$72+ Cheap flights from O'Hare Intl (ORD) to Caribbean Islands
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 2/28. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
Mar 16 — Mar 231
1 adult, Economy
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Find cheap flights from O'Hare Intl to Caribbean Islands with Cheapflights
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Cheapest flights from O'Hare Intl to Caribbean IslandsExplore the most affordable flight options available from O'Hare Intl to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 14, 2026.
Explore the most affordable flight options available from O'Hare Intl to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 14, 2026.
This Spirit deal was found by Cheapflights users on 2/10. 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 Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/2012:18 pm
ORD
- SJU
Nonstop4h 36m
Spirit Airlines
Thu 4/2312:30 pm
SJU
- ORD
Nonstop5h 08m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$179
This Cheapflightsfares deal was found by Cheapflights users on 2/11. 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.
Sun 3/15:15 am
ORD
- SJU
1 stop8h 16m
Spirit Airlines
Thu 3/511:52 am
SJU
- ORD
1 stop8h 26m
Spirit Airlines
Deal found 2/11![Spirit Airlines logo]()
$181
This CheapOair deal was found by Cheapflights users on 2/10. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/2212:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Thu 2/2611:52 am
SJU
- ORD
1 stop8h 26m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$182
This Kiwi.com deal was found by Cheapflights users on 2/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/91:27 pm
ORD
- SJU
1 stop22h 06m
Frontier
Fri 5/156:00 am
SJU
- ORD
1 stop17h 57m
Frontier
Deal found 2/10![Frontier logo]()
$184
This Kiwi.com deal was found by Cheapflights users on 2/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/2412:17 pm
ORD
- SJU
Nonstop4h 32m
Multiple Airlines
Mon 3/93:22 pm
SJU
- ORD
1 stop8h 17m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$185
This Kiwi.com deal was found by Cheapflights users on 2/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/212:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Tue 3/106:00 am
SJU
- ORD
1 stop12h 03m
Spirit Airlines
Deal found 2/11![Spirit Airlines logo]()
$186
This Kiwi.com deal was found by Cheapflights users on 2/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/2312:17 pm
ORD
- SJU
Nonstop4h 32m
Multiple Airlines
Fri 2/274:16 pm
SJU
- ORD
1 stop8h 23m
Multiple Airlines
Deal found 2/13![Multiple Airlines logo]()
$187
This Cheapflightsfares deal was found by Cheapflights users on 2/13. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/78:56 pm
ORD
- SJU
Nonstop4h 33m
Spirit Airlines
Wed 4/1512:30 pm
SJU
- ORD
Nonstop5h 08m
Spirit Airlines
Deal found 2/13![Spirit Airlines logo]()
$188
This Priceline deal was found by Cheapflights users on 2/11. 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.
Mon 4/1310:55 am
ORD
- SJU
1 stop12h 03m
Multiple Airlines
Fri 4/173:42 pm
SJU
- ORD
1 stop9h 16m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$189
This Kiwi.com deal was found by Cheapflights users on 2/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/712:29 pm
ORD
- SJU
Nonstop4h 31m
Spirit Airlines
Tue 4/71:29 am
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$190
This Kiwi.com deal was found by Cheapflights users on 2/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/22:13 pm
ORD
- SJU
1 stop10h 12m
Multiple Airlines
Thu 3/511:52 am
SJU
- ORD
1 stop8h 26m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$191
This Cheapflightsfares deal was found by Cheapflights users on 2/11. 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.
Sat 2/288:16 pm
ORD
- SXM
1 stop15h 59m
Spirit Airlines
Sat 3/73:20 pm
SXM
- ORD
1 stop10h 27m
Spirit Airlines
Deal found 2/11![Spirit Airlines logo]()
$237
Best flights from O'Hare Intl to Caribbean IslandsDiscover carefully curated flight deals from O'Hare Intl to Caribbean Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 14, 2026.
Discover carefully curated flight deals from O'Hare Intl to Caribbean Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated February 14, 2026.
This Delta deal was found by Cheapflights users on 2/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/158:10 am
ORD
- SJU
1 stop7h 05m
Delta
Sun 5/242:20 pm
SJU
- ORD
1 stop7h 14m
Delta
Deal found 2/14![Delta logo]()
$246
This United Airlines deal was found by Cheapflights users on 2/12. 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.
