$94+ 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 7/18. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJU
Jul 18 — Jul 251
Round-trip
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 June 18, 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 June 18, 2026.
This United Airlines deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/316:29 pm
ORD
- SJU
1 stop10h 00m
United Airlines
Fri 8/283:56 pm
SJU
- ORD
Nonstop5h 09m
United Airlines
Deal found 6/14![United Airlines logo]()
$254
This Delta deal was found by Cheapflights users on 6/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/226:40 am
ORD
- SJU
1 stop8h 58m
Delta
Mon 8/317:00 am
SJU
- ORD
1 stop8h 09m
Delta
Deal found 6/16![Delta logo]()
$256
This Southwest deal was found by Cheapflights users on 6/15. 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 8/2911:00 am
MDW
- SJU
1 stop6h 15m
Southwest
Sat 9/55:55 am
SJU
- MDW
2 stops8h 10m
Southwest
Deal found 6/15![Southwest logo]()
$256
This American Airlines deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/275:20 pm
ORD
- SJU
Nonstop4h 55m
American Airlines
Thu 9/31:38 pm
SJU
- ORD
1 stop11h 57m
American Airlines
Deal found 6/15![American Airlines logo]()
$257
This Kiwi.com deal was found by Cheapflights users on 6/15. 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.
Sun 8/1612:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Fri 8/216:11 pm
SJU
- ORD
Nonstop5h 15m
Frontier
Deal found 6/15![Frontier logo]()
$258
This Kiwi.com deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/1512:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Sat 8/226:11 pm
SJU
- ORD
Nonstop5h 15m
Frontier
Deal found 6/15![Frontier logo]()
$260
This American Airlines deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/154:59 pm
ORD
- SJU
Nonstop4h 55m
American Airlines
Sat 8/227:20 pm
SJU
- ORD
1 stop13h 14m
American Airlines
Deal found 6/18![American Airlines logo]()
$262
This Frontier deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1912:29 am
ORD
- SJU
Nonstop4h 57m
Frontier
Mon 8/246:11 pm
SJU
- ORD
Nonstop5h 15m
Frontier
Deal found 6/16![Frontier logo]()
$263
This eDestinos deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/612:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Tue 7/147:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 6/18![Frontier logo]()
$264
This Kiwi.com deal was found by Cheapflights users on 6/15. 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.
Mon 8/1712:29 am
ORD
- SJU
Nonstop4h 57m
Frontier
Sat 8/226:11 pm
SJU
- ORD
Nonstop5h 15m
Frontier
Deal found 6/15![Frontier logo]()
$265
This Delta deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 8/95:30 am
ORD
- SJU
1 stop10h 08m
Delta
Thu 8/132:59 pm
SJU
- ORD
1 stop9h 58m
Delta
Deal found 6/17![Delta logo]()
$266
This Kiwi.com deal was found by Cheapflights users on 6/15. 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 8/2512:29 am
ORD
- SJU
Nonstop4h 57m
Frontier
Sun 8/306:16 pm
SJU
- ORD
1 stop29h 58m
Frontier
Deal found 6/15![Frontier logo]()
$267
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 June 18, 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 June 18, 2026.
This Southwest deal was found by Cheapflights users on 6/16. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/227:50 am
MDW
- SJU
2 stops7h 50m
Southwest
Wed 8/2610:30 am
SJU
- MDW
1 stop8h 10m
Southwest
Deal found 6/16![Southwest logo]()
$256
This Delta deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/1412:46 pm
MDW
- SJU
1 stop8h 43m
Delta
Wed 8/192:59 pm
SJU
- MDW
1 stop8h 37m
Delta
Deal found 6/14![Delta logo]()
$276
This JetBlue deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/187:00 am
ORD
- NAS
1 stop9h 22m
JetBlue
Wed 7/2212:20 pm
NAS
- ORD
1 stop12h 24m
JetBlue
Deal found 6/17![JetBlue logo]()
$344
This United Airlines deal was found by Cheapflights users on 6/13. 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.
