$109+ Cheap flights from O'Hare Intl (ORD) to Caribbean
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 12/8. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
Oct 9 — Oct 161
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from O'Hare Intl to Caribbean with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
Review each provider’s pricing and select the best option for you! Book through your favorite provider’s website for a seamless experience.Cheap flight deals from O'Hare Intl to Caribbean
Cheapest
Best
Last-minute
One-way
Cheapest flights from O'Hare Intl to CaribbeanExplore the most affordable flight options available from O'Hare Intl to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 9, 2026.
Explore the most affordable flight options available from O'Hare Intl to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on September 9, 2026.
This Priceline deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 11/2311:53 pm -
Nonstop4h 39m
Thu 11/267:12 pm -
Nonstop5h 21m
Deal found 9/6![Frontier logo]()
$216
This United Airlines deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/58:55 am -
Nonstop4h 49m
Sat 10/103:56 pm -
Nonstop5h 09m
Deal found 9/7![United Airlines logo]()
$217
This deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/238:26 am -
1 stop9h 13m
Thu 11/57:00 am -
1 stop10h 37m
Deal found 9/8![Frontier logo]()
$219
This United Airlines deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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 9/285:00 am -
1 stop7h 45m
Mon 9/281:00 am -
1 stop9h 00m
Deal found 9/5![United Airlines logo]()
$221
This United Airlines deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/173:00 pm -
1 stop7h 50m
Wed 10/213:56 pm -
Nonstop5h 09m
Deal found 9/7![United Airlines logo]()
$222
This American Airlines deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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 10/166:40 pm -
1 stop15h 40m
Wed 10/2112:41 pm -
1 stop12h 27m
Deal found 9/5![American Airlines logo]()
$226
This JetBlue deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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 12/22:50 pm -
1 stop6h 38m
Sun 12/66:01 am -
1 stop9h 25m
Deal found 9/5![JetBlue logo]()
$227
This American Airlines deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/65:00 am -
1 stop9h 28m
Tue 10/136:30 am -
1 stop14h 25m
Deal found 9/7![American Airlines logo]()
$228
This American Airlines deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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 10/147:29 pm -
1 stop13h 17m
Wed 10/2810:36 am -
1 stop8h 38m
Deal found 9/5![American Airlines logo]()
$231
This American Airlines deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/188:15 am -
1 stop11h 23m
Fri 12/43:49 pm -
Nonstop5h 38m
Deal found 9/7![American Airlines logo]()
$232
This Orbitz deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/104:41 pm -
1 stop21h 38m
Fri 10/1612:59 am -
1 stop22h 40m
Deal found 9/8![Frontier logo]()
$233
This American Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/257:29 pm -
1 stop15h 02m
Tue 10/276:00 am -
1 stop13h 35m
Deal found 9/9![American Airlines logo]()
$234
Best flights from O'Hare Intl to CaribbeanDiscover carefully curated flight deals from O'Hare Intl to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 9, 2026.
Discover carefully curated flight deals from O'Hare Intl to Caribbean that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated September 9, 2026.
This United Airlines deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” 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.
Sun 9/278:55 am -
Nonstop4h 49m
Sat 10/31:00 am -
1 stop7h 42m
Deal found 9/4![United Airlines logo]()
$222
This Orbitz deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/191:55 pm -
2 stops21h 15m
Wed 11/252:25 pm -
1 stop30h 27m
Deal found 9/9![Air Canada logo]()
$367
This JetBlue deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 1/277:00 am -
1 stop5h 47m
Tue 2/212:35 pm -
1 stop12h 09m
Deal found 9/6![JetBlue logo]()
$442
This United Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/248:55 am -
Nonstop4h 49m
Tue 10/2712:00 pm -
1 stop10h 30m
Deal found 9/9![United Airlines logo]()
$222
This Arajet deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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 10/3111:27 am -
Nonstop4h 45m
Sun 11/86:10 pm -
Nonstop5h 10m
Deal found 9/5![Arajet logo]()
$460
This Delta deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 10/317:00 am -
2 stops8h 35m
Sat 11/75:50 pm -
2 stops14h 51m
Deal found 9/6![Delta logo]()
$467
This Copa Airlines deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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.
