$94+ 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 3/24. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
abr. 12 — abr. 191
Round-trip
1 adult, Economy
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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 marzo 13, 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 marzo 13, 2026.
This Kiwi.com deal was found by Cheapflights users on 3/9. 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.
dom. 5/178:24 pm
ORD
- SJU
1 stop25h 38m
Frontier
vie. 5/298:10 pm
SJU
- ORD
Nonstop5h 15m
Frontier
Deal found 3/9![Frontier logo]()
$192
This Cheapflightsfares deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 5/47:50 am
ORD
- SJU
1 stop17h 16m
Spirit Airlines
vie. 5/83:21 am
SJU
- ORD
1 stop11h 44m
Spirit Airlines
Deal found 3/9![Spirit Airlines logo]()
$193
This Expedia deal was found by Cheapflights users on 3/9. 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.
lun. 4/1310:55 am
ORD
- SJU
1 stop12h 03m
Multiple Airlines
jue. 4/303:03 pm
SJU
- ORD
1 stop8h 36m
Multiple Airlines
Deal found 3/9![Multiple Airlines logo]()
$200
This eDestinos deal was found by Cheapflights users on 3/11. 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.
vie. 4/1011:55 am
ORD
- SJU
1 stop11h 30m
Frontier
vie. 4/173:23 pm
SJU
- ORD
1 stop8h 16m
Frontier
Deal found 3/11![Frontier logo]()
$201
This Priceline deal was found by Cheapflights users on 3/9. 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.
sáb. 4/119:32 am
ORD
- SJU
1 stop14h 19m
Frontier
jue. 4/1611:30 am
SJU
- ORD
1 stop13h 29m
Frontier
Deal found 3/9![Frontier logo]()
$202
This Mytrip deal was found by Cheapflights users on 3/12. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 3/3110:55 am
ORD
- SJU
1 stop12h 03m
Multiple Airlines
jue. 4/1611:30 am
SJU
- ORD
1 stop13h 29m
Multiple Airlines
Deal found 3/12![Multiple Airlines logo]()
$204
This Kiwi.com deal was found by Cheapflights users on 3/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 4/242:09 pm
ORD
- SJU
1 stop8h 34m
Frontier
jue. 4/306:00 am
SJU
- ORD
1 stop16h 17m
Frontier
Deal found 3/8![Frontier logo]()
$205
This Cheapflightsfares deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 4/267:50 am
ORD
- SJU
1 stop16h 08m
Spirit Airlines
sáb. 5/24:34 pm
SJU
- ORD
Nonstop5h 15m
Spirit Airlines
Deal found 3/9![Spirit Airlines logo]()
$206
This Cheapflightsfares deal was found by Cheapflights users on 3/11. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 3/3110:55 am
ORD
- SJU
1 stop12h 03m
Spirit Airlines
mar. 4/71:29 am
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Deal found 3/11![Spirit Airlines logo]()
$208
This Kiwi.com deal was found by Cheapflights users on 3/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 5/28:00 am
ORD
- SJU
1 stop13h 48m
Multiple Airlines
mié. 5/133:21 am
SJU
- ORD
1 stop10h 44m
Multiple Airlines
Deal found 3/8![Multiple Airlines logo]()
$209
This Kiwi.com deal was found by Cheapflights users on 3/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 3/2410:55 am
ORD
- SJU
1 stop12h 03m
Spirit Airlines
mié. 4/81:29 am
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Deal found 3/8![Spirit Airlines logo]()
$210
This CheapOair deal was found by Cheapflights users on 3/8. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 4/75:05 am
ORD
- STT
1 stop9h 23m
Spirit Airlines
mar. 4/144:35 pm
STT
- ORD
1 stop18h 01m
Spirit Airlines
Deal found 3/8![Spirit Airlines logo]()
$268
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 marzo 13, 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 marzo 13, 2026.
