$79+ 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 5/2. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
May 19 — May 261
Round-trip
1 adult, Economy
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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 April 19, 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 April 19, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/192:00 pm
ORD
- SJU
1 stop8h 59m
Multiple Airlines
Wed 4/2910:59 am
SJU
- ORD
Nonstop5h 09m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$224
This Kiwi.com deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” 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 5/185:30 pm
ORD
- SJU
1 stop7h 38m
Multiple Airlines
Mon 5/2511:39 am
SJU
- ORD
Nonstop5h 10m
Multiple Airlines
Deal found 4/16![Multiple Airlines logo]()
$225
This Priceline deal was found by Cheapflights users on 4/14. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/14:58 pm
ORD
- SJU
1 stop29h 31m
Frontier
Sun 5/31:59 am
SJU
- ORD
1 stop19h 04m
Frontier
Deal found 4/14![Frontier logo]()
$226
This Kiwi.com deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” 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 4/2710:00 am
ORD
- SJU
Nonstop4h 39m
Spirit Airlines
Mon 5/411:39 am
SJU
- ORD
Nonstop5h 10m
Spirit Airlines
Deal found 4/15![Spirit Airlines logo]()
$227
This Kiwi.com deal was found by Cheapflights users on 4/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/2010:00 am
ORD
- SJU
Nonstop4h 39m
Spirit Airlines
Wed 4/2910:59 am
SJU
- ORD
Nonstop5h 09m
Spirit Airlines
Deal found 4/14![Spirit Airlines logo]()
$228
This Travelocity deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” 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.
Thu 5/144:44 pm
ORD
- SJU
Nonstop4h 37m
Multiple Airlines
Sun 5/176:46 pm
SJU
- ORD
1 stop24h 58m
Multiple Airlines
Deal found 4/16![Multiple Airlines logo]()
$229
This Kiwi.com deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” 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 4/305:10 am
ORD
- SJU
1 stop11h 57m
Multiple Airlines
Sat 5/24:34 pm
SJU
- ORD
Nonstop5h 15m
Multiple Airlines
Deal found 4/17![Multiple Airlines logo]()
$230
This Cheapflightsfares deal was found by Cheapflights users on 4/14. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/195:15 am
ORD
- SJU
1 stop12h 46m
Spirit Airlines
Wed 9/24:54 pm
SJU
- ORD
Nonstop5h 10m
Spirit Airlines
Deal found 4/14![Spirit Airlines logo]()
$231
This Kiwi.com deal was found by Cheapflights users on 4/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/85:30 pm
ORD
- SJU
1 stop7h 38m
Frontier
Mon 5/116:41 pm
SJU
- ORD
2 stops26h 10m
Frontier
Deal found 4/14![Frontier logo]()
$232
This Cheapflightsfares deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” 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 4/2110:00 am
ORD
- SJU
Nonstop4h 39m
Spirit Airlines
Thu 4/234:34 pm
SJU
- ORD
Nonstop5h 15m
Spirit Airlines
Deal found 4/17![Spirit Airlines logo]()
$233
This Frontier deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” 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 5/193:55 pm
ORD
- SJU
1 stop9h 13m
Frontier
Wed 5/276:00 am
SJU
- ORD
1 stop7h 37m
Frontier
Deal found 4/16![Frontier logo]()
$234
This CheapOair deal was found by Cheapflights users on 4/14. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/54:44 pm
ORD
- SJU
Nonstop4h 37m
Spirit Airlines
Thu 5/145:47 pm
SJU
- ORD
1 stop7h 09m
Spirit Airlines
Deal found 4/14![Spirit Airlines logo]()
$235
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 April 19, 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 April 19, 2026.