Wed 10/218:01 am -
1 stop26h 40m
Sat 10/3112:12 pm -
1 stop13h 59m
Deal found 9/6![Copa Airlines logo]()
$476
This United Airlines deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 12/51:10 pm -
1 stop9h 26m
Wed 12/98:05 am -
1 stop8h 07m
Deal found 9/8![United Airlines logo]()
$256
This United Airlines deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/201:55 pm -
1 stop8h 55m
Sat 10/241:05 am -
1 stop8h 57m
Deal found 9/7![United Airlines logo]()
$259
This United deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/201:55 pm -
2 stops16h 55m
Sun 10/2512:07 pm -
1 stop7h 47m
Deal found 9/7![Multiple Airlines logo]()
$689
This United Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/215:00 am -
1 stop7h 45m
Sat 9/262:55 pm -
1 stop9h 32m
Deal found 9/9![United Airlines logo]()
$266
This Air Canada deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/285:58 pm -
2 stops20h 27m
Sat 10/314:25 pm -
2 stops20h 42m
Deal found 9/9![Air Canada logo]()
$378
This United Airlines deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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 -
Nonstop4h 44m
Mon 11/93:46 pm -
1 stop9h 40m
Deal found 9/5![United Airlines logo]()
$274
This Copa Airlines deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/42:13 pm -
1 stop9h 55m
Sun 11/82:24 pm -
1 stop11h 47m
Deal found 9/7![Copa Airlines logo]()
$476
This JetBlue deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/27:00 am -
1 stop5h 47m
Sat 2/63:00 pm -
1 stop9h 44m
Deal found 9/8![JetBlue logo]()
$480
This United Airlines deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” 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 12/72:16 pm -
Nonstop4h 44m
Mon 12/72:05 am -
1 stop9h 40m
Deal found 9/4![United Airlines logo]()
$306
This Delta deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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 9/236:00 am -
1 stop11h 07m
Mon 9/287:35 pm -
1 stop14h 52m
Deal found 9/5![Delta logo]()
$520
This Copa Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/22:13 pm -
1 stop9h 55m
Wed 12/98:55 am -
1 stop17h 16m
Deal found 9/9![Copa Airlines logo]()
$484
This United Airlines deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” 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 12/72:16 pm -
Nonstop4h 44m
Fri 12/118:25 am -
Nonstop5h 24m
Deal found 9/4![United Airlines logo]()
$307
This Air Canada deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 1/253:45 pm -
2 stops22h 45m
Fri 1/293:25 pm -
1 stop25h 27m
Deal found 9/9![Air Canada logo]()
$517
This Delta deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/215:27 am -
2 stops11h 39m
Sat 10/312:57 pm -
1 stop10h 00m
Deal found 9/8![Delta logo]()
$525
This Copa Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/12:13 pm -
1 stop19h 29m
Fri 12/42:14 pm -
1 stop11h 57m
Deal found 9/9![Copa Airlines logo]()
$484
This United Airlines deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/238:55 am -
Nonstop4h 49m
Wed 10/287:25 am -
Nonstop5h 22m
Deal found 9/7![United Airlines logo]()
$346
This Copa Airlines deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 9/298:01 am -
1 stop27h 16m
Sat 10/312:22 pm -
1 stop12h 35m
Deal found 9/6![Copa Airlines logo]()
$508
This Booking.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/213:45 pm -
2 stops19h 25m
Wed 11/252:25 pm -
1 stop29h 21m
Deal found 9/9![Air Canada logo]()
$560
This JetBlue deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/237:00 am -
1 stop9h 21m
Tue 12/293:02 pm -
1 stop9h 47m
Deal found 9/8![JetBlue logo]()
$649
This Delta deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/101:55 pm -
2 stops21h 45m
Thu 10/224:05 pm -
1 stop8h 52m
Deal found 9/9![Delta logo]()
$593
This Copa Airlines deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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.