Sat 6/272:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Fri 7/31:00 am
SJU
- ORD
1 stop9h 00m
United Airlines
Deal found 6/13![United Airlines logo]()
$391
This Arajet deal was found by Cheapflights users on 6/15. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 8/35:30 am
ORD
- PUJ
Nonstop4h 45m
Arajet
Sat 8/87:02 am
PUJ
- ORD
Nonstop5h 10m
Arajet
Deal found 6/15![Arajet logo]()
$439
This Copa Airlines deal was found by Cheapflights users on 6/14. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/188:02 am
ORD
- MBJ
1 stop26h 09m
Copa Airlines
Fri 7/2411:16 am
MBJ
- ORD
1 stop16h 44m
Copa Airlines
Deal found 6/14![Copa Airlines logo]()
$468
This KAYAK deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure KAYAK is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/65:00 am
ORD
- SJU
1 stop16h 57m
American Airlines
Thu 7/912:59 am
SJU
- ORD
Nonstop5h 05m
American Airlines
Deal found 6/18![American Airlines logo]()
$480
This Southwest deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/141:00 pm
MDW
- SJU
2 stops8h 50m
Southwest
Sun 8/169:25 pm
SJU
- MDW
1 stop12h 20m
Southwest
Deal found 6/14![Southwest logo]()
$256
This CheapOair deal was found by Cheapflights users on 6/13. 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.
Fri 9/47:52 pm
ORD
- MBJ
1 stop13h 10m
Multiple Airlines
Tue 9/812:30 pm
MBJ
- ORD
1 stop24h 53m
Multiple Airlines
Deal found 6/13![Multiple Airlines logo]()
$525
This Air Canada deal was found by Cheapflights users on 6/13. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 9/46:21 pm
ORD
- MBJ
2 stops16h 59m
Air Canada
Tue 9/812:30 pm
MBJ
- ORD
2 stops21h 47m
Air Canada
Deal found 6/13![Air Canada logo]()
$548
This Delta deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/286:05 am
MDW
- SJU
1 stop9h 33m
Delta
Tue 9/112:56 pm
SJU
- MDW
1 stop10h 40m
Delta
Deal found 6/18![Delta logo]()
$276
This Orbitz deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/2112:44 am
ORD
- PUJ
1 stop18h 35m
Frontier
Sun 7/2611:52 am
PUJ
- ORD
1 stop8h 55m
Frontier
Deal found 6/18![Frontier logo]()
$635
This Southwest deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 8/201:00 pm
MDW
- SJU
2 stops8h 50m
Southwest
Mon 8/246:00 am
SJU
- MDW
2 stops9h 30m
Southwest
Deal found 6/18![Southwest logo]()
$326
This JetBlue deal was found by Cheapflights users on 6/16. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/257:00 am
ORD
- NAS
1 stop9h 22m
JetBlue
Fri 7/313:02 pm
NAS
- ORD
1 stop9h 42m
JetBlue
Deal found 6/16![JetBlue logo]()
$363
This United Airlines deal was found by Cheapflights users on 6/13. 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.
Thu 8/68:02 pm
ORD
- SJU
1 stop8h 27m
United Airlines
Tue 8/117:20 am
SJU
- ORD
1 stop8h 10m
United Airlines
Deal found 6/13![United Airlines logo]()
$395
This Southwest deal was found by Cheapflights users on 6/13. 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.
Thu 8/611:25 am
MDW
- SJU
2 stops9h 45m
Southwest
Wed 8/121:20 pm
SJU
- MDW
1 stop6h 50m
Southwest
Deal found 6/13![Southwest logo]()
$351
This Delta deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/56:05 am
MDW
- SDQ
1 stop6h 23m
Delta
Wed 8/192:53 pm
SDQ
- MDW
1 stop8h 43m
Delta
Deal found 6/18![Delta logo]()
$388
This United Airlines deal was found by Cheapflights users on 6/15. 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.
