$105+ 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 5/16. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJU
May 29 — Jun 51
Round-trip
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
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
Cheapest
Best
Last-minute
One-way
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 April 29, 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 April 29, 2026.
This Frontier deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 5/193:55 pm
ORD
- SJU
1 stop9h 13m
Frontier
Wed 5/206:24 pm
SJU
- ORD
Nonstop5h 22m
Frontier
Deal found 4/28![Frontier logo]()
$219
This Frontier deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 5/165:30 pm
ORD
- SJU
1 stop13h 34m
Frontier
Sat 5/236:00 am
SJU
- ORD
1 stop7h 37m
Frontier
Deal found 4/28![Frontier logo]()
$221
This Kiwi.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 5/174:44 pm
ORD
- SJU
Nonstop4h 37m
Multiple Airlines
Sat 5/233:58 pm
SJU
- ORD
1 stop8h 15m
Multiple Airlines
Deal found 4/28![Multiple Airlines logo]()
$222
This Orbitz deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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.
Sun 5/248:05 am
ORD
- SJU
1 stop6h 50m
Multiple Airlines
Fri 5/2911:39 am
SJU
- ORD
Nonstop5h 10m
Multiple Airlines
Deal found 4/28![Multiple Airlines logo]()
$223
This Frontier deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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 5/155:30 pm
ORD
- SJU
1 stop7h 38m
Frontier
Thu 5/216:24 pm
SJU
- ORD
Nonstop5h 22m
Frontier
Deal found 4/29![Frontier logo]()
$224
This Kiwi.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 5/2312:59 pm
ORD
- SJU
Nonstop4h 36m
Multiple Airlines
Sun 5/246:24 pm
SJU
- ORD
Nonstop5h 22m
Multiple Airlines
Deal found 4/28![Multiple Airlines logo]()
$225
This Delta deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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 8/191:15 pm
ORD
- SJU
1 stop8h 08m
Delta
Wed 9/22:40 pm
SJU
- ORD
1 stop10h 17m
Delta
Deal found 4/29![Delta logo]()
$226
This Delta deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 8/1110:35 am
MDW
- SJU
1 stop10h 48m
Delta
Tue 8/182:40 pm
SJU
- MDW
1 stop8h 06m
Delta
Deal found 4/28![Delta logo]()
$226
This Travelocity deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/157:52 pm
ORD
- SJU
1 stop18h 58m
Frontier
Sun 5/246:24 pm
SJU
- ORD
Nonstop5h 22m
Frontier
Deal found 4/28![Frontier logo]()
$227
This Frontier deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 5/126:00 am
MDW
- SJU
1 stop7h 07m
Frontier
Fri 5/156:00 am
SJU
- MDW
1 stop10h 57m
Frontier
Deal found 4/26![Frontier logo]()
$227
This Cheapflightsfares deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/114:44 pm
ORD
- SJU
Nonstop4h 37m
Spirit Airlines
Fri 5/2911:39 am
SJU
- ORD
Nonstop5h 10m
Spirit Airlines
Deal found 4/28![Spirit Airlines logo]()
$228
This Orbitz deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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.
Sun 5/174:44 pm
ORD
- SJU
Nonstop4h 37m
Multiple Airlines
Sun 5/246:24 pm
SJU
- ORD
Nonstop5h 22m
Multiple Airlines
Deal found 4/28![Multiple Airlines logo]()
$229
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 April 29, 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 April 29, 2026.
This Delta deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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 8/1910:35 am
MDW
- SJU
1 stop10h 48m
Delta
Wed 9/22:40 pm
SJU
- MDW
1 stop8h 06m
Delta
Deal found 4/29![Delta logo]()
$226
This United Airlines deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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.