This United Airlines deal was found by Cheapflights users on 3/8. 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.
dom. 4/198:40 am
ORD
- MBJ
Nonstop4h 10m
United Airlines
jue. 4/234:12 pm
MBJ
- ORD
1 stop7h 31m
United Airlines
Deal found 3/8![United Airlines logo]()
$308
This Delta deal was found by Cheapflights users on 3/8. 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.
mar. 4/215:15 am
ORD
- SJU
1 stop10h 08m
Delta
sáb. 4/256:15 am
SJU
- ORD
1 stop11h 27m
Delta
Deal found 3/8![Delta logo]()
$314
This Arajet deal was found by Cheapflights users on 3/10. 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.
mié. 4/85:35 am
ORD
- SDQ
1 stop9h 20m
Multiple Airlines
vie. 4/171:40 am
SDQ
- ORD
1 stop10h 32m
Multiple Airlines
Deal found 3/10![Multiple Airlines logo]()
$336
This Southwest deal was found by Cheapflights users on 3/8. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 8/136:05 am
ORD
- SJU
1 stop9h 50m
Southwest
dom. 8/1610:05 am
SJU
- ORD
1 stop8h 25m
Southwest
Deal found 3/8![Southwest logo]()
$356
This Copa Airlines deal was found by Cheapflights users on 3/10. 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.
vie. 7/311:20 am
ORD
- MBJ
1 stop9h 55m
Copa Airlines
jue. 8/612:22 pm
MBJ
- ORD
1 stop11h 40m
Copa Airlines
Deal found 3/10![Copa Airlines logo]()
$382
This CheapOair deal was found by Cheapflights users on 3/12. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 5/24:50 pm
ORD
- SXM
2 stops19h 47m
Spirit Airlines
sáb. 5/92:42 pm
SXM
- ORD
1 stop10h 45m
Spirit Airlines
Deal found 3/12![Spirit Airlines logo]()
$420
This JetBlue deal was found by Cheapflights users on 3/8. 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.
lun. 5/46:00 am
ORD
- SDQ
1 stop7h 42m
JetBlue
lun. 5/47:26 pm
SDQ
- ORD
1 stop13h 15m
JetBlue
Deal found 3/8![JetBlue logo]()
$619
This United Airlines deal was found by Cheapflights users on 3/8. 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.
lun. 4/138:45 am
ORD
- MBJ
1 stop6h 25m
United Airlines
vie. 4/174:12 pm
MBJ
- ORD
1 stop7h 31m
United Airlines
Deal found 3/8![United Airlines logo]()
$312
This Arajet deal was found by Cheapflights users on 3/10. 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.
vie. 8/146:45 am
ORD
- SDQ
1 stop8h 00m
Multiple Airlines
dom. 8/161:55 pm
SDQ
- ORD
1 stop9h 15m
Multiple Airlines
Deal found 3/10![Multiple Airlines logo]()
$376
This United Airlines deal was found by Cheapflights users on 3/12. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 4/188:40 am
ORD
- MBJ
Nonstop4h 10m
United Airlines
sáb. 4/252:40 pm
MBJ
- ORD
1 stop8h 35m
United Airlines
Deal found 3/12![United Airlines logo]()
$348
This Southwest deal was found by Cheapflights users on 3/10. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 7/243:20 pm
ORD
- SJU
1 stop7h 45m
Southwest
vie. 7/316:30 am
SJU
- ORD
1 stop9h 30m
Southwest
Deal found 3/10![Southwest logo]()
$406
This Copa Airlines deal was found by Cheapflights users on 3/7. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 4/288:06 am
ORD
- SDQ
1 stop13h 41m
Copa Airlines
dom. 5/36:04 am
SDQ
- ORD
1 stop20h 11m
Copa Airlines
Deal found 3/7![Copa Airlines logo]()
$419
This Delta deal was found by Cheapflights users on 3/8. 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.