Mon 4/208:49 am
ORD
- SJU
Nonstop4h 55m
United Airlines
Fri 4/247:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
Deal found 2/12![United Airlines logo]()
$260
This CheapOair deal was found by Cheapflights users on 2/10. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/94:43 pm
ORD
- STT
1 stop21h 51m
Spirit Airlines
Sun 3/152:36 pm
STT
- ORD
1 stop27h 20m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$265
This Orbitz deal was found by Cheapflights users on 2/11. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/45:15 am
ORD
- SXM
1 stop7h 00m
Multiple Airlines
Wed 3/114:00 pm
SXM
- ORD
2 stops27h 52m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$337
This Air Canada deal was found by Cheapflights users on 2/11. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/258:40 pm
ORD
- PLS
1 stop14h 40m
Air Canada
Sun 3/291:20 pm
PLS
- ORD
1 stop21h 30m
Air Canada
Deal found 2/11![Air Canada logo]()
$360
This American Airlines deal was found by Cheapflights users on 2/14. Clicking the “Pick Dates” 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 3/118:05 am
ORD
- MBJ
Nonstop4h 06m
American Airlines
Tue 3/171:14 pm
MBJ
- ORD
Nonstop4h 41m
American Airlines
Deal found 2/14![American Airlines logo]()
$374
This Flightnetwork deal was found by Cheapflights users on 2/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/2810:27 am
ORD
- PUJ
Nonstop4h 45m
Arajet
Sun 3/16:00 pm
PUJ
- ORD
Nonstop5h 10m
Arajet
Deal found 2/14![Arajet logo]()
$376
This Southwest deal was found by Cheapflights users on 2/10. 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.
Sun 5/36:00 am
ORD
- PLS
1 stop7h 50m
Southwest
Wed 5/63:50 pm
PLS
- ORD
1 stop7h 05m
Southwest
Deal found 2/10![Southwest logo]()
$456
This JetBlue deal was found by Cheapflights users on 2/10. 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.
Tue 3/106:04 am
ORD
- UVF
1 stop7h 54m
JetBlue
Sat 3/141:48 pm
UVF
- ORD
1 stop10h 08m
JetBlue
Deal found 2/10![JetBlue logo]()
$508
This Delta deal was found by Cheapflights users on 2/10. 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.
Mon 5/119:44 am
ORD
- SJU
1 stop11h 33m
Delta
Wed 5/207:30 am
SJU
- ORD
1 stop12h 11m
Delta
Deal found 2/10![Delta logo]()
$256
This United Airlines deal was found by Cheapflights users on 2/12. 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.
Tue 5/192:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Thu 6/47:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
Deal found 2/12![United Airlines logo]()
$266
This CheapOair deal was found by Cheapflights users on 2/12. 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.
Thu 2/268:16 pm
ORD
- STT
1 stop18h 18m
Spirit Airlines
Thu 3/55:40 pm
STT
- ORD
1 stop8h 07m
Spirit Airlines
Deal found 2/12![Spirit Airlines logo]()
$279
This Delta deal was found by Cheapflights users on 2/10. 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.
Tue 5/58:15 am
ORD
- SJU
1 stop7h 08m
Delta
Thu 5/145:15 pm
SJU
- ORD
1 stop7h 44m
Delta
Deal found 2/10![Delta logo]()
$256
This Delta deal was found by Cheapflights users on 2/10. 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.
Tue 4/218:15 am
ORD
- SJU
1 stop7h 08m
Delta
Thu 4/306:15 am
SJU
- ORD
1 stop7h 59m
Delta
Deal found 2/10![Delta logo]()
$256
This FlightHub deal was found by Cheapflights users on 2/11. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/244:36 pm
ORD
- STT
2 stops19h 50m
Spirit Airlines
Tue 3/312:36 pm
STT
- ORD
2 stops19h 14m
Spirit Airlines
Deal found 2/11![Spirit Airlines logo]()
$282
This United Airlines deal was found by Cheapflights users on 2/13. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/292:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Tue 6/27:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
Deal found 2/13![United Airlines logo]()
$285
This Kiwi.com deal was found by Cheapflights users on 2/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/295:05 am
ORD
- SXM
1 stop7h 11m
Multiple Airlines
Mon 5/42:35 pm
SXM
- ORD
1 stop31h 42m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$338
This Delta deal was found by Cheapflights users on 2/11. 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.
