
4.0
OkayDynasty,May 2026
LAX - EWR
Boarding
7.7
Comfort
7.3
Entertainment
7.1
Food
6.6
Overall
7.4
Crew
8.1
Reviews
1 / 20
4.0
OkayDynasty,May 2026
LAX - EWR
Boarding
7.7
Comfort
7.3
Entertainment
7.1
Food
6.6
Overall
7.4
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 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 June 8, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Fly to Caribbean countries
Consider these flights traveling to countries located in Caribbean.
O'Hare Intl to Caribbean flights
Consider these flights traveling from O'Hare Intl to Caribbean.
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 June 8, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$119 | Average$436 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$143 | Average$519 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$144 | Average$522 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$175 | Average$515 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$213 | Average$484 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$217 | Average$357 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$260 | Average$587 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$304 | Average$618 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$376 | Average$566 | FlexibilityNo cancel fee | On-time63% |