mar. 4/217:10 am
ORD
- PUJ
1 stop6h 22m
Delta
jue. 4/233:57 pm
PUJ
- ORD
2 stops17h 04m
Delta
Deal found 3/8![Delta logo]()
$452
This Mytrip deal was found by Cheapflights users on 3/12. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 4/99:50 am
ORD
- SXM
1 stop28h 05m
Multiple Airlines
lun. 4/132:35 pm
SXM
- ORD
2 stops19h 15m
Multiple Airlines
Deal found 3/12![Multiple Airlines logo]()
$416
This Copa Airlines deal was found by Cheapflights users on 3/9. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 5/303:21 pm
ORD
- SDQ
1 stop10h 04m
Copa Airlines
jue. 6/412:10 pm
SDQ
- ORD
1 stop16h 50m
Copa Airlines
Deal found 3/9![Copa Airlines logo]()
$419
This Kiwi.com deal was found by Cheapflights users on 3/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 4/45:05 am
ORD
- SXM
1 stop7h 25m
Spirit Airlines
dom. 4/52:35 pm
SXM
- ORD
2 stops43h 15m
Spirit Airlines
Deal found 3/12![Spirit Airlines logo]()
$482
This Southwest deal was found by Cheapflights users on 3/8. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 6/102:40 pm
ORD
- SJU
2 stops17h 20m
Southwest
dom. 6/149:05 pm
SJU
- ORD
1 stop13h 40m
Southwest
Deal found 3/8![Southwest logo]()
$446
This United Airlines deal was found by Cheapflights users on 3/10. 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.
dom. 7/55:30 am
ORD
- MBJ
1 stop9h 56m
United Airlines
jue. 7/94:12 pm
MBJ
- ORD
1 stop7h 14m
United Airlines
Deal found 3/10![United Airlines logo]()
$408
This Delta deal was found by Cheapflights users on 3/8. 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.
dom. 4/197:43 pm
ORD
- PUJ
1 stop16h 11m
Delta
jue. 4/233:57 pm
PUJ
- ORD
2 stops17h 04m
Delta
Deal found 3/8![Delta logo]()
$452
This Copa Airlines deal was found by Cheapflights users on 3/10. 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.
mar. 4/148:06 am
ORD
- SDQ
1 stop13h 41m
Copa Airlines
mié. 4/2912:38 pm
SDQ
- ORD
1 stop13h 35m
Copa Airlines
Deal found 3/10![Copa Airlines logo]()
$419
This United Airlines deal was found by Cheapflights users on 3/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 7/172:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
mar. 7/217:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
Deal found 3/11![United Airlines logo]()
$413
This Southwest deal was found by Cheapflights users on 3/11. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 8/144:00 pm
ORD
- SJU
2 stops16h 25m
Southwest
dom. 8/1610:05 am
SJU
- ORD
1 stop8h 25m
Southwest
Deal found 3/11![Southwest logo]()
$456
This Copa Airlines deal was found by Cheapflights users on 3/11. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 5/243:21 pm
ORD
- SDQ
1 stop18h 34m
Copa Airlines
mié. 5/276:39 pm
SDQ
- ORD
1 stop20h 27m
Copa Airlines
Deal found 3/11![Copa Airlines logo]()
$419
This Mytrip deal was found by Cheapflights users on 3/12. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 4/912:45 pm
ORD
- SXM
3 stops23h 45m
Spirit Airlines
lun. 4/132:35 pm
SXM
- ORD
2 stops19h 15m
Spirit Airlines
Deal found 3/12![Spirit Airlines logo]()
$507
This CheapOair deal was found by Cheapflights users on 3/12. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 5/28:31 am
ORD
- SXM
1 stop27h 03m
Multiple Airlines
sáb. 5/92:42 pm
SXM
- ORD
1 stop10h 45m
Multiple Airlines
Deal found 3/12![Multiple Airlines logo]()
$482
This United Airlines deal was found by Cheapflights users on 3/8. 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.
