$97+ Cheap flights from Caribbean to Chicago (CHI)
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 2/11. Fares are subject to change and may not be available on all flights or dates of travel.
SJU — CHI
Feb 28 — Mar 71
1 adult, Economy
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Find cheap flights from Caribbean to Chicago with Cheapflights
1. Tell us where you want to go
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Cheapest flights from Caribbean to ChicagoExplore the most affordable flight options available from Caribbean to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 29, 2026.
Explore the most affordable flight options available from Caribbean to Chicago. Find the lowest fares from popular airlines and budget airlines, with prices last updated on January 29, 2026.
This Expedia deal was found by Cheapflights users on 1/29. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/412:32 pm
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Mon 3/912:22 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Deal found 1/29![Spirit Airlines logo]()
$145
This Orbitz deal was found by Cheapflights users on 1/29. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 3/712:32 pm
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Mon 3/912:22 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Deal found 1/29![Spirit Airlines logo]()
$151
This Kiwi.com deal was found by Cheapflights users on 1/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/45:45 pm
SJU
- ORD
1 stop8h 55m
Multiple Airlines
Mon 3/99:05 pm
ORD
- SJU
1 stop27h 14m
Multiple Airlines
Deal found 1/29![Multiple Airlines logo]()
$160
This Priceline deal was found by Cheapflights users on 1/28. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/71:22 pm
SJU
- ORD
Nonstop5h 15m
Spirit Airlines
Wed 2/2512:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Deal found 1/28![Spirit Airlines logo]()
$161
This Priceline deal was found by Cheapflights users on 1/26. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/245:25 pm
SJU
- ORD
1 stop24h 27m
Multiple Airlines
Tue 3/312:17 pm
ORD
- SJU
Nonstop4h 32m
Multiple Airlines
Deal found 1/26![Multiple Airlines logo]()
$163
This Expedia deal was found by Cheapflights users on 1/29. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/244:31 pm
SJU
- ORD
1 stop9h 16m
Spirit Airlines
Sat 2/2812:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Deal found 1/29![Spirit Airlines logo]()
$164
This Travelocity deal was found by Cheapflights users on 1/29. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/265:40 pm
STT
- ORD
1 stop8h 07m
Spirit Airlines
Thu 3/57:00 am
ORD
- STT
1 stop7h 34m
Spirit Airlines
Deal found 1/29![Spirit Airlines logo]()
$165
This Expedia deal was found by Cheapflights users on 1/29. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/51:22 pm
SJU
- ORD
Nonstop5h 15m
Spirit Airlines
Mon 2/912:44 pm
ORD
- SJU
1 stop8h 49m
Spirit Airlines
Deal found 1/29![Spirit Airlines logo]()
$165
This SmartFares deal was found by Cheapflights users on 1/27. 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 SmartFares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/55:01 am
SJU
- ORD
1 stop8h 48m
JetBlue
Mon 3/912:41 pm
ORD
- SJU
1 stop7h 43m
JetBlue
Deal found 1/27![JetBlue logo]()
$167
This Cheapflightsfares deal was found by Cheapflights users on 1/27. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/51:22 pm
SJU
- ORD
Nonstop5h 15m
Spirit Airlines
Tue 2/1012:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Deal found 1/27![Spirit Airlines logo]()
$168
This Orbitz deal was found by Cheapflights users on 1/29. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/2812:32 pm
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Sat 3/78:16 pm
ORD
- SJU
1 stop16h 15m
Spirit Airlines
Deal found 1/29![Spirit Airlines logo]()
$170
This CheapOair deal was found by Cheapflights users on 1/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/185:25 pm
SJU
- MDW
1 stop23h 01m
Frontier
Mon 2/239:22 pm
MDW
- SJU
1 stop10h 32m
Frontier
Deal found 1/27![Frontier logo]()
$190
Best flights from Caribbean to ChicagoDiscover carefully curated flight deals from Caribbean to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated January 29, 2026.
Discover carefully curated flight deals from Caribbean to Chicago that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated January 29, 2026.
This Travelocity deal was found by Cheapflights users on 1/29. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/265:40 pm
STT
- ORD
1 stop8h 07m
Spirit Airlines
Thu 3/57:00 am
ORD
- STT
1 stop7h 34m
Spirit Airlines
Deal found 1/29![Spirit Airlines logo]()
$165
This JetBlue deal was found by Cheapflights users on 1/27. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 5/411:59 pm
SJU
- ORD
1 stop10h 49m
JetBlue
Thu 5/710:35 am
ORD
- SJU
1 stop9h 26m
JetBlue
Deal found 1/27![JetBlue logo]()
$171
This Frontier deal was found by Cheapflights users on 1/29. 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.