Sun 4/195:10 am
ORD
- SJU
1 stop7h 04m
Delta
Wed 4/226:15 am
SJU
- ORD
1 stop11h 27m
Delta
Deal found 2/11![Delta logo]()
$256
This Cheapflightsfares deal was found by Cheapflights users on 2/12. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/108:16 pm
ORD
- SXM
1 stop15h 59m
Spirit Airlines
Tue 3/172:20 pm
SXM
- ORD
1 stop9h 57m
Spirit Airlines
Deal found 2/12![Spirit Airlines logo]()
$305
This Kiwi.com deal was found by Cheapflights users on 2/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/45:15 am
ORD
- SXM
1 stop7h 00m
Multiple Airlines
Fri 3/132:20 pm
SXM
- ORD
2 stops21h 56m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$343
This Air Canada deal was found by Cheapflights users on 2/13. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/183:35 pm
ORD
- PUJ
1 stop20h 25m
Air Canada
Tue 2/245:45 pm
PUJ
- ORD
1 stop18h 05m
Air Canada
Deal found 2/13![Air Canada logo]()
$379
This American Airlines deal was found by Cheapflights users on 2/13. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/108:15 am
ORD
- PUJ
Nonstop4h 38m
American Airlines
Fri 4/173:34 pm
PUJ
- ORD
1 stop18h 16m
American Airlines
Deal found 2/13![American Airlines logo]()
$390
This CheapOair deal was found by Cheapflights users on 2/13. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 3/15:15 am
ORD
- STT
1 stop9h 19m
Spirit Airlines
Sun 3/84:40 pm
STT
- ORD
2 stops28h 07m
Spirit Airlines
Deal found 2/13![Spirit Airlines logo]()
$308
This Delta deal was found by Cheapflights users on 2/10. 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.
Tue 2/247:00 am
ORD
- SJU
1 stop7h 50m
Delta
Wed 2/256:37 pm
SJU
- ORD
1 stop7h 19m
Delta
Deal found 2/10![Delta logo]()
$296
This Priceline deal was found by Cheapflights users on 2/10. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/315:05 am
ORD
- SXM
1 stop7h 25m
Multiple Airlines
Mon 4/64:00 pm
SXM
- ORD
2 stops19h 53m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$359
This Air Canada deal was found by Cheapflights users on 2/10. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/2510:00 am
ORD
- GCM
1 stop25h 25m
Air Canada
Mon 3/3011:25 am
GCM
- ORD
1 stop26h 35m
Air Canada
Deal found 2/10![Air Canada logo]()
$403
This United Airlines deal was found by Cheapflights users on 2/13. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/118:42 am
ORD
- MBJ
Nonstop4h 04m
United Airlines
Sun 3/151:48 pm
MBJ
- ORD
Nonstop4h 25m
United Airlines
Deal found 2/13![United Airlines logo]()
$369
This FlightHub deal was found by Cheapflights users on 2/11. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/58:16 pm
ORD
- SXM
1 stop15h 59m
Spirit Airlines
Mon 3/92:20 pm
SXM
- ORD
1 stop10h 27m
Spirit Airlines
Deal found 2/11![Spirit Airlines logo]()
$324
This Delta deal was found by Cheapflights users on 2/12. 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 2/265:25 am
ORD
- SJU
1 stop10h 02m
Delta
Tue 3/106:15 am
SJU
- ORD
1 stop11h 34m
Delta
Deal found 2/12![Delta logo]()
$296
This Kiwi.com deal was found by Cheapflights users on 2/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/184:28 pm
ORD
- PUJ
3 stops18h 41m
Multiple Airlines
Thu 4/237:30 pm
PUJ
- ORD
Nonstop5h 10m
Multiple Airlines
Deal found 2/13![Multiple Airlines logo]()
$368
Last-minute flights from O'Hare Intl to Caribbean IslandsDiscover last-minute flight deals from O'Hare Intl to Caribbean Islands. Data last updated February 14, 2026 and is based on user searches.
Discover last-minute flight deals from O'Hare Intl to Caribbean Islands. Data last updated February 14, 2026 and is based on user searches.
