$106+ Cheap flights from O'Hare Intl (ORD) to Caribbean
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 5/8. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — SJU
Mai 27 — Jun 31
Round-trip
1 adult, Economy
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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 April 27, 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 April 27, 2026.
This Delta deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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.
Mi 8/1911:10 am
ORD
- SJU
1 stop10h 13m
Delta
Mi 9/25:45 pm
SJU
- ORD
1 stop7h 12m
Delta
Deal found 4/27![Delta logo]()
$226
This Frontier deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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.
Di 5/123:55 pm
ORD
- SJU
1 stop9h 13m
Frontier
Do 5/216:24 pm
SJU
- ORD
Nonstop5h 22m
Frontier
Deal found 4/25![Frontier logo]()
$227
This Cheapflightsfares deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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.
Fr 5/154:44 pm
ORD
- SJU
Nonstop4h 37m
Spirit Airlines
Di 5/1911:01 am
SJU
- ORD
Nonstop5h 10m
Spirit Airlines
Deal found 4/25![Spirit Airlines logo]()
$228
This Expedia deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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.
Mi 4/2910:00 am
ORD
- SJU
Nonstop4h 39m
Multiple Airlines
Do 4/301:59 am
SJU
- ORD
1 stop19h 04m
Multiple Airlines
Deal found 4/25![Multiple Airlines logo]()
$229
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Di 5/53:55 pm
ORD
- SJU
1 stop9h 13m
Frontier
Do 5/146:09 pm
SJU
- ORD
1 stop30h 04m
Frontier
Deal found 4/22![Frontier logo]()
$230
This Cheapflightsfares deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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.
So 5/175:05 am
ORD
- SJU
1 stop12h 54m
Spirit Airlines
Do 5/2111:39 am
SJU
- ORD
Nonstop5h 10m
Spirit Airlines
Deal found 4/27![Spirit Airlines logo]()
$231
This Kiwi.com deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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.
Di 5/2612:33 am
ORD
- SJU
Nonstop4h 51m
Frontier
Fr 5/296:00 am
SJU
- ORD
1 stop7h 37m
Frontier
Deal found 4/26![Frontier logo]()
$232
This Cheapflightsfares deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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.
Mi 4/2910:00 am
ORD
- SJU
Nonstop4h 39m
Spirit Airlines
Fr 5/14:34 pm
SJU
- ORD
Nonstop5h 15m
Spirit Airlines
Deal found 4/25![Spirit Airlines logo]()
$233
This Orbitz deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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.
So 5/247:52 pm
ORD
- SJU
1 stop7h 09m
Frontier
Fr 5/296:00 am
SJU
- ORD
1 stop7h 37m
Frontier
Deal found 4/26![Frontier logo]()
$234
This Trip.com deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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.
Sa 5/95:30 pm
ORD
- SJU
1 stop7h 38m
Frontier
Sa 5/166:30 am
SJU
- ORD
1 stop13h 14m
Frontier
Deal found 4/27![Frontier logo]()
$235
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.
Sa 8/81:49 pm
ORD
- SJU
1 stop7h 40m
Delta
Do 8/131:06 pm
SJU
- ORD
1 stop11h 51m
Delta
Deal found 4/23![Delta logo]()
$236
This United Airlines deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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.
So 5/102:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Fr 5/157:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
Deal found 4/24![United Airlines logo]()
$237
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 April 27, 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 April 27, 2026.
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.
So 7/265:15 am
ORD
- SJU
1 stop10h 30m
Delta
Fr 8/72:42 pm
SJU
- ORD
1 stop8h 26m
Delta
Deal found 4/23![Delta logo]()
$256
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.
Sa 5/25:30 am
ORD
- MBJ
1 stop8h 00m
United Airlines
Di 5/52:40 pm
MBJ
- ORD
1 stop17h 13m
United Airlines
Deal found 4/22![United Airlines logo]()
$332
This Arajet deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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.
Sa 8/112:12 pm
ORD
- SDQ
1 stop8h 28m
Multiple Airlines
So 8/301:55 pm
SDQ
- ORD
1 stop9h 15m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$393
This Arajet deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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.
Sa 5/1612:12 pm
ORD
- PUJ
Nonstop4h 45m
Arajet
Sa 5/237:02 am
PUJ
- ORD
Nonstop5h 10m
Arajet
Deal found 4/25![Arajet logo]()
$395
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.