Wed 3/43:53 am
SJU
- MDW
1 stop12h 33m
Frontier
Mon 3/99:51 pm
MDW
- SJU
1 stop11h 21m
Frontier
Deal found 1/29![Frontier logo]()
$220
This Kiwi.com deal was found by Cheapflights users on 1/29. 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 Kiwi.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/243:41 pm
AUA
- ORD
1 stop19h 55m
Multiple Airlines
Mon 3/308:41 pm
ORD
- AUA
1 stop16h 45m
Multiple Airlines
Deal found 1/29![Multiple Airlines logo]()
$276
This Delta deal was found by Cheapflights users on 1/29. 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.
Tue 4/142:09 pm
MBJ
- ORD
1 stop9h 50m
Delta
Mon 4/207:00 am
ORD
- MBJ
2 stops8h 17m
Delta
Deal found 1/29![Delta logo]()
$307
This American Airlines deal was found by Cheapflights users on 1/29. 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 American Airlines is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 4/141:15 pm
MBJ
- ORD
Nonstop4h 43m
American Airlines
Mon 4/205:00 am
ORD
- MBJ
1 stop8h 24m
American Airlines
Deal found 1/29![American Airlines logo]()
$320
This United Airlines deal was found by Cheapflights users on 1/27. 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 3/241:48 pm
MBJ
- ORD
Nonstop4h 25m
United Airlines
Tue 4/148:45 am
ORD
- MBJ
1 stop6h 25m
United Airlines
Deal found 1/27![United Airlines logo]()
$325
This Orbitz deal was found by Cheapflights users on 1/28. 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.
Thu 2/2612:32 pm
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Sun 3/112:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Deal found 1/28![Spirit Airlines logo]()
$169
This JetBlue deal was found by Cheapflights users on 1/27. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 3/183:26 am
SJU
- ORD
1 stop8h 59m
JetBlue
Tue 3/2412:20 pm
ORD
- SJU
1 stop7h 06m
JetBlue
Deal found 1/27![JetBlue logo]()
$171
This Southwest deal was found by Cheapflights users on 1/26. 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.
Sat 5/1610:00 am
SJU
- MDW
1 stop11h 40m
Southwest
Sun 5/177:45 am
MDW
- SJU
2 stops7h 45m
Southwest
Deal found 1/26![Southwest logo]()
$364
This Orbitz deal was found by Cheapflights users on 1/28. 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.
Thu 2/1912:32 pm
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Sun 2/2212:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Deal found 1/28![Spirit Airlines logo]()
$169
This Air Canada deal was found by Cheapflights users on 1/29. 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 Air Canada is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 5/71:35 pm
NAS
- ORD
1 stop7h 33m
Air Canada
Tue 5/129:55 am
ORD
- NAS
1 stop6h 35m
Air Canada
Deal found 1/29![Air Canada logo]()
$377
This JetBlue deal was found by Cheapflights users on 1/27. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/173:26 am
SJU
- ORD
1 stop8h 59m
JetBlue
Mon 3/2312:20 pm
ORD
- SJU
1 stop9h 31m
JetBlue
Deal found 1/27![JetBlue logo]()
$183
This JetBlue deal was found by Cheapflights users on 1/27. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/271:44 pm
SJU
- ORD
1 stop11h 15m
JetBlue
Mon 3/212:41 pm
ORD
- SJU
1 stop9h 48m
JetBlue
Deal found 1/27![JetBlue logo]()
$183
This Expedia deal was found by Cheapflights users on 1/28. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 5/63:08 am
SJU
- MDW
1 stop29h 56m
Frontier
Mon 5/116:00 am
MDW
- SJU
1 stop7h 08m
Frontier
Deal found 1/28![Frontier logo]()
$222
This Cheapflightsfares deal was found by Cheapflights users on 1/28. 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.
