$94+ Cheap flights from Chicago (CHI) to Caribbean
This is the cheapest one-way flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 4/5. Fares are subject to change and may not be available on all flights or dates of travel.
CHI — SJU
Apr 16 — Apr 231
Round-trip
1 adult, Economy
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Find cheap flights from Chicago to Caribbean with Cheapflights
1. Tell us where you want to go
Enter your travel information like dates, passengers, trip type (one-way or round trip), and preferred cabin class then click “Find deals”2. Select your favorite providers
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Cheapest flights from Chicago to CaribbeanExplore the most affordable flight options available from Chicago to Caribbean. Find the lowest fares from popular airlines and budget airlines, with prices last updated on March 17, 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 March 17, 2026.
This eDestinos deal was found by Cheapflights users on 3/13. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/107:20 am
ORD
- SJU
1 stop28h 13m
Frontier
Wed 4/1510:54 am
SJU
- ORD
1 stop29h 14m
Frontier
Deal found 3/13![Frontier logo]()
$201
This Cheapflightsfares deal was found by Cheapflights users on 3/17. 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.
Sun 4/126:10 pm
ORD
- SJU
1 stop16h 39m
Spirit Airlines
Wed 4/1510:59 am
SJU
- ORD
Nonstop5h 09m
Spirit Airlines
Deal found 3/17![Spirit Airlines logo]()
$202
This CheapOair deal was found by Cheapflights users on 3/14. 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.
Sat 4/116:10 pm
ORD
- SJU
1 stop16h 39m
Multiple Airlines
Thu 4/166:00 am
SJU
- ORD
1 stop16h 17m
Multiple Airlines
Deal found 3/14![Multiple Airlines logo]()
$208
This Cheapflightsfares deal was found by Cheapflights users on 3/17. 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.
Tue 4/710:55 am
ORD
- SJU
1 stop12h 03m
Spirit Airlines
Wed 4/1510:59 am
SJU
- ORD
Nonstop5h 09m
Spirit Airlines
Deal found 3/17![Spirit Airlines logo]()
$209
This Priceline deal was found by Cheapflights users on 3/17. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/1310:55 am
ORD
- SJU
1 stop12h 03m
Multiple Airlines
Thu 4/306:00 am
SJU
- ORD
1 stop16h 17m
Multiple Airlines
Deal found 3/17![Multiple Airlines logo]()
$210
This Kiwi.com deal was found by Cheapflights users on 3/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/710:55 am
ORD
- SJU
1 stop12h 03m
Multiple Airlines
Thu 4/166:00 am
SJU
- ORD
1 stop16h 17m
Multiple Airlines
Deal found 3/16![Multiple Airlines logo]()
$212
This Cheapflightsfares deal was found by Cheapflights users on 3/13. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/3110:55 am
ORD
- SJU
1 stop12h 03m
Spirit Airlines
Mon 4/61:29 am
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Deal found 3/13![Spirit Airlines logo]()
$213
This CheapOair deal was found by Cheapflights users on 3/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/3110:55 am
ORD
- SJU
1 stop12h 03m
Spirit Airlines
Wed 4/81:29 am
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Deal found 3/13![Spirit Airlines logo]()
$214
This CheapOair deal was found by Cheapflights users on 3/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/1310:55 am
ORD
- SJU
1 stop12h 03m
Multiple Airlines
Thu 4/166:00 am
SJU
- ORD
1 stop16h 17m
Multiple Airlines
Deal found 3/13![Multiple Airlines logo]()
$215
This Kiwi.com deal was found by Cheapflights users on 3/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/710:55 am
ORD
- SJU
1 stop12h 03m
Multiple Airlines
Wed 4/1510:54 am
SJU
- ORD
1 stop29h 14m
Multiple Airlines
Deal found 3/14![Multiple Airlines logo]()
$217
This Cheapflightsfares deal was found by Cheapflights users on 3/14. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/710:55 am
ORD
- SJU
1 stop12h 03m
Spirit Airlines
Wed 4/81:29 am
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Deal found 3/14![Spirit Airlines logo]()
$218
This Booking.com deal was found by Cheapflights users on 3/15. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/92:56 pm
MDW
- SJU
1 stop8h 56m
Frontier
Thu 4/163:03 pm
SJU
- MDW
1 stop8h 16m
Frontier
Deal found 3/15![Frontier logo]()
$220
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 March 17, 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 March 17, 2026.
