$109+ Cheap flights from Chicago (CHI) to Caribbean
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/15. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJU
Oct 18 — Oct 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
We find the providers serving your travel needs. Choose up to four travel providers to compare side-by-side for flights, hotels, or car rentals.3. Compare prices and book
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
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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 September 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 September 18, 2026.
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/296:00 am -
1 stop16h 25m
Mon 11/26:15 am -
1 stop18h 28m
Deal found 9/17![Frontier logo]()
$217
This CheapOair deal was found by Cheapflights users on 9/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/146:21 am -
1 stop8h 45m
Wed 10/283:59 pm -
1 stop8h 48m
Deal found 9/17![Frontier logo]()
$217
This Mytrip deal was found by Cheapflights users on 9/17. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/174:41 pm -
1 stop16h 38m
Fri 10/233:00 am -
2 stops20h 39m
Deal found 9/17![Frontier logo]()
$218
This Frontier deal was found by Cheapflights users on 9/17. 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.
Sun 10/256:00 am -
1 stop18h 17m
Sat 10/316:26 pm -
1 stop16h 20m
Deal found 9/17![Frontier logo]()
$219
This Cheapflightsfares deal was found by Cheapflights users on 9/17. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/164:41 pm -
1 stop22h 45m
Fri 10/232:51 pm -
1 stop8h 48m
Deal found 9/17![Frontier logo]()
$220
This Cheapflightsfares deal was found by Cheapflights users on 9/16. 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.
Wed 10/76:25 am -
1 stop7h 54m
Tue 11/173:59 pm -
1 stop9h 48m
Deal found 9/16![Frontier logo]()
$220
This Super.com deal was found by Cheapflights users on 9/15. 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 10/67:11 am -
1 stop7h 06m
Thu 10/157:00 am -
1 stop9h 30m
Deal found 9/15![Frontier logo]()
$221
This FlightHub deal was found by Cheapflights users on 9/17. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/304:42 pm -
1 stop22h 34m
Sat 11/77:26 pm -
1 stop15h 20m
Deal found 9/17![Frontier logo]()
$222
This Frontier deal was found by Cheapflights users on 9/16. 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 10/76:25 am -
1 stop7h 54m
Tue 10/273:59 pm -
1 stop8h 48m
Deal found 9/16![Frontier logo]()
$222
This FlightHub deal was found by Cheapflights users on 9/16. 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 10/104:41 pm -
1 stop16h 38m
Thu 10/157:00 am -
1 stop9h 30m
Deal found 9/16![Frontier logo]()
$223
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 11/210:26 am -
1 stop12h 33m
Fri 11/66:15 am -
1 stop18h 28m
Deal found 9/17![Frontier logo]()
$224
This CheapOair deal was found by Cheapflights users on 9/16. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/266:15 am -
1 stop8h 51m
Wed 11/43:59 pm -
1 stop9h 48m
Deal found 9/16![Frontier logo]()
$224
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 September 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 September 18, 2026.
This United Airlines deal was found by Cheapflights users on 9/13. 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.
Tue 10/272:16 pm -
Nonstop4h 44m
Wed 11/48:25 am -
Nonstop5h 22m
Deal found 9/13![United Airlines logo]()
$237
This JetBlue deal was found by Cheapflights users on 9/17. 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.
Wed 11/181:00 pm -
1 stop10h 13m
Fri 12/43:30 pm -
1 stop10h 03m
Deal found 9/17![JetBlue logo]()
$241
This Southwest deal was found by Cheapflights users on 9/15. 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 11/146:35 am -
1 stop8h 40m
Tue 11/176:10 am -
1 stop10h 50m
Deal found 9/15![Southwest logo]()
$266
This Delta deal was found by Cheapflights users on 9/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 9/2310:25 am -
1 stop12h 24m
Wed 9/307:30 am -
1 stop10h 29m
Deal found 9/14![Delta logo]()
$286
This Arajet deal was found by Cheapflights users on 9/14. 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.
Sat 10/3111:27 am -
Nonstop4h 45m
Sun 11/86:10 pm -
Nonstop5h 10m
Deal found 9/14![Arajet logo]()
$395
This Copa Airlines deal was found by Cheapflights users on 9/18. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/163:20 pm -
1 stop19h 57m
Sat 10/2412:22 pm -
1 stop12h 35m
Deal found 9/18![Copa Airlines logo]()
$470
This United Airlines deal was found by Cheapflights users on 9/15. 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.
Thu 10/295:00 am -
1 stop7h 11m
Thu 11/58:25 am -
Nonstop5h 22m
Deal found 9/15![United Airlines logo]()
$242
This Air Canada deal was found by Cheapflights users on 9/13. 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.