Mon 9/143:20 pm -
1 stop20h 53m
Sat 9/1912:42 pm -
1 stop26h 17m
Deal found 9/5![Copa Airlines logo]()
$516
This United Airlines deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/52:16 pm -
Nonstop4h 44m
Tue 11/108:25 am -
Nonstop5h 22m
Deal found 9/8![United Airlines logo]()
$359
This Copa Airlines deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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 9/253:20 pm -
1 stop23h 55m
Tue 9/296:41 pm -
1 stop20h 18m
Deal found 9/5![Copa Airlines logo]()
$516
Last-minute flights from O'Hare Intl to CaribbeanDiscover last-minute flight deals from O'Hare Intl to Caribbean. Data last updated September 9, 2026 and is based on user searches.
Discover last-minute flight deals from O'Hare Intl to Caribbean. Data last updated September 9, 2026 and is based on user searches.
This United Airlines deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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 9/285:00 am -
1 stop7h 45m
Mon 9/281:00 am -
1 stop9h 00m
Deal found 9/5![United Airlines logo]()
$221
This United Airlines deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/58:55 am -
Nonstop4h 49m
Sat 10/103:56 pm -
Nonstop5h 09m
Deal found 9/7![United Airlines logo]()
$217
This American Airlines deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/65:00 am -
1 stop9h 28m
Tue 10/136:30 am -
1 stop14h 25m
Deal found 9/7![American Airlines logo]()
$228
This Orbitz deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/104:41 pm -
1 stop21h 38m
Fri 10/1612:59 am -
1 stop22h 40m
Deal found 9/8![Frontier logo]()
$233
This American Airlines deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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 10/145:29 pm -
1 stop17h 02m
Wed 10/282:53 pm -
Nonstop5h 36m
Deal found 9/5![American Airlines logo]()
$227
This Priceline deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/158:04 am -
1 stop28h 27m
Thu 10/292:51 pm -
1 stop8h 52m
Deal found 9/9![Frontier logo]()
$237
This American Airlines deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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 10/166:40 pm -
1 stop15h 40m
Wed 10/2112:41 pm -
1 stop12h 27m
Deal found 9/5![American Airlines logo]()
$226
This United Airlines deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 -
Nonstop4h 49m
Fri 10/231:00 am -
1 stop7h 42m
Deal found 9/6![United Airlines logo]()
$222
This deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/238:26 am -
1 stop9h 13m
Thu 11/57:00 am -
1 stop10h 37m
Deal found 9/8![Frontier logo]()
$219
This American Airlines deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 10/257:29 pm -
1 stop15h 02m
Tue 10/276:00 am -
1 stop13h 35m
Deal found 9/9![American Airlines logo]()
$234
This Arajet deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/264:30 am -
1 stop11h 25m
Thu 10/293:30 pm -
1 stop9h 10m
Deal found 9/9![Multiple Airlines logo]()
$343
This Arajet deal was found by Cheapflights users on 9/6. Clicking the “Pick Dates” 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 10/3111:27 am -
1 stop9h 13m
Fri 11/61:40 am -
1 stop9h 17m
Deal found 9/6![Multiple Airlines logo]()
$344
One-way flights from O'Hare Intl to CaribbeanSearch for one-way flight options from O'Hare Intl to Caribbean. Find affordable one-way fares based on user searches. Data last updated September 9, 2026.
Search for one-way flight options from O'Hare Intl to Caribbean. Find affordable one-way fares based on user searches. Data last updated September 9, 2026.
