$107+ 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 8/28. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
Aug 2 — Aug 91
Round-trip
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 July 3, 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 July 3, 2026.
This Super.com deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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.
Sun 7/512:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Fri 7/107:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 7/1![Frontier logo]()
$257
This Kiwi.com deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” 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 8/208:05 am
ORD
- SJU
2 stops15h 29m
Multiple Airlines
Sun 9/67:14 pm
SJU
- ORD
Nonstop5h 13m
Multiple Airlines
Deal found 7/2![Multiple Airlines logo]()
$258
This Kiwi.com deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” 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 8/2712:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Sat 9/57:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 6/30![Frontier logo]()
$259
This Frontier deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2712:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Wed 9/27:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 6/30![Frontier logo]()
$261
This American Airlines deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/156:00 am
ORD
- SJU
1 stop11h 30m
American Airlines
Fri 8/2812:55 am
SJU
- ORD
Nonstop5h 05m
American Airlines
Deal found 6/30![American Airlines logo]()
$262
This Kiwi.com deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” 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 7/312:44 am
ORD
- SJU
Nonstop4h 57m
Frontier
Sat 7/47:14 pm
SJU
- ORD
Nonstop5h 15m
Frontier
Deal found 6/30![Frontier logo]()
$263
This Kiwi.com deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 8/1712:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Sun 8/236:35 am
SJU
- ORD
1 stop31h 15m
Frontier
Deal found 7/1![Frontier logo]()
$264
This Super.com deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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.
Sun 8/912:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Sun 8/167:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 7/1![Frontier logo]()
$265
This Frontier deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” 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 7/612:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Sat 7/117:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 6/30![Frontier logo]()
$266
This American Airlines deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” 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 8/275:20 pm
ORD
- SJU
Nonstop4h 55m
American Airlines
Thu 9/31:38 pm
SJU
- ORD
1 stop11h 57m
American Airlines
Deal found 6/30![American Airlines logo]()
$267
This Frontier deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/1612:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Sun 8/237:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 6/30![Frontier logo]()
$268
This SmartFares deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/147:00 am
ORD
- NAS
1 stop9h 22m
JetBlue
Fri 8/2112:20 pm
NAS
- ORD
1 stop12h 24m
JetBlue
Deal found 6/30![JetBlue logo]()
$298
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 July 3, 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 July 3, 2026.
This Delta deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” 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 8/165:30 am
ORD
- SJU
1 stop7h 12m
Delta
Sat 8/295:49 pm
SJU
- ORD
1 stop7h 08m
Delta
Deal found 6/30![Delta logo]()
$291
This JetBlue deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/127:00 am
ORD
- NAS
1 stop9h 22m
JetBlue
Wed 8/193:02 pm
NAS
- ORD
1 stop9h 42m
JetBlue
Deal found 7/2![JetBlue logo]()
$322
This United Airlines deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” 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 10/292:16 pm
ORD
- SJU
Nonstop4h 44m
United Airlines
Tue 11/31:00 pm
SJU
- ORD
1 stop9h 14m
United Airlines
Deal found 6/29![United Airlines logo]()
$372
This WorldTicket deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” 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.