lun. 4/132:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
jue. 4/161:00 am
SJU
- ORD
1 stop10h 43m
United Airlines
Deal found 3/8![United Airlines logo]()
$415
This Southwest deal was found by Cheapflights users on 3/8. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 5/176:00 am
ORD
- GCM
1 stop5h 55m
Southwest
vie. 5/221:05 pm
GCM
- ORD
1 stop8h 50m
Southwest
Deal found 3/8![Southwest logo]()
$478
This Delta deal was found by Cheapflights users on 3/11. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 5/281:04 pm
ORD
- SDQ
1 stop10h 37m
Delta
mar. 6/26:05 am
SDQ
- ORD
2 stops15h 21m
Delta
Deal found 3/11![Delta logo]()
$538
This Copa Airlines deal was found by Cheapflights users on 3/11. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 8/208:02 am
ORD
- SDQ
1 stop13h 54m
Copa Airlines
dom. 8/2312:43 pm
SDQ
- ORD
1 stop13h 19m
Copa Airlines
Deal found 3/11![Copa Airlines logo]()
$459
This United Airlines deal was found by Cheapflights users on 3/11. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
lun. 4/208:40 am
ORD
- MBJ
Nonstop4h 10m
United Airlines
jue. 4/231:52 pm
MBJ
- ORD
Nonstop4h 23m
United Airlines
Deal found 3/11![United Airlines logo]()
$428
Last-minute flights from O'Hare Intl to CaribbeanDiscover last-minute flight deals from O'Hare Intl to Caribbean. Data last updated marzo 13, 2026 and is based on user searches.
Discover last-minute flight deals from O'Hare Intl to Caribbean. Data last updated marzo 13, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 3/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 3/2410:55 am
ORD
- SJU
1 stop12h 03m
Spirit Airlines
mar. 4/71:29 am
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Deal found 3/8![Spirit Airlines logo]()
$210
This Mytrip deal was found by Cheapflights users on 3/12. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 3/3110:55 am
ORD
- SJU
1 stop12h 03m
Multiple Airlines
jue. 4/1611:30 am
SJU
- ORD
1 stop13h 29m
Multiple Airlines
Deal found 3/12![Multiple Airlines logo]()
$204
This Cheapflightsfares deal was found by Cheapflights users on 3/11. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 3/3110:55 am
ORD
- SJU
1 stop12h 03m
Spirit Airlines
mar. 4/71:29 am
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Deal found 3/11![Spirit Airlines logo]()
$208
This Mytrip deal was found by Cheapflights users on 3/11. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 3/3110:55 am
ORD
- SJU
1 stop12h 03m
Multiple Airlines
mar. 4/73:16 am
SJU
- ORD
1 stop21h 20m
Multiple Airlines
Deal found 3/11![Multiple Airlines logo]()
$211
This Cheapflightsfares deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 3/3110:55 am
ORD
- SJU
1 stop12h 03m
Spirit Airlines
mié. 4/81:29 am
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Deal found 3/9![Spirit Airlines logo]()
$213
This Kiwi.com deal was found by Cheapflights users on 3/12. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 4/710:55 am
ORD
- SJU
1 stop12h 03m
Multiple Airlines
vie. 4/173:37 pm
SJU
- ORD
1 stop8h 29m
Multiple Airlines
Deal found 3/12![Multiple Airlines logo]()
$212
This CheapOair deal was found by Cheapflights users on 3/8. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 4/75:05 am
ORD
- STT
1 stop9h 23m
Spirit Airlines
mar. 4/144:35 pm
STT
- ORD
1 stop18h 01m
Spirit Airlines
Deal found 3/8![Spirit Airlines logo]()
$268
This eDestinos deal was found by Cheapflights users on 3/11. 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.
vie. 4/1011:55 am
ORD
- SJU
1 stop11h 30m
Frontier
vie. 4/173:23 pm
SJU
- ORD
1 stop8h 16m
Frontier
Deal found 3/11![Frontier logo]()
$201
This Priceline deal was found by Cheapflights users on 3/9. 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.
sáb. 4/119:32 am
ORD
- SJU
1 stop14h 19m
Frontier
jue. 4/1611:30 am
SJU
- ORD
1 stop13h 29m
Frontier
Deal found 3/9![Frontier logo]()
$202
This Expedia deal was found by Cheapflights users on 3/9. 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.
lun. 4/1310:55 am
ORD
- SJU
1 stop12h 03m
Multiple Airlines
jue. 4/303:03 pm
SJU
- ORD
1 stop8h 36m
Multiple Airlines
Deal found 3/9![Multiple Airlines logo]()
$200
This Kiwi.com deal was found by Cheapflights users on 3/8. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 4/242:09 pm
ORD
- SJU
1 stop8h 34m
Frontier
vie. 5/13:23 pm
SJU
- ORD
1 stop8h 16m
Frontier
Deal found 3/8![Frontier logo]()
$205
This Cheapflightsfares deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
dom. 4/267:50 am
ORD
- SJU
1 stop16h 08m
Spirit Airlines
sáb. 5/24:34 pm
SJU
- ORD
Nonstop5h 15m
Spirit Airlines
Deal found 3/9![Spirit Airlines logo]()
$206
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 marzo 13, 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 marzo 13, 2026.