This Southwest deal was found by Cheapflights users on 3/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/118:35 pm
MDW
- SJU
1 stop13h 00m
Southwest
Fri 5/151:00 pm
SJU
- MDW
1 stop8h 50m
Southwest
Deal found 3/13![Southwest logo]()
$316
This Booking.com deal was found by Cheapflights users on 3/17. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/134:30 am
ORD
- PUJ
Nonstop4h 45m
Arajet
Thu 4/167:30 pm
PUJ
- ORD
Nonstop5h 10m
Arajet
Deal found 3/17![Arajet logo]()
$317
This Delta deal was found by Cheapflights users on 3/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/91:15 pm
ORD
- SJU
1 stop8h 33m
Delta
Tue 6/166:15 am
SJU
- ORD
1 stop11h 29m
Delta
Deal found 3/15![Delta logo]()
$326
This Kiwi.com deal was found by Cheapflights users on 3/17. 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 4/95:05 am
ORD
- STT
1 stop9h 23m
Multiple Airlines
Mon 4/132:36 pm
STT
- ORD
2 stops44h 47m
Multiple Airlines
Deal found 3/17![Multiple Airlines logo]()
$329
This United Airlines deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/711:00 pm
ORD
- MBJ
1 stop14h 30m
United Airlines
Sun 5/104:12 pm
MBJ
- ORD
1 stop7h 32m
United Airlines
Deal found 3/12![United Airlines logo]()
$332
This Frontier deal was found by Cheapflights users on 3/17. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/135:15 am
ORD
- PUJ
1 stop7h 30m
Frontier
Thu 4/161:37 pm
PUJ
- ORD
2 stops11h 07m
Frontier
Deal found 3/17![Frontier logo]()
$389
This Flighttix deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Flighttix is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/86:22 pm
ORD
- PLS
2 stops42h 38m
Air Canada
Sat 6/132:10 pm
PLS
- ORD
2 stops18h 35m
Air Canada
Deal found 3/12![Air Canada logo]()
$507
This American Airlines deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 6/110:01 am
ORD
- NAS
1 stop6h 49m
American Airlines
Mon 6/82:18 pm
NAS
- ORD
1 stop6h 30m
American Airlines
Deal found 3/12![American Airlines logo]()
$527
This Delta deal was found by Cheapflights users on 3/14. 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 6/106:00 am
ORD
- SJU
1 stop9h 38m
Delta
Tue 6/166:15 am
SJU
- ORD
1 stop11h 29m
Delta
Deal found 3/14![Delta logo]()
$326
This United Airlines deal was found by Cheapflights users on 3/15. 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.
Sun 5/248:40 am
ORD
- MBJ
1 stop6h 30m
United Airlines
Sun 5/314:33 pm
MBJ
- ORD
1 stop8h 12m
United Airlines
Deal found 3/15![United Airlines logo]()
$342
This Delta deal was found by Cheapflights users on 3/14. 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.
