$88+ Cheap flights from Chicago (CHI) 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 8/12. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJU
Jun 18 — Jun 251
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Caribbean Islands 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
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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 Chicago to Caribbean Islands
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Cheapest flights from Chicago to Caribbean IslandsExplore the most affordable flight options available from Chicago to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 19, 2026.
Explore the most affordable flight options available from Chicago to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on May 19, 2026.
This Kiwi.com deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/812:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Thu 8/137:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 5/15![Frontier logo]()
$226
This Frontier deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/812:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Tue 8/186:11 pm
SJU
- ORD
Nonstop5h 15m
Frontier
Deal found 5/16![Frontier logo]()
$229
This Kiwi.com deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/812:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Mon 8/177:00 am
SJU
- ORD
2 stops26h 03m
Frontier
Deal found 5/16![Frontier logo]()
$230
This American Airlines deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/115:14 pm
ORD
- SJU
Nonstop4h 53m
American Airlines
Tue 8/187:14 pm
SJU
- ORD
1 stop13h 20m
American Airlines
Deal found 5/18![American Airlines logo]()
$232
This Kiwi.com deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/812:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Tue 8/117:00 am
SJU
- ORD
2 stops25h 53m
Frontier
Deal found 5/15![Frontier logo]()
$233
This American Airlines deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/65:14 pm
ORD
- SJU
Nonstop4h 53m
American Airlines
Tue 8/117:14 pm
SJU
- ORD
1 stop14h 46m
American Airlines
Deal found 5/15![American Airlines logo]()
$235
This Delta deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/198:02 am
ORD
- SJU
1 stop7h 35m
Delta
Thu 8/275:49 pm
SJU
- ORD
1 stop7h 09m
Delta
Deal found 5/15![Delta logo]()
$236
This Southwest deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1912:45 pm
MDW
- SJU
2 stops8h 15m
Southwest
Wed 8/261:45 pm
SJU
- MDW
1 stop8h 15m
Southwest
Deal found 5/18![Southwest logo]()
$236
This American Airlines deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/195:14 pm
ORD
- SJU
Nonstop4h 53m
American Airlines
Wed 9/26:51 am
SJU
- ORD
1 stop8h 24m
American Airlines
Deal found 5/19![American Airlines logo]()
$237
This American Airlines deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/154:59 pm
ORD
- SJU
Nonstop4h 53m
American Airlines
Tue 8/187:14 pm
SJU
- ORD
1 stop14h 46m
American Airlines
Deal found 5/19![American Airlines logo]()
$242
This Expedia deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2112:29 am
ORD
- SJU
Nonstop4h 57m
Frontier
Fri 8/286:11 pm
SJU
- ORD
Nonstop5h 15m
Frontier
Deal found 5/14![Frontier logo]()
$243
This Kiwi.com deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/1512:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Mon 8/246:11 pm
SJU
- ORD
Nonstop5h 15m
Frontier
Deal found 5/16![Frontier logo]()
$244
Best flights from Chicago to Caribbean IslandsDiscover carefully curated flight deals from Chicago to Caribbean Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 19, 2026.
Discover carefully curated flight deals from Chicago to Caribbean Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated May 19, 2026.