Sun 5/102:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Fri 5/157:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
Deal found 4/24![United Airlines logo]()
$237
This Arajet deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 5/912:12 pm
ORD
- PUJ
Nonstop4h 45m
Arajet
Sat 5/167:02 am
PUJ
- ORD
Nonstop5h 10m
Arajet
Deal found 4/28![Arajet logo]()
$388
This CheapOair deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 7/175:10 am
ORD
- STT
1 stop7h 17m
Spirit Airlines
Fri 7/242:32 pm
STT
- ORD
1 stop10h 27m
Spirit Airlines
Deal found 4/28![Spirit Airlines logo]()
$404
This Southwest deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 9/1712:15 pm
MDW
- SJU
2 stops9h 50m
Southwest
Sun 9/205:00 am
SJU
- MDW
2 stops8h 55m
Southwest
Deal found 4/27![Southwest logo]()
$426
This Copa Airlines deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 10/73:20 pm
ORD
- NAS
1 stop19h 12m
Copa Airlines
Sun 10/1112:43 pm
NAS
- ORD
1 stop13h 14m
Copa Airlines
Deal found 4/28![Copa Airlines logo]()
$544
This American Airlines deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 7/175:10 am
ORD
- STT
2 stops9h 50m
American Airlines
Fri 7/241:42 pm
STT
- ORD
2 stops9h 18m
American Airlines
Deal found 4/28![American Airlines logo]()
$580
This Delta deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 8/266:00 am
MDW
- SJU
1 stop9h 35m
Delta
Tue 9/11:06 pm
SJU
- MDW
1 stop9h 40m
Delta
Deal found 4/26![Delta logo]()
$296
This United Airlines deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 5/122:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Sat 5/164:55 pm
SJU
- ORD
1 stop7h 49m
United Airlines
Deal found 4/26![United Airlines logo]()
$345
This United Airlines deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” 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 6/208:40 am
ORD
- MBJ
1 stop6h 30m
United Airlines
Wed 6/244:12 pm
MBJ
- ORD
1 stop7h 14m
United Airlines
Deal found 4/25![United Airlines logo]()
$354
This Arajet deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 5/1612:12 pm
ORD
- PUJ
Nonstop4h 45m
Arajet
Sat 5/237:02 am
PUJ
- ORD
Nonstop5h 10m
Arajet
Deal found 4/27![Arajet logo]()
$395
This United Airlines deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 7/48:40 am
ORD
- MBJ
Nonstop4h 10m
United Airlines
Tue 7/74:12 pm
MBJ
- ORD
1 stop15h 15m
United Airlines
Deal found 4/26![United Airlines logo]()
$356
This Southwest deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 5/178:50 pm
MDW
- SJU
1 stop11h 20m
Southwest
Fri 5/223:45 pm
SJU
- MDW
1 stop9h 30m
Southwest
Deal found 4/27![Southwest logo]()
$447
This Arajet deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 6/294:30 am
ORD
- PUJ
Nonstop4h 45m
Arajet
Thu 7/97:30 pm
PUJ
- ORD
Nonstop5h 10m
Arajet
Deal found 4/26![Arajet logo]()
$430
This United Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 5/72:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Mon 5/117:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
Deal found 4/27![United Airlines logo]()
$360
This Southwest deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/181:00 pm
MDW
- SJU
1 stop9h 25m
Southwest
Fri 5/226:50 am
SJU
- MDW
2 stops8h 50m
Southwest
Deal found 4/27![Southwest logo]()
$447
This Delta deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 10/196:00 am
MDW
- MBJ
1 stop7h 20m
Delta
Fri 10/232:45 pm
MBJ
- MDW
1 stop7h 00m
Delta
Deal found 4/24![Delta logo]()
$452
This United Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 7/148:40 am
ORD
- MBJ
1 stop6h 30m
United Airlines
Wed 8/52:40 pm
MBJ
- ORD
1 stop10h 05m
United Airlines
Deal found 4/27![United Airlines logo]()
$369
This Copa Airlines deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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
ORD
- NAS
1 stop19h 12m
Copa Airlines
Sun 10/2512:35 pm
NAS
- ORD
1 stop13h 49m
Copa Airlines
Deal found 4/28![Copa Airlines logo]()
$544
This Southwest deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 6/182:25 pm
MDW
- SJU
1 stop8h 10m
Southwest
Thu 6/2510:20 pm
SJU
- MDW
2 stops12h 40m
Southwest
Deal found 4/28![Southwest logo]()
$456
This Arajet deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 7/205:30 am