Mi 7/155:00 am
ORD
- MBJ
1 stop8h 09m
American Airlines
So 7/192:23 pm
MBJ
- ORD
Nonstop4h 53m
American Airlines
Deal found 4/22![American Airlines logo]()
$447
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.
Mo 6/83:21 pm
ORD
- SDQ
1 stop19h 21m
Copa Airlines
Mi 7/82:17 pm
SDQ
- ORD
1 stop14h 43m
Copa Airlines
Deal found 4/23![Copa Airlines logo]()
$490
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.
Sa 7/259:45 am
ORD
- SJU
1 stop11h 44m
Delta
Mi 8/52:05 pm
SJU
- ORD
1 stop7h 26m
Delta
Deal found 4/23![Delta logo]()
$266
This Mytrip deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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.
Fr 5/297:33 pm
ORD
- STT
2 stops17h 43m
Spirit Airlines
Do 6/111:52 pm
STT
- ORD
2 stops23h 12m
Spirit Airlines
Deal found 4/26![Spirit Airlines logo]()
$557
This JetBlue deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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.
So 5/36:00 am
ORD
- PUJ
1 stop10h 41m
JetBlue
Do 5/712:30 pm
PUJ
- ORD
1 stop9h 23m
JetBlue
Deal found 4/26![JetBlue logo]()
$618
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.
So 7/266:30 am
ORD
- SJU
1 stop9h 15m
Delta
Mo 8/32:42 pm
SJU
- ORD
1 stop8h 26m
Delta
Deal found 4/22![Delta logo]()
$286
This United Airlines deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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.
Di 5/122:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Sa 5/164:55 pm
SJU
- ORD
1 stop7h 49m
United Airlines
Deal found 4/26![United Airlines logo]()
$345
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.
Fr 6/198:03 am
ORD
- SJU
1 stop11h 40m
Delta
Mi 6/241:10 pm
SJU
- ORD
1 stop9h 38m
Delta
Deal found 4/23![Delta logo]()
$296
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.
Mi 5/132:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Sa 5/307:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
Deal found 4/22![United Airlines logo]()
$350
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.
Sa 7/259:45 am
ORD
- SJU
1 stop11h 44m
Delta
Sa 8/17:30 am
SJU
- ORD
1 stop10h 27m
Delta
Deal found 4/22![Delta logo]()
$302
This United Airlines deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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.
Sa 6/208:40 am
ORD
- MBJ
1 stop6h 30m
United Airlines
Mi 6/244:12 pm
MBJ
- ORD
1 stop7h 14m
United Airlines
Deal found 4/25![United Airlines logo]()
$354
This Arajet deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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.
Mo 7/205:30 am
ORD
- PUJ
Nonstop4h 45m
Arajet
Sa 7/257:02 am
PUJ
- ORD
Nonstop5h 10m
Arajet
Deal found 4/24![Arajet logo]()
$454
This United Airlines deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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.
Sa 7/48:40 am
ORD
- MBJ
Nonstop4h 10m
United Airlines
Di 7/74:12 pm
MBJ
- ORD
1 stop15h 15m
United Airlines
Deal found 4/26![United Airlines logo]()
$356
This Copa 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Do 10/18:01 am
ORD
- SDQ
1 stop13h 55m
Copa Airlines
Mo 10/58:47 am
SDQ
- ORD
1 stop17h 10m
Copa Airlines
Deal found 4/22![Copa Airlines logo]()
$490
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sa 5/308:40 am
ORD
- MBJ
Nonstop4h 10m
United Airlines
Mi 6/34:12 pm
MBJ
- ORD
1 stop7h 14m
United Airlines
Deal found 4/23![United Airlines logo]()
$363
This Copa Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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.
So 5/313:21 pm
ORD
- SDQ
1 stop19h 21m
Copa Airlines
Di 6/26:39 pm
SDQ
- ORD
1 stop20h 27m
Copa Airlines
Deal found 4/27![Copa Airlines logo]()
$490
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.
Sa 7/259:45 am
ORD
- SJU
1 stop11h 44m
Delta
So 8/212:56 pm
SJU
- ORD
1 stop10h 12m
Delta
Deal found 4/23![Delta logo]()
$401
This United 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mo 5/48:49 am
ORD
- SJU
Nonstop4h 55m
United Airlines
Fr 5/87:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
Deal found 4/23![United Airlines logo]()
$367
This Copa 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mi 8/193:21 pm
ORD
- SDQ
1 stop10h 04m
Copa Airlines
Mi 8/262:17 pm
SDQ
- ORD
1 stop11h 45m
Copa Airlines
Deal found 4/22![Copa Airlines logo]()
$490
This Mytrip deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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.