This Delta deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” 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 5/56:04 am
ORD
- SJU
1 stop9h 27m
Delta
Sat 5/95:43 pm
SJU
- ORD
1 stop7h 16m
Delta
Deal found 4/18![Delta logo]()
$251
This Frontier deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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 7/95:30 pm
ORD
- SJU
1 stop7h 24m
Frontier
Mon 7/136:11 pm
SJU
- ORD
Nonstop5h 15m
Frontier
Deal found 4/19![Frontier logo]()
$257
This United Airlines deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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 7/76:30 am
ORD
- MBJ
1 stop8h 40m
United Airlines
Sat 7/114:33 pm
MBJ
- ORD
1 stop8h 12m
United Airlines
Deal found 4/19![United Airlines logo]()
$332
This Orbitz deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/201:04 pm
ORD
- SJU
Nonstop4h 44m
Multiple Airlines
Wed 6/247:14 pm
SJU
- ORD
Nonstop5h 15m
Multiple Airlines
Deal found 4/19![Multiple Airlines logo]()
$334
This Arajet deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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 9/256:45 am
ORD
- PUJ
Nonstop4h 45m
Arajet
Sun 9/276:00 pm
PUJ
- ORD
Nonstop5h 10m
Arajet
Deal found 4/19![Arajet logo]()
$395
This Copa Airlines deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” 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 stop18h 50m
Copa Airlines
Fri 7/2411:16 am
MBJ
- ORD
1 stop16h 44m
Copa Airlines
Deal found 4/15![Copa Airlines logo]()
$440
This Southwest deal was found by Cheapflights users on 4/14. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/57:35 pm
ORD
- PUJ
2 stops17h 40m
Southwest
Fri 5/81:40 pm
PUJ
- ORD
2 stops20h 30m
Southwest
Deal found 4/14![Southwest logo]()
$513
This Cheapflightsfares deal was found by Cheapflights users on 4/14. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/185:10 am
ORD
- SXM
1 stop7h 32m
Spirit Airlines
Thu 6/252:49 pm
SXM
- ORD
1 stop9h 19m
Spirit Airlines
Deal found 4/14![Spirit Airlines logo]()
$521
This Orbitz deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/186:22 pm
ORD
- PLS
2 stops41h 23m
Air Canada
Tue 7/211:40 pm
PLS
- ORD
1 stop21h 10m
Air Canada
Deal found 4/19![Air Canada logo]()
$573
This Kiwi.com deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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 6/205:25 pm
ORD
- SJU
1 stop7h 44m
Frontier
Wed 6/247:30 am
SJU
- ORD
2 stops13h 23m
Frontier
Deal found 4/19![Frontier logo]()
$287
This American Airlines deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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 6/198:52 pm
ORD
- NAS
1 stop12h 11m
American Airlines
Fri 6/2612:42 pm
NAS
- ORD
Nonstop3h 53m
American Airlines
Deal found 4/19![American Airlines logo]()
$581
This Delta deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” 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 7/65:30 am
ORD
- SJU
1 stop7h 01m
Delta
Fri 7/105:56 pm
SJU
- ORD
1 stop6h 57m
Delta
Deal found 4/18![Delta logo]()
$296
This WorldTicket deal was found by Cheapflights users on 4/14. 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 WorldTicket is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/1112:12 pm
ORD
- PUJ
Nonstop4h 45m
WorldTicket
Sat 7/187:02 am
PUJ
- ORD
Nonstop5h 10m
WorldTicket
Deal found 4/14![WorldTicket logo]()
$651
This United Airlines deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” 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 5/55:30 am
ORD
- MBJ
1 stop8h 00m
United Airlines
Wed 5/134:12 pm
MBJ
- ORD
1 stop7h 32m
United Airlines
Deal found 4/18![United Airlines logo]()
$332
This Delta deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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 6/295:30 am
ORD
- SJU
1 stop7h 01m
Delta
Fri 7/35:56 pm
SJU
- ORD
1 stop7h 03m
Delta
Deal found 4/19![Delta logo]()
$326
This United Airlines deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” 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 5/412:55 pm
ORD
- SJU
1 stop7h 29m
United Airlines
Fri 5/83:56 pm
SJU
- ORD
Nonstop5h 19m
United Airlines
Deal found 4/17![United Airlines logo]()
$337
This JetBlue deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” 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 4/276:00 am
ORD
- AUA
1 stop9h 05m
JetBlue
Fri 5/15:35 pm
AUA
- ORD
1 stop15h 06m
JetBlue
Deal found 4/15![JetBlue logo]()
$764
This Delta deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” 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 7/165:15 am
ORD
- SJU
1 stop10h 30m
Delta
Thu 7/232:42 pm
SJU
- ORD
1 stop10h 11m
Delta
Deal found 4/15![Delta logo]()
$326
This United Airlines deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” 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 5/12:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Wed 5/62:55 pm
SJU
- ORD
1 stop11h 32m
United Airlines
Deal found 4/16![United Airlines logo]()
$342
This Arajet deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” 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 4/18![Arajet logo]()
$433
This Delta deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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 6/510:15 am
ORD
- SJU
1 stop12h 20m
Delta
Wed 6/105:56 pm
SJU
- ORD
1 stop7h 03m
Delta
Deal found 4/19![Delta logo]()
$366
This Mytrip deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” 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.