ORD
- PUJ
Nonstop4h 45m
Arajet
Sat 7/257:02 am
PUJ
- ORD
Nonstop5h 10m
Arajet
Deal found 4/28![Arajet logo]()
$463
This Delta deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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 5/1310:59 am
MDW
- SJU
1 stop10h 18m
Delta
Wed 5/201:14 pm
SJU
- MDW
1 stop8h 55m
Delta
Deal found 4/24![Delta logo]()
$487
This Southwest deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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 7/18:10 am
MDW
- MBJ
1 stop6h 45m
Southwest
Sun 7/52:30 pm
MBJ
- MDW
Nonstop4h 05m
Southwest
Deal found 4/24![Southwest logo]()
$460
This United Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 7/136:30 am
ORD
- MBJ
1 stop8h 40m
United Airlines
Sat 7/181:52 pm
MBJ
- ORD
Nonstop4h 23m
United Airlines
Deal found 4/27![United Airlines logo]()
$391
This Arajet deal was found by Cheapflights users on 4/24. Clicking the “Pick Dates” 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 6/14:30 am
ORD
- PUJ
Nonstop4h 45m
Arajet
Thu 6/47:30 pm
PUJ
- ORD
Nonstop5h 10m
Arajet
Deal found 4/24![Arajet logo]()
$474
This Delta deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 9/136:00 am
MDW
- SJU
1 stop6h 16m
Delta
Sat 9/192:26 pm
SJU
- MDW
1 stop8h 20m
Delta
Deal found 4/26![Delta logo]()
$496
This Southwest deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 10/211:25 pm
MDW
- SJU
1 stop7h 15m
Southwest
Mon 10/265:30 am
SJU
- MDW
1 stop9h 25m
Southwest
Deal found 4/26![Southwest logo]()
$466
This United Airlines deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 5/611:00 am
ORD
- SJU
1 stop9h 24m
United Airlines
Mon 5/117:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
Deal found 4/28![United Airlines logo]()
$394
This American Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 7/18:56 pm
ORD
- STT
2 stops13h 07m
American Airlines
Wed 7/84:50 pm
STT
- ORD
1 stop8h 36m
American Airlines
Deal found 4/27![American Airlines logo]()
$705
This Copa Airlines deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 10/78:01 am
ORD
- AUA
1 stop12h 58m
Copa Airlines
Sun 10/113:46 pm
AUA
- ORD
1 stop10h 11m
Copa Airlines
Deal found 4/28![Copa Airlines logo]()
$673
Last-minute flights from Chicago to CaribbeanDiscover last-minute flight deals from Chicago to Caribbean. Data last updated April 29, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Caribbean. Data last updated April 29, 2026 and is based on user searches.
This Priceline deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 5/95:30 pm
ORD
- SJU
1 stop7h 38m
Frontier
Fri 5/1511:00 am
SJU
- ORD
1 stop13h 59m
Frontier
Deal found 4/27![Frontier logo]()
$226
This Cheapflightsfares deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/114:44 pm
ORD
- SJU
Nonstop4h 37m
Spirit Airlines
Fri 5/2911:39 am
SJU
- ORD
Nonstop5h 10m
Spirit Airlines
Deal found 4/28![Spirit Airlines logo]()
$228
This Priceline deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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.
Tue 5/126:00 am
MDW
- SJU
1 stop7h 07m
Frontier
Thu 5/143:03 am
SJU
- MDW
1 stop13h 54m
Frontier
Deal found 4/27![Frontier logo]()
$226
This Frontier deal was found by Cheapflights users on 4/29. Clicking the “Pick Dates” 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 5/155:30 pm
ORD
- SJU
1 stop7h 38m
Frontier
Thu 5/216:24 pm
SJU
- ORD
Nonstop5h 22m
Frontier
Deal found 4/29![Frontier logo]()
$224
This Travelocity deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/157:52 pm
ORD
- SJU
1 stop18h 58m
Frontier
Sun 5/246:24 pm
SJU
- ORD
Nonstop5h 22m
Frontier
Deal found 4/28![Frontier logo]()
$227
This Frontier deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 5/165:30 pm
ORD
- SJU
1 stop13h 34m
Frontier
Sat 5/236:00 am
SJU
- ORD
1 stop7h 37m
Frontier
Deal found 4/28![Frontier logo]()
$221
This Kiwi.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 5/174:44 pm
ORD
- SJU
Nonstop4h 37m
Multiple Airlines
Sat 5/233:58 pm
SJU
- ORD
1 stop8h 15m
Multiple Airlines
Deal found 4/28![Multiple Airlines logo]()
$222
This Orbitz deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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.
