$79+ 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 3/17. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJU
Mar 18 — Mar 251
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 February 16, 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 February 16, 2026.
This Cheapflightsfares deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” 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.
Mon 2/2312:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Thu 2/265:45 pm
SJU
- ORD
1 stop8h 55m
Spirit Airlines
Deal found 2/12![Spirit Airlines logo]()
$182
This eDestinos deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” 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.
Fri 4/171:12 pm
ORD
- SJU
1 stop10h 28m
Frontier
Sun 4/191:59 am
SJU
- ORD
1 stop19h 09m
Frontier
Deal found 2/12![Frontier logo]()
$183
This Cheapflightsfares deal was found by Cheapflights users on 2/15. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/2212:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Fri 2/274:31 pm
SJU
- ORD
1 stop9h 16m
Spirit Airlines
Deal found 2/15![Spirit Airlines logo]()
$184
This Kiwi.com deal was found by Cheapflights users on 2/15. 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.
Tue 8/1812:59 am
ORD
- SJU
Nonstop4h 57m
Multiple Airlines
Sat 8/2212:38 pm
SJU
- ORD
Nonstop4h 59m
Multiple Airlines
Deal found 2/15![Multiple Airlines logo]()
$185
This Cheapflightsfares deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” 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.
Mon 3/212:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Thu 3/511:52 am
SJU
- ORD
1 stop8h 26m
Spirit Airlines
Deal found 2/12![Spirit Airlines logo]()
$186
This Cheapflightsfares deal was found by Cheapflights users on 2/15. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/810:55 am
ORD
- SJU
1 stop12h 03m
Spirit Airlines
Mon 4/131:29 am
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Deal found 2/15![Spirit Airlines logo]()
$187
This Cheapflightsfares deal was found by Cheapflights users on 2/15. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/712:29 pm
ORD
- SJU
Nonstop4h 31m
Spirit Airlines
Thu 4/91:29 am
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Deal found 2/15![Spirit Airlines logo]()
$188
This CheapOair deal was found by Cheapflights users on 2/15. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/212:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Fri 3/612:32 pm
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Deal found 2/15![Spirit Airlines logo]()
$189
This Kiwi.com deal was found by Cheapflights users on 2/16. 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.
Tue 2/2412:17 pm
ORD
- SJU
Nonstop4h 32m
Multiple Airlines
Mon 3/23:53 am
SJU
- ORD
1 stop13h 59m
Multiple Airlines
Deal found 2/16![Multiple Airlines logo]()
$191
This Kiwi.com deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” 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 4/84:34 pm
ORD
- SJU
1 stop7h 18m
Multiple Airlines
Mon 4/131:29 am
SJU
- ORD
Nonstop5h 16m
Multiple Airlines
Deal found 2/12![Multiple Airlines logo]()
$192
This Kiwi.com deal was found by Cheapflights users on 2/15. 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.
Fri 4/104:34 pm
ORD
- SJU
1 stop7h 18m
Multiple Airlines
Mon 4/131:29 am
SJU
- ORD
Nonstop5h 16m
Multiple Airlines
Deal found 2/15![Multiple Airlines logo]()
$193
This Frontier deal was found by Cheapflights users on 2/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/1011:19 am
MDW
- SJU
1 stop10h 26m
Frontier
Wed 3/116:30 am
SJU
- MDW
1 stop12h 43m
Frontier
Deal found 2/14![Frontier logo]()
$197
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 February 16, 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 February 16, 2026.
This Delta deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” 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 3/1111:10 am
ORD
- SJU
1 stop11h 05m
Delta
Tue 3/177:30 am
SJU
- ORD
1 stop10h 19m
Delta
Deal found 2/12![Delta logo]()
$246
This Southwest deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” 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 5/61:00 pm
MDW
- SJU
1 stop8h 40m
Southwest
Wed 5/135:05 am
SJU
- MDW
1 stop12h 10m
Southwest
Deal found 2/13![Southwest logo]()
$246
This United Airlines deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” 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 4/278:49 am
ORD
- SJU
Nonstop4h 55m
United Airlines
Mon 5/47:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
Deal found 2/13![United Airlines logo]()
$267
This CheapOair deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” 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.
