$97+ 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 4/25. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJU
May 2 — May 91
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 April 2, 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 April 2, 2026.
This Mytrip deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/115:05 am
ORD
- SJU
1 stop12h 50m
Spirit Airlines
Sat 4/187:00 am
SJU
- ORD
1 stop8h 05m
Spirit Airlines
Deal found 3/30![Spirit Airlines logo]()
$212
This Kiwi.com deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/97:17 am
ORD
- SJU
1 stop10h 38m
Multiple Airlines
Tue 4/1411:00 am
SJU
- ORD
1 stop8h 31m
Multiple Airlines
Deal found 3/29![Multiple Airlines logo]()
$213
This Kiwi.com deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/225:05 am
ORD
- SJU
1 stop13h 17m
Spirit Airlines
Fri 4/244:34 pm
SJU
- ORD
Nonstop5h 15m
Spirit Airlines
Deal found 3/29![Spirit Airlines logo]()
$214
This Cheapflightsfares deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/167:50 am
ORD
- SJU
1 stop16h 08m
Spirit Airlines
Sat 4/254:34 pm
SJU
- ORD
Nonstop5h 15m
Spirit Airlines
Deal found 3/30![Spirit Airlines logo]()
$215
This Travelocity deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/224:44 pm
ORD
- SJU
Nonstop4h 37m
Multiple Airlines
Fri 5/296:00 am
SJU
- ORD
1 stop7h 37m
Multiple Airlines
Deal found 3/29![Multiple Airlines logo]()
$216
This Frontier deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/267:55 am
ORD
- SJU
1 stop7h 03m
Frontier
Tue 9/16:11 pm
SJU
- ORD
Nonstop5h 15m
Frontier
Deal found 3/30![Frontier logo]()
$217
This Kiwi.com deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/66:10 pm
ORD
- SJU
1 stop16h 39m
Spirit Airlines
Tue 4/1412:55 pm
SJU
- ORD
2 stops29h 16m
Spirit Airlines
Deal found 3/30![Spirit Airlines logo]()
$218
This Kiwi.com deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/63:15 pm
ORD
- SJU
1 stop8h 46m
Frontier
Thu 4/1611:30 am
SJU
- ORD
1 stop13h 29m
Frontier
Deal found 3/31![Frontier logo]()
$219
This Kiwi.com deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 4/2110:00 am
ORD
- SJU
Nonstop4h 39m
Multiple Airlines
Sat 4/2511:30 am
SJU
- ORD
1 stop13h 29m
Multiple Airlines
Deal found 3/31![Multiple Airlines logo]()
$220
This Frontier deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 5/53:55 pm
ORD
- SJU
1 stop9h 13m
Frontier
Sat 5/96:30 am
SJU
- ORD
1 stop13h 14m
Frontier
Deal found 3/31![Frontier logo]()
$221
This Frontier deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/179:14 am
MDW
- SJU
1 stop12h 34m
Frontier
Fri 4/173:08 am
SJU
- MDW
1 stop13h 52m
Frontier
Deal found 3/30![Frontier logo]()
$221
This Frontier deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 8/1812:29 am
ORD
- SJU
Nonstop4h 57m
Frontier
Wed 9/26:25 am
SJU
- ORD
1 stop10h 45m
Frontier
Deal found 3/31![Frontier logo]()
$222
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 April 2, 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 April 2, 2026.