Sun 5/174:44 pm
ORD
- SJU
Nonstop4h 37m
Multiple Airlines
Sun 5/246:24 pm
SJU
- ORD
Nonstop5h 22m
Multiple Airlines
Deal found 4/28![Multiple Airlines logo]()
$229
This Frontier deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 5/193:55 pm
ORD
- SJU
1 stop9h 13m
Frontier
Wed 5/206:24 pm
SJU
- ORD
Nonstop5h 22m
Frontier
Deal found 4/28![Frontier logo]()
$219
This Kiwi.com deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 5/2312:59 pm
ORD
- SJU
Nonstop4h 36m
Multiple Airlines
Sun 5/246:24 pm
SJU
- ORD
Nonstop5h 22m
Multiple Airlines
Deal found 4/28![Multiple Airlines logo]()
$225
This Orbitz deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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.
Sun 5/248:05 am
ORD
- SJU
1 stop6h 50m
Multiple Airlines
Fri 5/2911:39 am
SJU
- ORD
Nonstop5h 10m
Multiple Airlines
Deal found 4/28![Multiple Airlines logo]()
$223
This Frontier deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 5/2512:33 am
ORD
- SJU
Nonstop4h 51m
Frontier
Fri 5/296:00 am
SJU
- ORD
1 stop7h 37m
Frontier
Deal found 4/27![Frontier logo]()
$230
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 April 29, 2026.
Search for one-way flight options from Chicago to Caribbean. Find affordable one-way fares based on user searches. Data last updated April 29, 2026.
This Kiwi.com deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 5/1612:59 pm
ORD
- SJU
Nonstop4h 36m
Spirit Airlines
Deal found 4/27![Spirit Airlines logo]()
$105
This Frontier deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 7/1812:44 am
ORD
- SJU
Nonstop5h 00m
Frontier
Deal found 4/26![Frontier logo]()
$107
This Super.com deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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.
Mon 5/116:00 am
MDW
- SJU
1 stop7h 07m
Frontier
Deal found 4/27![Frontier logo]()
$107
This Priceline deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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.
Tue 5/196:00 am
MDW
- MBJ
1 stop6h 11m
Frontier
Deal found 4/27![Frontier logo]()
$108
This eDestinos deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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.
Tue 5/2612:33 am
ORD
- SJU
Nonstop4h 51m
Frontier
Deal found 4/26![Frontier logo]()
$108
This United Airlines deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 8/118:55 am
ORD
- SJU
Nonstop4h 49m
United Airlines
Deal found 4/27![United Airlines logo]()
$109
This Kiwi.com deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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 5/297:52 pm
ORD
- SJU
1 stop7h 09m
Frontier
Deal found 4/26![Frontier logo]()
$110
This eDestinos deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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.
Tue 5/268:05 am
ORD
- SJU
1 stop6h 50m
Frontier
Deal found 4/26![Frontier logo]()
$112
This American Airlines deal was found by Cheapflights users on 4/28. Clicking the “Pick Dates” 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 5/196:40 am
ORD
- SJU
1 stop14h 25m
American Airlines
Deal found 4/28![American Airlines logo]()
$113
This Delta deal was found by Cheapflights users on 4/27. Clicking the “Pick Dates” 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 8/1110:35 am
MDW
- SJU
1 stop10h 48m
Delta
Deal found 4/27![Delta logo]()
$113
This eDestinos deal was found by Cheapflights users on 4/26. Clicking the “Pick Dates” 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.
Sat 8/15:13 pm
ORD
- SJU
1 stop29h 16m
Frontier
Deal found 4/26![Frontier logo]()
$114
This eDestinos deal was found by Cheapflights users on 4/25. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/84:44 pm
ORD
- SJU
Nonstop4h 37m
Spirit Airlines
Deal found 4/25![Spirit Airlines logo]()
$117
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 April 29, 2026.