Mon 8/245:30 am
ORD
- PUJ
Nonstop4h 45m
WorldTicket
Sun 8/306:00 pm
PUJ
- ORD
Nonstop5h 10m
WorldTicket
Deal found 6/29![WorldTicket logo]()
$488
This Avianca deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/1311:20 pm
ORD
- CUR
1 stop16h 40m
Avianca
Wed 8/1911:35 am
CUR
- ORD
1 stop10h 45m
Avianca
Deal found 7/1![Avianca logo]()
$570
This Copa Airlines deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” 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 11/127:35 am
ORD
- CUR
1 stop8h 47m
Copa Airlines
Thu 11/193:34 pm
CUR
- ORD
1 stop23h 12m
Copa Airlines
Deal found 6/28![Copa Airlines logo]()
$604
This JetBlue deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/196:00 am
ORD
- NAS
1 stop9h 00m
JetBlue
Wed 9/235:57 pm
NAS
- ORD
1 stop6h 34m
JetBlue
Deal found 6/29![JetBlue logo]()
$322
This American Airlines deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” 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 7/318:54 pm
ORD
- SXM
1 stop13h 39m
American Airlines
Sat 8/84:39 pm
SXM
- ORD
1 stop15h 55m
American Airlines
Deal found 6/28![American Airlines logo]()
$665
This Delta deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/210:33 am
ORD
- SJU
1 stop10h 56m
Delta
Mon 9/142:59 pm
SJU
- ORD
1 stop10h 00m
Delta
Deal found 7/3![Delta logo]()
$356
This JetBlue deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” 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.
Thu 8/137:00 am
ORD
- NAS
1 stop9h 22m
JetBlue
Sat 8/1512:20 pm
NAS
- ORD
1 stop12h 24m
JetBlue
Deal found 7/2![JetBlue logo]()
$340
This United Airlines deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” 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 11/710:30 am
ORD
- SJU
1 stop8h 54m
United Airlines
Sat 11/148:05 am
SJU
- ORD
1 stop8h 16m
United Airlines
Deal found 6/29![United Airlines logo]()
$376
This United Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 10/28:55 am
ORD
- SJU
Nonstop4h 49m
United Airlines
Sun 10/113:56 pm
SJU
- ORD
Nonstop5h 09m
United Airlines
Deal found 7/1![United Airlines logo]()
$391
This JetBlue deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/157:00 am
ORD
- NAS
1 stop9h 22m
JetBlue
Sat 8/226:27 pm
NAS
- ORD
1 stop6h 17m
JetBlue
Deal found 7/1![JetBlue logo]()
$358
This JetBlue deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/207:00 am
ORD
- NAS
1 stop5h 44m
JetBlue
Mon 10/2612:25 pm
NAS
- ORD
1 stop12h 19m
JetBlue
Deal found 7/3![JetBlue logo]()
$373
This Delta deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” 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 11/41:26 pm
ORD
- MBJ
2 stops21h 59m
Delta
Tue 11/106:00 pm
MBJ
- ORD
1 stop17h 07m
Delta
Deal found 7/2![Delta logo]()
$453
This United Airlines deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” 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 10/178:55 am
ORD
- SJU
Nonstop4h 49m
United Airlines
Sun 10/253:55 pm
SJU
- ORD
Nonstop5h 31m
United Airlines
Deal found 7/2![United Airlines logo]()
$457
This Delta deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” 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 11/297:35 pm
ORD
- PUJ
2 stops18h 05m
Delta
Sat 12/53:45 pm
PUJ
- ORD
1 stop18h 58m
Delta
Deal found 7/2![Delta logo]()
$470
This Copa Airlines deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” 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 10/103:20 pm
ORD
- CUR
1 stop26h 00m
Copa Airlines
Sat 10/173:38 pm
CUR
- ORD
1 stop10h 19m
Copa Airlines
Deal found 6/29![Copa Airlines logo]()
$604
This United Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 11/62:16 pm
ORD
- SJU
Nonstop4h 44m
United Airlines
Sat 11/148:25 am
SJU
- ORD
Nonstop5h 24m
United Airlines
Deal found 7/1![United Airlines logo]()
$457
This JetBlue deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” 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.
Sun 11/17:00 am
ORD
- MBJ
1 stop6h 54m
JetBlue
Thu 11/53:59 pm
MBJ
- ORD
1 stop8h 45m
JetBlue
Deal found 7/2![JetBlue logo]()
$421
This Avianca deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1911:20 pm
ORD
- CUR
1 stop16h 40m
Avianca
Wed 8/2611:35 am
CUR
- ORD
1 stop10h 45m
Avianca
Deal found 7/2![Avianca logo]()
$617
This Copa Airlines deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” 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.
