$104+ Cheap flights from Chicago (CHI) to Caribbean Islands
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 10/15. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJU
Sep 20 — Sep 271
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Caribbean Islands with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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 Islands
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Cheapest flights from Chicago to Caribbean IslandsExplore the most affordable flight options available from Chicago to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 21, 2026.
Explore the most affordable flight options available from Chicago to Caribbean Islands. Find the lowest fares from popular airlines and budget airlines, with prices last updated on August 21, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/17. 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.
Fri 8/2112:44 am -
Nonstop5h 00m
Thu 8/277:14 pm -
Nonstop5h 13m
Deal found 8/17![Frontier logo]()
$208
This Kiwi.com deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” 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 10/198:04 am -
1 stop30h 14m
Thu 11/57:00 am -
1 stop10h 24m
Deal found 8/19![Frontier logo]()
$209
This Kiwi.com deal was found by Cheapflights users on 8/18. 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.
Sun 8/3012:44 am -
Nonstop5h 00m
Sun 9/1312:59 am -
1 stop13h 31m
Deal found 8/18![Frontier logo]()
$210
This Priceline deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2812:44 am -
Nonstop5h 00m
Wed 9/27:14 pm -
Nonstop5h 13m
Deal found 8/20![Frontier logo]()
$211
This Super.com deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” 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 8/2712:44 am -
Nonstop5h 00m
Sun 8/307:14 pm -
Nonstop5h 13m
Deal found 8/19![Frontier logo]()
$212
This Super.com deal was found by Cheapflights users on 8/18. 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.
Tue 8/2512:44 am -
Nonstop5h 00m
Sat 8/297:14 pm -
Nonstop5h 13m
Deal found 8/18![Frontier logo]()
$213
This CheapOair deal was found by Cheapflights users on 8/17. 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.
Sat 9/512:44 am -
Nonstop5h 00m
Wed 9/162:32 pm -
1 stop9h 36m
Deal found 8/17![Multiple Airlines logo]()
$214
This Super.com deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” 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 8/2912:44 am -
Nonstop5h 00m
Tue 9/17:14 pm -
Nonstop5h 13m
Deal found 8/19![Frontier logo]()
$215
This Kiwi.com deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” 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 8/3112:44 am -
Nonstop5h 00m
Thu 9/1011:54 am -
2 stops13h 51m
Deal found 8/20![Frontier logo]()
$217
This Priceline deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” 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.
Sat 8/2212:44 am -
Nonstop5h 00m
Wed 8/267:14 pm -
Nonstop5h 13m
Deal found 8/19![Frontier logo]()
$220
This Southwest deal was found by Cheapflights users on 8/18. 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.
Sun 9/138:05 pm -
1 stop12h 05m
Tue 9/225:15 am -
2 stops7h 50m
Deal found 8/18![Southwest logo]()
$226
This Southwest deal was found by Cheapflights users on 8/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/213:15 pm -
1 stop6h 55m
Fri 9/256:30 am -
2 stops8h 15m
Deal found 8/17![Southwest logo]()
$246
Best flights from Chicago to Caribbean IslandsDiscover carefully curated flight deals from Chicago to Caribbean Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 21, 2026.
Discover carefully curated flight deals from Chicago to Caribbean Islands that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated August 21, 2026.
This Southwest deal was found by Cheapflights users on 8/15. 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 9/252:55 pm -
1 stop6h 20m
Wed 9/305:15 am -
2 stops7h 50m
Deal found 8/15![Southwest logo]()
$246
This American Airlines deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” 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 9/15:20 pm -
Nonstop4h 55m
Fri 9/47:30 am -
1 stop10h 18m
Deal found 8/20![American Airlines logo]()
$262
This United Airlines deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” 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 9/510:40 am -
1 stop8h 58m
Fri 9/112:55 pm -
1 stop8h 20m
Deal found 8/19![United Airlines logo]()
$346
This Orbitz deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” 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.