Thu 5/712:22 pm
SJU
- ORD
Nonstop5h 15m
Spirit Airlines
Mon 5/1112:22 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Deal found 1/28![Spirit Airlines logo]()
$198
This Cheapflightsfares deal was found by Cheapflights users on 1/27. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Mon 4/61:29 am
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Tue 4/1412:22 pm
ORD
- SJU
Nonstop4h 31m
Spirit Airlines
Deal found 1/27![Spirit Airlines logo]()
$198
This Flightnetwork deal was found by Cheapflights users on 1/27. 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 Flightnetwork is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/215:47 am
PUJ
- ORD
Nonstop5h 10m
Multiple Airlines
Sun 2/227:00 am
ORD
- PUJ
1 stop7h 36m
Multiple Airlines
Deal found 1/27![Multiple Airlines logo]()
$289
This CheapOair deal was found by Cheapflights users on 1/29. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/2412:22 pm
SJU
- ORD
Nonstop5h 15m
Spirit Airlines
Mon 4/276:34 pm
ORD
- SJU
1 stop22h 24m
Spirit Airlines
Deal found 1/29![Spirit Airlines logo]()
$201
This Trip.com deal was found by Cheapflights users on 1/27. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/133:53 am
SJU
- MDW
1 stop13h 02m
Frontier
Mon 2/166:00 am
MDW
- SJU
1 stop7h 02m
Frontier
Deal found 1/27![Frontier logo]()
$289
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
Mon 3/233:41 pm
AUA
- ORD
1 stop19h 55m
Multiple Airlines
Tue 3/316:36 pm
ORD
- AUA
1 stop18h 50m
Multiple Airlines
Deal found 1/28![Multiple Airlines logo]()
$293
This Cheapflightsfares deal was found by Cheapflights users on 1/28. 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.
Wed 4/2211:07 am
SJU
- ORD
1 stop8h 08m
Spirit Airlines
Sat 4/2512:22 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Deal found 1/28![Spirit Airlines logo]()
$204
This American Airlines deal was found by Cheapflights users on 1/27. 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.
Thu 5/143:20 pm
MBJ
- ORD
1 stop8h 33m
American Airlines
Mon 5/186:58 pm
ORD
- MBJ
1 stop16h 53m
American Airlines
Deal found 1/27![American Airlines logo]()
$335
This Delta deal was found by Cheapflights users on 1/27. 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.
Thu 5/144:55 pm
MBJ
- ORD
2 stops14h 31m
Delta
Mon 5/187:10 am
ORD
- MBJ
1 stop6h 06m
Delta
Deal found 1/27![Delta logo]()
$351
This Kiwi.com deal was found by Cheapflights users on 1/28. 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.
Tue 3/243:41 pm
AUA
- ORD
1 stop19h 55m
Multiple Airlines
Wed 4/15:05 am
ORD
- AUA
1 stop8h 21m
Multiple Airlines
Deal found 1/28![Multiple Airlines logo]()
$299
This Southwest deal was found by Cheapflights users on 1/29. 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 Southwest is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/245:35 am
SJU
- MDW
1 stop7h 30m
Southwest
Mon 4/271:00 pm
MDW
- SJU
2 stops9h 40m
Southwest
Deal found 1/29![Southwest logo]()
$364
This United Airlines deal was found by Cheapflights users on 1/27. 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 4/134:12 pm
MBJ
- ORD
1 stop7h 31m
United Airlines
Tue 4/218:45 am
ORD
- MBJ
1 stop6h 25m
United Airlines
Deal found 1/27![United Airlines logo]()
$365
This Priceline deal was found by Cheapflights users on 1/29. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 4/243:19 pm
SJU
- MDW
1 stop25h 54m
Frontier
Mon 4/276:00 am
MDW
- SJU
1 stop7h 08m
Frontier
Deal found 1/29![Frontier logo]()
$302
This American Airlines deal was found by Cheapflights users on 1/27. 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.
Mon 4/131:15 pm
MBJ
- ORD
Nonstop4h 43m
American Airlines
Tue 4/215:00 am
ORD
- MBJ
1 stop6h 24m
American Airlines
Deal found 1/27![American Airlines logo]()
$350
This Delta deal was found by Cheapflights users on 1/27. 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 3/2411:15 am
MBJ
- ORD
1 stop12h 39m
Delta
Tue 4/147:00 am
ORD
- MBJ
2 stops8h 17m
Delta
Deal found 1/27![Delta logo]()
$351
Last-minute flights from Caribbean to ChicagoDiscover last-minute flight deals from Caribbean to Chicago. Data last updated January 29, 2026 and is based on user searches.
Discover last-minute flight deals from Caribbean to Chicago. Data last updated January 29, 2026 and is based on user searches.