Tue 6/232:21 pm
ORD
- SJU
1 stop8h 29m
United Airlines
Fri 6/261:00 am
SJU
- ORD
1 stop9h 00m
United Airlines
Deal found 6/15![United Airlines logo]()
$404
This Arajet deal was found by Cheapflights users on 6/14. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/64:30 am
ORD
- PUJ
Nonstop4h 45m
Arajet
Thu 7/97:30 pm
PUJ
- ORD
Nonstop5h 10m
Arajet
Deal found 6/14![Arajet logo]()
$460
This Southwest deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/157:50 am
MDW
- SJU
2 stops9h 15m
Southwest
Sun 8/236:35 am
SJU
- MDW
2 stops10h 15m
Southwest
Deal found 6/14![Southwest logo]()
$351
This JetBlue deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/42:35 pm
ORD
- SJU
1 stop7h 45m
JetBlue
Sat 8/155:35 am
SJU
- ORD
1 stop9h 04m
JetBlue
Deal found 6/14![JetBlue logo]()
$427
This Copa Airlines deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/88:02 am
ORD
- SDQ
1 stop13h 54m
Copa Airlines
Tue 7/1412:43 pm
SDQ
- ORD
1 stop16h 17m
Copa Airlines
Deal found 6/17![Copa Airlines logo]()
$472
This Delta deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/155:30 am
ORD
- SDQ
2 stops11h 55m
Delta
Tue 9/227:40 pm
SDQ
- ORD
2 stops15h 57m
Delta
Deal found 6/17![Delta logo]()
$393
This United Airlines deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 6/262:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Sun 6/281:00 am
SJU
- ORD
1 stop9h 00m
United Airlines
Deal found 6/18![United Airlines logo]()
$407
This Delta deal was found by Cheapflights users on 6/13. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1112:46 pm
MDW
- SJU
1 stop8h 43m
Delta
Mon 8/172:59 pm
SJU
- MDW
1 stop8h 37m
Delta
Deal found 6/13![Delta logo]()
$396
This JetBlue deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/176:00 am
ORD
- NAS
1 stop9h 04m
JetBlue
Mon 7/203:02 pm
NAS
- ORD
1 stop9h 42m
JetBlue
Deal found 6/17![JetBlue logo]()
$441
This Arajet deal was found by Cheapflights users on 6/15. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/275:30 am
ORD
- PUJ
Nonstop4h 45m
Arajet
Sat 8/17:02 am
PUJ
- ORD
Nonstop5h 10m
Arajet
Deal found 6/15![Arajet logo]()
$494
This CheapOair deal was found by Cheapflights users on 6/13. 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.
Sat 7/186:22 pm
ORD
- MBJ
2 stops16h 58m
Multiple Airlines
Sat 7/2510:27 am
MBJ
- ORD
1 stop9h 20m
Multiple Airlines
Deal found 6/13![Multiple Airlines logo]()
$559
This Copa Airlines deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 7/83:21 pm
ORD
- MBJ
1 stop19h 54m
Copa Airlines
Sun 7/1212:22 pm
MBJ
- ORD
1 stop25h 35m
Copa Airlines
Deal found 6/17![Copa Airlines logo]()
$514
This Air Canada deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 8/18:40 pm
ORD
- NAS
2 stops15h 55m
Air Canada
Sat 8/86:30 pm
NAS
- ORD
2 stops41h 50m
Air Canada
Deal found 6/18![Air Canada logo]()
$566
Last-minute flights from Chicago to CaribbeanDiscover last-minute flight deals from Chicago to Caribbean. Data last updated June 18, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Caribbean. Data last updated June 18, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 6/16. 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.