This Delta deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/195:28 am
ORD
- SJU
1 stop10h 09m
Delta
Wed 9/25:45 pm
SJU
- ORD
1 stop7h 12m
Delta
Deal found 5/17![Delta logo]()
$236
This Southwest deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/305:00 am
MDW
- SJU
1 stop7h 00m
Southwest
Thu 9/36:00 am
SJU
- MDW
1 stop7h 40m
Southwest
Deal found 5/15![Southwest logo]()
$256
This United Airlines deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 11/118:42 am
ORD
- MBJ
Nonstop4h 04m
United Airlines
Wed 11/183:36 pm
MBJ
- ORD
1 stop9h 06m
United Airlines
Deal found 5/17![United Airlines logo]()
$338
This JetBlue deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/217:00 am
ORD
- NAS
1 stop9h 14m
JetBlue
Sat 7/256:24 pm
NAS
- ORD
1 stop6h 20m
JetBlue
Deal found 5/18![JetBlue logo]()
$374
This Arajet deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/35:30 am
ORD
- PUJ
Nonstop4h 45m
Arajet
Sat 8/87:02 am
PUJ
- ORD
Nonstop5h 10m
Arajet
Deal found 5/17![Arajet logo]()
$393
This Delta deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/221:48 pm
ORD
- SJU
1 stop7h 41m
Delta
Fri 8/2812:56 pm
SJU
- ORD
1 stop12h 02m
Delta
Deal found 5/18![Delta logo]()
$246
This Southwest deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1912:45 pm
MDW
- SJU
1 stop8h 15m
Southwest
Sat 8/225:05 am
SJU
- MDW
2 stops9h 05m
Southwest
Deal found 5/18![Southwest logo]()
$266
This Delta deal was found by Cheapflights users on 5/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/221:48 pm
ORD
- SJU
1 stop7h 41m
Delta
Mon 8/317:00 am
SJU
- ORD
1 stop11h 41m
Delta
Deal found 5/19![Delta logo]()
$256
This American Airlines deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/115:07 am
ORD
- STT
2 stops9h 53m
American Airlines
Sat 7/1812:47 pm
STT
- ORD
1 stop11h 12m
American Airlines
Deal found 5/18![American Airlines logo]()
$590
This Copa Airlines deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/88:01 am
ORD
- PUJ
1 stop8h 39m
Copa Airlines
Tue 10/132:03 pm
PUJ
- ORD
1 stop24h 56m
Copa Airlines
Deal found 5/17![Copa Airlines logo]()
$658
This United Airlines deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/48:40 am
ORD
- MBJ
Nonstop4h 10m
United Airlines
Sat 7/111:52 pm
MBJ
- ORD
Nonstop4h 23m
United Airlines
Deal found 5/15![United Airlines logo]()
$395
This Delta deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/289:45 am
ORD
- SJU
1 stop11h 45m
Delta
Mon 8/32:11 pm
SJU
- ORD
1 stop7h 11m
Delta
Deal found 5/18![Delta logo]()
$331
This JetBlue deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/293:27 pm
ORD
- SJU
1 stop9h 11m
JetBlue
Sat 6/131:12 pm
SJU
- ORD
1 stop9h 18m
JetBlue
Deal found 5/18![JetBlue logo]()
$452
This Delta deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 9/37:10 am
ORD
- SJU
1 stop8h 25m
Delta
Tue 9/87:30 am
SJU
- ORD
1 stop10h 15m
Delta
Deal found 5/18![Delta logo]()
$341
This United Airlines deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/148:40 am
ORD
- MBJ
1 stop6h 30m
United Airlines
Sat 7/184:33 pm
MBJ
- ORD
1 stop8h 12m
United Airlines
Deal found 5/14![United Airlines logo]()
$415
This Southwest deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/272:30 pm
MDW
- SJU
1 stop8h 45m
Southwest
Sat 8/19:25 pm
SJU
- MDW
1 stop12h 05m
Southwest
Deal found 5/17![Southwest logo]()
$431
This Arajet deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/710:27 am
ORD
- PUJ
Nonstop4h 45m
Arajet
Thu 11/127:30 pm
PUJ
- ORD
Nonstop5h 10m
Arajet
Deal found 5/16![Arajet logo]()
$476
This United Airlines deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/278:40 am
ORD
- MBJ
1 stop6h 30m
United Airlines
Thu 7/24:12 pm
MBJ
- ORD
1 stop7h 19m
United Airlines
Deal found 5/15![United Airlines logo]()
$419
This Southwest deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/284:40 pm
MDW
- SJU
1 stop6h 35m
Southwest
Mon 8/36:00 am
SJU
- MDW
2 stops12h 45m
Southwest
Deal found 5/18![Southwest logo]()
$451
This JetBlue deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/147:00 am
ORD
- PUJ
1 stop7h 27m
JetBlue
Tue 7/2111:24 am
PUJ
- ORD
1 stop11h 31m
JetBlue
Deal found 5/15![JetBlue logo]()
$505
This United Airlines deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/288:42 am
ORD
- MBJ
Nonstop4h 04m
United Airlines
Sun 11/12:48 pm
MBJ
- ORD
Nonstop4h 28m
United Airlines
Deal found 5/17![United Airlines logo]()
$458
This Southwest deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/2012:50 pm
MDW
- SJU
2 stops9h 10m
Southwest
Thu 7/910:20 pm
SJU
- MDW
1 stop11h 55m
Southwest
Deal found 5/14![Southwest logo]()
$466
This Delta deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/296:05 am
MDW
- SJU
1 stop6h 37m