Thu 3/57:00 am
ORD
- STT
1 stop7h 34m
Spirit Airlines
Sat 3/75:40 pm
STT
- ORD
1 stop8h 07m
Spirit Airlines
Deal found 2/13![Spirit Airlines logo]()
$274
This Kiwi.com deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” 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 3/187:18 pm
ORD
- STT
2 stops17h 08m
Multiple Airlines
Mon 3/234:35 pm
STT
- ORD
1 stop19h 01m
Multiple Airlines
Deal found 2/12![Multiple Airlines logo]()
$280
This American Airlines deal was found by Cheapflights users on 2/15. 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.
Mon 4/208:15 am
ORD
- PUJ
Nonstop4h 38m
American Airlines
Tue 4/283:34 pm
PUJ
- ORD
1 stop9h 14m
American Airlines
Deal found 2/15![American Airlines logo]()
$386
This Air Canada deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 3/2312:50 pm
ORD
- PLS
1 stop27h 50m
Air Canada
Mon 3/306:40 pm
PLS
- ORD
1 stop26h 10m
Air Canada
Deal found 2/12![Air Canada logo]()
$398
This Delta deal was found by Cheapflights users on 2/15. 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 4/286:04 am
ORD
- SJU
1 stop9h 27m
Delta
Tue 5/57:30 am
SJU
- ORD
1 stop10h 12m
Delta
Deal found 2/15![Delta logo]()
$246
This Delta deal was found by Cheapflights users on 2/15. 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 4/296:04 am
ORD
- SJU
1 stop9h 27m
Delta
Tue 5/57:30 am
SJU
- ORD
1 stop10h 12m
Delta
Deal found 2/15![Delta logo]()
$246
This United Airlines deal was found by Cheapflights users on 2/15. 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 3/22:20 pm
ORD
- SJU
Nonstop4h 40m
United Airlines
Wed 3/44:52 pm
SJU
- ORD
Nonstop5h 28m
United Airlines
Deal found 2/15![United Airlines logo]()
$287
This CheapOair deal was found by Cheapflights users on 2/15. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/144:36 pm
ORD
- STT
2 stops19h 55m
Spirit Airlines
Tue 4/211:23 pm
STT
- ORD
2 stops11h 51m
Spirit Airlines
Deal found 2/15![Spirit Airlines logo]()
$295
This Southwest deal was found by Cheapflights users on 2/15. 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.
Fri 5/158:35 pm
MDW
- SJU
1 stop11h 20m
Southwest
Wed 5/203:45 pm
SJU
- MDW
1 stop6h 40m
Southwest
Deal found 2/15![Southwest logo]()
$296
This Delta deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” 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 4/206:00 am
MDW
- SJU
1 stop9h 23m
Delta
Wed 4/292:34 pm
SJU
- MDW
1 stop8h 54m
Delta
Deal found 2/12![Delta logo]()
$246
This United Airlines deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” 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 5/22:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Wed 5/67:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
Deal found 2/12![United Airlines logo]()
$287
This Flightnetwork deal was found by Cheapflights users on 2/16. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/195:05 am
ORD
- PUJ
1 stop7h 45m
Multiple Airlines
Sun 4/266:00 pm
PUJ
- ORD
Nonstop5h 10m
Multiple Airlines
Deal found 2/16![Multiple Airlines logo]()
$321
This Southwest deal was found by Cheapflights users on 2/15. 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.
Sat 5/25:00 am
MDW
- SJU
1 stop9h 35m
Southwest
Wed 5/611:25 am
SJU
- MDW
2 stops9h 20m
Southwest
Deal found 2/15![Southwest logo]()
$296
This Delta deal was found by Cheapflights users on 2/15. 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 4/1512:52 pm
MDW
- SJU
1 stop9h 20m
Delta
Tue 4/2112:55 pm
SJU
- MDW
1 stop10h 33m
Delta
Deal found 2/15![Delta logo]()
$246
This CheapOair deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” 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.
Wed 3/184:36 pm
ORD
- STT
2 stops19h 50m
Spirit Airlines
Mon 3/234:35 pm
STT
- ORD
2 stops25h 21m
Spirit Airlines
Deal found 2/12![Spirit Airlines logo]()
$309
This Southwest deal was found by Cheapflights users on 2/15. 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.