Fr 5/2912:59 pm
ORD
- STT
3 stops24h 17m
Multiple Airlines
Do 6/111:52 pm
STT
- ORD
3 stops22h 38m
Multiple Airlines
Deal found 4/26![Multiple Airlines logo]()
$657
This United Airlines deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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.
Sa 5/98:40 am
ORD
- MBJ
Nonstop4h 10m
United Airlines
Di 5/122:40 pm
MBJ
- ORD
1 stop8h 35m
United Airlines
Deal found 4/24![United Airlines logo]()
$383
This Arajet deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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.
Mo 6/84:30 am
ORD
- PUJ
Nonstop4h 45m
Arajet
So 6/146:00 pm
PUJ
- ORD
Nonstop5h 10m
Arajet
Deal found 4/24![Arajet logo]()
$617
This Copa Airlines deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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.
Di 6/308:02 am
ORD
- SDQ
1 stop13h 54m
Copa Airlines
Di 7/712:43 pm
SDQ
- ORD
1 stop12h 18m
Copa Airlines
Deal found 4/25![Copa Airlines logo]()
$530
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.
So 5/175:30 am
ORD
- PUJ
1 stop8h 05m
Delta
Fr 5/224:00 pm
PUJ
- ORD
1 stop8h 59m
Delta
Deal found 4/23![Delta logo]()
$460
This Copa 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mi 7/13:21 pm
ORD
- SDQ
1 stop18h 34m
Copa Airlines
Mi 7/152:17 pm
SDQ
- ORD
1 stop14h 43m
Copa Airlines
Deal found 4/22![Copa Airlines logo]()
$530
This United Airlines deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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.
Mi 5/276:30 am
ORD
- MBJ
1 stop8h 40m
United Airlines
Di 6/24:12 pm
MBJ
- ORD
1 stop7h 14m
United Airlines
Deal found 4/25![United Airlines logo]()
$409
Last-minute flights from O'Hare Intl to CaribbeanDiscover last-minute flight deals from O'Hare Intl to Caribbean. Data last updated April 27, 2026 and is based on user searches.
Discover last-minute flight deals from O'Hare Intl to Caribbean. Data last updated April 27, 2026 and is based on user searches.
This Expedia deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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.
Mi 4/2910:00 am
ORD
- SJU
Nonstop4h 39m
Multiple Airlines
Do 4/301:59 am
SJU
- ORD
1 stop19h 04m
Multiple Airlines
Deal found 4/25![Multiple Airlines logo]()
$229
This Cheapflightsfares deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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.
Mi 4/2910:00 am
ORD
- SJU
Nonstop4h 39m
Spirit Airlines
Fr 5/14:34 pm
SJU
- ORD
Nonstop5h 15m
Spirit Airlines
Deal found 4/25![Spirit Airlines logo]()
$233
This American Airlines deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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.
Mo 5/48:05 am
ORD
- MBJ
Nonstop4h 08m
American Airlines
Mi 5/131:15 pm
MBJ
- ORD
Nonstop4h 40m
American Airlines
Deal found 4/26![American Airlines logo]()
$319
This Priceline 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Di 5/53:55 pm
ORD
- SJU
1 stop9h 13m
Frontier
Do 5/146:09 pm
SJU
- ORD
1 stop30h 04m
Frontier
Deal found 4/22![Frontier logo]()
$230
This Frontier deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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.
Sa 5/95:30 pm
ORD
- SJU
1 stop7h 38m
Frontier
Sa 5/166:30 am
SJU
- ORD
1 stop13h 14m
Frontier
Deal found 4/25![Frontier logo]()
$226
This United Airlines deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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.
So 5/102:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Fr 5/157:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
Deal found 4/24![United Airlines logo]()
$237
This Frontier deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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.
Di 5/123:55 pm
ORD
- SJU
1 stop9h 13m
Frontier
Do 5/216:24 pm
SJU
- ORD
Nonstop5h 22m
Frontier
Deal found 4/25![Frontier logo]()
$227
This Cheapflightsfares deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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.