Sun 11/85:58 pm -
2 stops22h 22m
Sat 11/146:20 pm -
1 stop16h 03m
Deal found 9/13![Air Canada logo]()
$510
This Southwest deal was found by Cheapflights users on 9/15. 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.
Thu 10/18:40 pm -
1 stop11h 40m
Tue 10/66:35 am -
1 stop7h 20m
Deal found 9/15![Southwest logo]()
$266
This Orbitz deal was found by Cheapflights users on 9/13. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 12/165:58 pm -
2 stops25h 27m
Mon 12/2112:24 pm -
1 stop12h 25m
Deal found 9/13![Multiple Airlines logo]()
$540
This JetBlue deal was found by Cheapflights users on 9/16. 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 10/107:00 am -
1 stop7h 23m
Mon 10/124:40 pm -
1 stop7h 50m
Deal found 9/16![JetBlue logo]()
$285
This Southwest deal was found by Cheapflights users on 9/13. 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.
Sat 10/172:40 pm -
1 stop6h 35m
Wed 10/215:50 am -
1 stop11h 15m
Deal found 9/13![Southwest logo]()
$266
This JetBlue deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/71:00 pm -
1 stop10h 13m
Mon 11/96:25 am -
1 stop9h 17m
Deal found 9/18![JetBlue logo]()
$300
This Southwest deal was found by Cheapflights users on 9/15. 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 11/161:20 pm -
1 stop7h 05m
Mon 11/232:20 pm -
1 stop10h 25m
Deal found 9/15![Southwest logo]()
$285
This United Airlines deal was found by Cheapflights users on 9/16. 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.
Wed 10/148:55 am -
Nonstop4h 49m
Wed 10/213:56 pm -
Nonstop5h 09m
Deal found 9/16![United Airlines logo]()
$319
This Southwest deal was found by Cheapflights users on 9/15. 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 10/162:15 pm -
1 stop9h 10m
Mon 10/1910:50 pm -
1 stop12h 00m
Deal found 9/15![Southwest logo]()
$288
This United Airlines deal was found by Cheapflights users on 9/15. 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 11/172:16 pm -
Nonstop4h 44m
Wed 11/188:25 am -
Nonstop5h 22m
Deal found 9/15![United Airlines logo]()
$322
This Arajet deal was found by Cheapflights users on 9/13. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 12/63:20 am -
Nonstop4h 45m
Sun 12/136:10 pm -
Nonstop5h 10m
Deal found 9/13![Arajet logo]()
$415
This United Airlines deal was found by Cheapflights users on 9/15. 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 10/65:00 am -
1 stop7h 45m
Wed 10/283:55 pm -
Nonstop5h 31m
Deal found 9/15![United Airlines logo]()
$332
This Southwest deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 10/61:40 pm -
2 stops8h 30m
Thu 10/158:50 pm -
1 stop12h 55m
Deal found 9/18![Southwest logo]()
$321
This Copa Airlines deal was found by Cheapflights users on 9/16. 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 Copa Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/132:13 pm -
1 stop20h 57m
Mon 11/1612:45 pm -
1 stop26h 01m
Deal found 9/16![Copa Airlines logo]()
$478
This United Airlines deal was found by Cheapflights users on 9/18. 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.
Mon 9/215:00 am -
1 stop7h 45m
Fri 9/253:56 pm -
Nonstop5h 09m
Deal found 9/18![United Airlines logo]()
$341
This Delta deal was found by Cheapflights users on 9/13. 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.
Wed 10/286:04 am -
1 stop6h 28m
Wed 11/43:57 pm -
1 stop8h 36m
Deal found 9/13![Delta logo]()
$520
This Air Canada deal was found by Cheapflights users on 9/13. 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.
Mon 1/43:45 pm -
2 stops22h 45m
Mon 1/115:25 pm -
1 stop17h 43m
Deal found 9/13![Air Canada logo]()
$523
This JetBlue deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 11/67:00 am -
1 stop6h 57m
Mon 11/91:07 pm -
1 stop11h 48m
Deal found 9/18![JetBlue logo]()
$433
This Southwest deal was found by Cheapflights users on 9/15. 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 10/234:15 pm -
2 stops8h 10m
Sun 10/255:40 pm -
1 stop7h 00m
Deal found 9/15![Southwest logo]()
$333
This Copa Airlines deal was found by Cheapflights users on 9/17. 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.