This Travelocity deal was found by Cheapflights users on 3/8. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 3/2410:55 am
ORD
- SJU
1 stop12h 03m
Spirit Airlines
Deal found 3/8![Spirit Airlines logo]()
$94
This Super.com deal was found by Cheapflights users on 3/10. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 4/810:55 am
ORD
- SJU
1 stop12h 03m
Spirit Airlines
Deal found 3/10![Spirit Airlines logo]()
$97
This Cheapflightsfares deal was found by Cheapflights users on 3/10. 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.
lun. 4/1310:55 am
ORD
- SJU
1 stop12h 03m
Spirit Airlines
Deal found 3/10![Spirit Airlines logo]()
$98
This Booking.com deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 4/114:21 pm
ORD
- SJU
1 stop14h 35m
Frontier
Deal found 3/9![Frontier logo]()
$101
This Priceline deal was found by Cheapflights users on 3/12. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 4/115:05 am
ORD
- GCM
1 stop7h 15m
Spirit Airlines
Deal found 3/12![Spirit Airlines logo]()
$102
This Kiwi.com deal was found by Cheapflights users on 3/9. 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.
mar. 4/74:21 pm
ORD
- SJU
1 stop15h 57m
Frontier
Deal found 3/9![Frontier logo]()
$103
This WAYA deal was found by Cheapflights users on 3/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 3/244:51 pm
ORD
- SJU
1 stop7h 28m
Multiple Airlines
Deal found 3/13![Multiple Airlines logo]()
$104
This Super.com deal was found by Cheapflights users on 3/9. 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.
mié. 4/85:05 am
ORD
- SXM
1 stop7h 25m
Spirit Airlines
Deal found 3/9![Spirit Airlines logo]()
$104
This Cheapflightsfares deal was found by Cheapflights users on 3/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mié. 3/2510:55 am
ORD
- SJU
1 stop12h 03m
Spirit Airlines
Deal found 3/9![Spirit Airlines logo]()
$105
This Cheapflightsfares deal was found by Cheapflights users on 3/8. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
mar. 4/75:05 am
ORD
- SXM
1 stop7h 25m
Spirit Airlines
Deal found 3/8![Spirit Airlines logo]()
$105
This FlightHub deal was found by Cheapflights users on 3/8. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 4/25:05 am
ORD
- SXM
1 stop7h 25m
Spirit Airlines
Deal found 3/8![Spirit Airlines logo]()
$106
This Priceline deal was found by Cheapflights users on 3/9. 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.
sáb. 4/251:27 pm
ORD
- SJU
1 stop21h 56m
Frontier
Deal found 3/9![Frontier logo]()
$107
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 marzo 13, 2026.