This FlightHub deal was found by Cheapflights users on 1/28. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/41:22 pm
SJU
- ORD
Nonstop5h 15m
Spirit Airlines
Sun 2/88:43 pm
ORD
- SJU
1 stop16h 52m
Spirit Airlines
Deal found 1/28![Spirit Airlines logo]()
$175
This Cheapflightsfares deal was found by Cheapflights users on 1/27. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/51:22 pm
SJU
- ORD
Nonstop5h 15m
Spirit Airlines
Tue 2/1012:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Deal found 1/27![Spirit Airlines logo]()
$168
This Cheapflightsfares deal was found by Cheapflights users on 1/26. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 2/61:22 pm
SJU
- ORD
Nonstop5h 15m
Spirit Airlines
Sun 2/812:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Deal found 1/26![Spirit Airlines logo]()
$176
This Priceline deal was found by Cheapflights users on 1/28. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 2/71:22 pm
SJU
- ORD
Nonstop5h 15m
Spirit Airlines
Wed 2/2512:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Deal found 1/28![Spirit Airlines logo]()
$161
This Priceline deal was found by Cheapflights users on 1/27. 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 2/1412:32 pm
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Mon 2/1612:17 pm
ORD
- SJU
Nonstop4h 32m
Spirit Airlines
Deal found 1/27![Spirit Airlines logo]()
$180
This Frontier deal was found by Cheapflights users on 1/27. 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.
Tue 2/173:53 am
SJU
- ORD
1 stop13h 59m
Frontier
Mon 2/2310:15 am
ORD
- SJU
1 stop13h 09m
Frontier
Deal found 1/27![Frontier logo]()
$178
This CheapOair deal was found by Cheapflights users on 1/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/185:25 pm
SJU
- MDW
1 stop23h 01m
Frontier
Mon 2/239:22 pm
MDW
- SJU
1 stop10h 32m
Frontier
Deal found 1/27![Frontier logo]()
$190
This Priceline deal was found by Cheapflights users on 1/26. 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 Priceline is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/245:25 pm
SJU
- ORD
1 stop24h 27m
Multiple Airlines
Tue 3/312:17 pm
ORD
- SJU
Nonstop4h 32m
Multiple Airlines
Deal found 1/26![Multiple Airlines logo]()
$163
This Expedia deal was found by Cheapflights users on 1/26. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 2/245:10 am
SJU
- ORD
1 stop8h 49m
JetBlue
Tue 3/312:41 pm
ORD
- SJU
1 stop9h 48m
JetBlue
Deal found 1/26![JetBlue logo]()
$171
This Expedia deal was found by Cheapflights users on 1/27. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/253:53 am
SJU
- MDW
1 stop12h 33m
Frontier
Sun 3/16:15 am
MDW
- SJU
1 stop17h 54m
Frontier
Deal found 1/27![Frontier logo]()
$217
This Travelocity deal was found by Cheapflights users on 1/29. 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 Travelocity is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/265:40 pm
STT
- ORD
1 stop8h 07m
Spirit Airlines
Thu 3/57:00 am
ORD
- STT
1 stop7h 34m
Spirit Airlines
Deal found 1/29![Spirit Airlines logo]()
$165
This Frontier deal was found by Cheapflights users on 1/27. 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.
Fri 2/273:53 am
SJU
- MDW
1 stop13h 02m
Frontier
Mon 3/29:22 pm
MDW
- SJU
1 stop10h 32m
Frontier
Deal found 1/27![Frontier logo]()
$203
One-way flights from Caribbean to ChicagoSearch for one-way flight options from Caribbean to Chicago. Find affordable one-way fares based on user searches. Data last updated January 29, 2026.
Search for one-way flight options from Caribbean to Chicago. Find affordable one-way fares based on user searches. Data last updated January 29, 2026.
This CheapOair deal was found by Cheapflights users on 1/27. 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 CheapOair is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/115:25 pm
SJU
- MDW
1 stop23h 01m
Frontier
Deal found 1/27![Frontier logo]()
$97
This Orbitz deal was found by Cheapflights users on 1/27. 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 Orbitz is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 2/44:40 pm
SJU
- ORD
1 stop9h 07m
Spirit Airlines
Deal found 1/27![Spirit Airlines logo]()
$97
This Super.com deal was found by Cheapflights users on 1/27. 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.