This CheapOair deal was found by Cheapflights users on 2/10. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/2212:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Thu 2/2611:52 am
SJU
- ORD
1 stop8h 26m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$182
This Kiwi.com deal was found by Cheapflights users on 2/13. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/2312:17 pm
ORD
- SJU
Nonstop4h 32m
Multiple Airlines
Fri 2/274:16 pm
SJU
- ORD
1 stop8h 23m
Multiple Airlines
Deal found 2/13![Multiple Airlines logo]()
$187
This Kiwi.com deal was found by Cheapflights users on 2/12. 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.
Mon 2/2312:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Thu 3/512:32 pm
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Deal found 2/12![Spirit Airlines logo]()
$189
This Kiwi.com deal was found by Cheapflights users on 2/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/2412:17 pm
ORD
- SJU
Nonstop4h 32m
Multiple Airlines
Mon 3/93:22 pm
SJU
- ORD
1 stop8h 17m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$185
This Kiwi.com deal was found by Cheapflights users on 2/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/247:00 am
ORD
- SJU
1 stop6h 31m
Spirit Airlines
Thu 3/511:52 am
SJU
- ORD
1 stop8h 26m
Spirit Airlines
Deal found 2/11![Spirit Airlines logo]()
$193
This Priceline deal was found by Cheapflights users on 2/10. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/258:30 am
ORD
- SJU
1 stop14h 13m
Frontier
Tue 3/33:53 am
SJU
- ORD
1 stop13h 59m
Frontier
Deal found 2/10![Frontier logo]()
$188
This Cheapflightsfares deal was found by Cheapflights users on 2/11. 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.
Sat 2/288:16 pm
ORD
- SXM
1 stop15h 59m
Spirit Airlines
Sat 3/73:20 pm
SXM
- ORD
1 stop10h 27m
Spirit Airlines
Deal found 2/11![Spirit Airlines logo]()
$237
This Cheapflightsfares deal was found by Cheapflights users on 2/11. 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.
Sun 3/15:15 am
ORD
- SJU
1 stop8h 16m
Spirit Airlines
Thu 3/511:52 am
SJU
- ORD
1 stop8h 26m
Spirit Airlines
Deal found 2/11![Spirit Airlines logo]()
$181
This Cheapflightsfares deal was found by Cheapflights users on 2/12. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/212:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Thu 3/511:52 am
SJU
- ORD
1 stop8h 26m
Spirit Airlines
Deal found 2/12![Spirit Airlines logo]()
$186
This Kiwi.com deal was found by Cheapflights users on 2/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/22:13 pm
ORD
- SJU
1 stop10h 12m
Multiple Airlines
Thu 3/511:52 am
SJU
- ORD
1 stop8h 26m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$191
This Kiwi.com deal was found by Cheapflights users on 2/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/312:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Fri 3/612:32 pm
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Deal found 2/11![Spirit Airlines logo]()
$190
This Priceline deal was found by Cheapflights users on 2/11. 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.
Sun 3/88:16 pm
ORD
- SXM
1 stop15h 59m
Spirit Airlines
Wed 3/112:20 pm
SXM
- ORD
1 stop10h 27m
Spirit Airlines
Deal found 2/11![Spirit Airlines logo]()
$238
One-way flights from O'Hare Intl to Caribbean IslandsSearch for one-way flight options from O'Hare Intl to Caribbean Islands. Find affordable one-way fares based on user searches. Data last updated February 14, 2026.
Search for one-way flight options from O'Hare Intl to Caribbean Islands. Find affordable one-way fares based on user searches. Data last updated February 14, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 2/10. 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 2/288:16 pm
ORD
- SXM
1 stop15h 59m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$72
This Super.com deal was found by Cheapflights users on 2/11. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/105:15 am
ORD
- SXM
1 stop7h 00m
Spirit Airlines
Deal found 2/11![Spirit Airlines logo]()
$74
This FlightHub deal was found by Cheapflights users on 2/10. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/115:05 am
ORD
- GCM
1 stop7h 15m
Spirit Airlines
Deal found 2/10![Spirit Airlines logo]()
$75
This Cheapflightsfares deal was found by Cheapflights users on 2/11. 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.