This Spirit deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/2912:59 pm
ORD
- SJU
1 stop8h 43m
Spirit Airlines
Sat 5/304:59 pm
SJU
- ORD
Nonstop5h 15m
Spirit Airlines
Deal found 4/1![Spirit Airlines logo]()
$267
This Delta deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/2211:19 am
ORD
- SJU
1 stop8h 05m
Delta
Wed 4/292:45 pm
SJU
- ORD
1 stop7h 40m
Delta
Deal found 4/1![Delta logo]()
$316
This United Airlines deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/98:40 am
ORD
- MBJ
Nonstop4h 10m
United Airlines
Sat 5/161:52 pm
MBJ
- ORD
Nonstop4h 23m
United Airlines
Deal found 3/28![United Airlines logo]()
$318
This Southwest deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/1312:45 pm
MDW
- SJU
1 stop6h 15m
Southwest
Tue 4/285:35 am
SJU
- MDW
1 stop9h 10m
Southwest
Deal found 4/2![Southwest logo]()
$346
This Priceline deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/196:00 am
MDW
- MBJ
1 stop6h 11m
Frontier
Sat 5/231:16 pm
MBJ
- MDW
1 stop8h 46m
Frontier
Deal found 3/28![Frontier logo]()
$352
This Travelocity deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/1612:42 pm
ORD
- SJU
1 stop8h 47m
Multiple Airlines
Sun 4/1911:25 pm
SJU
- ORD
1 stop10h 35m
Multiple Airlines
Deal found 4/2![Multiple Airlines logo]()
$427
This Copa Airlines deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/298:06 am
ORD
- AUA
1 stop12h 51m
Copa Airlines
Sun 5/33:43 pm
AUA
- ORD
1 stop10h 32m
Copa Airlines
Deal found 3/29![Copa Airlines logo]()
$541
This United Airlines deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/111:00 pm
ORD
- MBJ
1 stop14h 30m
United Airlines
Sat 5/91:52 pm
MBJ
- ORD
Nonstop4h 23m
United Airlines
Deal found 4/1![United Airlines logo]()
$322
This United Airlines deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/195:30 am
ORD
- MBJ
1 stop8h 00m
United Airlines
Sat 5/231:52 pm
MBJ
- ORD
Nonstop4h 23m
United Airlines
Deal found 3/28![United Airlines logo]()
$322
This Southwest deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/131:00 pm
MDW
- SJU
1 stop9h 25m
Southwest
Wed 4/155:05 am
SJU
- MDW
2 stops11h 45m
Southwest
Deal found 3/30![Southwest logo]()
$356
This Delta deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/119:45 am
ORD
- SJU
1 stop11h 44m
Delta
Mon 7/202:05 pm
SJU
- ORD
1 stop7h 26m
Delta
Deal found 3/31![Delta logo]()
$366
This Frontier deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/812:29 am
ORD
- SJU
Nonstop4h 57m
Frontier
Mon 7/134:05 pm
SJU
- ORD
1 stop8h 09m
Frontier
Deal found 4/2![Frontier logo]()
$370
This Southwest deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/121:25 pm
MDW
- SJU
1 stop9h 15m
Southwest
Fri 5/152:00 pm
SJU
- MDW
1 stop11h 15m
Southwest
Deal found 4/2![Southwest logo]()
$356
This United Airlines deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/286:30 am
ORD
- MBJ
1 stop7h 00m
United Airlines
Sat 7/44:12 pm
MBJ
- ORD
1 stop7h 14m
United Airlines
Deal found 3/28![United Airlines logo]()
$332
This FlightHub deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/29:14 am
MDW
- PUJ
2 stops25h 46m
Frontier
Sat 5/93:35 pm
PUJ
- MDW
1 stop20h 37m
Frontier
Deal found 3/28![Frontier logo]()
$398
This United Airlines deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/28:45 am
ORD
- MBJ
1 stop6h 25m
United Airlines
Mon 5/42:40 pm
MBJ
- ORD
1 stop17h 14m
United Airlines
Deal found 3/29![United Airlines logo]()
$332
This CheapOair deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/248:27 pm
ORD
- STT
2 stops17h 14m
Spirit Airlines
Fri 8/283:46 pm
STT
- ORD
2 stops29h 58m
Spirit Airlines
Deal found 3/28![Spirit Airlines logo]()
$448
This Southwest deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/512:50 pm
MDW
- SJU
2 stops8h 50m
Southwest
Fri 5/85:35 am
SJU
- MDW
2 stops8h 35m
Southwest
Deal found 3/31![Southwest logo]()
$371
This Southwest deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/111:45 am
MDW
- SJU
2 stops10h 40m
Southwest