Thu 5/145:05 am
ORD
- SXM
1 stop7h 25m
Multiple Airlines
Sun 5/1711:30 am
SXM
- ORD
3 stops21h 52m
Multiple Airlines
Deal found 4/17![Multiple Airlines logo]()
$494
This United Airlines deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” 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 4/232:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Sat 5/27:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
Deal found 4/16![United Airlines logo]()
$377
This United Airlines deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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 5/52:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Sun 5/103:56 pm
SJU
- ORD
Nonstop5h 19m
United Airlines
Deal found 4/19![United Airlines logo]()
$377
This Arajet deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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 7/2512:12 pm
ORD
- PUJ
Nonstop4h 45m
Arajet
Sat 8/17:02 am
PUJ
- ORD
Nonstop5h 10m
Arajet
Deal found 4/19![Arajet logo]()
$511
This Priceline deal was found by Cheapflights users on 4/14. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/226:00 am
ORD
- SXM
1 stop27h 04m
Multiple Airlines
Sat 6/276:00 pm
SXM
- ORD
2 stops14h 45m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$557
This Southwest deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” 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.
Sat 5/96:00 am
ORD
- PLS
1 stop8h 35m
Southwest
Wed 5/133:50 pm
PLS
- ORD
1 stop7h 05m
Southwest
Deal found 4/16![Southwest logo]()
$619
This Mytrip deal was found by Cheapflights users on 4/14. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/15:05 am
ORD
- STT
1 stop6h 42m
Spirit Airlines
Sun 6/73:21 pm
STT
- ORD
3 stops32h 54m
Spirit Airlines
Deal found 4/14![Spirit Airlines logo]()
$634
This United Airlines deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/45:30 am
ORD
- MBJ
1 stop8h 00m
United Airlines
Sat 7/111:52 pm
MBJ
- ORD
Nonstop4h 23m
United Airlines
Deal found 4/16![United Airlines logo]()
$402
This Copa Airlines deal was found by Cheapflights users on 4/14. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/88:01 am
ORD
- PUJ
1 stop8h 39m
Copa Airlines
Mon 10/1212:11 pm
PUJ
- ORD
1 stop13h 46m
Copa Airlines
Deal found 4/14![Copa Airlines logo]()
$648
Last-minute flights from O'Hare Intl to Caribbean IslandsDiscover last-minute flight deals from O'Hare Intl to Caribbean Islands. Data last updated April 19, 2026 and is based on user searches.
Discover last-minute flight deals from O'Hare Intl to Caribbean Islands. Data last updated April 19, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 4/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/192:00 pm
ORD
- SJU
1 stop8h 59m
Multiple Airlines
Wed 4/2910:59 am
SJU
- ORD
Nonstop5h 09m
Multiple Airlines
Deal found 4/14![Multiple Airlines logo]()
$224
This Kiwi.com deal was found by Cheapflights users on 4/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/2010:00 am
ORD
- SJU
Nonstop4h 39m
Spirit Airlines
Wed 4/2910:59 am
SJU
- ORD
Nonstop5h 09m
Spirit Airlines
Deal found 4/14![Spirit Airlines logo]()
$228
This Cheapflightsfares deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” 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 4/2110:00 am
ORD
- SJU
Nonstop4h 39m
Spirit Airlines
Thu 4/234:34 pm
SJU
- ORD
Nonstop5h 15m
Spirit Airlines
Deal found 4/17![Spirit Airlines logo]()
$233
This Kiwi.com deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” 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 4/2710:00 am
ORD
- SJU
Nonstop4h 39m
Spirit Airlines
Mon 5/411:39 am
SJU
- ORD
Nonstop5h 10m
Spirit Airlines
Deal found 4/15![Spirit Airlines logo]()
$227
This Kiwi.com deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” 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 4/305:10 am
ORD
- SJU
1 stop11h 57m
Multiple Airlines
Sat 5/24:34 pm
SJU
- ORD
Nonstop5h 15m
Multiple Airlines
Deal found 4/17![Multiple Airlines logo]()
$230
This Priceline deal was found by Cheapflights users on 4/14. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/14:58 pm
ORD
- SJU
1 stop29h 31m
Frontier
Sun 5/31:59 am
SJU
- ORD
1 stop19h 04m
Frontier
Deal found 4/14![Frontier logo]()
$226
This CheapOair deal was found by Cheapflights users on 4/14. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/54:44 pm
ORD
- SJU
Nonstop4h 37m
Spirit Airlines
Thu 5/145:47 pm
SJU
- ORD
1 stop7h 09m
Spirit Airlines
Deal found 4/14![Spirit Airlines logo]()
$235
This Kiwi.com deal was found by Cheapflights users on 4/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/85:30 pm
ORD
- SJU
1 stop7h 38m
Frontier
Mon 5/116:41 pm
SJU
- ORD
2 stops26h 10m
Frontier
Deal found 4/14![Frontier logo]()
$232
This Cheapflightsfares deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” 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 5/115:05 am
ORD
- SJU
1 stop12h 54m
Spirit Airlines
Fri 5/2911:39 am
SJU
- ORD
Nonstop5h 10m
Spirit Airlines
Deal found 4/16![Spirit Airlines logo]()
$231
This Travelocity deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” 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.