Sun 10/118:01 am
ORD
- CUR
1 stop9h 19m
Copa Airlines
Fri 10/163:38 pm
CUR
- ORD
1 stop10h 19m
Copa Airlines
Deal found 6/28![Copa Airlines logo]()
$604
This American Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 9/257:00 pm
ORD
- SXM
1 stop17h 22m
American Airlines
Tue 9/292:22 pm
SXM
- ORD
1 stop18h 07m
American Airlines
Deal found 7/1![American Airlines logo]()
$665
This United Airlines deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” 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 9/118:55 am
ORD
- SJU
Nonstop4h 49m
United Airlines
Thu 9/172:55 pm
SJU
- ORD
1 stop10h 33m
United Airlines
Deal found 6/29![United Airlines logo]()
$462
This Avianca deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1811:20 pm
ORD
- CUR
1 stop16h 40m
Avianca
Wed 8/266:15 pm
CUR
- ORD
1 stop28h 05m
Avianca
Deal found 7/2![Avianca logo]()
$617
This Delta deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 7/257:00 am
ORD
- PUJ
1 stop7h 58m
Delta
Sat 8/15:25 pm
PUJ
- ORD
1 stop16h 10m
Delta
Deal found 7/1![Delta logo]()
$540
This Copa Airlines deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/93:20 pm
ORD
- CUR
1 stop22h 16m
Copa Airlines
Sat 10/173:38 pm
CUR
- ORD
1 stop10h 19m
Copa Airlines
Deal found 6/28![Copa Airlines logo]()
$604
This JetBlue deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/17:00 am
ORD
- PUJ
1 stop7h 29m
JetBlue
Tue 9/84:41 pm
PUJ
- ORD
1 stop8h 03m
JetBlue
Deal found 7/2![JetBlue logo]()
$454
This United Airlines deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” 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 11/72:16 pm
ORD
- SJU
Nonstop4h 44m
United Airlines
Fri 11/138:05 am
SJU
- ORD
1 stop8h 16m
United Airlines
Deal found 6/28![United Airlines logo]()
$462
This American Airlines deal was found by Cheapflights users on 6/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/198:53 pm
ORD
- SXM
2 stops15h 29m
American Airlines
Sun 8/232:22 pm
SXM
- ORD
2 stops10h 34m
American Airlines
Deal found 6/28![American Airlines logo]()
$680
Last-minute flights from O'Hare Intl to Caribbean IslandsDiscover last-minute flight deals from O'Hare Intl to Caribbean Islands. Data last updated July 3, 2026 and is based on user searches.
Discover last-minute flight deals from O'Hare Intl to Caribbean Islands. Data last updated July 3, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” 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 7/312:44 am
ORD
- SJU
Nonstop4h 57m
Frontier
Sat 7/47:14 pm
SJU
- ORD
Nonstop5h 15m
Frontier
Deal found 6/30![Frontier logo]()
$263
This Super.com deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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.
Sun 7/512:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Fri 7/107:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 7/1![Frontier logo]()
$257
This Frontier deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” 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 7/612:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Sat 7/117:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 6/30![Frontier logo]()
$266
This Super.com deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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.