Mon 5/118:35 pm
MDW
- SJU
1 stop13h 00m
Southwest
Sun 5/179:45 pm
SJU
- MDW
2 stops15h 05m
Southwest
Deal found 2/15![Southwest logo]()
$296
This Delta deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” 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 4/1510:43 am
MDW
- SJU
1 stop8h 41m
Delta
Wed 4/227:30 am
SJU
- MDW
1 stop9h 55m
Delta
Deal found 2/12![Delta logo]()
$256
This Kiwi.com deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” 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 5/44:28 pm
ORD
- PUJ
3 stops18h 41m
Multiple Airlines
Sat 5/95:47 am
PUJ
- ORD
Nonstop5h 10m
Multiple Airlines
Deal found 2/13![Multiple Airlines logo]()
$355
This Southwest deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” 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 5/48:35 pm
MDW
- SJU
1 stop13h 00m
Southwest
Thu 5/146:50 am
SJU
- MDW
2 stops14h 45m
Southwest
Deal found 2/13![Southwest logo]()
$296
This Booking.com deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/141:55 pm
ORD
- PLS
2 stops50h 45m
Air Canada
Tue 3/176:40 pm
PLS
- ORD
2 stops25h 12m
Air Canada
Deal found 2/12![Air Canada logo]()
$410
This Cheapflightsfares deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 4/265:15 am
ORD
- PUJ
1 stop9h 21m
Spirit Airlines
Wed 4/294:47 pm
PUJ
- ORD
1 stop7h 54m
Spirit Airlines
Deal found 2/12![Spirit Airlines logo]()
$346
This United Airlines deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” 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 3/118:42 am
ORD
- MBJ
Nonstop4h 04m
United Airlines
Sun 3/151:48 pm
MBJ
- ORD
Nonstop4h 25m
United Airlines
Deal found 2/13![United Airlines logo]()
$369
This Southwest deal was found by Cheapflights users on 2/15. 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 4/267:35 am
MDW
- SJU
1 stop6h 05m
Southwest
Fri 5/16:50 am
SJU
- MDW
2 stops14h 45m
Southwest
Deal found 2/15![Southwest logo]()
$310
This CheapOair deal was found by Cheapflights users on 2/15. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/111:55 pm
ORD
- MBJ
2 stops45h 25m
Multiple Airlines
Wed 4/1512:00 pm
MBJ
- ORD
1 stop7h 47m
Multiple Airlines
Deal found 2/15![Multiple Airlines logo]()
$378
This Delta deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” 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 2/2411:18 am
ORD
- SJU
1 stop7h 54m
Delta
Tue 3/36:37 pm
SJU
- ORD
1 stop7h 19m
Delta
Deal found 2/12![Delta logo]()
$286
This Air Canada deal was found by Cheapflights users on 2/16. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/258:40 pm
ORD
- PLS
1 stop14h 40m
Air Canada
Wed 4/11:20 pm
PLS
- ORD
1 stop20h 50m
Air Canada
Deal found 2/16![Air Canada logo]()
$421
This FlightHub deal was found by Cheapflights users on 2/16. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/165:34 pm
ORD
- STT
2 stops17h 54m
Spirit Airlines
Sat 5/234:40 pm
STT
- ORD
1 stop8h 34m
Spirit Airlines
Deal found 2/16![Spirit Airlines logo]()
$356
Last-minute flights from Chicago to Caribbean IslandsDiscover last-minute flight deals from Chicago to Caribbean Islands. Data last updated February 16, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Caribbean Islands. Data last updated February 16, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 2/15. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 2/2212:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Fri 2/274:31 pm
SJU
- ORD
1 stop9h 16m
Spirit Airlines
Deal found 2/15![Spirit Airlines logo]()
$184
This Cheapflightsfares deal was found by Cheapflights users on 2/15. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 2/238:16 pm
ORD
- SJU
1 stop17h 15m
Spirit Airlines
Thu 2/2612:32 pm
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Deal found 2/15![Spirit Airlines logo]()
$182
This Kiwi.com deal was found by Cheapflights users on 2/16. 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.
Mon 2/2312:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Thu 3/512:32 pm
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Deal found 2/16![Spirit Airlines logo]()
$194
This Kiwi.com deal was found by Cheapflights users on 2/16. 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.
Tue 2/2412:17 pm
ORD
- SJU
Nonstop4h 32m
Multiple Airlines
Mon 3/23:53 am
SJU
- ORD
1 stop13h 59m
Multiple Airlines
Deal found 2/16![Multiple Airlines logo]()
$191
This Kiwi.com deal was found by Cheapflights users on 2/16. 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.