Thu 5/144:44 pm
ORD
- SJU
Nonstop4h 37m
Multiple Airlines
Sun 5/176:46 pm
SJU
- ORD
1 stop24h 58m
Multiple Airlines
Deal found 4/16![Multiple Airlines logo]()
$229
This Kiwi.com deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” 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 5/185:30 pm
ORD
- SJU
1 stop7h 38m
Multiple Airlines
Mon 5/2511:39 am
SJU
- ORD
Nonstop5h 10m
Multiple Airlines
Deal found 4/16![Multiple Airlines logo]()
$225
This Frontier deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” 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 5/193:55 pm
ORD
- SJU
1 stop9h 13m
Frontier
Wed 5/276:00 am
SJU
- ORD
1 stop7h 37m
Frontier
Deal found 4/16![Frontier logo]()
$234
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 April 19, 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 April 19, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 4/18. Clicking the “Pick Dates” 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 5/27:15 pm
ORD
- SXM
1 stop17h 22m
Spirit Airlines
Deal found 4/18![Spirit Airlines logo]()
$79
This Booking.com deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” 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.
Thu 4/305:05 am
ORD
- SXM
1 stop7h 32m
Spirit Airlines
Deal found 4/16![Spirit Airlines logo]()
$97
This Super.com deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/157:33 pm
ORD
- SXM
1 stop16h 57m
Spirit Airlines
Deal found 4/16![Spirit Airlines logo]()
$109
This Spirit deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” 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.
Sun 5/35:05 am
ORD
- SXM
1 stop7h 32m
Spirit Airlines
Deal found 4/15![Spirit Airlines logo]()
$110
This Kiwi.com deal was found by Cheapflights users on 4/19. Clicking the “Pick Dates” 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 5/103:44 pm
ORD
- AUA
1 stop21h 52m
Multiple Airlines
Deal found 4/19![Multiple Airlines logo]()
$111
This American Airlines deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” 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 5/196:40 am
ORD
- SJU
1 stop14h 25m
American Airlines
Deal found 4/16![American Airlines logo]()
$113
This eDestinos deal was found by Cheapflights users on 4/16. Clicking the “Pick Dates” 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.
Sun 4/2612:38 pm
ORD
- SJU
1 stop10h 21m
Frontier
Deal found 4/16![Frontier logo]()
$116
This Kiwi.com deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” 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 4/281:27 pm
ORD
- SJU
1 stop28h 55m
Multiple Airlines
Deal found 4/15![Multiple Airlines logo]()
$117
This Super.com deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” 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.
Sat 4/257:15 pm
ORD
- SXM
1 stop17h 22m
Spirit Airlines
Deal found 4/15![Spirit Airlines logo]()
$117
This Kiwi.com deal was found by Cheapflights users on 4/17. Clicking the “Pick Dates” 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 6/112:33 am
ORD
- SJU
Nonstop4h 51m
Frontier
Deal found 4/17![Frontier logo]()
$118
This Kiwi.com deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” 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 5/115:05 am
ORD
- AUA
1 stop8h 31m
Spirit Airlines
Deal found 4/15![Spirit Airlines logo]()
$118
This Kiwi.com deal was found by Cheapflights users on 4/15. Clicking the “Pick Dates” 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 4/265:05 am
ORD
- SXM
1 stop7h 32m
Spirit Airlines
Deal found 4/15![Spirit Airlines logo]()
$118
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 April 19, 2026.