Round-trip from | $219 (Frontier) |
|---|---|
One-way from | $105 (Kiwi.com) |
Popular in | December |
Cheapest in | January |
Average price | $381 |
Good round-trip deal | $309 or less |
Good one-way deal | $138 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 April 29, 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
Wed 8/19
10:35 am-10:23 pm
1 stop10h 48m
San Juan Luis Munoz Marin Intl
Wed 9/2
2:40 pm-9:46 pm
1 stop8h 06m
$226
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Sun 5/10
2:38 pm-8:34 pm
Nonstop4h 56m
San Juan Luis Munoz Marin Intl
Fri 5/15
7:40 am-11:53 am
Nonstop5h 13m
$237
ChicagoSan Juan
MDW - SJU
MDWSJU
Chicago Midway
Wed 8/26
6:00 am-4:35 pm
1 stop9h 35m
San Juan Luis Munoz Marin Intl
Tue 9/1
1:06 pm-9:46 pm
1 stop9h 40m
$296
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 5/12
2:38 pm-8:34 pm
Nonstop4h 56m
San Juan Luis Munoz Marin Intl
Sat 5/16
4:55 pm-11:44 pm
1 stop7h 49m
$345
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Sat 6/20
8:40 am-3:10 pm
1 stop6h 30m
Montego Bay Sangster Intl
Wed 6/24
4:12 pm-11:26 pm
1 stop7h 14m
$354
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Sat 7/4
8:40 am-12:50 pm
Nonstop4h 10m
Montego Bay Sangster Intl
Tue 7/7
4:12 pm-7:27 am
1 stop15h 15m
$356
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Thu 5/7
2:38 pm-8:34 pm
Nonstop4h 56m
San Juan Luis Munoz Marin Intl
Mon 5/11
7:40 am-11:53 am
Nonstop5h 13m
$360
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Tue 7/14
8:40 am-3:10 pm
1 stop6h 30m
Montego Bay Sangster Intl
Wed 8/5
2:40 pm-12:45 am
1 stop10h 05m
$369
Quickest round-trip
ChicagoPunta Cana
ORD - PUJ
ORDPUJ
Chicago O'Hare Intl
Sat 5/9
12:12 pm-5:57 pm
Nonstop4h 45m
Punta Cana
Sat 5/16
7:02 am-11:12 am
Nonstop5h 10m
$388
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Mon 7/13
6:30 am-3:10 pm
1 stop8h 40m
Montego Bay Sangster Intl
Sat 7/18
1:52 pm-6:15 pm
Nonstop4h 23m
$391
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.
MDW-SJU
ORD-SJU
MDW-MBJ
ORD-MBJ
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
CHI-0CB
MDW-SJU
ORD-SJU
MDW-MBJ
ORD-MBJ
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 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 $392). Flying from Chicago to Caribbean in December is currently the most expensive (average of $585). 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 April 29, 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 33% on airfare.
What is the cheapest day to fly from Chicago to Caribbean?
Use this chart to determine the cheapest time to fly round-trip from Chicago to Caribbean. Price data was last updated on April 25, 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. Saturday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Weekly flight availability from Chicago to Caribbean
Explore weekly flight availability from Chicago to Caribbean. Discover flights operating on different days of the week, giving you the flexibility to choose a travel day that best fits your plans. Compare info to find the most convenient option for your journey. Data last updated April 29, 2026.
The most flights from CHI to 0CB are scheduled on a Monday (9 on average). You will have fewer flight options on Thursday, which is when the least amount of flights are scheduled (7 on average).
Reviews of airlines servicing Caribbean
Get insights into the airlines that provide service to Caribbean. Read reviews, discover amenities, and learn about the overall travel experience offered by airlines. Use this information to make informed decisions when choosing an airline for your flight to Caribbean. Reviews last updated April 29, 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.
Entertainment
7.5
Crew
8.6
Food
7.0
Boarding
8.1
Comfort
8.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Crew
8.6
Food
7.0
Boarding
8.1
Comfort
8.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Crew
8.6
Food
7.0
Boarding
8.1
Comfort
8.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Crew
8.6
Food
7.0
Boarding
8.1
Comfort
8.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Crew
8.6
Food
7.0
Boarding
8.1
Comfort
8.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
Entertainment
7.5
Crew
8.6
Food
7.0
Boarding
8.1
Comfort
8.0
Overall
8.0
Reviews
1 / 20
2.0
MediocreDominic,Mar 2026
MCO - SMF
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.
Browse thousands of different options on Cheapflights for your next trip
Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
Alternative routes
Complete your trip
Flights by cabin class
Other flight options
Popular flights
Top countries
Top destinations
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 April 29, 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 April 29, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$100 | Average$394 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$118 | Average$455 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$119 | Average$421 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$132 | Average$522 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$175 | Average$480 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$202 | Average$342 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$213 | Average$484 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$255 | Average$580 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$311 | Average$593 | FlexibilityNo cancel fee | On-time71% |