Tue 2/2412:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Fri 3/67:00 am
SJU
- ORD
1 stop12h 03m
Spirit Airlines
Deal found 2/16![Spirit Airlines logo]()
$193
This Kiwi.com deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” 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 2/2612:15 pm
ORD
- SJU
1 stop12h 10m
Multiple Airlines
Thu 3/512:32 pm
SJU
- ORD
Nonstop5h 16m
Multiple Airlines
Deal found 2/12![Multiple Airlines logo]()
$192
This Cheapflightsfares deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” 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.
Mon 3/212:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Thu 3/511:52 am
SJU
- ORD
1 stop8h 26m
Spirit Airlines
Deal found 2/12![Spirit Airlines logo]()
$186
This Frontier deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” 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 3/29:22 pm
MDW
- SJU
1 stop10h 32m
Frontier
Wed 3/116:30 am
SJU
- MDW
1 stop12h 43m
Frontier
Deal found 2/12![Frontier logo]()
$202
This Cheapflightsfares deal was found by Cheapflights users on 2/16. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/35:15 am
ORD
- SJU
1 stop8h 16m
Spirit Airlines
Wed 3/412:32 pm
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Deal found 2/16![Spirit Airlines logo]()
$188
This Frontier deal was found by Cheapflights users on 2/14. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/1011:19 am
MDW
- SJU
1 stop10h 26m
Frontier
Wed 3/116:30 am
SJU
- MDW
1 stop12h 43m
Frontier
Deal found 2/14![Frontier logo]()
$197
This Trip.com deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” 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.
Tue 3/1710:55 am
ORD
- SJU
1 stop12h 03m
Spirit Airlines
Tue 3/241:29 am
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Deal found 2/12![Spirit Airlines logo]()
$185
This Super.com deal was found by Cheapflights users on 2/16. 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.
Tue 3/1710:55 am
ORD
- SJU
1 stop12h 03m
Spirit Airlines
Mon 3/231:29 am
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Deal found 2/16![Spirit Airlines logo]()
$187
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 February 16, 2026.
Search for one-way flight options from Chicago to Caribbean Islands. Find affordable one-way fares based on user searches. Data last updated February 16, 2026.
This FlightHub deal was found by Cheapflights users on 2/15. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/175:05 am
ORD
- AUA
1 stop8h 30m
Spirit Airlines
Deal found 2/15![Spirit Airlines logo]()
$79
This Super.com deal was found by Cheapflights users on 2/15. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/145:05 am
ORD
- AUA
1 stop8h 30m
Spirit Airlines
Deal found 2/15![Spirit Airlines logo]()
$84
This Priceline deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” 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.
Sun 4/125:05 am
ORD
- GCM
1 stop7h 52m
Spirit Airlines
Deal found 2/13![Spirit Airlines logo]()
$89
This eDestinos deal was found by Cheapflights users on 2/15. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/176:57 am
ORD
- SJU
1 stop14h 51m
Frontier
Deal found 2/15![Frontier logo]()
$92
This Cheapflightsfares deal was found by Cheapflights users on 2/16. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/710:55 am
ORD
- SJU
1 stop12h 03m
Spirit Airlines
Deal found 2/16![Spirit Airlines logo]()
$93
This Frontier deal was found by Cheapflights users on 2/15. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/112:59 am
ORD
- SJU
Nonstop4h 57m
Frontier
Deal found 2/15![Frontier logo]()
$94
This Spirit deal was found by Cheapflights users on 2/14. 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 Spirit is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/1812:18 pm
ORD
- SJU
Nonstop4h 36m
Spirit Airlines
Deal found 2/14![Spirit Airlines logo]()
$95
This Kiwi.com deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” 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 4/1310:55 am
ORD
- SJU
1 stop12h 03m
Spirit Airlines
Deal found 2/13![Spirit Airlines logo]()
$98
This Kiwi.com deal was found by Cheapflights users on 2/15. 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.
Wed 5/131:27 pm
ORD
- AUA
1 stop24h 08m
Multiple Airlines
Deal found 2/15![Multiple Airlines logo]()
$98
This Priceline deal was found by Cheapflights users on 2/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/812:59 am
ORD
- SJU
Nonstop4h 57m
Frontier
Deal found 2/12![Frontier logo]()
$99
This Kiwi.com deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” 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 4/1112:29 pm
ORD
- SJU
Nonstop4h 31m
Spirit Airlines
Deal found 2/13![Spirit Airlines logo]()
$100
This Super.com deal was found by Cheapflights users on 2/13. Clicking the “Pick Dates” 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.
Sat 2/288:00 am
MDW
- SJU
1 stop14h 43m
Frontier
Deal found 2/13![Frontier logo]()
$100
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 February 16, 2026.