Sun 8/912:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Sun 8/167:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 7/1![Frontier logo]()
$265
This SmartFares deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/147:00 am
ORD
- NAS
1 stop9h 22m
JetBlue
Fri 8/2112:20 pm
NAS
- ORD
1 stop12h 24m
JetBlue
Deal found 6/30![JetBlue logo]()
$298
This American Airlines deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/156:00 am
ORD
- SJU
1 stop11h 30m
American Airlines
Fri 8/2812:55 am
SJU
- ORD
Nonstop5h 05m
American Airlines
Deal found 6/30![American Airlines logo]()
$262
This Frontier deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/1612:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Sun 8/237:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 6/30![Frontier logo]()
$268
This Kiwi.com deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 8/1712:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Sun 8/236:35 am
SJU
- ORD
1 stop31h 15m
Frontier
Deal found 7/1![Frontier logo]()
$264
This Kiwi.com deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” 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 8/208:05 am
ORD
- SJU
2 stops15h 29m
Multiple Airlines
Sun 9/67:14 pm
SJU
- ORD
Nonstop5h 13m
Multiple Airlines
Deal found 7/2![Multiple Airlines logo]()
$258
This Kiwi.com deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” 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 8/2712:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Sat 9/57:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 6/30![Frontier logo]()
$259
This Frontier deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2712:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Wed 9/27:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 6/30![Frontier logo]()
$261
This American Airlines deal was found by Cheapflights users on 6/30. Clicking the “Pick Dates” 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 8/275:20 pm
ORD
- SJU
Nonstop4h 55m
American Airlines
Thu 9/31:38 pm
SJU
- ORD
1 stop11h 57m
American Airlines
Deal found 6/30![American Airlines logo]()
$267
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 July 3, 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 July 3, 2026.
This JetBlue deal was found by Cheapflights users on 7/3. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/297:00 am
ORD
- NAS
1 stop9h 22m
JetBlue
Deal found 7/3![JetBlue logo]()
$107
This Cheapflightsfares deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” 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 9/276:00 am
ORD
- SXM
1 stop7h 00m
JetBlue
Deal found 6/29![JetBlue logo]()
$117
This JetBlue deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/266:00 am
ORD
- SXM
1 stop7h 00m
JetBlue
Deal found 7/1![JetBlue logo]()
$118
This JetBlue deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/297:00 am
ORD
- NAS
1 stop9h 22m
JetBlue
Deal found 7/2![JetBlue logo]()
$125
This eDestinos deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 8/2912:12 pm
ORD
- PUJ
Nonstop4h 45m
Arajet
Deal found 7/1![Arajet logo]()
$126
This American Airlines deal was found by Cheapflights users on 7/2. Clicking the “Pick Dates” 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 7/308:29 am
ORD
- SJU
1 stop13h 28m
American Airlines
Deal found 7/2![American Airlines logo]()
$126
This American Airlines deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/296:10 am
ORD
- SJU
1 stop7h 02m
American Airlines
Deal found 7/1![American Airlines logo]()
$128
This Expedia deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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.
Tue 7/712:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 7/1![Frontier logo]()
$129
This American Airlines deal was found by Cheapflights users on 6/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/154:59 pm
ORD
- SJU
Nonstop4h 55m
American Airlines
Deal found 6/29![American Airlines logo]()
$131
This Mytrip deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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.
Sat 8/1512:12 pm
ORD
- PUJ
Nonstop4h 45m
Arajet
Deal found 7/1![Arajet logo]()
$132
This Frontier deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” 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 7/912:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 7/1![Frontier logo]()
$132
This Delta deal was found by Cheapflights users on 7/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/2711:23 am
ORD
- SJU
1 stop10h 06m
Delta
Deal found 7/1![Delta logo]()
$133
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 July 3, 2026.
