$109+ Cheap flights from Caribbean to O'Hare Intl (ORD)
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 5/13. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — ORD
May 23 — May 301
Round-trip
1 adult, Economy
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Find cheap flights from Caribbean to O'Hare Intl with Cheapflights
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Cheapest flights from Caribbean to O'Hare IntlExplore the most affordable flight options available from Caribbean to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 23, 2026.
Explore the most affordable flight options available from Caribbean to O'Hare Intl. Find the lowest fares from popular airlines and budget airlines, with prices last updated on April 23, 2026.
This eDestinos deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” 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.
Fri 5/14:34 pm
SJU
- ORD
Nonstop5h 15m
Spirit Airlines
Mon 5/44:44 pm
ORD
- SJU
Nonstop4h 37m
Spirit Airlines
Deal found 4/22![Spirit Airlines logo]()
$142
This eDestinos deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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.
Thu 4/304:34 pm
SJU
- ORD
Nonstop5h 15m
Spirit Airlines
Mon 5/44:44 pm
ORD
- SJU
Nonstop4h 37m
Spirit Airlines
Deal found 4/20![Spirit Airlines logo]()
$148
This Kiwi.com deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 5/14:34 pm
SJU
- ORD
Nonstop5h 15m
Spirit Airlines
Tue 5/54:44 pm
ORD
- SJU
Nonstop4h 37m
Spirit Airlines
Deal found 4/20![Spirit Airlines logo]()
$158
This eDestinos deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” 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.
Wed 5/206:24 pm
SJU
- ORD
Nonstop5h 22m
Frontier
Wed 5/2712:33 am
ORD
- SJU
Nonstop4h 51m
Frontier
Deal found 4/22![Frontier logo]()
$160
This eDestinos 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/24:34 pm
SJU
- ORD
Nonstop5h 15m
Spirit Airlines
Tue 5/54:44 pm
ORD
- SJU
Nonstop4h 37m
Spirit Airlines
Deal found 4/18![Spirit Airlines logo]()
$161
This Cheapflightsfares deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” 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 4/2910:59 am
SJU
- ORD
Nonstop5h 09m
Spirit Airlines
Mon 5/44:44 pm
ORD
- SJU
Nonstop4h 37m
Spirit Airlines
Deal found 4/22![Spirit Airlines logo]()
$167
This Cheapflightsfares deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” 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.
Fri 5/811:39 am
SJU
- ORD
Nonstop5h 10m
Spirit Airlines
Mon 5/114:44 pm
ORD
- SJU
Nonstop4h 37m
Spirit Airlines
Deal found 4/21![Spirit Airlines logo]()
$168
This eDestinos 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/2810:59 am
SJU
- ORD
Nonstop5h 09m
Spirit Airlines
Sun 5/310:00 am
ORD
- SJU
Nonstop4h 39m
Spirit Airlines
Deal found 4/19![Spirit Airlines logo]()
$171
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.
Fri 4/241:52 pm
MBJ
- ORD
Nonstop4h 23m
United Airlines
Sun 4/268:40 am
ORD
- MBJ
Nonstop4h 10m
United Airlines
Deal found 4/18![United Airlines logo]()
$281
This United Airlines deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” 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 4/251:52 pm
MBJ
- ORD
Nonstop4h 23m
United Airlines
Fri 5/19:56 pm
ORD
- MBJ
1 stop15h 34m
United Airlines
Deal found 4/22![United Airlines logo]()
$285
This American Airlines deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/301:15 pm
MBJ
- ORD
Nonstop4h 40m
American Airlines
Wed 5/68:05 am
ORD
- MBJ
Nonstop4h 08m
American Airlines
Deal found 4/22![American Airlines logo]()
$286
This United Airlines deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” 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 4/302:40 pm
MBJ
- ORD
1 stop10h 46m
United Airlines
Wed 5/62:27 pm
ORD
- MBJ
1 stop24h 43m
United Airlines
Deal found 4/22![United Airlines logo]()
$291
Best flights from Caribbean to O'Hare IntlDiscover carefully curated flight deals from Caribbean to O'Hare Intl that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 23, 2026.
Discover carefully curated flight deals from Caribbean to O'Hare Intl that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated April 23, 2026.