Tue 6/25:30 am
ORD
- SJU
1 stop10h 03m
Delta
Tue 6/97:00 am
SJU
- ORD
1 stop11h 41m
Delta
Deal found 3/14![Delta logo]()
$326
This Kiwi.com deal was found by Cheapflights users on 3/17. 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 4/1310:55 am
ORD
- PUJ
1 stop9h 34m
Multiple Airlines
Thu 4/161:37 pm
PUJ
- ORD
1 stop8h 12m
Multiple Airlines
Deal found 3/17![Multiple Airlines logo]()
$380
This United Airlines deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/188:40 am
ORD
- MBJ
Nonstop4h 10m
United Airlines
Sat 4/252:40 pm
MBJ
- ORD
1 stop8h 35m
United Airlines
Deal found 3/12![United Airlines logo]()
$348
This Southwest deal was found by Cheapflights users on 3/16. 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 4/138:35 pm
MDW
- SJU
1 stop13h 00m
Southwest
Thu 4/166:50 am
SJU
- MDW
2 stops14h 45m
Southwest
Deal found 3/16![Southwest logo]()
$391
This Southwest deal was found by Cheapflights users on 3/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/112:40 pm
ORD
- SJU
2 stops8h 15m
Southwest
Fri 5/155:35 am
SJU
- ORD
2 stops17h 20m
Southwest
Deal found 3/13![Southwest logo]()
$408
This United Airlines deal was found by Cheapflights users on 3/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 6/68:40 am
ORD
- MBJ
1 stop6h 30m
United Airlines
Sat 6/134:12 pm
MBJ
- ORD
1 stop7h 14m
United Airlines
Deal found 3/13![United Airlines logo]()
$371
This United Airlines deal was found by Cheapflights users on 3/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 5/82:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Tue 5/127:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
Deal found 3/17![United Airlines logo]()
$372
This Southwest deal was found by Cheapflights users on 3/16. 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 4/151:55 pm
MDW
- SJU
2 stops8h 45m
Southwest
Fri 4/176:50 am
SJU
- MDW
2 stops14h 45m
Southwest
Deal found 3/16![Southwest logo]()
$422
This Southwest deal was found by Cheapflights users on 3/15. 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.
Tue 6/99:10 am
MDW
- SJU
2 stops9h 35m
Southwest
Tue 6/168:35 pm
SJU
- MDW
1 stop13h 25m
Southwest
Deal found 3/15![Southwest logo]()
$426
This Delta deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/276:00 am
MDW
- PUJ
1 stop7h 32m
Delta
Thu 4/302:46 pm
PUJ
- MDW
1 stop8h 42m
Delta
Deal found 3/12![Delta logo]()
$479
This Southwest deal was found by Cheapflights users on 3/17. 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 5/119:00 am
MDW
- SJU
2 stops10h 00m
Southwest
Sat 5/169:40 am
SJU
- MDW
2 stops8h 45m
Southwest
Deal found 3/17![Southwest logo]()
$426
This United Airlines deal was found by Cheapflights users on 3/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/208:40 am
ORD
- MBJ
Nonstop4h 10m
United Airlines
Thu 4/231:52 pm
MBJ
- ORD
Nonstop4h 23m
United Airlines
Deal found 3/13![United Airlines logo]()
$428
This American Airlines deal was found by Cheapflights users on 3/17. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 6/216:08 am
ORD
- GCM
1 stop10h 03m
American Airlines
Sun 6/2812:01 pm
GCM
- ORD
1 stop10h 32m
American Airlines
Deal found 3/17![American Airlines logo]()
$651
This Mytrip deal was found by Cheapflights users on 3/17. 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.
Thu 4/169:44 pm
ORD
- PUJ
2 stops21h 10m
Multiple Airlines
Sun 4/191:25 pm
PUJ
- ORD
3 stops21h 11m
Multiple Airlines
Deal found 3/17![Multiple Airlines logo]()
$601
This Southwest deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 5/191:55 pm
MDW
- SJU
2 stops8h 45m
Southwest
Mon 5/258:40 pm
SJU
- MDW
1 stop13h 30m
Southwest
Deal found 3/14![Southwest logo]()
$431
This United Airlines deal was found by Cheapflights users on 3/17. 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 United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/98:40 am
ORD
- MBJ
Nonstop4h 10m
United Airlines
Mon 5/112:40 pm
MBJ
- ORD
1 stop10h 47m
United Airlines
Deal found 3/17![United Airlines logo]()
$438
This Avianca deal was found by Cheapflights users on 3/17. 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 Avianca is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/1511:20 pm
ORD
- PUJ
1 stop16h 25m
Multiple Airlines
Mon 4/206:35 pm
PUJ
- ORD
2 stops16h 03m
Multiple Airlines
Deal found 3/17![Multiple Airlines logo]()
$612
This American Airlines deal was found by Cheapflights users on 3/12. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sun 5/315:00 am
ORD
- PLS
1 stop8h 30m
American Airlines
Sun 6/71:31 pm
PLS
- ORD
1 stop9h 06m
American Airlines
Deal found 3/12![American Airlines logo]()
$680
This Delta deal was found by Cheapflights users on 3/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Delta is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 6/96:10 pm
ORD
- NAS
1 stop16h 19m
Delta
Thu 6/181:20 pm
NAS
- ORD
1 stop8h 56m
Delta
Deal found 3/15![Delta logo]()
$566
This United Airlines deal was found by Cheapflights users on 3/14. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure United Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/172:38 pm
ORD
- SJU
Nonstop4h 56m
United Airlines
Tue 4/217:40 am
SJU
- ORD
Nonstop5h 13m
United Airlines
Deal found 3/14![United Airlines logo]()
$440
Last-minute flights from Chicago to CaribbeanDiscover last-minute flight deals from Chicago to Caribbean. Data last updated March 17, 2026 and is based on user searches.