Fr 5/154:44 pm
ORD
- SJU
Nonstop4h 37m
Spirit Airlines
Di 5/1911:01 am
SJU
- ORD
Nonstop5h 10m
Spirit Airlines
Deal found 4/25![Spirit Airlines logo]()
$228
This Cheapflightsfares deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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.
So 5/175:05 am
ORD
- SJU
1 stop12h 54m
Spirit Airlines
Do 5/2111:39 am
SJU
- ORD
Nonstop5h 10m
Spirit Airlines
Deal found 4/27![Spirit Airlines logo]()
$231
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.
Mo 5/188:05 am
ORD
- MBJ
Nonstop4h 08m
American Airlines
Do 5/212:30 pm
MBJ
- ORD
Nonstop4h 45m
American Airlines
Deal found 4/22![American Airlines logo]()
$318
This Orbitz deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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.
So 5/247:52 pm
ORD
- SJU
1 stop7h 09m
Frontier
Fr 5/296:00 am
SJU
- ORD
1 stop7h 37m
Frontier
Deal found 4/26![Frontier logo]()
$234
This Kiwi.com deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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.
Di 5/2612:33 am
ORD
- SJU
Nonstop4h 51m
Frontier
Fr 5/296:00 am
SJU
- ORD
1 stop7h 37m
Frontier
Deal found 4/26![Frontier logo]()
$232
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 April 27, 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 April 27, 2026.
This Trip.com deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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.
Fr 5/84:44 pm
ORD
- SJU
Nonstop4h 37m
Spirit Airlines
Deal found 4/27![Spirit Airlines logo]()
$106
This Frontier deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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.
Sa 7/1812:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 4/26![Frontier logo]()
$107
This eDestinos deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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.
Di 5/2612:33 am
ORD
- SJU
Nonstop4h 51m
Frontier
Deal found 4/26![Frontier logo]()
$108
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.
Mo 5/185:30 pm
ORD
- SJU
1 stop7h 38m
Frontier
Deal found 4/22![Frontier logo]()
$112
This Super.com 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Do 5/147:56 pm
ORD
- PUJ
1 stop14h 01m
Frontier
Deal found 4/23![Frontier logo]()
$113
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.
Di 5/196:40 am
ORD
- SJU
1 stop14h 25m
American Airlines
Deal found 4/22![American Airlines logo]()
$113
This eDestinos deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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.
Fr 5/12:09 pm
ORD
- SJU
1 stop8h 34m
Frontier
Deal found 4/24![Frontier logo]()
$116
This American Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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.
Mi 5/278:32 am
ORD
- SJU
1 stop13h 29m
American Airlines
Deal found 4/27![American Airlines logo]()
$118
This Frontier 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fr 5/2912:33 am
ORD
- SJU
Nonstop4h 51m
Frontier
Deal found 4/23![Frontier logo]()
$119
This Travelocity deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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.
Mo 5/2512:33 am
ORD
- PUJ
1 stop18h 46m
Frontier
Deal found 4/26![Frontier logo]()
$120
This eDestinos deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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.
Do 4/3012:16 pm
ORD
- SJU
1 stop10h 43m
Frontier
Deal found 4/24![Frontier logo]()
$121
This Kiwi.com 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fr 5/85:30 pm
ORD
- PUJ
1 stop14h 48m
Frontier
Deal found 4/22![Frontier logo]()
$123
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 April 27, 2026.