This Delta deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/145:56 pm
SJU
- ORD
1 stop6h 57m
Delta
Fri 8/71:44 pm
ORD
- SJU
1 stop7h 45m
Delta
Deal found 4/20![Delta logo]()
$236
This United Airlines deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 8/262:20 pm
SJU
- ORD
1 stop9h 57m
United Airlines
Sun 8/308:55 am
ORD
- SJU
Nonstop4h 49m
United Airlines
Deal found 4/20![United Airlines logo]()
$284
This American Airlines deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” 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 5/810:17 am
MBJ
- ORD
1 stop7h 41m
American Airlines
Fri 5/156:41 pm
ORD
- MBJ
1 stop14h 32m
American Airlines
Deal found 4/23![American Airlines logo]()
$296
This CheapOair deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” 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 5/281:52 pm
STT
- ORD
1 stop10h 23m
Spirit Airlines
Thu 6/47:33 pm
ORD
- STT
1 stop16h 14m
Spirit Airlines
Deal found 4/22![Spirit Airlines logo]()
$370
This Arajet deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” 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 9/267:02 am
PUJ
- ORD
Nonstop5h 10m
Arajet
Fri 10/26:45 am
ORD
- PUJ
Nonstop4h 45m
Arajet
Deal found 4/21![Arajet logo]()
$387
This Arajet deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/131:45 pm
SDQ
- ORD
1 stop10h 55m
Multiple Airlines
Sat 8/2212:12 pm
ORD
- SDQ
1 stop8h 28m
Multiple Airlines
Deal found 4/21![Multiple Airlines logo]()
$435
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/303:35 pm
PUJ
- ORD
1 stop17h 20m
Frontier
Sat 6/137:52 pm
ORD
- PUJ
1 stop15h 03m
Frontier
Deal found 4/18![Frontier logo]()
$461
This Southwest deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” 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 5/55:05 am
SJU
- ORD
2 stops17h 50m
Southwest
Mon 5/114:15 pm
ORD
- SJU
2 stops17h 20m
Southwest
Deal found 4/21![Southwest logo]()
$466
This Air Canada 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/183:05 pm
KIN
- ORD
1 stop17h 55m
Air Canada
Tue 9/18:40 pm
ORD
- KIN
1 stop17h 15m
Air Canada
Deal found 4/18![Air Canada logo]()
$476
This Delta deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/95:43 pm
SJU
- ORD
1 stop7h 16m
Delta
Tue 5/126:07 am
ORD
- SJU
1 stop9h 22m
Delta
Deal found 4/21![Delta logo]()
$241
This Delta deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/17:30 am
SJU
- ORD
1 stop10h 27m
Delta
Sat 8/81:49 pm
ORD
- SJU
1 stop7h 40m
Delta
Deal found 4/20![Delta logo]()
$246
This Copa Airlines deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” 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.
Tue 5/1212:40 pm
SDQ
- ORD
1 stop13h 35m
Copa Airlines
Wed 9/98:01 am
ORD
- SDQ
1 stop13h 55m
Copa Airlines
Deal found 4/23![Copa Airlines logo]()
$568
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.
Sat 5/161:52 pm
MBJ
- ORD
Nonstop4h 23m
United Airlines
Mon 5/189:56 pm
ORD
- MBJ
1 stop15h 34m
United Airlines
Deal found 4/18![United Airlines logo]()
$286
This United Airlines deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 5/72:40 pm
MBJ
- ORD
1 stop10h 05m
United Airlines
Tue 7/76:30 am
ORD
- MBJ
1 stop8h 40m
United Airlines
Deal found 4/20![United Airlines logo]()
$291
This Delta deal was found by Cheapflights users on 4/23. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/51:19 pm
SJU
- ORD
1 stop9h 33m
Delta
Wed 8/125:30 am
ORD
- SJU
1 stop10h 05m
Delta
Deal found 4/23![Delta logo]()
$286
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.
Thu 6/44:12 pm
MBJ
- ORD
1 stop15h 15m
United Airlines
Tue 6/96:30 am
ORD
- MBJ
1 stop8h 40m
United Airlines
Deal found 4/19![United Airlines logo]()
$292
This CheapOair deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” 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.
Fri 5/151:52 pm
STT
- ORD
1 stop10h 23m
Spirit Airlines
Thu 5/287:33 pm
ORD
- STT
2 stops17h 43m
Spirit Airlines
Deal found 4/22![Spirit Airlines logo]()
$388
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.