Discover last-minute flight deals from Chicago to Caribbean. Data last updated March 17, 2026 and is based on user searches.
This Cheapflightsfares deal was found by Cheapflights users on 3/13. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/3110:55 am
ORD
- SJU
1 stop12h 03m
Spirit Airlines
Mon 4/61:29 am
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Deal found 3/13![Spirit Airlines logo]()
$213
This CheapOair deal was found by Cheapflights users on 3/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/3110:55 am
ORD
- SJU
1 stop12h 03m
Spirit Airlines
Wed 4/81:29 am
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Deal found 3/13![Spirit Airlines logo]()
$214
This Cheapflightsfares deal was found by Cheapflights users on 3/17. 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.
Tue 4/710:55 am
ORD
- SJU
1 stop12h 03m
Spirit Airlines
Wed 4/1510:59 am
SJU
- ORD
Nonstop5h 09m
Spirit Airlines
Deal found 3/17![Spirit Airlines logo]()
$209
This Kiwi.com deal was found by Cheapflights users on 3/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/710:55 am
ORD
- SJU
1 stop12h 03m
Multiple Airlines
Thu 4/166:00 am
SJU
- ORD
1 stop16h 17m
Multiple Airlines
Deal found 3/16![Multiple Airlines logo]()
$212
This Kiwi.com deal was found by Cheapflights users on 3/14. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/710:55 am
ORD
- SJU
1 stop12h 03m
Multiple Airlines
Wed 4/1510:54 am
SJU
- ORD
1 stop29h 14m
Multiple Airlines
Deal found 3/14![Multiple Airlines logo]()
$217
This Cheapflightsfares deal was found by Cheapflights users on 3/14. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/710:55 am
ORD
- SJU
1 stop12h 03m
Spirit Airlines
Wed 4/81:29 am
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Deal found 3/14![Spirit Airlines logo]()
$218
This Booking.com deal was found by Cheapflights users on 3/15. 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 Booking.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/92:56 pm
MDW
- SJU
1 stop8h 56m
Frontier
Thu 4/163:03 pm
SJU
- MDW
1 stop8h 16m
Frontier
Deal found 3/15![Frontier logo]()
$220
This eDestinos deal was found by Cheapflights users on 3/13. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/107:20 am
ORD
- SJU
1 stop28h 13m
Frontier
Wed 4/1510:54 am
SJU
- ORD
1 stop29h 14m
Frontier
Deal found 3/13![Frontier logo]()
$201
This CheapOair deal was found by Cheapflights users on 3/14. 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.
Sat 4/116:10 pm
ORD
- SJU
1 stop16h 39m
Multiple Airlines
Thu 4/166:00 am
SJU
- ORD
1 stop16h 17m
Multiple Airlines
Deal found 3/14![Multiple Airlines logo]()
$208
This Cheapflightsfares deal was found by Cheapflights users on 3/17. 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.
Sun 4/126:10 pm
ORD
- SJU
1 stop16h 39m
Spirit Airlines
Wed 4/1510:59 am
SJU
- ORD
Nonstop5h 09m
Spirit Airlines
Deal found 3/17![Spirit Airlines logo]()
$202
This Priceline deal was found by Cheapflights users on 3/17. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/1310:55 am
ORD
- SJU
1 stop12h 03m
Multiple Airlines
Thu 4/306:00 am
SJU
- ORD
1 stop16h 17m
Multiple Airlines
Deal found 3/17![Multiple Airlines logo]()
$210
This CheapOair deal was found by Cheapflights users on 3/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/1310:55 am
ORD
- SJU
1 stop12h 03m
Multiple Airlines
Thu 4/166:00 am
SJU
- ORD
1 stop16h 17m
Multiple Airlines
Deal found 3/13![Multiple Airlines logo]()
$215
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 March 17, 2026.
