$79+ Cheap flights from Chicago (CHI) to Caribbean
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 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 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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Cheapest flights from Chicago to CaribbeanExplore the most affordable flight options available from Chicago to Caribbean. 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. 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 CaribbeanDiscover carefully curated flight deals from Chicago to Caribbean 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 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 2/15. 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.
Sun 4/125:05 am
ORD
- STT
1 stop9h 23m
Spirit Airlines
Thu 4/164:40 pm
STT
- ORD
2 stops17h 30m
Spirit Airlines
Deal found 2/15![Spirit Airlines logo]()
$280
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 2/288:16 pm
ORD
- STT
1 stop18h 18m
Multiple Airlines
Thu 3/122:36 pm
STT
- ORD
1 stop10h 02m
Multiple Airlines
Deal found 2/13![Multiple Airlines logo]()
$298
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 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.
Fri 4/105:05 am
ORD
- STT
1 stop9h 23m
Spirit Airlines
Mon 4/132:36 pm
STT
- ORD
1 stop27h 20m
Spirit Airlines
Deal found 2/15![Spirit Airlines logo]()
$286
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 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 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 3/78:16 pm
ORD
- STT
2 stops15h 15m
Spirit Airlines
Thu 3/124:35 pm
STT
- ORD
1 stop7h 42m
Spirit Airlines
Deal found 2/16![Spirit Airlines logo]()
$291
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 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.
Tue 4/144:36 pm
ORD
- STT
2 stops18h 52m
Spirit Airlines
Tue 4/212:36 pm
STT
- ORD
2 stops10h 38m
Spirit Airlines
Deal found 2/16![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.
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 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.
Sun 3/15:15 am
ORD
- STT
1 stop9h 19m
Spirit Airlines
Sun 3/84:40 pm
STT
- ORD
2 stops28h 07m
Spirit Airlines
Deal found 2/13![Spirit Airlines logo]()
$308
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 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
Last-minute flights from Chicago to CaribbeanDiscover last-minute flight deals from Chicago to Caribbean. Data last updated February 16, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Caribbean. 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 CaribbeanSearch for one-way flight options from Chicago to Caribbean. 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. 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
Keep the following information in mind while searching for Chicago to Caribbean 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 |
Good round-trip deal | $280 or less |
Good one-way deal | $120 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Caribbean that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated February 16, 2026.
Use the filters below to find and compare flights from Chicago to Caribbean that are best for you.
Fly from
Chicago
Fly to
Caribbean
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
Sun 4/12
5:05 am-3:28 pm
1 stop9h 23m
Saint Thomas Island Cyril E King
Thu 4/16
4:40 pm-9:10 am
2 stops17h 30m
$280
ChicagoSaint Thomas Island
ORD - STT
ORDSTT
Chicago O'Hare Intl
Fri 4/10
5:05 am-3:28 pm
1 stop9h 23m
Saint Thomas Island Cyril E King
Mon 4/13
2:36 pm-4:56 pm
1 stop27h 20m
$286
Showing 1-10 of 60 results
Best time to book a flight from Chicago to Caribbean
Have a flexible travel schedule? Discover the best time to fly to Caribbean 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
CHI-0CB
ORD-SJU
MDW-SJU
ORD-STT
ORD-PUJ
What is the cheapest month to book a flight from Chicago to Caribbean?
Currently, April is the cheapest month in which you can book a flight from Chicago to Caribbean (average of $91). Flying from Chicago to Caribbean 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 CB?
Find hourly flight availability from Chicago to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated February 16, 2026.
One of the essential ways to save on airfare from Chicago to Caribbean is to remain as flexible as possible. Flights that are in the morning tend to be the most expensive. A flight in the evening could potentially save you up to 41% on airfare.
What is the cheapest day to fly from Chicago to Caribbean?
Use this chart to determine the cheapest time to fly round-trip from Chicago to Caribbean. Price data was last updated on February 7, 2026.
Travelers seeking maximum savings on their Chicago to Caribbean 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
Explore weekly flight availability from Chicago to Caribbean. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated February 16, 2026.
The most flights from CHI to 0CB 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
Get insights into the airlines that provide service to Caribbean. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean. Reviews last updated February 16, 2026.
Read reviews from past customers who have flown Delta, United Airlines, and American Airlines from Chicago to Caribbean. 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.
Comfort
7.9
Boarding
8.1
Entertainment
7.8
Crew
8.5
Food
7.2
Overall
7.9
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Comfort
7.9
Boarding
8.1
Entertainment
7.8
Crew
8.5
Food
7.2
Overall
7.9
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Comfort
7.9
Boarding
8.1
Entertainment
7.8
Crew
8.5
Food
7.2
Overall
7.9
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Comfort
7.9
Boarding
8.1
Entertainment
7.8
Crew
8.5
Food
7.2
Overall
7.9
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Comfort
7.9
Boarding
8.1
Entertainment
7.8
Crew
8.5
Food
7.2
Overall
7.9
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Comfort
7.9
Boarding
8.1
Entertainment
7.8
Crew
8.5
Food
7.2
Overall
7.9
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. 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
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Caribbean by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Caribbean by cabin class
Find flights from Chicago to Caribbean, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Caribbean flights
Browse other Chicago and Caribbean flight options. Last updated on February 16, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Fly to Caribbean countries
Consider these flights traveling to countries located in Caribbean.
Chicago to Caribbean flights
Consider these flights traveling from Chicago to Caribbean.
Top 9 airlines flying from Chicago to Caribbean
Discover the top 9 airlines that operate flights from Chicago to Caribbean. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 2,558,603 searches. Data last updated 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% |