Fri 5/82:40 pm
MBJ
- ORD
1 stop10h 47m
United Airlines
Sun 5/105:30 am
ORD
- MBJ
1 stop8h 00m
United Airlines
Deal found 4/18![United Airlines logo]()
$292
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.
Wed 9/22:40 pm
SJU
- ORD
1 stop10h 17m
Delta
Mon 9/75:30 am
ORD
- SJU
1 stop7h 00m
Delta
Deal found 4/19![Delta logo]()
$296
This American 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/161:15 pm
MBJ
- ORD
Nonstop4h 40m
American Airlines
Mon 5/188:05 am
ORD
- MBJ
Nonstop4h 08m
American Airlines
Deal found 4/18![American Airlines logo]()
$399
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.
Thu 8/137:30 pm
PUJ
- ORD
Nonstop5h 10m
Arajet
Sat 8/2212:12 pm
ORD
- PUJ
Nonstop4h 45m
Arajet
Deal found 4/18![Arajet logo]()
$415
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.
Thu 6/44:12 pm
MBJ
- ORD
1 stop15h 15m
United Airlines
Mon 6/89:40 pm
ORD
- MBJ
1 stop17h 30m
United Airlines
Deal found 4/19![United Airlines logo]()
$296
This Delta deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/222:05 pm
SJU
- ORD
1 stop7h 26m
Delta
Tue 7/286:30 am
ORD
- SJU
1 stop9h 15m
Delta
Deal found 4/22![Delta logo]()
$296
This Air Canada deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” 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.
Mon 5/253:05 pm
KIN
- ORD
2 stops21h 06m
Air Canada
Tue 9/110:40 am
ORD
- KIN
2 stops27h 15m
Air Canada
Deal found 4/21![Air Canada logo]()
$483
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 8/17:02 am
PUJ
- ORD
Nonstop5h 10m
Arajet
Mon 8/35:30 am
ORD
- PUJ
Nonstop4h 45m
Arajet
Deal found 4/19![Arajet logo]()
$447
This CheapOair 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/234:20 pm
PUJ
- ORD
1 stop20h 01m
Multiple Airlines
Tue 7/712:29 am
ORD
- PUJ
1 stop18h 49m
Multiple Airlines
Deal found 4/18![Multiple Airlines logo]()
$492
This CheapOair deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” 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.
Sat 5/301:52 pm
STT
- ORD
1 stop19h 30m
Spirit Airlines
Mon 6/15:05 am
ORD
- STT
1 stop6h 42m
Spirit Airlines
Deal found 4/22![Spirit Airlines logo]()
$450
This Delta deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 7/106:00 am
SJU
- ORD
1 stop11h 44m
Delta
Mon 7/209:45 am
ORD
- SJU
1 stop11h 44m
Delta
Deal found 4/20![Delta logo]()
$326
This Air Canada deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/106:30 pm
NAS
- ORD
1 stop15h 30m
Air Canada
Wed 7/158:40 pm
ORD
- NAS
2 stops15h 55m
Air Canada
Deal found 4/22![Air Canada logo]()
$515
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.
Fri 7/314:55 pm
SJU
- ORD
1 stop7h 31m
United Airlines
Fri 8/72:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Deal found 4/18![United Airlines logo]()
$352
Last-minute flights from Caribbean to O'Hare IntlDiscover last-minute flight deals from Caribbean to O'Hare Intl. Data last updated April 23, 2026 and is based on user searches.
Discover last-minute flight deals from Caribbean to O'Hare Intl. Data last updated April 23, 2026 and is based on user searches.
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.
Fri 4/241:52 pm
MBJ
- ORD
Nonstop4h 23m
United Airlines
Sun 4/268:40 am
ORD
- MBJ
Nonstop4h 10m
United Airlines
Deal found 4/18![United Airlines logo]()
$281
This United Airlines deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” 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 4/251:52 pm
MBJ
- ORD
Nonstop4h 23m
United Airlines
Fri 5/19:56 pm
ORD
- MBJ
1 stop15h 34m
United Airlines
Deal found 4/22![United Airlines logo]()
$285
This eDestinos 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/2810:59 am
SJU
- ORD
Nonstop5h 09m
Spirit Airlines
Sun 5/310:00 am
ORD
- SJU
Nonstop4h 39m
Spirit Airlines
Deal found 4/19![Spirit Airlines logo]()
$171
This Cheapflightsfares deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” 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 4/2910:59 am
SJU
- ORD
Nonstop5h 09m
Spirit Airlines
Mon 5/44:44 pm
ORD
- SJU
Nonstop4h 37m
Spirit Airlines
Deal found 4/22![Spirit Airlines logo]()
$167
This eDestinos deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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.