Round-trip from | $183 (eDestinos) |
|---|---|
One-way from | $79 (FlightHub) |
Popular in | December |
Cheapest in | April |
Average price | $392 |
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 February 16, 2026.
Use the filters below to find and compare flights from Chicago to Caribbean Islands that are best for you.
Fly from
Chicago
Fly to
Caribbean Islands
Route
Depart
Return
Price
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Wed 3/11
11:10 am-11:15 pm
1 stop11h 05m
San Juan Luis Munoz Marin Intl
Tue 3/17
7:30 am-4:49 pm
1 stop10h 19m
$246
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Wed 5/6
1:00 pm-10:40 pm
1 stop8h 40m
San Juan Luis Munoz Marin Intl
Wed 5/13
5:05 am-4:15 pm
1 stop12h 10m
$246
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 4/28
6:04 am-4:31 pm
1 stop9h 27m
San Juan Luis Munoz Marin Intl
Tue 5/5
7:30 am-4:42 pm
1 stop10h 12m
$246
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Wed 4/29
6:04 am-4:31 pm
1 stop9h 27m
San Juan Luis Munoz Marin Intl
Tue 5/5
7:30 am-4:42 pm
1 stop10h 12m
$246
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Mon 4/20
6:00 am-4:23 pm
1 stop9h 23m
San Juan Luis Munoz Marin Intl
Wed 4/29
2:34 pm-10:28 pm
1 stop8h 54m
$246
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Wed 4/15
12:52 pm-11:12 pm
1 stop9h 20m
San Juan Luis Munoz Marin Intl
Tue 4/21
12:55 pm-10:28 pm
1 stop10h 33m
$246
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Wed 4/15
10:43 am-8:24 pm
1 stop8h 41m
San Juan Luis Munoz Marin Intl
Wed 4/22
7:30 am-4:25 pm
1 stop9h 55m
$256
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Mon 4/27
8:49 am-2:44 pm
Nonstop4h 55m
San Juan Luis Munoz Marin Intl
Mon 5/4
7:40 am-11:53 am
Nonstop5h 13m
$267
ChicagoSaint Thomas Island
ORD - STT
ORDSTT
Chicago O'Hare Intl
Thu 3/5
7:00 am-4:34 pm
1 stop7h 34m
Saint Thomas Island Cyril E King
Sat 3/7
5:40 pm-11:47 pm
1 stop8h 07m
$274
ChicagoSaint Thomas Island
ORD - STT
ORDSTT
Chicago O'Hare Intl
Wed 3/18
7:18 pm-1:26 pm
2 stops17h 08m
Saint Thomas Island Cyril E King
Mon 3/23
4:35 pm-10:36 am
1 stop19h 01m
$280
Showing 1-10 of 60 results
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-STT
ORD-PUJ
ORD-PLS
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-STT
ORD-PUJ
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 February 16, 2026.
Unlike in the morning, when flights are generally more expensive, you can save up to 41% 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 February 7, 2026.
Travelers seeking maximum savings on their Chicago to Caribbean Islands flight should consider departing on Tuesday mornings 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 February 16, 2026.
The most flights from CHI to zzEPX are scheduled on a Saturday (13 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (7 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 February 16, 2026.
Read through reviews of airlines operating flights from Chicago to Caribbean Islands, such as Delta, United Airlines, and American 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.
Crew
8.5
Comfort
7.9
Food
7.2
Boarding
8.1
Overall
7.9
Entertainment
7.8
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Crew
8.5
Comfort
7.9
Food
7.2
Boarding
8.1
Overall
7.9
Entertainment
7.8
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Crew
8.5
Comfort
7.9
Food
7.2
Boarding
8.1
Overall
7.9
Entertainment
7.8
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Crew
8.5
Comfort
7.9
Food
7.2
Boarding
8.1
Overall
7.9
Entertainment
7.8
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Crew
8.5
Comfort
7.9
Food
7.2
Boarding
8.1
Overall
7.9
Entertainment
7.8
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Crew
8.5
Comfort
7.9
Food
7.2
Boarding
8.1
Overall
7.9
Entertainment
7.8
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.
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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 February 16, 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 February 16, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$106 | Average$450 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$119 | Average$444 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$130 | Average$354 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$132 | Average$552 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$180 | Average$321 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$188 | Average$431 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$193 | Average$576 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$213 | Average$343 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$251 | Average$615 | FlexibilityNo cancel fee | On-time69% |