Fri 9/42:25 pm -
1 stop7h 55m
Sat 9/57:14 pm -
Nonstop5h 13m
Deal found 8/20![Frontier logo]()
$352
This Arajet deal was found by Cheapflights users on 8/17. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 11/13:20 am -
Nonstop4h 45m
Sat 11/75:47 am -
Nonstop5h 10m
Deal found 8/17![Arajet logo]()
$355
This Arajet deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” 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 10/1712:12 pm -
1 stop8h 28m
Fri 10/231:40 am -
1 stop10h 32m
Deal found 8/20![Multiple Airlines logo]()
$397
This Delta deal was found by Cheapflights users on 8/18. 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 9/111:29 pm -
1 stop9h 20m
Thu 9/175:59 pm -
1 stop7h 00m
Deal found 8/18![Delta logo]()
$401
This WorldTicket deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure WorldTicket is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 12/255:45 am -
Nonstop4h 45m
Thu 1/77:30 pm -
Nonstop5h 10m
Deal found 8/20![WorldTicket logo]()
$435
This Copa Airlines deal was found by Cheapflights users on 8/17. 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 11/112:13 pm -
1 stop23h 59m
Sun 11/158:55 am -
1 stop17h 16m
Deal found 8/17![Copa Airlines logo]()
$476
This Southwest deal was found by Cheapflights users on 8/18. 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 9/173:15 pm -
1 stop6h 55m
Thu 9/2411:35 am -
1 stop10h 55m
Deal found 8/18![Southwest logo]()
$246
This JetBlue deal was found by Cheapflights users on 8/18. 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 10/177:00 am -
1 stop5h 44m
Tue 10/2012:18 pm -
1 stop12h 26m
Deal found 8/18![JetBlue logo]()
$542
This Southwest deal was found by Cheapflights users on 8/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/18:30 am -
1 stop6h 55m
Sat 9/55:05 am -
1 stop8h 30m
Deal found 8/17![Southwest logo]()
$261
This Avianca deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 11/510:20 pm -
1 stop11h 05m
Tue 11/1012:35 pm -
1 stop9h 45m
Deal found 8/19![Avianca logo]()
$590
This Southwest deal was found by Cheapflights users on 8/16. 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.
Wed 9/3012:20 pm -
1 stop7h 50m
Wed 10/78:15 am -
2 stops12h 05m
Deal found 8/16![Southwest logo]()
$281
This Arajet deal was found by Cheapflights users on 8/17. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 10/236:45 am -
Nonstop4h 45m
Sun 11/16:10 pm -
Nonstop5h 10m
Deal found 8/17![Arajet logo]()
$365
This Southwest deal was found by Cheapflights users on 8/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 10/294:15 pm -
2 stops8h 05m
Thu 11/55:50 pm -
1 stop7h 15m
Deal found 8/17![Southwest logo]()
$281
This Arajet deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” 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 9/2612:12 pm -
1 stop8h 28m
Fri 10/21:40 am -
1 stop10h 32m
Deal found 8/20![Multiple Airlines logo]()
$397
This United Airlines deal was found by Cheapflights users on 8/18. 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 10/239:38 pm -
1 stop16h 52m
Tue 10/271:55 pm -
Nonstop5h 15m
Deal found 8/18![United Airlines logo]()
$400
This Arajet deal was found by Cheapflights users on 8/16. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 10/2412:12 pm -
Nonstop4h 45m
Sun 11/16:10 pm -
Nonstop5h 10m
Deal found 8/16![Arajet logo]()
$365
This Southwest deal was found by Cheapflights users on 8/16. 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.