This United Airlines deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/82:16 pm -
Nonstop4h 44m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![United Airlines logo]()
$109
This Super.com deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/287:00 am -
1 stop8h 12m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![JetBlue logo]()
$112
This American Airlines deal was found by Cheapflights users on 9/4. Clicking the “Pick Dates” 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 10/94:31 pm -
1 stop16h 15m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/4![American Airlines logo]()
$113
This American Airlines deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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 10/288:13 am -
Nonstop4h 50m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![American Airlines logo]()
$114
This Super.com deal was found by Cheapflights users on 9/9. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/17:25 am -
1 stop15h 36m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/9![Frontier logo]()
$115
This American Airlines deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/288:50 am -
2 stops10h 57m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![American Airlines logo]()
$116
This Trip.com deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/307:11 am -
1 stop7h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![Frontier logo]()
$117
This American Airlines deal was found by Cheapflights users on 9/7. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/304:35 pm -
1 stop15h 49m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/7![American Airlines logo]()
$121
This eDestinos deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/77:11 am -
1 stop7h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Frontier logo]()
$122
This Travelocity deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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.
Sun 10/49:55 am -
1 stop25h 30m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![Air Canada logo]()
$125
This Frontier deal was found by Cheapflights users on 9/5. Clicking the “Pick Dates” 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 10/67:11 am -
1 stop7h 06m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/5![Frontier logo]()
$126
This Orbitz deal was found by Cheapflights users on 9/8. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/78:45 am -
1 stop27h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/8![Air Canada logo]()
$128
Find flight deals from O'Hare Intl to Caribbean
Keep the following information in mind while searching for O'Hare Intl to Caribbean flight deals. Data was last updated September 9, 2026.
Round-trip from | $216 (Priceline) |
|---|---|
One-way from | $109 (United Airlines) |
Popular in | December |
Cheapest in | August |
Average price | $376 |
Good round-trip deal | $319 or less |
Good one-way deal | $156 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from O'Hare Intl to Caribbean that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated September 9, 2026.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Caribbean that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoSan Juan
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Wed 11/18
1:00 pm-1:13 am
1 stop10h 13m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$113
ChicagoSan Juan
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Mon 9/14
1:30 pm-11:50 pm
1 stop9h 20m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$133
ChicagoGeorge Town
ORD Chicago O'Hare Intl - GCM George Town Owen Roberts Intl
ORDGCM
Chicago O'Hare Intl
Wed 11/18
3:45 pm-12:10 pm
2 stops19h 25m
George Town Owen Roberts Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$141
ChicagoGeorge Town
ORD Chicago O'Hare Intl - GCM George Town Owen Roberts Intl
ORDGCM
Chicago O'Hare Intl
Wed 12/2
7:02 am-12:10 pm
1 stop28h 08m
George Town Owen Roberts Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$143
ChicagoGeorge Town
ORD Chicago O'Hare Intl - GCM George Town Owen Roberts Intl
ORDGCM
Chicago O'Hare Intl
Sun 12/6
8:45 am-12:10 pm
1 stop26h 25m
George Town Owen Roberts Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$143
ChicagoNassau
ORD Chicago O'Hare Intl - NAS Nassau Intl
ORDNAS
Chicago O'Hare Intl
Sat 10/10
10:50 am-5:30 pm
2 stops29h 40m
Nassau Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$144
ChicagoSan Juan
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Tue 10/6
8:55 am-2:44 pm
Nonstop4h 49m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$154
ChicagoSan Juan
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Sun 12/6
2:16 pm-9:00 pm
Nonstop4h 44m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$154
ChicagoSan Juan
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Sun 10/4
8:55 am-2:44 pm
Nonstop4h 49m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$154
ChicagoSanto Domingo
ORD Chicago O'Hare Intl - SDQ Santo Domingo Las Americas
ORDSDQ
Chicago O'Hare Intl
Mon 10/26
4:30 am-4:55 pm
1 stop11h 25m
Santo Domingo Las Americas
Wed 12/31
12:00 am-10:30 pm
Nonstop0h 00m
$158
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from O'Hare Intl to Caribbean
Have a flexible travel schedule? Discover the best time to fly to Caribbean from O'Hare Intl with our price prediction graph.