Round-trip from | $257 (Super.com) |
|---|---|
One-way from | $107 (JetBlue) |
Popular in | December |
Cheapest in | January |
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 July 3, 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
Sun 8/16
5:30 am-1:42 pm
1 stop7h 12m
San Juan Luis Munoz Marin Intl
Sat 8/29
5:49 pm-11:57 pm
1 stop7h 08m
$291
ChicagoNassau
ORD - NAS
ORDNAS
Chicago O'Hare Intl
Wed 8/12
7:00 am-5:22 pm
1 stop9h 22m
Nassau Intl
Wed 8/19
3:02 pm-11:44 pm
1 stop9h 42m
$322
ChicagoNassau
ORD - NAS
ORDNAS
Chicago O'Hare Intl
Sat 9/19
6:00 am-4:00 pm
1 stop9h 00m
Nassau Intl
Wed 9/23
5:57 pm-11:31 pm
1 stop6h 34m
$322
ChicagoNassau
ORD - NAS
ORDNAS
Chicago O'Hare Intl
Thu 8/13
7:00 am-5:22 pm
1 stop9h 22m
Nassau Intl
Sat 8/15
12:20 pm-11:44 pm
1 stop12h 24m
$340
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Wed 9/2
10:33 am-10:29 pm
1 stop10h 56m
San Juan Luis Munoz Marin Intl
Mon 9/14
2:59 pm-11:59 pm
1 stop10h 00m
$356
ChicagoNassau
ORD - NAS
ORDNAS
Chicago O'Hare Intl
Sat 8/15
7:00 am-5:22 pm
1 stop9h 22m
Nassau Intl
Sat 8/22
6:27 pm-11:44 pm
1 stop6h 17m
$358
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Thu 10/29
2:16 pm-8:00 pm
Nonstop4h 44m
San Juan Luis Munoz Marin Intl
Tue 11/3
1:00 pm-8:14 pm
1 stop9h 14m
$372
ChicagoNassau
ORD - NAS
ORDNAS
Chicago O'Hare Intl
Tue 10/20
7:00 am-1:44 pm
1 stop5h 44m
Nassau Intl
Mon 10/26
12:25 pm-11:44 pm
1 stop12h 19m
$373
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Sat 11/7
10:30 am-9:24 pm
1 stop8h 54m
San Juan Luis Munoz Marin Intl
Sat 11/14
8:05 am-2:21 pm
1 stop8h 16m
$376
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Fri 10/2
8:55 am-2:44 pm
Nonstop4h 49m
San Juan Luis Munoz Marin Intl
Sun 10/11
3:56 pm-8:05 pm
Nonstop5h 09m
$391
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-NAS
ORD-PUJ
ORD-SXM
ORD-CUR
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-NAS
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 $186). Flying from Chicago O'Hare Intl Airport to Caribbean Islands in July is currently the most expensive (average of $827). 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 July 3, 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.
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 July 3, 2026.
The most flights from ORD to zzEPX are scheduled on a Monday (9 on average). You will have fewer flight options on Wednesday, which is when the least amount of flights are scheduled (6 on average).
How far ahead should I book a flight from Chicago O'Hare Intl Airport to Caribbean Islands?
To ensure you get the cheapest price possible for a flight from Chicago O'Hare Intl Airport to Caribbean Islands, you should look to book at least 48 days in advance of your intended travel date. The price of your flight may increase if you delay and leave booking until a week or so before departure.
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 June 27, 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. Thursday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
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 July 3, 2026.
See what other customers who have flown with Delta,United Airlines, andAmerican 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.
Overall
7.8
Food
7.2
Crew
8.5
Entertainment
7.8
Boarding
8.1
Comfort
7.8
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Overall
7.8
Food
7.2
Crew
8.5
Entertainment
7.8
Boarding
8.1
Comfort
7.8
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Overall
7.8
Food
7.2
Crew
8.5
Entertainment
7.8
Boarding
8.1
Comfort
7.8
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Overall
7.8
Food
7.2
Crew
8.5
Entertainment
7.8
Boarding
8.1
Comfort
7.8
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
Overall
7.8
Food
7.2
Crew
8.5
Entertainment
7.8
Boarding
8.1
Comfort
7.8
Reviews
1 / 20
10.0
ExcellentAnonymous,May 2026
SEA - KOA
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 July 3, 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 July 3, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$118 | Average$508 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$119 | Average$433 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$144 | Average$586 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$175 | Average$472 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$216 | Average$365 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$228 | Average$486 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$262 | Average$588 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$300 | Average$610 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$324 | Average$628 | FlexibilityNo cancel fee | On-time71% |