Sun 9/61:55 pm -
2 stops8h 15m
Thu 9/106:00 am -
2 stops9h 30m
Deal found 8/16![Southwest logo]()
$295
This United Airlines deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” 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 12/88:55 am -
1 stop6h 33m
Tue 12/1512:56 pm -
1 stop12h 19m
Deal found 8/20![United Airlines logo]()
$410
This Arajet deal was found by Cheapflights users on 8/18. 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 Arajet is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/75:30 am -
1 stop10h 25m
Fri 9/111:40 am -
1 stop10h 32m
Deal found 8/18![Multiple Airlines logo]()
$429
This Southwest deal was found by Cheapflights users on 8/16. 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.
Mon 10/192:15 pm -
1 stop9h 05m
Mon 10/265:30 am -
2 stops8h 55m
Deal found 8/16![Southwest logo]()
$295
This Copa Airlines deal was found by Cheapflights users on 8/17. 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 10/213:20 pm -
1 stop10h 05m
Sat 10/3112:12 pm -
1 stop13h 59m
Deal found 8/17![Copa Airlines logo]()
$476
This Delta deal was found by Cheapflights users on 8/17. 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 10/276:04 am -
1 stop7h 36m
Sat 10/314:05 pm -
1 stop7h 28m
Deal found 8/17![Delta logo]()
$480
This United Airlines deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” 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
Sat 11/142:05 am -
1 stop8h 57m
Deal found 8/20![United Airlines logo]()
$422
This Copa Airlines deal was found by Cheapflights users on 8/17. 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 11/42:13 pm -
1 stop19h 32m
Wed 11/188:55 am -
1 stop17h 16m
Deal found 8/17![Copa Airlines logo]()
$476
This Southwest deal was found by Cheapflights users on 8/16. 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.
Sun 11/18:40 pm -
1 stop13h 10m
Tue 11/106:40 am -
1 stop14h 15m
Deal found 8/16![Southwest logo]()
$301
This Delta deal was found by Cheapflights users on 8/17. 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 11/36:30 am -
1 stop6h 30m
Tue 11/106:00 pm -
2 stops14h 46m
Deal found 8/17![Delta logo]()
$510
This United Airlines deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” 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 11/29:15 am -
1 stop10h 09m
Mon 11/94:55 pm -
Nonstop5h 31m
Deal found 8/20![United Airlines logo]()
$422
Last-minute flights from Chicago to Caribbean IslandsDiscover last-minute flight deals from Chicago to Caribbean Islands. Data last updated August 21, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Caribbean Islands. Data last updated August 21, 2026 and is based on user searches.
This Kiwi.com deal was found by Cheapflights users on 8/17. 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.
Fri 8/2112:44 am -
Nonstop5h 00m
Thu 8/277:14 pm -
Nonstop5h 13m
Deal found 8/17![Frontier logo]()
$208
This Priceline deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” 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.
Sat 8/2212:44 am -
Nonstop5h 00m
Wed 8/267:14 pm -
Nonstop5h 13m
Deal found 8/19![Frontier logo]()
$220
This Super.com deal was found by Cheapflights users on 8/18. 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.
Tue 8/2512:44 am -
Nonstop5h 00m
Sat 8/297:14 pm -
Nonstop5h 13m
Deal found 8/18![Frontier logo]()
$213
This Super.com deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” 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 8/2712:44 am -
Nonstop5h 00m
Sun 8/307:14 pm -
Nonstop5h 13m
Deal found 8/19![Frontier logo]()
$212
This Priceline deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 8/2812:44 am -
Nonstop5h 00m
Wed 9/27:14 pm -
Nonstop5h 13m
Deal found 8/20![Frontier logo]()
$211
This Kiwi.com deal was found by Cheapflights users on 8/16. 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 8/2812:44 am -
Nonstop5h 00m
Wed 9/912:59 am -
1 stop13h 31m
Deal found 8/16![Frontier logo]()
$221
This Super.com deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” 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 8/2912:44 am -
Nonstop5h 00m
Tue 9/17:14 pm -
Nonstop5h 13m
Deal found 8/19![Frontier logo]()
$215
This Kiwi.com deal was found by Cheapflights users on 8/18. 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.