Fri 2/2712:32 pm
SJU
- ORD
Nonstop5h 16m
Spirit Airlines
Deal found 1/27![Spirit Airlines logo]()
$98
This Trip.com deal was found by Cheapflights users on 1/28. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 2/123:18 pm
SJU
- MDW
1 stop9h 16m
Multiple Airlines
Deal found 1/28![Multiple Airlines logo]()
$99
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
Fri 2/273:53 am
SJU
- ORD
1 stop13h 44m
Frontier
Deal found 1/27![Frontier logo]()
$99
This Cheapflightsfares deal was found by Cheapflights users on 1/29. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Sat 5/1612:22 pm
SJU
- ORD
Nonstop5h 15m
Spirit Airlines
Deal found 1/29![Spirit Airlines logo]()
$100
This JetBlue deal was found by Cheapflights users on 1/28. 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 JetBlue is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Tue 3/104:15 am
SJU
- ORD
1 stop8h 33m
JetBlue
Deal found 1/28![JetBlue logo]()
$101
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
Wed 3/1811:07 am
SJU
- MDW
1 stop27h 34m
Multiple Airlines
Deal found 1/27![Multiple Airlines logo]()
$102
This Kiwi.com deal was found by Cheapflights users on 1/27. 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.
Wed 3/1110:52 am
SJU
- MDW
1 stop27h 49m
Multiple Airlines
Deal found 1/27![Multiple Airlines logo]()
$103
This Cheapflightsfares deal was found by Cheapflights users on 1/29. 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 Cheapflightsfares is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Fri 3/611:52 am
SJU
- ORD
1 stop8h 26m
Spirit Airlines
Deal found 1/29![Spirit Airlines logo]()
$103
This Trip.com deal was found by Cheapflights users on 1/27. 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 Trip.com is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 3/56:00 am
SJU
- MDW
1 stop9h 56m
Frontier
Deal found 1/27![Frontier logo]()
$104
This Expedia deal was found by Cheapflights users on 1/29. 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 Expedia is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Thu 4/911:07 am
SJU
- ORD
1 stop8h 28m
Spirit Airlines
Deal found 1/29![Spirit Airlines logo]()
$104
Find flight deals from Caribbean to Chicago
Keep the following information in mind while searching for Caribbean to Chicago flight deals. Data was last updated January 29, 2026.
Round-trip from | $145 (Expedia) |
|---|---|
One-way from | $97 (CheapOair) |
Popular in | December |
Cheapest in | February |
Average price | $301 |
Good round-trip deal | $160 or less |
Good one-way deal | $187 or less |
Cheapflights Fare Finder
Customize your flight search to find flights from Caribbean to Chicago 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 January 29, 2026.
Use the filters below to find and compare flights from Caribbean to Chicago that are best for you.
Fly from
Caribbean
Fly to
Chicago
Route
Depart
Return
Price
Saint Thomas IslandChicago
STT - ORD
STTORD
Saint Thomas Island Cyril E King
Thu 2/26
5:40 pm-11:47 pm
1 stop8h 07m
Chicago O'Hare Intl
Thu 3/5
7:00 am-4:34 pm
1 stop7h 34m
$165
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Thu 2/26
12:32 pm-3:48 pm
Nonstop5h 16m
Chicago O'Hare Intl
Sun 3/1
12:17 pm-6:49 pm
Nonstop4h 32m
$169
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Thu 2/19
12:32 pm-3:48 pm
Nonstop5h 16m
Chicago O'Hare Intl
Sun 2/22
12:17 pm-6:49 pm
Nonstop4h 32m
$169
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Mon 5/4
11:59 pm-9:48 am
1 stop10h 49m
Chicago O'Hare Intl
Thu 5/7
10:35 am-9:01 pm
1 stop9h 26m
$171
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Wed 3/18
3:26 am-11:25 am
1 stop8h 59m
Chicago O'Hare Intl
Tue 3/24
12:20 pm-8:26 pm
1 stop7h 06m
$171
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Tue 3/17
3:26 am-11:25 am
1 stop8h 59m
Chicago O'Hare Intl
Mon 3/23
12:20 pm-10:51 pm
1 stop9h 31m
$183
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Fri 2/27
1:44 pm-10:59 pm
1 stop11h 15m
Chicago O'Hare Intl
Mon 3/2
12:41 pm-12:29 am
1 stop9h 48m
$183
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Thu 5/7
12:22 pm-4:37 pm
Nonstop5h 15m
Chicago O'Hare Intl
Mon 5/11
12:22 pm-5:54 pm
Nonstop4h 32m
$198
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Mon 4/6
1:29 am-5:45 am
Nonstop5h 16m
Chicago O'Hare Intl
Tue 4/14
12:22 pm-5:53 pm
Nonstop4h 31m
$198
San JuanChicago
SJU - ORD
SJUORD
San Juan Luis Munoz Marin Intl
Fri 4/24
12:22 pm-4:37 pm
Nonstop5h 15m
Chicago O'Hare Intl
Mon 4/27
6:34 pm-5:58 pm
1 stop22h 24m
$201
Showing 1-10 of 60 results
Best time to book a flight from Caribbean to Chicago
Have a flexible travel schedule? Discover the best time to fly to Chicago from Caribbean with our price prediction graph.