Delta
Mon 8/312:40 pm
SJU
- MDW
1 stop8h 06m
Delta
Deal found 5/14![Delta logo]()
$426
This JetBlue deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/66:00 am
ORD
- NAS
1 stop9h 03m
JetBlue
Thu 7/96:24 pm
NAS
- ORD
1 stop6h 20m
JetBlue
Deal found 5/17![JetBlue logo]()
$520
This United Airlines deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/128:55 am
ORD
- SJU
Nonstop4h 49m
United Airlines
Sat 9/194:55 pm
SJU
- ORD
1 stop7h 45m
United Airlines
Deal found 5/16![United Airlines logo]()
$462
This Southwest deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/302:30 pm
MDW
- SJU
1 stop8h 45m
Southwest
Mon 8/310:20 pm
SJU
- MDW
1 stop12h 00m
Southwest
Deal found 5/14![Southwest logo]()
$466
This Copa Airlines deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/218:02 am
ORD
- AUA
1 stop12h 58m
Copa Airlines
Sun 6/287:10 am
AUA
- ORD
1 stop21h 50m
Copa Airlines
Deal found 5/15![Copa Airlines logo]()
$683
This Delta deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/2610:54 am
MDW
- SJU
1 stop10h 35m
Delta
Sun 8/3012:56 pm
SJU
- MDW
1 stop10h 40m
Delta
Deal found 5/14![Delta logo]()
$431
This JetBlue deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 6/43:27 pm
ORD
- SJU
1 stop9h 11m
JetBlue
Tue 6/2312:00 pm
SJU
- ORD
1 stop10h 29m
JetBlue
Deal found 5/17![JetBlue logo]()
$545
This United Airlines deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/292:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Tue 7/77:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
Deal found 5/15![United Airlines logo]()
$468
Last-minute flights from Chicago to Caribbean IslandsDiscover last-minute flight deals from Chicago to Caribbean Islands. Data last updated May 19, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Caribbean Islands. Data last updated May 19, 2026 and is based on user searches.
This American Airlines deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/185:00 am
ORD
- SJU
1 stop7h 49m
American Airlines
Sat 5/236:20 am
SJU
- ORD
1 stop14h 18m
American Airlines
Deal found 5/14![American Airlines logo]()
$316
This American Airlines deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/188:05 am
ORD
- MBJ
Nonstop4h 08m
American Airlines
Thu 5/212:55 pm
MBJ
- ORD
1 stop16h 15m
American Airlines
Deal found 5/14![American Airlines logo]()
$348
This Super.com deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/2512:33 am
ORD
- SJU
Nonstop4h 51m
Frontier
Fri 5/297:04 pm
SJU
- ORD
Nonstop5h 22m
Frontier
Deal found 5/18![Frontier logo]()
$308
This Super.com deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/2512:33 am
ORD
- SJU
Nonstop4h 51m
Frontier
Thu 5/286:24 pm
SJU
- ORD
Nonstop5h 22m
Frontier
Deal found 5/16![Frontier logo]()
$309
This Frontier deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/2612:33 am
ORD
- SJU
Nonstop4h 51m
Frontier
Thu 5/286:24 pm
SJU
- ORD
Nonstop5h 22m
Frontier
Deal found 5/18![Frontier logo]()
$269
This Kiwi.com deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/2612:33 am
ORD
- SJU
Nonstop4h 51m
Frontier
Tue 6/97:00 am
SJU
- ORD
2 stops26h 03m
Frontier
Deal found 5/18![Frontier logo]()
$285
This eDestinos deal was found by Cheapflights users on 5/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/2612:33 am
ORD
- SJU
Nonstop4h 51m
Frontier
Sun 8/167:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 5/16![Frontier logo]()
$300
This Frontier deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/2612:33 am
ORD
- SJU
Nonstop4h 51m
Frontier
Thu 6/116:00 am
SJU
- ORD
1 stop7h 24m
Frontier
Deal found 5/18![Frontier logo]()
$317
This American Airlines deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/286:00 pm
ORD
- MBJ
1 stop19h 08m
American Airlines
Wed 6/32:40 pm
MBJ
- ORD
Nonstop4h 45m
American Airlines
Deal found 5/17![American Airlines logo]()
$357
This United Airlines deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/67:30 am
ORD
- MBJ
1 stop7h 56m
United Airlines
Tue 6/94:12 pm
MBJ
- ORD
1 stop7h 14m
United Airlines
Deal found 5/15![United Airlines logo]()
$384
This United Airlines deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/278:40 am
ORD
- MBJ
Nonstop4h 10m
United Airlines
Thu 7/24:12 pm
MBJ
- ORD
1 stop7h 19m
United Airlines
Deal found 5/18![United Airlines logo]()
$380
This Arajet deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/294:30 am
ORD
- PUJ
Nonstop4h 45m
Arajet
Thu 7/97:30 pm
PUJ
- ORD
Nonstop5h 10m
Arajet
Deal found 5/17![Arajet logo]()
$382
One-way flights from Chicago to Caribbean IslandsSearch for one-way flight options from Chicago to Caribbean Islands. Find affordable one-way fares based on user searches. Data last updated May 19, 2026.