Mon 3/87:08 am -
1 stop26h 28m
Mon 3/152:37 pm -
1 stop23h 57m
Deal found 9/17![Copa Airlines logo]()
$488
This United Airlines deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 11/72:16 pm -
Nonstop4h 44m
Mon 11/98:25 am -
Nonstop5h 22m
Deal found 9/18![United Airlines logo]()
$347
This Delta deal was found by Cheapflights users on 9/16. 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 9/296:05 am -
1 stop6h 22m
Tue 10/62:57 pm -
1 stop8h 36m
Deal found 9/16![Delta logo]()
$522
This Copa Airlines deal was found by Cheapflights users on 9/17. 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.
Tue 10/278:35 am -
1 stop26h 10m
Tue 11/312:10 pm -
1 stop14h 01m
Deal found 9/17![Copa Airlines logo]()
$490
Last-minute flights from Chicago to CaribbeanDiscover last-minute flight deals from Chicago to Caribbean. Data last updated September 18, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Caribbean. Data last updated September 18, 2026 and is based on user searches.
This deal was found by Cheapflights users on 9/15. 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 is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 9/266:20 am -
1 stop8h 46m
Tue 9/298:45 am -
1 stop7h 35m
Deal found 9/15![Frontier logo]()
$225
This Super.com deal was found by Cheapflights users on 9/15. 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 10/67:11 am -
1 stop7h 06m
Thu 10/157:00 am -
1 stop9h 30m
Deal found 9/15![Frontier logo]()
$221
This Cheapflightsfares deal was found by Cheapflights users on 9/16. 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.
Wed 10/76:25 am -
1 stop7h 54m
Tue 11/173:59 pm -
1 stop9h 48m
Deal found 9/16![Frontier logo]()
$220
This Frontier deal was found by Cheapflights users on 9/16. 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 10/76:25 am -
1 stop7h 54m
Tue 10/273:59 pm -
1 stop8h 48m
Deal found 9/16![Frontier logo]()
$222
This FlightHub deal was found by Cheapflights users on 9/16. 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 10/104:41 pm -
1 stop16h 38m
Thu 10/157:00 am -
1 stop9h 30m
Deal found 9/16![Frontier logo]()
$223
This CheapOair deal was found by Cheapflights users on 9/17. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/146:21 am -
1 stop8h 45m
Wed 10/283:59 pm -
1 stop8h 48m
Deal found 9/17![Frontier logo]()
$217
This Cheapflightsfares deal was found by Cheapflights users on 9/17. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/164:41 pm -
1 stop22h 45m
Fri 10/232:51 pm -
1 stop8h 48m
Deal found 9/17![Frontier logo]()
$220
This Mytrip deal was found by Cheapflights users on 9/17. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/174:41 pm -
1 stop16h 38m
Fri 10/233:00 am -
2 stops20h 39m
Deal found 9/17![Frontier logo]()
$218
This Frontier deal was found by Cheapflights users on 9/17. 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.
Sun 10/256:00 am -
1 stop18h 17m
Sat 10/316:26 pm -
1 stop16h 20m
Deal found 9/17![Frontier logo]()
$219
This CheapOair deal was found by Cheapflights users on 9/16. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/266:15 am -
1 stop8h 51m
Wed 11/43:59 pm -
1 stop9h 48m
Deal found 9/16![Frontier logo]()
$224
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/296:00 am -
1 stop16h 25m
Mon 11/26:15 am -
1 stop18h 28m
Deal found 9/17![Frontier logo]()
$217
This Kiwi.com deal was found by Cheapflights users on 9/16. 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 10/304:42 pm -
1 stop22h 34m
Thu 11/57:00 am -
1 stop10h 37m
Deal found 9/16![Frontier logo]()
$222
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 September 18, 2026.
Search for one-way flight options from Chicago to Caribbean. Find affordable one-way fares based on user searches. Data last updated September 18, 2026.
This Super.com deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/156:00 am -
1 stop18h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Frontier logo]()
$109
This Super.com deal was found by Cheapflights users on 9/15. 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 10/136:21 am -
1 stop8h 45m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Frontier logo]()
$110
This Trip.com deal was found by Cheapflights users on 9/18. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 11/1712:50 pm -
1 stop21h 40m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Air Canada logo]()
$111
This Frontier deal was found by Cheapflights users on 9/15. 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.
Sun 10/116:24 am -
1 stop8h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Frontier logo]()
$111
This Frontier deal was found by Cheapflights users on 9/15. 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 10/318:00 am -
1 stop13h 17m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Frontier logo]()
$113
This CheapOair deal was found by Cheapflights users on 9/14. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 10/76:25 am -
1 stop7h 54m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/14![Frontier logo]()
$113
This Kiwi.com deal was found by Cheapflights users on 9/15. 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 10/164:41 pm -
1 stop16h 38m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Frontier logo]()
$115
This Priceline deal was found by Cheapflights users on 9/15. 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.