Tue 5/55:05 am
SJU
- MDW
2 stops11h 45m
Southwest
Deal found 4/1![Southwest logo]()
$371
This Delta deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 9/76:00 am
MDW
- MBJ
1 stop7h 04m
Delta
Sat 9/122:35 pm
MBJ
- MDW
1 stop7h 11m
Delta
Deal found 3/31![Delta logo]()
$452
This United Airlines deal was found by Cheapflights users on 4/1. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/98:40 am
ORD
- MBJ
Nonstop4h 10m
United Airlines
Tue 5/122:40 pm
MBJ
- ORD
1 stop10h 05m
United Airlines
Deal found 4/1![United Airlines logo]()
$345
This Delta deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/196:00 am
MDW
- MBJ
1 stop9h 34m
Delta
Wed 9/231:25 pm
MBJ
- MDW
1 stop8h 21m
Delta
Deal found 3/30![Delta logo]()
$452
This Southwest deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/228:15 am
MDW
- SJU
2 stops8h 55m
Southwest
Tue 5/125:05 am
SJU
- MDW
2 stops11h 45m
Southwest
Deal found 3/29![Southwest logo]()
$376
This United Airlines deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/276:30 am
ORD
- MBJ
1 stop8h 40m
United Airlines
Sat 6/64:33 pm
MBJ
- ORD
1 stop8h 12m
United Airlines
Deal found 3/30![United Airlines logo]()
$349
This Delta deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/16:38 pm
MDW
- MBJ
1 stop16h 55m
Delta
Tue 5/122:21 pm
MBJ
- MDW
1 stop6h 48m
Delta
Deal found 4/2![Delta logo]()
$452
This Southwest deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/187:45 am
MDW
- SJU
Nonstop4h 35m
Southwest
Wed 4/2211:25 am
SJU
- MDW
1 stop7h 05m
Southwest
Deal found 4/2![Southwest logo]()
$382
This United Airlines deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/265:30 am
ORD
- MBJ
1 stop8h 00m
United Airlines
Sun 5/314:33 pm
MBJ
- ORD
1 stop8h 12m
United Airlines
Deal found 3/30![United Airlines logo]()
$349
This Delta deal was found by Cheapflights users on 4/2. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/16:38 pm
MDW
- MBJ
1 stop16h 55m
Delta
Wed 5/131:18 pm
MBJ
- MDW
1 stop7h 51m
Delta
Deal found 4/2![Delta logo]()
$452
This Southwest deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/141:00 pm
MDW
- SJU
1 stop8h 40m
Southwest
Sat 4/1811:15 am
SJU
- MDW
1 stop6h 50m
Southwest
Deal found 3/29![Southwest logo]()
$396
This United Airlines deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/26:30 am
ORD
- MBJ
1 stop8h 40m
United Airlines
Sun 7/54:12 pm
MBJ
- ORD
1 stop7h 14m
United Airlines
Deal found 3/29![United Airlines logo]()
$369
Last-minute flights from Chicago to Caribbean IslandsDiscover last-minute flight deals from Chicago to Caribbean Islands. Data last updated April 2, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Caribbean Islands. Data last updated April 2, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/66:10 pm
ORD
- SJU
1 stop16h 39m
Spirit Airlines
Tue 4/1412:55 pm
SJU
- ORD
2 stops29h 16m
Spirit Airlines
Deal found 3/30![Spirit Airlines logo]()
$218
This Kiwi.com deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/63:15 pm
ORD
- SJU
1 stop8h 46m
Frontier
Thu 4/1611:30 am
SJU
- ORD
1 stop13h 29m
Frontier
Deal found 3/31![Frontier logo]()
$219
This Kiwi.com deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/97:17 am
ORD
- SJU
1 stop10h 38m
Multiple Airlines
Tue 4/1411:00 am
SJU
- ORD
1 stop8h 31m
Multiple Airlines
Deal found 3/29![Multiple Airlines logo]()
$213
This Mytrip deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/115:05 am
ORD
- SJU
1 stop12h 50m
Spirit Airlines
Sat 4/187:00 am
SJU
- ORD
1 stop8h 05m
Spirit Airlines
Deal found 3/30![Spirit Airlines logo]()
$212
This Cheapflightsfares deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/167:50 am
ORD
- SJU
1 stop16h 08m
Spirit Airlines
Sat 4/254:34 pm
SJU
- ORD
Nonstop5h 15m
Spirit Airlines
Deal found 3/30![Spirit Airlines logo]()
$215
This Frontier deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/179:14 am
MDW
- SJU
1 stop12h 34m
Frontier
Fri 4/173:08 am
SJU
- MDW
1 stop13h 52m
Frontier