Sun 8/3012:44 am -
Nonstop5h 00m
Sun 9/1312:59 am -
1 stop13h 31m
Deal found 8/18![Frontier logo]()
$210
This Kiwi.com deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” 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 8/3112:44 am -
Nonstop5h 00m
Thu 9/1011:54 am -
2 stops13h 51m
Deal found 8/20![Frontier logo]()
$217
This CheapOair deal was found by Cheapflights users on 8/17. 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.
Sat 9/512:44 am -
Nonstop5h 00m
Wed 9/162:32 pm -
1 stop9h 36m
Deal found 8/17![Multiple Airlines logo]()
$214
This Southwest deal was found by Cheapflights users on 8/18. 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.
Sun 9/138:05 pm -
1 stop12h 05m
Tue 9/225:15 am -
2 stops7h 50m
Deal found 8/18![Southwest logo]()
$226
This Southwest deal was found by Cheapflights users on 8/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/213:15 pm -
1 stop6h 55m
Fri 9/252:35 pm -
1 stop9h 10m
Deal found 8/17![Southwest logo]()
$246
One-way flights from Chicago to Caribbean IslandsSearch for one-way flight options from Chicago to Caribbean Islands. Find affordable one-way fares based on user searches. Data last updated August 21, 2026.
Search for one-way flight options from Chicago to Caribbean Islands. Find affordable one-way fares based on user searches. Data last updated August 21, 2026.
This Kiwi.com deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” 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 10/158:04 am -
1 stop28h 27m
Deal found 8/19![Frontier logo]()
$104
This Kiwi.com deal was found by Cheapflights users on 8/17. 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.
Sat 9/197:11 am -
1 stop8h 52m
Deal found 8/17![Frontier logo]()
$105
This Kiwi.com deal was found by Cheapflights users on 8/18. 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.
Mon 10/198:04 am -
1 stop30h 14m
Deal found 8/18![Frontier logo]()
$106
This Kiwi.com deal was found by Cheapflights users on 8/18. 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.
Sat 10/108:04 am -
1 stop28h 27m
Deal found 8/18![Frontier logo]()
$107
This Kiwi.com deal was found by Cheapflights users on 8/20. Clicking the “Pick Dates” 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 9/127:11 am -
1 stop8h 52m
Deal found 8/20![Frontier logo]()
$108
This Kiwi.com deal was found by Cheapflights users on 8/17. 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.
Wed 10/148:04 am -
1 stop28h 27m
Deal found 8/17![Frontier logo]()
$109
This Kiwi.com deal was found by Cheapflights users on 8/18. 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.
Wed 10/218:04 am -
1 stop28h 27m
Deal found 8/18![Frontier logo]()
$110
This American Airlines deal was found by Cheapflights users on 8/15. 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.
Sun 9/65:00 am -
1 stop7h 24m
Deal found 8/15![American Airlines logo]()
$113
This Southwest deal was found by Cheapflights users on 8/17. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 9/156:15 am -
1 stop9h 10m
Deal found 8/17![Southwest logo]()
$113
This American Airlines deal was found by Cheapflights users on 8/16. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 9/75:00 am -
1 stop7h 24m
Deal found 8/16![American Airlines logo]()
$116
This eDestinos deal was found by Cheapflights users on 8/18. 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.
Thu 8/2712:44 am -
Nonstop5h 00m
Deal found 8/18![Frontier logo]()
$120
This Kiwi.com deal was found by Cheapflights users on 8/19. Clicking the “Pick Dates” 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 10/17:11 am -
1 stop29h 23m
Deal found 8/19![Frontier logo]()
$122
Find flight deals from Chicago to Caribbean Islands
Keep the following information in mind while searching for Chicago to Caribbean Islands flight deals. Data was last updated August 21, 2026.