Search for one-way flight options from Chicago to Caribbean Islands. Find affordable one-way fares based on user searches. Data last updated May 19, 2026.
This JetBlue deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure 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 14m
JetBlue
Deal found 5/14![JetBlue logo]()
$88
This JetBlue deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/157:00 am
ORD
- NAS
1 stop5h 47m
JetBlue
Deal found 5/17![JetBlue logo]()
$107
This Kiwi.com deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/612:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 5/18![Frontier logo]()
$108
This Orbitz deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/512:29 am
ORD
- SJU
Nonstop4h 57m
Frontier
Deal found 5/18![Frontier logo]()
$109
This Delta deal was found by Cheapflights users on 5/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/109:52 am
ORD
- SJU
1 stop11h 37m
Delta
Deal found 5/14![Delta logo]()
$113
This American Airlines deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/115:14 pm
ORD
- SJU
Nonstop4h 53m
American Airlines
Deal found 5/17![American Airlines logo]()
$114
This Kiwi.com deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/1512:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 5/18![Frontier logo]()
$116
This eDestinos deal was found by Cheapflights users on 5/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/2612:33 am
ORD
- SJU
Nonstop4h 51m
Frontier
Deal found 5/18![Frontier logo]()
$117
This Delta deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1112:46 pm
MDW
- SJU
1 stop8h 43m
Delta
Deal found 5/15![Delta logo]()
$118
This American Airlines deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/55:14 pm
ORD
- SJU
Nonstop4h 53m
American Airlines
Deal found 5/17![American Airlines logo]()
$119
This American Airlines deal was found by Cheapflights users on 5/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/125:14 pm
ORD
- SJU
Nonstop4h 53m
American Airlines
Deal found 5/17![American Airlines logo]()
$120
This American Airlines deal was found by Cheapflights users on 5/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/166:34 am
ORD
- SJU
1 stop14h 50m
American Airlines
Deal found 5/15![American Airlines logo]()
$121
Find flight deals from Chicago to Caribbean Islands
Keep the following information in mind while searching for Chicago to Caribbean Islands flight deals. Data was last updated May 19, 2026.
Round-trip from | $226 (Kiwi.com) |
|---|---|
One-way from | $88 (JetBlue) |
Popular in | December |
Cheapest in | January |
Average price | $363 |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago 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 May 19, 2026.
Use the filters below to find and compare flights from Chicago 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
Wed 8/19
5:28 am-4:37 pm
1 stop10h 09m
San Juan Luis Munoz Marin Intl
Wed 9/2
5:45 pm-11:57 pm
1 stop7h 12m
$236
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Sat 8/22
1:48 pm-10:29 pm
1 stop7h 41m
San Juan Luis Munoz Marin Intl
Fri 8/28
12:56 pm-11:58 pm
1 stop12h 02m
$246
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Sun 8/30
5:00 am-1:00 pm
1 stop7h 00m
San Juan Luis Munoz Marin Intl
Thu 9/3
6:00 am-12:40 pm
1 stop7h 40m
$256
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Sat 8/22
1:48 pm-10:29 pm
1 stop7h 41m
San Juan Luis Munoz Marin Intl
Mon 8/31
7:00 am-5:41 pm
1 stop11h 41m
$256
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Wed 8/19
12:45 pm-10:00 pm
1 stop8h 15m
San Juan Luis Munoz Marin Intl
Sat 8/22
5:05 am-1:10 pm
2 stops9h 05m
$266
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 7/28
9:45 am-10:30 pm
1 stop11h 45m
San Juan Luis Munoz Marin Intl
Mon 8/3
2:11 pm-8:22 pm
1 stop7h 11m
$331
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Wed 11/11
8:42 am-1:46 pm
Nonstop4h 04m
Montego Bay Sangster Intl
Wed 11/18
3:36 pm-11:42 pm
1 stop9h 06m
$338
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Thu 9/3
7:10 am-4:35 pm
1 stop8h 25m
San Juan Luis Munoz Marin Intl
Tue 9/8
7:30 am-4:45 pm
1 stop10h 15m
$341
ChicagoNassau
ORD - NAS
ORDNAS
Chicago O'Hare Intl
Tue 7/21
7:00 am-5:14 pm
1 stop9h 14m
Nassau Intl
Sat 7/25
6:24 pm-11:44 pm
1 stop6h 20m
$374
ChicagoPunta Cana
ORD - PUJ
ORDPUJ
Chicago O'Hare Intl
Mon 8/3
5:30 am-11:15 am
Nonstop4h 45m
Punta Cana
Sat 8/8
7:02 am-11:12 am
Nonstop5h 10m
$393
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Chicago to Caribbean Islands
Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands from Chicago with our price prediction graph.