Fri 7/312:44 am
ORD
- SJU
Nonstop4h 57m
Frontier
Sat 7/117:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 6/16![Frontier logo]()
$267
This Frontier deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/312:44 am
ORD
- SJU
Nonstop4h 57m
Frontier
Fri 7/107:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 6/16![Frontier logo]()
$277
This United Airlines deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/48:49 am
ORD
- SJU
Nonstop4h 55m
United Airlines
Sat 7/117:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
Deal found 6/16![United Airlines logo]()
$279
This Frontier deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 7/512:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Thu 7/97:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 6/16![Frontier logo]()
$276
This eDestinos deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/612:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Tue 7/147:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 6/18![Frontier logo]()
$264
This Frontier deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/612:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Sat 7/117:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 6/17![Frontier logo]()
$278
This Frontier deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/712:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Sat 7/117:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 6/17![Frontier logo]()
$282
This Priceline deal was found by Cheapflights users on 6/15. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/912:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Fri 7/177:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 6/15![Frontier logo]()
$281
This Frontier deal was found by Cheapflights users on 6/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/1112:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Fri 7/177:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 6/16![Frontier logo]()
$286
This Super.com deal was found by Cheapflights users on 6/15. 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 7/1412:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Mon 7/207:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 6/15![Frontier logo]()
$273
This Frontier deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 7/2012:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Fri 7/317:14 pm
SJU
- ORD
Nonstop5h 13m
Frontier
Deal found 6/17![Frontier logo]()
$283
This United Airlines deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 7/316:29 pm
ORD
- SJU
1 stop10h 00m
United Airlines
Fri 8/283:56 pm
SJU
- ORD
Nonstop5h 09m
United Airlines
Deal found 6/14![United Airlines logo]()
$254
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 June 18, 2026.
Search for one-way flight options from Chicago to Caribbean. Find affordable one-way fares based on user searches. Data last updated June 18, 2026.
This American Airlines deal was found by Cheapflights users on 6/15. 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.
Sat 7/187:00 am
ORD
- NAS
Nonstop3h 29m
American Airlines
Deal found 6/15![American Airlines logo]()
$94
This SmartFares deal was found by Cheapflights users on 6/14. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 7/167:00 am
ORD
- NAS
1 stop9h 22m
JetBlue
Deal found 6/14![JetBlue logo]()
$103
This JetBlue deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 7/117:00 am
ORD
- NAS
1 stop9h 22m
JetBlue
Deal found 6/14![JetBlue logo]()
$113
This American Airlines deal was found by Cheapflights users on 6/15. 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.
Fri 9/45:20 pm
ORD
- SJU
Nonstop4h 55m
American Airlines
Deal found 6/15![American Airlines logo]()
$114
This JetBlue deal was found by Cheapflights users on 6/16. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/127:00 am
ORD
- NAS
1 stop9h 14m
JetBlue
Deal found 6/16![JetBlue logo]()
$118
This Delta deal was found by Cheapflights users on 6/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/116:40 am
ORD
- SJU
1 stop8h 58m
Delta
Deal found 6/15![Delta logo]()
$118
This Delta deal was found by Cheapflights users on 6/16. 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 Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 8/1112:46 pm
MDW
- SJU
1 stop8h 43m
Delta
Deal found 6/16![Delta logo]()
$118
This Frontier deal was found by Cheapflights users on 6/15. 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.
Sat 8/812:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 6/15![Frontier logo]()
$119
This American Airlines deal was found by Cheapflights users on 6/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 7/219:45 am
ORD
- SJU
1 stop12h 12m
American Airlines
Deal found 6/14![American Airlines logo]()
$121
This Delta deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1210:33 am
ORD
- SJU
1 stop10h 56m
Delta
Deal found 6/17![Delta logo]()
$123
This Delta deal was found by Cheapflights users on 6/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 8/1210:54 am
MDW
- SJU
1 stop10h 35m
Delta
Deal found 6/17![Delta logo]()
$123
This American Airlines deal was found by Cheapflights users on 6/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/25:20 pm
ORD
- SJU
Nonstop4h 55m
American Airlines
Deal found 6/18![American Airlines logo]()
$124
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 June 18, 2026.
Round-trip from | $254 (United Airlines) |
|---|---|
One-way from | $94 (American Airlines) |
Popular in | December |
Cheapest in | January |
Average price | $455 |
Good round-trip deal | $396 or less |
Good one-way deal | $148 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 June 18, 2026.