Round-trip from | $192 (Kiwi.com) |
|---|---|
One-way from | $94 (Travelocity) |
Popular in | December |
Cheapest in | October |
Average price | $408 |
Good round-trip deal | $282 or less |
Good one-way deal | $142 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 marzo 13, 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
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
dom. 4/19
8:40 am-12:50 pm
Nonstop4h 10m
Montego Bay Sangster Intl
jue. 4/23
4:12 pm-11:43 pm
1 stop7h 31m
$308
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
lun. 4/13
8:45 am-3:10 pm
1 stop6h 25m
Montego Bay Sangster Intl
vie. 4/17
4:12 pm-11:43 pm
1 stop7h 31m
$312
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
mar. 4/21
5:15 am-4:23 pm
1 stop10h 08m
San Juan Luis Munoz Marin Intl
sáb. 4/25
6:15 am-4:42 pm
1 stop11h 27m
$314
ChicagoSanto Domingo
ORD - SDQ
ORDSDQ
Chicago O'Hare Intl
mié. 4/8
5:35 am-3:55 pm
1 stop9h 20m
Santo Domingo Las Americas
vie. 4/17
1:40 am-11:12 am
1 stop10h 32m
$336
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
sáb. 4/18
8:40 am-12:50 pm
Nonstop4h 10m
Montego Bay Sangster Intl
sáb. 4/25
2:40 pm-11:15 pm
1 stop8h 35m
$348
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
jue. 8/13
6:05 am-4:55 pm
1 stop9h 50m
San Juan Luis Munoz Marin Intl
dom. 8/16
10:05 am-5:30 pm
1 stop8h 25m
$356
ChicagoSanto Domingo
ORD - SDQ
ORDSDQ
Chicago O'Hare Intl
vie. 8/14
6:45 am-3:45 pm
1 stop8h 00m
Santo Domingo Las Americas
dom. 8/16
1:55 pm-10:10 pm
1 stop9h 15m
$376
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
vie. 7/31
1:20 am-11:15 am
1 stop9h 55m
Montego Bay Sangster Intl
jue. 8/6
12:22 pm-12:02 am
1 stop11h 40m
$382
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
vie. 7/24
3:20 pm-12:05 am
1 stop7h 45m
San Juan Luis Munoz Marin Intl
vie. 7/31
6:30 am-3:00 pm
1 stop9h 30m
$406
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
dom. 7/5
5:30 am-3:26 pm
1 stop9h 56m
Montego Bay Sangster Intl
jue. 7/9
4:12 pm-11:26 pm
1 stop7h 14m
$408
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-GCM
ORD-SXM
ORD-STT
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-SJU
ORD-GCM
ORD-SXM
ORD-STT
What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Caribbean?
Currently, January is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Caribbean (average of $95). Flying from Chicago O'Hare Intl Airport to Caribbean in December is currently the most expensive (average of $195). 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 marzo 13, 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 35% on your trip compared to booking a flight in the morning.
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 March 12, 2026.
Travelers seeking maximum savings on their Chicago O'Hare Intl Airport to Caribbean flight should consider departing on Tuesday evenings when fares are most often at their lowest. Saturday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
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 marzo 13, 2026.
The most flights from ORD to 0CB are scheduled on a Thursday (13 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (6 on average).
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 marzo 13, 2026.
See what other customers who have flown with United Airlines,JetBlue, andAmerican Airlines 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.
Entertainment
7.1
Comfort
7.3
Boarding
7.7
Overall
7.4
Crew
8.1
Food
6.6
Reviews
1 / 20
10.0
ExcellentDane,Jan 2026
TYS - IAD
Entertainment
7.1
Comfort
7.3
Boarding
7.7
Overall
7.4
Crew
8.1
Food
6.6
Reviews
1 / 20
10.0
ExcellentDane,Jan 2026
TYS - IAD
Entertainment
7.1
Comfort
7.3
Boarding
7.7
Overall
7.4
Crew
8.1
Food
6.6
Reviews
1 / 20
10.0
ExcellentDane,Jan 2026
TYS - IAD
Entertainment
7.1
Comfort
7.3
Boarding
7.7
Overall
7.4
Crew
8.1
Food
6.6
Reviews
1 / 20
10.0
ExcellentDane,Jan 2026
TYS - IAD
Entertainment
7.1
Comfort
7.3
Boarding
7.7
Overall
7.4
Crew
8.1
Food
6.6
Reviews
1 / 20
10.0
ExcellentDane,Jan 2026
TYS - IAD
Entertainment
7.1
Comfort
7.3
Boarding
7.7
Overall
7.4
Crew
8.1
Food
6.6
Reviews
1 / 20
10.0
ExcellentDane,Jan 2026
TYS - IAD
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.
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 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 marzo 13, 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 marzo 13, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$100 | Average$393 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$106 | Average$506 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$119 | Average$439 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$136 | Average$509 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$175 | Average$522 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$186 | Average$323 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$188 | Average$431 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$213 | Average$343 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$253 | Average$597 | FlexibilityNo cancel fee | On-time69% |