Round-trip from | $208 (Kiwi.com) |
|---|---|
One-way from | $104 (Kiwi.com) |
Popular in | December |
Cheapest in | August |
Average price | $320 |
Cheapflights Fare Finder
Customize your flight search to find flights from Chicago to Caribbean Islands that fit within your specific budget. Explore options based on user searches and filter the results based on your desired price range. Find flights that match your budget for a cost-effective journey. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated August 21, 2026.
Use the filters below to find and compare flights from Chicago to Caribbean Islands that are best for you.
Fly from
Fly to
Route
Depart
Return
Cheapest round-trip
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Fri 9/25
2:55 pm-10:15 pm
1 stop6h 20m
San Juan Luis Munoz Marin Intl
Wed 9/30
5:15 am-12:05 pm
2 stops7h 50m
$246
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Thu 9/17
3:15 pm-11:10 pm
1 stop6h 55m
San Juan Luis Munoz Marin Intl
Thu 9/24
11:35 am-9:30 pm
1 stop10h 55m
$246
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Tue 9/1
8:30 am-4:25 pm
1 stop6h 55m
San Juan Luis Munoz Marin Intl
Sat 9/5
5:05 am-12:35 pm
1 stop8h 30m
$261
ChicagoSan Juan
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Tue 9/1
5:20 pm-11:15 pm
Nonstop4h 55m
San Juan Luis Munoz Marin Intl
Fri 9/4
7:30 am-4:48 pm
1 stop10h 18m
$262
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Wed 9/30
12:20 pm-9:10 pm
1 stop7h 50m
San Juan Luis Munoz Marin Intl
Wed 10/7
8:15 am-7:20 pm
2 stops12h 05m
$281
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Thu 10/29
4:15 pm-1:20 am
2 stops8h 05m
San Juan Luis Munoz Marin Intl
Thu 11/5
5:50 pm-11:05 pm
1 stop7h 15m
$281
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Sun 9/6
1:55 pm-11:10 pm
2 stops8h 15m
San Juan Luis Munoz Marin Intl
Thu 9/10
6:00 am-2:30 pm
2 stops9h 30m
$295
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Mon 10/19
2:15 pm-12:20 am
1 stop9h 05m
San Juan Luis Munoz Marin Intl
Mon 10/26
5:30 am-1:25 pm
2 stops8h 55m
$295
ChicagoSan Juan
MDW Chicago Midway - SJU San Juan Luis Munoz Marin Intl
MDWSJU
Chicago Midway
Sun 11/1
8:40 pm-11:50 am
1 stop13h 10m
San Juan Luis Munoz Marin Intl
Tue 11/10
6:40 am-6:55 pm
1 stop14h 15m
$301
ChicagoSan Juan
ORD Chicago O'Hare Intl - SJU San Juan Luis Munoz Marin Intl
ORDSJU
Chicago O'Hare Intl
Sat 9/5
10:40 am-8:38 pm
1 stop8h 58m
San Juan Luis Munoz Marin Intl
Fri 9/11
2:55 pm-10:15 pm
1 stop8h 20m
$346
Showing 1-10 of 60 resultsSorted by cheapest first
Best time to book a flight from Chicago to Caribbean Islands
Have a flexible travel schedule? Discover the best time to fly to Caribbean Islands from Chicago with our price prediction graph.
MDW-SJU
ORD-SJU
ORD-PUJ
ORD-SDQ
ORD-NAS
Estimated round-trip price
Rates are based on past data. Find the cheapest month and day to book your flight based on your travel requirements, then search for cheap deals.
Cheapflights Insights
Everything you need to know about your flight from Chicago to Caribbean Islands
CHI-zzEPX
MDW-SJU
ORD-SJU
ORD-PUJ
ORD-SDQ
What is the cheapest month to book a flight from Chicago to Caribbean Islands?
Currently, January is the cheapest month in which you can book a flight from Chicago to Caribbean Islands (average of $534). Flying from Chicago to Caribbean Islands in June is currently the most expensive (average of $698). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from CHI to EPX?