Round-trip from | $226 (Delta) |
|---|---|
One-way from | $106 (Trip.com) |
Popular in | December |
Cheapest in | January |
Average price | $381 |
Good round-trip deal | $309 or less |
Good one-way deal | $138 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 2,558,603 searches. Data last updated April 27, 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 - SJU
ORDSJU
Chicago O'Hare Intl
So 7/26
5:15 am-4:45 pm
1 stop10h 30m
San Juan Luis Munoz Marin Intl
Fr 8/7
2:42 pm-10:08 pm
1 stop8h 26m
$256
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Sa 7/25
9:45 am-10:29 pm
1 stop11h 44m
San Juan Luis Munoz Marin Intl
Mi 8/5
2:05 pm-8:31 pm
1 stop7h 26m
$266
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
So 7/26
6:30 am-4:45 pm
1 stop9h 15m
San Juan Luis Munoz Marin Intl
Mo 8/3
2:42 pm-10:08 pm
1 stop8h 26m
$286
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Fr 6/19
8:03 am-8:43 pm
1 stop11h 40m
San Juan Luis Munoz Marin Intl
Mi 6/24
1:10 pm-9:48 pm
1 stop9h 38m
$296
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Sa 7/25
9:45 am-10:29 pm
1 stop11h 44m
San Juan Luis Munoz Marin Intl
Sa 8/1
7:30 am-4:57 pm
1 stop10h 27m
$302
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Sa 5/2
5:30 am-1:30 pm
1 stop8h 00m
Montego Bay Sangster Intl
Di 5/5
2:40 pm-7:53 am
1 stop17h 13m
$332
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Di 5/12
2:38 pm-8:34 pm
Nonstop4h 56m
San Juan Luis Munoz Marin Intl
Sa 5/16
4:55 pm-11:44 pm
1 stop7h 49m
$345
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Mi 5/13
2:38 pm-8:34 pm
Nonstop4h 56m
San Juan Luis Munoz Marin Intl
Sa 5/30
7:40 am-11:53 am
Nonstop5h 13m
$350
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Sa 6/20
8:40 am-3:10 pm
1 stop6h 30m
Montego Bay Sangster Intl
Mi 6/24
4:12 pm-11:26 pm
1 stop7h 14m
$354
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Sa 7/4
8:40 am-12:50 pm
Nonstop4h 10m
Montego Bay Sangster Intl
Di 7/7
4:12 pm-7:27 am
1 stop15h 15m
$356
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-MBJ
ORD-SDQ
ORD-PUJ
ORD-STT
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-MBJ
ORD-SDQ
ORD-PUJ
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 29 days in advance of your trip. Fares are likely to increase a fortnight or so before your departure date.
What is the cheapest month to book a flight from Chicago O'Hare Intl Airport to Caribbean?
Currently, July is the cheapest month in which you can book a flight from Chicago O'Hare Intl Airport to Caribbean (average of $397). Flying from Chicago O'Hare Intl Airport to Caribbean in December is currently the most expensive (average of $661). 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 April 27, 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 31% on your trip compared to booking a flight in the morning.
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 April 25, 2026.
Travelers seeking maximum savings on their Chicago O'Hare Intl Airport to Caribbean flight should consider departing on Wednesday evenings when fares are most often at their lowest. Saturday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Weekly flight availability from Chicago O'Hare Intl Airport to Caribbean
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 April 27, 2026.
The most flights from ORD to 0CB are scheduled on a Monday (9 on average). You will have fewer flight options on Monday, which is when the least amount of flights are scheduled (9 on average).
Reviews of airlines servicing Caribbean
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 April 27, 2026.
See what other customers who have flown with United Airlines,American Airlines, andSpirit Airlines 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.
Boarding
7.7
Crew
8.1
Food
6.6
Comfort
7.3
Entertainment
7.1
Overall
7.4
Reviews
1 / 20
8.0
ExcellentAnonymous,Apr 2026
DFW - EWR
Boarding
7.7
Crew
8.1
Food
6.6
Comfort
7.3
Entertainment
7.1
Overall
7.4
Reviews
1 / 20
8.0
ExcellentAnonymous,Apr 2026
DFW - EWR
Boarding
7.7
Crew
8.1
Food
6.6
Comfort
7.3
Entertainment
7.1
Overall
7.4
Reviews
1 / 20
8.0
ExcellentAnonymous,Apr 2026
DFW - EWR
Boarding
7.7
Crew
8.1
Food
6.6
Comfort
7.3
Entertainment
7.1
Overall
7.4
Reviews
1 / 20
8.0
ExcellentAnonymous,Apr 2026
DFW - EWR
Boarding
7.7
Crew
8.1
Food
6.6
Comfort
7.3
Entertainment
7.1
Overall
7.4
Reviews
1 / 20
8.0
ExcellentAnonymous,Apr 2026
DFW - EWR
Related info for your journey
Find useful and relevant information for your journey from O'Hare Intl to Caribbean. 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
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 April 27, 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 2,558,603 searches. Data last updated April 27, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$100 | Average$394 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$118 | Average$511 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$119 | Average$421 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$143 | Average$494 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$175 | Average$480 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$202 | Average$342 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$213 | Average$484 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$255 | Average$580 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$311 | Average$599 | FlexibilityNo cancel fee | On-time71% |