Deal found 3/30![Frontier logo]()
$221
This Kiwi.com deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/2010:00 am
ORD
- SJU
Nonstop4h 39m
Spirit Airlines
Sat 4/254:34 pm
SJU
- ORD
Nonstop5h 15m
Spirit Airlines
Deal found 3/31![Spirit Airlines logo]()
$222
This Kiwi.com deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 4/2110:00 am
ORD
- SJU
Nonstop4h 39m
Multiple Airlines
Sat 4/2511:30 am
SJU
- ORD
1 stop13h 29m
Multiple Airlines
Deal found 3/31![Multiple Airlines logo]()
$220
This Kiwi.com deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/225:05 am
ORD
- SJU
1 stop13h 17m
Spirit Airlines
Thu 4/234:34 pm
SJU
- ORD
Nonstop5h 15m
Spirit Airlines
Deal found 3/29![Spirit Airlines logo]()
$214
This CheapOair deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/258:00 am
ORD
- SJU
1 stop17h 01m
Multiple Airlines
Wed 4/2912:57 pm
SJU
- ORD
1 stop12h 27m
Multiple Airlines
Deal found 3/29![Multiple Airlines logo]()
$217
This Frontier deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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 5/53:55 pm
ORD
- SJU
1 stop9h 13m
Frontier
Sat 5/96:30 am
SJU
- ORD
1 stop13h 14m
Frontier
Deal found 3/31![Frontier logo]()
$221
This Travelocity deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/224:44 pm
ORD
- SJU
Nonstop4h 37m
Multiple Airlines
Fri 5/296:00 am
SJU
- ORD
1 stop7h 37m
Multiple Airlines
Deal found 3/29![Multiple Airlines logo]()
$216
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 April 2, 2026.
Search for one-way flight options from Chicago to Caribbean Islands. Find affordable one-way fares based on user searches. Data last updated April 2, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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.
Sat 4/255:05 am
ORD
- AUA
1 stop8h 31m
Spirit Airlines
Deal found 3/31![Spirit Airlines logo]()
$97
This Kiwi.com deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/275:05 am
ORD
- AUA
1 stop8h 31m
Spirit Airlines
Deal found 3/30![Spirit Airlines logo]()
$103
This Super.com deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/135:05 am
ORD
- MBJ
1 stop6h 00m
Spirit Airlines
Deal found 3/29![Spirit Airlines logo]()
$104
This Kiwi.com deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/261:22 pm
ORD
- AUA
1 stop24h 14m
Multiple Airlines
Deal found 3/30![Multiple Airlines logo]()
$104
This Kiwi.com deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/285:05 am
ORD
- MBJ
1 stop7h 11m
Spirit Airlines
Deal found 3/28![Spirit Airlines logo]()
$105
This Frontier deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/116:00 am
MDW
- MBJ
1 stop6h 11m
Frontier
Deal found 3/28![Frontier logo]()
$108
This Frontier deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/255:50 am
ORD
- MBJ
1 stop6h 22m
Frontier
Deal found 3/28![Frontier logo]()
$108
This Kiwi.com deal was found by Cheapflights users on 3/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/134:36 pm
ORD
- AUA
1 stop20h 59m
Spirit Airlines
Deal found 3/28![Spirit Airlines logo]()
$113
This Kiwi.com deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/301:27 pm
ORD
- AUA
1 stop24h 09m
Multiple Airlines
Deal found 3/30![Multiple Airlines logo]()
$115
This Cheapflightsfares deal was found by Cheapflights users on 3/31. Clicking the “Pick Dates” 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.
Sat 4/1112:29 pm
ORD
- SJU
Nonstop4h 31m
Spirit Airlines
Deal found 3/31![Spirit Airlines logo]()
$119
This Cheapflightsfares deal was found by Cheapflights users on 3/30. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/17:15 pm
ORD
- AUA
1 stop18h 21m
Spirit Airlines
Deal found 3/30![Spirit Airlines logo]()
$119
This Priceline deal was found by Cheapflights users on 3/29. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/108:56 pm
ORD
- SJU
Nonstop4h 33m
Spirit Airlines
Deal found 3/29![Spirit Airlines logo]()
$120
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 April 2, 2026.