Thu 4/304:34 pm
SJU
- ORD
Nonstop5h 15m
Spirit Airlines
Mon 5/44:44 pm
ORD
- SJU
Nonstop4h 37m
Spirit Airlines
Deal found 4/20![Spirit Airlines logo]()
$148
This American Airlines deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/301:15 pm
MBJ
- ORD
Nonstop4h 40m
American Airlines
Wed 5/68:05 am
ORD
- MBJ
Nonstop4h 08m
American Airlines
Deal found 4/22![American Airlines logo]()
$286
This United Airlines deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” 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 4/302:40 pm
MBJ
- ORD
1 stop10h 46m
United Airlines
Wed 5/62:27 pm
ORD
- MBJ
1 stop24h 43m
United Airlines
Deal found 4/22![United Airlines logo]()
$291
This eDestinos deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” 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.
Fri 5/14:34 pm
SJU
- ORD
Nonstop5h 15m
Spirit Airlines
Mon 5/44:44 pm
ORD
- SJU
Nonstop4h 37m
Spirit Airlines
Deal found 4/22![Spirit Airlines logo]()
$142
This Kiwi.com deal was found by Cheapflights users on 4/20. Clicking the “Pick Dates” 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 5/14:34 pm
SJU
- ORD
Nonstop5h 15m
Spirit Airlines
Tue 5/54:44 pm
ORD
- SJU
Nonstop4h 37m
Spirit Airlines
Deal found 4/20![Spirit Airlines logo]()
$158
This eDestinos 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/24:34 pm
SJU
- ORD
Nonstop5h 15m
Spirit Airlines
Tue 5/54:44 pm
ORD
- SJU
Nonstop4h 37m
Spirit Airlines
Deal found 4/18![Spirit Airlines logo]()
$161
This Cheapflightsfares deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” 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.
Fri 5/811:39 am
SJU
- ORD
Nonstop5h 10m
Spirit Airlines
Mon 5/114:44 pm
ORD
- SJU
Nonstop4h 37m
Spirit Airlines
Deal found 4/21![Spirit Airlines logo]()
$168
This eDestinos deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” 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.
Wed 5/206:24 pm
SJU
- ORD
Nonstop5h 22m
Frontier
Wed 5/2712:33 am
ORD
- SJU
Nonstop4h 51m
Frontier
Deal found 4/22![Frontier logo]()
$160
One-way flights from Caribbean to O'Hare IntlSearch for one-way flight options from Caribbean to O'Hare Intl. Find affordable one-way fares based on user searches. Data last updated April 23, 2026.
Search for one-way flight options from Caribbean to O'Hare Intl. Find affordable one-way fares based on user searches. Data last updated April 23, 2026.
This United Airlines deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” 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 5/133:56 pm
SJU
- ORD
Nonstop5h 19m
United Airlines
Deal found 4/21![United Airlines logo]()
$109
This Expedia 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 6/36:00 am
SJU
- ORD
1 stop7h 37m
Frontier
Deal found 4/19![Frontier logo]()
$111
This eDestinos deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” 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 5/245:15 pm
SJU
- ORD
1 stop14h 09m
Frontier
Deal found 4/21![Frontier logo]()
$112
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.
Thu 5/147:25 am
SJU
- ORD
1 stop9h 56m
American Airlines
Deal found 4/19![American Airlines logo]()
$113
This eDestinos deal was found by Cheapflights users on 4/22. Clicking the “Pick Dates” 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.
Tue 4/2810:59 am
SJU
- ORD
Nonstop5h 09m
Spirit Airlines
Deal found 4/22![Spirit Airlines logo]()
$114
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.
Thu 8/271:38 pm
SJU
- ORD
1 stop10h 22m
American Airlines
Deal found 4/19![American Airlines logo]()
$116
This eDestinos deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” 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.
Mon 5/113:03 am
SJU
- ORD
1 stop21h 10m
Frontier
Deal found 4/21![Frontier logo]()
$117
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.
Tue 6/26:24 pm
SJU
- ORD
Nonstop5h 22m
Frontier
Deal found 4/19![Frontier logo]()
$118
This Frontier deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” 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.