Round-trip from | $224 (Kiwi.com) |
|---|---|
One-way from | $79 (Cheapflightsfares) |
Popular in | December |
Cheapest in | January |
Average price | $381 |
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 April 19, 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
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 5/5
6:04 am-4:31 pm
1 stop9h 27m
San Juan Luis Munoz Marin Intl
Sat 5/9
5:43 pm-11:59 pm
1 stop7h 16m
$251
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Thu 7/9
5:30 pm-1:54 am
1 stop7h 24m
San Juan Luis Munoz Marin Intl
Mon 7/13
6:11 pm-10:26 pm
Nonstop5h 15m
$257
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Sat 6/20
5:25 pm-2:09 am
1 stop7h 44m
San Juan Luis Munoz Marin Intl
Wed 6/24
7:30 am-7:53 pm
2 stops13h 23m
$287
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Mon 7/6
5:30 am-1:31 pm
1 stop7h 01m
San Juan Luis Munoz Marin Intl
Fri 7/10
5:56 pm-11:53 pm
1 stop6h 57m
$296
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Mon 6/29
5:30 am-1:31 pm
1 stop7h 01m
San Juan Luis Munoz Marin Intl
Fri 7/3
5:56 pm-11:59 pm
1 stop7h 03m
$326
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Thu 7/16
5:15 am-4:45 pm
1 stop10h 30m
San Juan Luis Munoz Marin Intl
Thu 7/23
2:42 pm-11:53 pm
1 stop10h 11m
$326
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Tue 7/7
6:30 am-3:10 pm
1 stop8h 40m
Montego Bay Sangster Intl
Sat 7/11
4:33 pm-12:45 am
1 stop8h 12m
$332
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Tue 5/5
5:30 am-1:30 pm
1 stop8h 00m
Montego Bay Sangster Intl
Wed 5/13
4:12 pm-11:44 pm
1 stop7h 32m
$332
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Sat 6/20
1:04 pm-6:48 pm
Nonstop4h 44m
San Juan Luis Munoz Marin Intl
Wed 6/24
7:14 pm-11:29 pm
Nonstop5h 15m
$334
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Mon 5/4
12:55 pm-9:24 pm
1 stop7h 29m
San Juan Luis Munoz Marin Intl
Fri 5/8
3:56 pm-8:15 pm
Nonstop5h 19m
$337
Showing 1-10 of 60 resultsSorted by cheapest first
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-SJU
ORD-MBJ
ORD-PUJ
ORD-SXM
ORD-PLS
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-SJU
ORD-MBJ
ORD-PUJ
ORD-SXM
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 $158). Flying from Chicago O'Hare Intl Airport to Caribbean Islands in August is currently the most expensive (average of $865). 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 April 19, 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 32% 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 April 11, 2026.
Travelers seeking maximum savings on their Chicago O'Hare Intl Airport to Caribbean Islands flight should consider departing on Wednesday 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 April 19, 2026.
The most flights from ORD to zzEPX are scheduled on a Monday (9 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (9 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 April 19, 2026.
See what other customers who have flown with United Airlines,American Airlines, andSpirit 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
Comfort
7.3
Food
6.6
Overall
7.4
Boarding
7.7
Entertainment
7.1
Reviews
1 / 20
8.0
ExcellentAnonymous,Apr 2026
DFW - EWR
Crew
8.1
Comfort
7.3
Food
6.6
Overall
7.4
Boarding
7.7
Entertainment
7.1
Reviews
1 / 20
8.0
ExcellentAnonymous,Apr 2026
DFW - EWR
Crew
8.1
Comfort
7.3
Food
6.6
Overall
7.4
Boarding
7.7
Entertainment
7.1
Reviews
1 / 20
8.0
ExcellentAnonymous,Apr 2026
DFW - EWR
Crew
8.1
Comfort
7.3
Food
6.6
Overall
7.4
Boarding
7.7
Entertainment
7.1
Reviews
1 / 20
8.0
ExcellentAnonymous,Apr 2026
DFW - EWR
Crew
8.1
Comfort
7.3
Food
6.6
Overall
7.4
Boarding
7.7
Entertainment
7.1
Reviews
1 / 20
8.0
ExcellentAnonymous,Apr 2026
DFW - EWR
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
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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 April 19, 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 April 19, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$100 | Average$393 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$115 | Average$510 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$119 | Average$437 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$143 | Average$500 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$175 | Average$480 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$197 | Average$333 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$213 | Average$484 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$254 | Average$578 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$312 | Average$602 | FlexibilityNo cancel fee | On-time71% |