ORD-NAS
ORD-SJU
MDW-SJU
ORD-MBJ
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 to Caribbean Islands
CHI-zzEPX
ORD-NAS
ORD-SJU
MDW-SJU
ORD-MBJ
How far ahead should I book a flight from Chicago to Caribbean Islands?
Booking 46 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to Caribbean Islands. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
What is the cheapest month to book a flight from Chicago to Caribbean Islands?
Currently, October is the cheapest month in which you can book a flight from Chicago to Caribbean Islands (average of $507). Flying from Chicago to Caribbean Islands in December is currently the most expensive (average of $685). 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 CHI to EPX?
Find hourly flight availability from Chicago 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 May 19, 2026.
Unlike in the morning, when flights are generally more expensive, you can save up to 33% on flights from Chicago to Caribbean Islands by exploring options for tickets in the afternoon.
What is the cheapest day to fly from Chicago to Caribbean Islands?
Use this chart to determine the cheapest time to fly round-trip from Chicago to Caribbean Islands. Price data was last updated on May 16, 2026.
Travelers seeking maximum savings on their Chicago to Caribbean Islands flight should consider departing on Wednesday evenings when fares are most often at their lowest. Saturday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Weekly flight availability from Chicago to Caribbean Islands
Explore weekly flight availability from Chicago 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 May 19, 2026.
The most flights from CHI to zzEPX are scheduled on a Saturday (9 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (6 on average).
Reviews of airlines servicing Caribbean Islands
Get insights into the airlines that provide service to Caribbean Islands. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean Islands. Reviews last updated May 19, 2026.
Read through reviews of airlines operating flights from Chicago to Caribbean Islands, such as United Airlines,American Airlines, andSpirit Airlines. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Boarding
7.7
Food
6.6
Comfort
7.3
Crew
8.1
Overall
7.4
Entertainment
7.1
Reviews
1 / 20
4.0
OkayDynasty,May 2026
LAX - EWR
Boarding
7.7
Food
6.6
Comfort
7.3
Crew
8.1
Overall
7.4
Entertainment
7.1
Reviews
1 / 20
4.0
OkayDynasty,May 2026
LAX - EWR
Boarding
7.7
Food
6.6
Comfort
7.3
Crew
8.1
Overall
7.4
Entertainment
7.1
Reviews
1 / 20
4.0
OkayDynasty,May 2026
LAX - EWR
Boarding
7.7
Food
6.6
Comfort
7.3
Crew
8.1
Overall
7.4
Entertainment
7.1
Reviews
1 / 20
4.0
OkayDynasty,May 2026
LAX - EWR
Boarding
7.7
Food
6.6
Comfort
7.3
Crew
8.1
Overall
7.4
Entertainment
7.1
Reviews
1 / 20
4.0
OkayDynasty,May 2026
LAX - EWR
Related info for your journey
Find useful and relevant information for your journey from Chicago 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 Chicago to Caribbean Islands
See prices for flight routes from nearby airports that may be better suited for you.
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 Chicago to Caribbean Islands by cabin class
Find flights from Chicago to Caribbean Islands, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Caribbean Islands flights
Browse other Chicago and Caribbean Islands flight options. Last updated on May 19, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Chicago to Caribbean Islands flights
Consider these flights traveling from Chicago to Caribbean Islands.
Top 9 airlines flying from Chicago to Caribbean Islands
Discover the top 9 airlines that operate flights from Chicago 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 May 19, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$100 | Average$402 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$119 | Average$425 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$130 | Average$452 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$132 | Average$517 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$175 | Average$480 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$213 | Average$486 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$216 | Average$352 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$256 | Average$583 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$307 | Average$602 | FlexibilityNo cancel fee | On-time71% |