Mon 7/136:11 pm
SJU
- ORD
Nonstop5h 15m
Frontier
Deal found 4/21![Frontier logo]()
$119
This eDestinos deal was found by Cheapflights users on 4/21. Clicking the “Pick Dates” 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.
Mon 5/43:37 pm
SJU
- ORD
1 stop8h 29m
Frontier
Deal found 4/21![Frontier logo]()
$120
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/143:21 pm
STT
- ORD
1 stop8h 52m
Multiple Airlines
Deal found 4/18![Multiple Airlines logo]()
$156
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/151:52 pm
STT
- ORD
1 stop11h 07m
Multiple Airlines
Deal found 4/18![Multiple Airlines logo]()
$165
Find flight deals from Caribbean to O'Hare Intl
Keep the following information in mind while searching for Caribbean to O'Hare Intl flight deals. Data was last updated April 23, 2026.
Round-trip from | $160 (eDestinos) |
|---|---|
One-way from | $109 (United Airlines) |
Popular in | December |
Cheapest in | February |
Average price | $324 |
Good round-trip deal | $299 or less |
Good one-way deal | $207 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Caribbean to O'Hare Intl that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 23, 2026.
Use the filters below to find and compare flights from Caribbean to Chicago O'Hare Intl Airport that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Tue 7/14
5:56 pm-11:53 pm
1 stop6h 57m
Chicago O'Hare Intl
Fri 8/7
1:44 pm-10:29 pm
1 stop7h 45m
$236
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Sat 5/9
5:43 pm-11:59 pm
1 stop7h 16m
Chicago O'Hare Intl
Tue 5/12
6:07 am-4:29 pm
1 stop9h 22m
$241
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Sat 8/1
7:30 am-4:57 pm
1 stop10h 27m
Chicago O'Hare Intl
Sat 8/8
1:49 pm-10:29 pm
1 stop7h 40m
$246
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Wed 8/26
2:20 pm-11:17 pm
1 stop9h 57m
Chicago O'Hare Intl
Sun 8/30
8:55 am-2:44 pm
Nonstop4h 49m
$284
Montego BayChicago
MBJ - ORD
MBJORD
Montego Bay Sangster Intl
Sat 5/16
1:52 pm-6:15 pm
Nonstop4h 23m
Chicago O'Hare Intl
Mon 5/18
9:56 pm-1:30 pm
1 stop15h 34m
$286
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Wed 8/5
1:19 pm-9:52 pm
1 stop9h 33m
Chicago O'Hare Intl
Wed 8/12
5:30 am-4:35 pm
1 stop10h 05m
$286
Montego BayChicago
MBJ - ORD
MBJORD
Montego Bay Sangster Intl
Thu 5/7
2:40 pm-12:45 am
1 stop10h 05m
Chicago O'Hare Intl
Tue 7/7
6:30 am-3:10 pm
1 stop8h 40m
$291
Montego BayChicago
MBJ - ORD
MBJORD
Montego Bay Sangster Intl
Thu 6/4
4:12 pm-7:27 am
1 stop15h 15m
Chicago O'Hare Intl
Tue 6/9
6:30 am-3:10 pm
1 stop8h 40m
$292
Montego BayChicago
MBJ - ORD
MBJORD
Montego Bay Sangster Intl
Fri 5/8
2:40 pm-1:27 am
1 stop10h 47m
Chicago O'Hare Intl
Sun 5/10
5:30 am-1:30 pm
1 stop8h 00m
$292
Montego BayChicago
MBJ - ORD
MBJORD
Montego Bay Sangster Intl
Fri 5/8
10:17 am-5:58 pm
1 stop7h 41m
Chicago O'Hare Intl
Fri 5/15
6:41 pm-9:13 am
1 stop14h 32m
$296
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Caribbean to O'Hare Intl
Have a flexible travel schedule? Discover the best time to fly to O'Hare Intl from Caribbean with our price prediction graph.
SJU-ORD
MBJ-ORD
STT-ORD
PUJ-ORD
STI-ORD
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Caribbean to Chicago O'Hare Intl Airport
0CB-ORD
SJU-ORD
MBJ-ORD
STT-ORD
PUJ-ORD
What is the cheapest month to book a flight from Caribbean to Chicago O'Hare Intl Airport?
Currently, May is the cheapest month in which you can book a flight from Caribbean to Chicago O'Hare Intl Airport (average of $64). Flying from Caribbean to Chicago O'Hare Intl Airport in July is currently the most expensive (average of $662). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from CB to ORD?