Round-trip from | $212 (Kiwi.com) |
|---|---|
One-way from | $97 (Cheapflightsfares) |
Popular in | December |
Cheapest in | January |
Average price | $361 |
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 April 2, 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
Fri 5/29
12:59 pm-10:42 pm
1 stop8h 43m
San Juan Luis Munoz Marin Intl
Sat 5/30
4:59 pm-9:14 pm
Nonstop5h 15m
$267
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Wed 4/22
11:19 am-8:24 pm
1 stop8h 05m
San Juan Luis Munoz Marin Intl
Wed 4/29
2:45 pm-9:25 pm
1 stop7h 40m
$316
Quickest round-trip
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Sat 5/9
8:40 am-12:50 pm
Nonstop4h 10m
Montego Bay Sangster Intl
Sat 5/16
1:52 pm-6:15 pm
Nonstop4h 23m
$318
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Fri 5/1
11:00 pm-1:30 pm
1 stop14h 30m
Montego Bay Sangster Intl
Sat 5/9
1:52 pm-6:15 pm
Nonstop4h 23m
$322
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Tue 5/19
5:30 am-1:30 pm
1 stop8h 00m
Montego Bay Sangster Intl
Sat 5/23
1:52 pm-6:15 pm
Nonstop4h 23m
$322
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Sun 6/28
6:30 am-1:30 pm
1 stop7h 00m
Montego Bay Sangster Intl
Sat 7/4
4:12 pm-11:26 pm
1 stop7h 14m
$332
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Sat 5/2
8:45 am-3:10 pm
1 stop6h 25m
Montego Bay Sangster Intl
Mon 5/4
2:40 pm-7:54 am
1 stop17h 14m
$332
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Sat 5/9
8:40 am-12:50 pm
Nonstop4h 10m
Montego Bay Sangster Intl
Tue 5/12
2:40 pm-12:45 am
1 stop10h 05m
$345
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Mon 4/13
12:45 pm-8:00 pm
1 stop6h 15m
San Juan Luis Munoz Marin Intl
Tue 4/28
5:35 am-1:45 pm
1 stop9h 10m
$346
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Wed 5/27
6:30 am-3:10 pm
1 stop8h 40m
Montego Bay Sangster Intl
Sat 6/6
4:33 pm-12:45 am
1 stop8h 12m
$349
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-SJU
MDW-SJU
ORD-MBJ
ORD-PLS
MDW-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-SJU
MDW-SJU
ORD-MBJ
ORD-PLS
What is the cheapest month to book a flight from Chicago to Caribbean Islands?
Currently, April is the cheapest month in which you can book a flight from Chicago to Caribbean Islands (average of $91). Flying from Chicago to Caribbean Islands in December is currently the most expensive (average of $195). 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 April 2, 2026.
Unlike in the morning, when flights are generally more expensive, you can save up to 35% on flights from Chicago to Caribbean Islands by exploring options for tickets in the evening.
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 March 28, 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 April 2, 2026.
The most flights from CHI to zzEPX are scheduled on a Monday (12 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (8 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 April 2, 2026.
Read through reviews of airlines operating flights from Chicago to Caribbean Islands, such as Delta,United Airlines, andAmerican 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.
Overall
7.9
Food
7.2
Boarding
8.1
Entertainment
7.8
Comfort
7.9
Crew
8.5
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Overall
7.9
Food
7.2
Boarding
8.1
Entertainment
7.8
Comfort
7.9
Crew
8.5
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Overall
7.9
Food
7.2
Boarding
8.1
Entertainment
7.8
Comfort
7.9
Crew
8.5
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Overall
7.9
Food
7.2
Boarding
8.1
Entertainment
7.8
Comfort
7.9
Crew
8.5
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Overall
7.9
Food
7.2
Boarding
8.1
Entertainment
7.8
Comfort
7.9
Crew
8.5
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Overall
7.9
Food
7.2
Boarding
8.1
Entertainment
7.8
Comfort
7.9
Crew
8.5
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
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.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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Alternative routes for 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 April 2, 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 April 2, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$81 | Average$374 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$114 | Average$455 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$119 | Average$432 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$132 | Average$538 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$188 | Average$431 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$193 | Average$522 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$199 | Average$329 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$213 | Average$476 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$254 | Average$574 | FlexibilityNo cancel fee | On-time69% |