Find hourly flight availability from Chicago to Caribbean Islands. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated August 21, 2026.
Unlike in the morning, when flights are generally more expensive, you can save up to 33% on flights from Chicago to Caribbean Islands by exploring options for tickets in the evening.
Weekly flight availability from Chicago to Caribbean Islands
Explore weekly flight availability from Chicago to Caribbean Islands. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated August 21, 2026.
The most flights from CHI to zzEPX are scheduled on a Wednesday (7 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (4 on average).
How far ahead should I book a flight from Chicago to Caribbean Islands?
Booking 48 days in advance of your planned departure date is, on average, the best time to get cheap flights from Chicago to Caribbean Islands. The general trend is that the closer you book to the departure date, the more expensive your flight will be.
What is the cheapest day to fly from Chicago to Caribbean Islands?
Use this chart to determine the cheapest time to fly round-trip from Chicago to Caribbean Islands. Price data was last updated on August 15, 2026.
Travelers seeking maximum savings on their Chicago to Caribbean Islands 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 Islands
Get insights into the airlines that provide service to Caribbean Islands. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean Islands. Reviews last updated August 21, 2026.
Read through reviews of airlines operating flights from Chicago to Caribbean Islands, such as Delta,United Airlines, andAmerican Airlines. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Entertainment
7.8
Boarding
8.1
Crew
8.5
Food
7.2
Comfort
7.8
Overall
7.8
Reviews
1 / 20
10.0
ExcellentSalvador,Aug 2026
PHL - DTW
Entertainment
7.8
Boarding
8.1
Crew
8.5
Food
7.2
Comfort
7.8
Overall
7.8
Reviews
1 / 20
10.0
ExcellentSalvador,Aug 2026
PHL - DTW
Entertainment
7.8
Boarding
8.1
Crew
8.5
Food
7.2
Comfort
7.8
Overall
7.8
Reviews
1 / 20
10.0
ExcellentSalvador,Aug 2026
PHL - DTW
Entertainment
7.8
Boarding
8.1
Crew
8.5
Food
7.2
Comfort
7.8
Overall
7.8
Reviews
1 / 20
10.0
ExcellentSalvador,Aug 2026
PHL - DTW
Entertainment
7.8
Boarding
8.1
Crew
8.5
Food
7.2
Comfort
7.8
Overall
7.8
Reviews
1 / 20
10.0
ExcellentSalvador,Aug 2026
PHL - DTW
Related info for your journey
Find useful and relevant information for your journey from Chicago to Caribbean Islands. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Alternative routes for Chicago to Caribbean Islands
See prices for flight routes from nearby airports that may be better suited for you.
Complete your trip
Complete your trip to Caribbean Islands by adding a car rental and/or hotel reservation to your travel itinerary.
Search flights from Chicago to Caribbean Islands by cabin class
Find flights from Chicago to Caribbean Islands, based on your preferred cabin class, be it economy, premium economy, business, or first class.
Chicago and Caribbean Islands flights
Browse other Chicago and Caribbean Islands flight options. Last updated on August 21, 2026.
Popular flight searches
Check out other popular destinations found by fellow travelers in 2026
Chicago to Caribbean Islands flights
Consider these flights traveling from Chicago to Caribbean Islands.
Top 9 airlines flying from Chicago to Caribbean Islands
Discover the top 9 airlines that operate flights from Chicago to Caribbean Islands. Compare their services, reliability, and customer satisfaction ratings to choose the airline that best suits your travel preferences and needs. Over the last 7 days, Cheapflights users made 7,457,451 searches. Data last updated August 21, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$91 | Average$597 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$118 | Average$525 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$119 | Average$442 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$175 | Average$518 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$213 | Average$486 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$222 | Average$374 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$264 | Average$594 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$296 | Average$695 | FlexibilityNo cancel fee | On-time63% | |
| Cheapest$297 | Average$605 | FlexibilityNo cancel fee | On-time71% |