Find hourly flight availability from Caribbean to O'Hare Intl. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated April 23, 2026.
A simple way to save on the total cost of your ticket is to fly from Caribbean to Chicago O'Hare Intl Airport in the evening. If you’re flexible enough to do this you can expect to save up to 44% on your trip compared to booking a flight in the afternoon.
What is the cheapest day to fly from Caribbean to Chicago O'Hare Intl Airport?
Use this chart to determine the cheapest time to fly round-trip from Caribbean to O'Hare Intl. Price data was last updated on April 18, 2026.
Travelers seeking maximum savings on their Caribbean to Chicago O'Hare Intl Airport flight should consider departing on Friday evenings when fares are most often at their lowest. Monday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Weekly flight availability from Caribbean to Chicago O'Hare Intl Airport
Explore weekly flight availability from Caribbean to O'Hare Intl. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated April 23, 2026.
The most flights from 0CB to ORD 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 O'Hare Intl
Get insights into the airlines that provide service to O'Hare Intl. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to O'Hare Intl. Reviews last updated April 23, 2026.
Get a feel of what it's like to fly with United Airlines,JetBlue, andAmerican Airlines from Caribbean to Chicago O'Hare Intl Airport by reading reviews from past customers. Users have also rated airlines in terms of entertainment options, comfort, food, crew/service, and boarding process.
Crew
8.1
Boarding
7.7
Entertainment
7.1
Comfort
7.3
Overall
7.4
Food
6.6
Reviews
1 / 20
8.0
ExcellentAnonymous,Apr 2026
DFW - EWR
Crew
8.1
Boarding
7.7
Entertainment
7.1
Comfort
7.3
Overall
7.4
Food
6.6
Reviews
1 / 20
8.0
ExcellentAnonymous,Apr 2026
DFW - EWR
Crew
8.1
Boarding
7.7
Entertainment
7.1
Comfort
7.3
Overall
7.4
Food
6.6
Reviews
1 / 20
8.0
ExcellentAnonymous,Apr 2026
DFW - EWR
Crew
8.1
Boarding
7.7
Entertainment
7.1
Comfort
7.3
Overall
7.4
Food
6.6
Reviews
1 / 20
8.0
ExcellentAnonymous,Apr 2026
DFW - EWR
Crew
8.1
Boarding
7.7
Entertainment
7.1
Comfort
7.3
Overall
7.4
Food
6.6
Reviews
1 / 20
8.0
ExcellentAnonymous,Apr 2026
DFW - EWR
Crew
8.1
Boarding
7.7
Entertainment
7.1
Comfort
7.3
Overall
7.4
Food
6.6
Reviews
1 / 20
8.0
ExcellentAnonymous,Apr 2026
DFW - EWR
Related info for your journey
Find useful and relevant information for your journey from Caribbean to O'Hare Intl. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago O'Hare Intl Airport?
Book flights to Chicago O'Hare Intl Airport if you plan to visit one of these locationsRosemont
Schaumburg
Naperville
Gurnee
Lake Geneva
Delavan
Hoffman Estates
Downers Grove
Oakbrook Terrace
Benton Harbor
Des Plaines
Oak Brook
South Holland
Libertyville
Elgin
Warrenville
Elk Grove Village
Bridgeview
Great Lakes
Lansing
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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Alternative routes for Caribbean to O'Hare Intl
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to O'Hare Intl by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Caribbean to O'Hare Intl by cabin class
Find flights from Caribbean to O'Hare Intl, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Other flights to O'Hare Intl
Explore flights to O'Hare Intl departing from other origins. Flights are based on user searches made on Cheapflights and were last updated on April 23, 2026.
Caribbean and O'Hare Intl flights
Browse other Caribbean and O'Hare Intl flight options. Last updated on April 23, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Caribbean to O'Hare Intl flights
Consider these flights traveling from Caribbean to O'Hare Intl.
Top 8 airlines flying from Caribbean to O'Hare Intl
Discover the top 8 airlines that operate flights from Caribbean to O'Hare Intl. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated April 23, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$116 | Average$577 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$123 | Average$338 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$128 | Average$254 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$131 | Average$201 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$195 | Average$380 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$246 | Average$530 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$256 | Average$490 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$292 | Average$439 | FlexibilityNo cancel fee | On-time63% |