Sun 11/228:42 pm -
1 stop27h 42m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/15![Frontier logo]()
$117
This Kiwi.com deal was found by Cheapflights users on 9/17. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/156:00 am -
1 stop15h 28m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Frontier logo]()
$118
This JetBlue deal was found by Cheapflights users on 9/17. 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.
Tue 11/171:00 pm -
1 stop10h 13m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![JetBlue logo]()
$119
This Kiwi.com deal was found by Cheapflights users on 9/18. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 12/152:04 pm -
1 stop9h 03m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/18![Frontier logo]()
$119
This Orbitz deal was found by Cheapflights users on 9/17. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 12/107:05 am -
1 stop29h 10m
Wed 12/3112:00 am -
Nonstop0h 00m
Deal found 9/17![Air Canada logo]()
$120
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 September 18, 2026.
Round-trip from | $217 (Kiwi.com) |
|---|---|
One-way from | $109 (Super.com) |
Popular in | December |
Cheapest in | August |
Average price | $340 |
Good round-trip deal | $315 or less |
Good one-way deal | $159 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 7,457,451 searches. Data last updated September 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
Quickest round-trip
ChicagoSan Juan
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Sat 11/7
2:16 pm-9:00 pm
Nonstop4h 44m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$119
ChicagoNassau
ORD Chicago O'Hare Intl - NAS Nassau Intl
ORDNAS
Chicago O'Hare Intl
Sat 11/21
3:45 pm-1:15 pm
1 stop20h 30m
Nassau Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$120
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Tue 11/10
1:05 pm-11:15 pm
1 stop8h 10m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$120
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Fri 10/30
2:50 pm-12:10 am
2 stops8h 20m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$120
ChicagoSan Juan
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Wed 11/11
12:59 pm-12:36 am
1 stop9h 37m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$123
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Wed 11/11
4:25 pm-12:50 am
1 stop6h 25m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$123
ChicagoNassau
ORD Chicago O'Hare Intl - NAS Nassau Intl
ORDNAS
Chicago O'Hare Intl
Sun 12/13
5:58 pm-1:15 pm
2 stops18h 17m
Nassau Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$125
ChicagoSan Juan
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Fri 11/13
1:35 pm-11:54 pm
1 stop8h 19m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$125
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Mon 11/16
1:05 pm-11:15 pm
1 stop8h 10m
San Juan Luis Munoz Marin Intl
Wed 12/31
12:00 am-10:00 pm
Nonstop0h 00m
$125
ChicagoNassau
ORD Chicago O'Hare Intl - NAS Nassau Intl
ORDNAS
Chicago O'Hare Intl
Wed 9/30
3:40 pm-1:25 pm
1 stop20h 45m
Nassau Intl
Wed 12/31
12:00 am-11:00 pm
Nonstop0h 00m
$128
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-SDQ
ORD-PUJ
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago to Caribbean
CHI-0CB
ORD-SJU
MDW-SJU
ORD-NAS
ORD-SDQ
What is the cheapest month to book a flight from Chicago to Caribbean?
Currently, August is the cheapest month in which you can book a flight from Chicago to Caribbean (average of $429). Flying from Chicago to Caribbean in December is currently the most expensive (average of $612). 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 September 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 31% 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 September 18, 2026.
The most flights from CHI to 0CB are scheduled on a Monday (3 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (1 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 64 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 September 12, 2026.
Travelers seeking maximum savings on their Chicago to Caribbean flight should consider departing on Sunday 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 September 18, 2026.
Read reviews from past customers who have flown United Airlines,American Airlines, andJetBlue 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.
Food
6.7
Boarding
7.7
Entertainment
7.1
Overall
7.4
Comfort
7.3
Crew
8.1
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Food
6.7
Boarding
7.7
Entertainment
7.1
Overall
7.4
Comfort
7.3
Crew
8.1
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Food
6.7
Boarding
7.7
Entertainment
7.1
Overall
7.4
Comfort
7.3
Crew
8.1
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Food
6.7
Boarding
7.7
Entertainment
7.1
Overall
7.4
Comfort
7.3
Crew
8.1
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
Food
6.7
Boarding
7.7
Entertainment
7.1
Overall
7.4
Comfort
7.3
Crew
8.1
Reviews
1 / 20
2.0
MediocreDawn,Aug 2026
ORD - DEN
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 September 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 7,457,451 searches. Data last updated September 18, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$91 | Average$520 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$118 | Average$561 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$118 | Average$461 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$223 | Average$376 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$231 | Average$554 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$235 | Average$586 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$262 | Average$597 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$276 | Average$674 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$286 | Average$624 | FlexibilityNo cancel fee | On-time71% |