Tue 3/35:15 am
ORD
- SXM
1 stop7h 00m
Spirit Airlines
Deal found 2/11![Spirit Airlines logo]()
$75
This Kiwi.com deal was found by Cheapflights users on 2/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/78:16 pm
ORD
- SXM
1 stop14h 59m
Spirit Airlines
Deal found 2/11![Spirit Airlines logo]()
$80
This Kiwi.com deal was found by Cheapflights users on 2/10. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/61:27 pm
ORD
- GCM
1 stop23h 16m
Multiple Airlines
Deal found 2/10![Multiple Airlines logo]()
$86
This Priceline deal was found by Cheapflights users on 2/13. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/125:05 am
ORD
- GCM
1 stop7h 52m
Spirit Airlines
Deal found 2/13![Spirit Airlines logo]()
$89
This Cheapflightsfares deal was found by Cheapflights users on 2/11. 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.
Thu 2/268:16 pm
ORD
- SXM
1 stop15h 59m
Spirit Airlines
Deal found 2/11![Spirit Airlines logo]()
$91
This Super.com deal was found by Cheapflights users on 2/12. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/1610:55 am
ORD
- SJU
1 stop12h 03m
Spirit Airlines
Deal found 2/12![Spirit Airlines logo]()
$92
This Kiwi.com deal was found by Cheapflights users on 2/11. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/116:36 pm
ORD
- GCM
1 stop18h 21m
Multiple Airlines
Deal found 2/11![Multiple Airlines logo]()
$93
This Cheapflightsfares deal was found by Cheapflights users on 2/13. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/710:55 am
ORD
- SJU
1 stop12h 03m
Spirit Airlines
Deal found 2/13![Spirit Airlines logo]()
$93
This Kiwi.com deal was found by Cheapflights users on 2/12. 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.
Sun 3/15:15 am
ORD
- SXM
1 stop7h 00m
Spirit Airlines
Deal found 2/12![Spirit Airlines logo]()
$93
Find flight deals from O'Hare Intl to Caribbean Islands
Keep the following information in mind while searching for O'Hare Intl to Caribbean Islands flight deals. Data was last updated February 14, 2026.
Round-trip from | $179 (Spirit) |
|---|---|
One-way from | $72 (Cheapflightsfares) |
Popular in | December |
Cheapest in | April |
Average price | $387 |
Cheapflights Fare Finder
Customize your flight search to find flights from O'Hare Intl to Caribbean Islands 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 February 14, 2026.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Caribbean Islands that are best for you.
Fly from
O'Hare Intl
Fly to
Caribbean Islands
Route
Depart
Return
Price
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Fri 5/15
8:10 am-4:15 pm
1 stop7h 05m
San Juan Luis Munoz Marin Intl
Sun 5/24
2:20 pm-8:34 pm
1 stop7h 14m
$246
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Mon 5/11
9:44 am-10:17 pm
1 stop11h 33m
San Juan Luis Munoz Marin Intl
Wed 5/20
7:30 am-6:41 pm
1 stop12h 11m
$256
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 5/5
8:15 am-4:23 pm
1 stop7h 08m
San Juan Luis Munoz Marin Intl
Thu 5/14
5:15 pm-11:59 pm
1 stop7h 44m
$256
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 4/21
8:15 am-4:23 pm
1 stop7h 08m
San Juan Luis Munoz Marin Intl
Thu 4/30
6:15 am-1:14 pm
1 stop7h 59m
$256
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Sun 4/19
5:10 am-1:14 pm
1 stop7h 04m
San Juan Luis Munoz Marin Intl
Wed 4/22
6:15 am-4:42 pm
1 stop11h 27m
$256
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Mon 4/20
8:49 am-2:44 pm
Nonstop4h 55m
San Juan Luis Munoz Marin Intl
Fri 4/24
7:40 am-11:53 am
Nonstop5h 13m
$260
ChicagoSaint Thomas Island
ORD - STT
ORDSTT
Chicago O'Hare Intl
Mon 3/9
4:43 pm-3:34 pm
1 stop21h 51m
Saint Thomas Island Cyril E King
Sun 3/15
2:36 pm-4:56 pm
1 stop27h 20m
$265
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 5/19
2:38 pm-8:34 pm
Nonstop4h 56m
San Juan Luis Munoz Marin Intl
Thu 6/4
7:40 am-11:53 am
Nonstop5h 13m
$266
ChicagoSaint Thomas Island
ORD - STT
ORDSTT
Chicago O'Hare Intl
Thu 2/26
8:16 pm-4:34 pm
1 stop18h 18m
Saint Thomas Island Cyril E King
Thu 3/5
5:40 pm-11:47 pm
1 stop8h 07m
$279
ChicagoSaint Thomas Island
ORD - STT
ORDSTT
Chicago O'Hare Intl
Tue 3/24
4:36 pm-1:26 pm
2 stops19h 50m
Saint Thomas Island Cyril E King
Tue 3/31
2:36 pm-8:50 am
2 stops19h 14m
$282
Showing 1-10 of 60 results
Best time to book a flight from O'Hare Intl to Caribbean Islands
Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands from O'Hare Intl with our price prediction graph.