Use the filters below to find and compare flights from Chicago to Caribbean that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Sat 8/22
7:50 am-4:40 pm
2 stops7h 50m
San Juan Luis Munoz Marin Intl
Wed 8/26
10:30 am-5:40 pm
1 stop8h 10m
$256
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Fri 8/14
1:00 pm-10:50 pm
2 stops8h 50m
San Juan Luis Munoz Marin Intl
Sun 8/16
9:25 pm-8:45 am
1 stop12h 20m
$256
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Fri 8/14
12:46 pm-10:29 pm
1 stop8h 43m
San Juan Luis Munoz Marin Intl
Wed 8/19
2:59 pm-10:36 pm
1 stop8h 37m
$276
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Fri 8/28
6:05 am-4:38 pm
1 stop9h 33m
San Juan Luis Munoz Marin Intl
Tue 9/1
12:56 pm-10:36 pm
1 stop10h 40m
$276
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Thu 8/20
1:00 pm-10:50 pm
2 stops8h 50m
San Juan Luis Munoz Marin Intl
Mon 8/24
6:00 am-2:30 pm
2 stops9h 30m
$326
ChicagoNassau
ORD - NAS
ORDNAS
Chicago O'Hare Intl
Sat 7/18
7:00 am-5:22 pm
1 stop9h 22m
Nassau Intl
Wed 7/22
12:20 pm-11:44 pm
1 stop12h 24m
$344
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Thu 8/6
11:25 am-10:10 pm
2 stops9h 45m
San Juan Luis Munoz Marin Intl
Wed 8/12
1:20 pm-7:10 pm
1 stop6h 50m
$351
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Sat 8/15
7:50 am-6:05 pm
2 stops9h 15m
San Juan Luis Munoz Marin Intl
Sun 8/23
6:35 am-3:50 pm
2 stops10h 15m
$351
ChicagoNassau
ORD - NAS
ORDNAS
Chicago O'Hare Intl
Sat 7/25
7:00 am-5:22 pm
1 stop9h 22m
Nassau Intl
Fri 7/31
3:02 pm-11:44 pm
1 stop9h 42m
$363
ChicagoSanto Domingo
MDW - SDQ
MDWSDQ
Chicago Midway
Wed 8/5
6:05 am-1:28 pm
1 stop6h 23m
Santo Domingo Las Americas
Wed 8/19
2:53 pm-10:36 pm
1 stop8h 43m
$388
Showing 1-10 of 60 resultsSorted by cheapest first
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-NAS
ORD-PUJ
ORD-MBJ
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-NAS
ORD-PUJ
What is the cheapest month to book a flight from Chicago to Caribbean?
Currently, September is the cheapest month in which you can book a flight from Chicago to Caribbean (average of $371). Flying from Chicago to Caribbean in December is currently the most expensive (average of $580). 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 June 18, 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 32% on airfare.
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 June 18, 2026.
The most flights from CHI to 0CB are scheduled on a Monday (9 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (6 on average).
How far ahead should I book a flight from Chicago to Caribbean?
The best time to book flights from Chicago to Caribbean is 48 days before your desired departure date. The cost of your flight will likely increase significantly if you book two weeks in advance of your flight.
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 June 13, 2026.
Travelers seeking maximum savings on their Chicago to Caribbean flight should consider departing on Wednesday evenings when fares are most often at their lowest. Thursday mornings flights should be avoided if possible as fares are typically the most expensive at this time.
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 June 18, 2026.
Read reviews from past customers who have flown Southwest,United Airlines, andAmerican 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
8.0
Boarding
8.1
Food
7.0
Overall
7.9
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Comfort
8.0
Boarding
8.1
Food
7.0
Overall
7.9
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Comfort
8.0
Boarding
8.1
Food
7.0
Overall
7.9
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Comfort
8.0
Boarding
8.1
Food
7.0
Overall
7.9
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
Comfort
8.0
Boarding
8.1
Food
7.0
Overall
7.9
Crew
8.6
Entertainment
7.5
Reviews
1 / 20
8.0
ExcellentLa Tracimeldamarcos,Jun 2026
LAX - SLC
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 June 18, 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 June 18, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$119 | Average$425 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$132 | Average$525 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$138 | Average$546 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$175 | Average$515 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$216 | Average$357 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$228 | Average$486 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$261 | Average$588 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$303 | Average$609 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$324 | Average$628 | FlexibilityNo cancel fee | On-time71% |