ORD-SJU
ORD-GCM
ORD-NAS
ORD-PLS
ORD-PUJ
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago O'Hare Intl Airport to Caribbean
ORD-0CB
ORD-SJU
ORD-GCM
ORD-NAS
ORD-PLS
What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Caribbean?
Currently, August is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Caribbean (average of $423). Flying from Chicago O'Hare Intl Airport to Caribbean in December is currently the most expensive (average of $608). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from ORD to CB?
Find hourly flight availability from O'Hare Intl to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated September 9, 2026.
A simple way to save on the total cost of your ticket is to fly from Chicago O'Hare Intl Airport to Caribbean in the evening. If you’re flexible enough to do this you can expect to save up to 32% on your trip compared to booking a flight in the morning.
Weekly flight availability from Chicago O'Hare Intl Airport to Caribbean
Explore weekly flight availability from O'Hare Intl to Caribbean. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated September 9, 2026.
The most flights from ORD to 0CB are scheduled on a Monday (4 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (1 on average).
How far ahead should I book a flight from Chicago O'Hare Intl Airport to Caribbean?
The price you pay for your flight from Chicago O'Hare Intl Airport to Caribbean may vary depending on when you book. For the best chance of a lower fare, look to book 19 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
What is the cheapest day to fly from Chicago O'Hare Intl Airport to Caribbean?
Use this chart to determine the cheapest time to fly round-trip from O'Hare Intl to Caribbean. Price data was last updated on September 5, 2026.
Travelers seeking maximum savings on their Chicago O'Hare Intl Airport to Caribbean flight should consider departing on Saturday 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
Get insights into the airlines that provide service to Caribbean. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean. Reviews last updated September 9, 2026.
See what other customers who have flown with United Airlines,American Airlines, andJetBlue from Chicago O'Hare Intl Airport to Caribbean have to say. You can also see how each airline compares in terms of entertainment options, comfort, food, crew/service, and boarding process.
Comfort
7.3
Entertainment
7.1
Overall
7.4
Boarding
7.7
Crew
8.1
Food
6.7
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Comfort
7.3
Entertainment
7.1
Overall
7.4
Boarding
7.7
Crew
8.1
Food
6.7
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Comfort
7.3
Entertainment
7.1
Overall
7.4
Boarding
7.7
Crew
8.1
Food
6.7
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Comfort
7.3
Entertainment
7.1
Overall
7.4
Boarding
7.7
Crew
8.1
Food
6.7
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Comfort
7.3
Entertainment
7.1
Overall
7.4
Boarding
7.7
Crew
8.1
Food
6.7
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Related info for your journey
Find useful and relevant information for your journey from O'Hare Intl to Caribbean. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Top countries
Top destinations
Alternative routes for O'Hare Intl to Caribbean
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Caribbean by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from O'Hare Intl to Caribbean by cabin class
Find flights from O'Hare Intl to Caribbean, based on your preferred cabin class, be it economy, premium economy, business, or first class.
O'Hare Intl and Caribbean flights
Browse other O'Hare Intl and Caribbean flight options. Last updated on September 9, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Fly to Caribbean countries
Consider these flights traveling to countries located in Caribbean.
O'Hare Intl to Caribbean flights
Consider these flights traveling from O'Hare Intl to Caribbean.
Top 9 airlines flying from O'Hare Intl to Caribbean
Discover the top 9 airlines that operate flights from O'Hare Intl to Caribbean. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated September 9, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$118 | Average$484 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$118 | Average$457 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$144 | Average$440 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$223 | Average$376 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$231 | Average$554 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$235 | Average$586 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$264 | Average$593 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$292 | Average$629 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$372 | Average$566 | FlexibilityNo cancel fee | On-time63% |