ORD-SXM
ORD-AUA
ORD-SJU
ORD-MBJ
ORD-PUJ
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 Islands
ORD-zzEPX
ORD-SXM
ORD-AUA
ORD-SJU
ORD-MBJ
What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Caribbean Islands?
Currently, September is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Caribbean Islands (average of $124). Flying from Chicago O'Hare Intl Airport to Caribbean Islands 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 EPX?
Find hourly flight availability from O'Hare Intl to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 14, 2026.
One of the essential ways to save on airfare from Chicago O'Hare Intl Airport to Caribbean Islands is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the evening could potentially save you up to 40% on airfare.
What is the cheapest day to fly from Chicago O'Hare Intl Airport to Caribbean Islands?
Use this chart to determine the cheapest time to fly round-trip from O'Hare Intl to Caribbean Islands. Price data was last updated on February 7, 2026.
Travelers seeking maximum savings on their Chicago O'Hare Intl Airport to Caribbean Islands 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 Islands
Explore weekly flight availability from O'Hare Intl to Caribbean Islands. 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 February 14, 2026.
The most flights from ORD to zzEPX are scheduled on a Thursday (12 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 Islands
Get insights into the airlines that provide service to Caribbean Islands. 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 Islands. Reviews last updated February 14, 2026.
See what other customers who have flown with United Airlines, American Airlines, and Spirit Airlines from Chicago O'Hare Intl Airport to Caribbean Islands have to say. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.1
Entertainment
7.1
Food
6.6
Boarding
7.7
Comfort
7.3
Overall
7.4
Reviews
1 / 20
10.0
ExcellentDane,Jan 2026
TYS - IAD
Crew
8.1
Entertainment
7.1
Food
6.6
Boarding
7.7
Comfort
7.3
Overall
7.4
Reviews
1 / 20
10.0
ExcellentDane,Jan 2026
TYS - IAD
Crew
8.1
Entertainment
7.1
Food
6.6
Boarding
7.7
Comfort
7.3
Overall
7.4
Reviews
1 / 20
10.0
ExcellentDane,Jan 2026
TYS - IAD
Crew
8.1
Entertainment
7.1
Food
6.6
Boarding
7.7
Comfort
7.3
Overall
7.4
Reviews
1 / 20
10.0
ExcellentDane,Jan 2026
TYS - IAD
Crew
8.1
Entertainment
7.1
Food
6.6
Boarding
7.7
Comfort
7.3
Overall
7.4
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 Islands. 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 Islands
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Caribbean Islands by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from O'Hare Intl to Caribbean Islands by cabin class
Find flights from O'Hare Intl to Caribbean Islands, based on your preferred cabin class, be it economy, premium economy, business, or first class.
O'Hare Intl and Caribbean Islands flights
Browse other O'Hare Intl and Caribbean Islands flight options. Last updated on February 14, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
O'Hare Intl to Caribbean Islands flights
Consider these flights traveling from O'Hare Intl to Caribbean Islands.
Top 9 airlines flying from O'Hare Intl to Caribbean Islands
Discover the top 9 airlines that operate flights from O'Hare Intl to Caribbean Islands. 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 February 14, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$106 | Average$506 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$119 | Average$444 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$130 | Average$354 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$136 | Average$531 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$180 | Average$321 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$188 | Average$431 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$193 | Average$576 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$213 | Average$343 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$251 | Average$615 | FlexibilityNo cancel fee | On-time69% |