Search for one-way flight options from Chicago to Caribbean. Find affordable one-way fares based on user searches. Data last updated March 17, 2026.
This FlightHub deal was found by Cheapflights users on 3/16. 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.
Sun 4/55:05 am
ORD
- GCM
1 stop7h 52m
Spirit Airlines
Deal found 3/16![Spirit Airlines logo]()
$94
This Super.com deal was found by Cheapflights users on 3/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/710:55 am
ORD
- SJU
1 stop12h 03m
Spirit Airlines
Deal found 3/15![Spirit Airlines logo]()
$97
This Cheapflightsfares deal was found by Cheapflights users on 3/17. 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.
Mon 4/1310:55 am
ORD
- SJU
1 stop12h 03m
Spirit Airlines
Deal found 3/17![Spirit Airlines logo]()
$98
This eDestinos deal was found by Cheapflights users on 3/15. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/314:18 pm
ORD
- SJU
1 stop8h 45m
Frontier
Deal found 3/15![Frontier logo]()
$101
This Super.com deal was found by Cheapflights users on 3/17. 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 Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/106:10 pm
ORD
- SJU
1 stop16h 39m
Spirit Airlines
Deal found 3/17![Spirit Airlines logo]()
$102
This Cheapflightsfares deal was found by Cheapflights users on 3/13. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 4/115:05 am
ORD
- SJU
1 stop12h 50m
Spirit Airlines
Deal found 3/13![Spirit Airlines logo]()
$103
This WAYA deal was found by Cheapflights users on 3/13. 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 WAYA is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/244:51 pm
ORD
- SJU
1 stop7h 28m
Multiple Airlines
Deal found 3/13![Multiple Airlines logo]()
$104
This eDestinos deal was found by Cheapflights users on 3/17. 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 eDestinos is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/176:04 pm
ORD
- SJU
1 stop27h 44m
Frontier
Deal found 3/17![Frontier logo]()
$106
This Kiwi.com deal was found by Cheapflights users on 3/13. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/147:17 am
ORD
- SJU
1 stop10h 38m
Spirit Airlines
Deal found 3/13![Spirit Airlines logo]()
$109
This Super.com deal was found by Cheapflights users on 3/15. 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.
Wed 4/14:21 pm
ORD
- SJU
1 stop8h 40m
Frontier
Deal found 3/15![Frontier logo]()
$110
This Super.com deal was found by Cheapflights users on 3/16. Clicking the “Pick Dates” button in this card will allow you to select your dates and further customize your flight criteria. From there, click “Find deals”, make sure Super.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/314:33 pm
MDW
- SJU
1 stop8h 30m
Frontier
Deal found 3/16![Frontier logo]()
$110
This Frontier deal was found by Cheapflights users on 3/13. 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 Frontier is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/94:31 pm
ORD
- SJU
1 stop7h 21m
Frontier
Deal found 3/13![Frontier logo]()
$111
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 March 17, 2026.
Round-trip from | $201 (eDestinos) |
|---|---|
One-way from | $94 (FlightHub) |
Popular in | December |
Cheapest in | October |
Average price | $416 |
Good round-trip deal | $302 or less |
Good one-way deal | $132 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 March 17, 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
Mon 5/11
8:35 pm-10:35 am
1 stop13h 00m
San Juan Luis Munoz Marin Intl
Fri 5/15
1:00 pm-8:50 pm
1 stop8h 50m
$316
ChicagoPunta Cana
ORD - PUJ
ORDPUJ
Chicago O'Hare Intl
Mon 4/13
4:30 am-10:15 am
Nonstop4h 45m
Punta Cana
Thu 4/16
7:30 pm-11:40 pm
Nonstop5h 10m
$317
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 6/9
1:15 pm-10:48 pm
1 stop8h 33m
San Juan Luis Munoz Marin Intl
Tue 6/16
6:15 am-4:44 pm
1 stop11h 29m
$326
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Wed 6/10
6:00 am-4:38 pm
1 stop9h 38m
San Juan Luis Munoz Marin Intl
Tue 6/16
6:15 am-4:44 pm
1 stop11h 29m
$326
ChicagoSan Juan
ORD - SJU
ORDSJU
Chicago O'Hare Intl
Tue 6/2
5:30 am-4:33 pm
1 stop10h 03m
San Juan Luis Munoz Marin Intl
Tue 6/9
7:00 am-5:41 pm
1 stop11h 41m
$326
ChicagoSaint Thomas Island
ORD - STT
ORDSTT
Chicago O'Hare Intl
Thu 4/9
5:05 am-3:28 pm
1 stop9h 23m
Saint Thomas Island Cyril E King
Mon 4/13
2:36 pm-10:23 am
2 stops44h 47m
$329
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Thu 5/7
11:00 pm-1:30 pm
1 stop14h 30m
Montego Bay Sangster Intl
Sun 5/10
4:12 pm-11:44 pm
1 stop7h 32m
$332
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Sun 5/24
8:40 am-3:10 pm
1 stop6h 30m
Montego Bay Sangster Intl
Sun 5/31
4:33 pm-12:45 am
1 stop8h 12m
$342
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Sat 4/18
8:40 am-12:50 pm
Nonstop4h 10m
Montego Bay Sangster Intl
Sat 4/25
2:40 pm-11:15 pm
1 stop8h 35m
$348
ChicagoMontego Bay
ORD - MBJ
ORDMBJ
Chicago O'Hare Intl
Sat 6/6
8:40 am-3:10 pm
1 stop6h 30m
Montego Bay Sangster Intl
Sat 6/13
4:12 pm-11:26 pm
1 stop7h 14m
$371
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-MBJ
ORD-PUJ
ORD-STT
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-MBJ
ORD-PUJ
What is the cheapest month to book a flight from Chicago to Caribbean?
Currently, April is the cheapest month in which you can book a flight from Chicago to Caribbean (average of $91). Flying from Chicago to Caribbean in December is currently the most expensive (average of $195). There are several factors that can impact the price of a flight, so comparing airlines, departure airports and flight times can provide users with more options.
What is the cheapest time of day to fly from CHI to CB?
Find hourly flight availability from Chicago to Caribbean. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated March 17, 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 37% 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 March 14, 2026.
Travelers seeking maximum savings on their Chicago to Caribbean flight should consider departing on Tuesday 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 March 17, 2026.
The most flights from CHI to 0CB are scheduled on a Monday (13 on average). You will have fewer flight options on Tuesday, which is when the least amount of flights are scheduled (12 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 March 17, 2026.
Read reviews from past customers who have flown Delta,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.
Boarding
8.1
Crew
8.5
Overall
7.9
Comfort
7.9
Entertainment
7.8
Food
7.2
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Boarding
8.1
Crew
8.5
Overall
7.9
Comfort
7.9
Entertainment
7.8
Food
7.2
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Boarding
8.1
Crew
8.5
Overall
7.9
Comfort
7.9
Entertainment
7.8
Food
7.2
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Boarding
8.1
Crew
8.5
Overall
7.9
Comfort
7.9
Entertainment
7.8
Food
7.2
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Boarding
8.1
Crew
8.5
Overall
7.9
Comfort
7.9
Entertainment
7.8
Food
7.2
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Boarding
8.1
Crew
8.5
Overall
7.9
Comfort
7.9
Entertainment
7.8
Food
7.2
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Related info for your journey
Find useful and relevant information for your journey from Chicago to Caribbean. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
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Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.
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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 March 17, 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 March 17, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$100 | Average$394 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$112 | Average$454 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$119 | Average$443 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$132 | Average$528 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$175 | Average$522 | FlexibilityNo cancel fee | On-time67% | |
| Cheapest$188 | Average$458 | FlexibilityNo cancel fee | On-time70% | |
| Cheapest$191 | Average$325 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$213 | Average$395 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$254 | Average$595 | FlexibilityNo cancel fee | On-time69% |