STT-ORD
SJU-ORD
SJU-MDW
AUA-ORD
MBJ-ORD
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 Caribbean to Chicago
0CB-CHI
STT-ORD
SJU-ORD
SJU-MDW
AUA-ORD
What is the cheapest month to book a flight from Caribbean to Chicago?
Currently, February is the cheapest month in which you can book a flight from Caribbean to Chicago (average of $118). Flying from Caribbean to Chicago in December is currently the most expensive (average of $157). 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 CB to CHI?
Find hourly flight availability from Caribbean to Chicago. Discover flight options and departure times throughout the day, allowing you to choose a departure time that suits your schedule. Data last updated January 29, 2026.
It’s optimal to fly from Caribbean to Chicago in the evening. By choosing this option you can save up to 55% on the cost of your flight, compared to a flight in the afternoon.
What is the cheapest day to fly from Caribbean to Chicago?
Use this chart to determine the cheapest time to fly round-trip from Caribbean to Chicago. Price data was last updated on January 24, 2026.
Travelers seeking maximum savings on their Caribbean to Chicago flight should consider departing on Friday evenings when fares are most often at their lowest. Monday at noon flights should be avoided if possible as fares are typically the most expensive at this time.
Weekly flight availability from Caribbean to Chicago
Explore weekly flight availability from Caribbean to Chicago. 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 January 29, 2026.
The most flights from 0CB to CHI are scheduled on a Thursday (12 on average). You will have fewer flight options on Saturday, which is when the least amount of flights are scheduled (7 on average).
Reviews of airlines servicing Chicago
Get insights into the airlines that provide service to Chicago. 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 Chicago. Reviews last updated January 29, 2026.
Read reviews from past customers who have flown Delta, United Airlines, and American Airlines from Caribbean to Chicago. Users can see the overall rating for each airline as well as how each is rated in terms of entertainment options, comfort, food, crew/service, and boarding process.
Food
7.2
Overall
7.9
Boarding
8.1
Crew
8.5
Entertainment
7.8
Comfort
7.9
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Food
7.2
Overall
7.9
Boarding
8.1
Crew
8.5
Entertainment
7.8
Comfort
7.9
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Food
7.2
Overall
7.9
Boarding
8.1
Crew
8.5
Entertainment
7.8
Comfort
7.9
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Food
7.2
Overall
7.9
Boarding
8.1
Crew
8.5
Entertainment
7.8
Comfort
7.9
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Food
7.2
Overall
7.9
Boarding
8.1
Crew
8.5
Entertainment
7.8
Comfort
7.9
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Food
7.2
Overall
7.9
Boarding
8.1
Crew
8.5
Entertainment
7.8
Comfort
7.9
Reviews
1 / 20
6.0
GoodJim,Nov 2025
AVL - ATL
Related info for your journey
Find useful and relevant information for your journey from Caribbean to Chicago. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.
Traveling to a place near Chicago?
Book flights to Chicago if you plan to visit one of these locationsLansing
Merrillville
Hammond
Porter
Benton Harbor
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 for Caribbean to Chicago
See prices for flight routes from nearby airports that may be better suited for you.
Top 7 airlines flying from Caribbean to Chicago
Discover the top 7 airlines that operate flights from Caribbean to Chicago. 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 January 29, 2026.
| Airline | Cheapest | Average | Flexibility | On-time |
|---|---|---|---|---|
| Cheapest$116 | Average$626 | FlexibilityNo cancel fee | On-timeN/A | |
| Cheapest$118 | Average$316 | FlexibilityNo cancel fee | On-time65% | |
| Cheapest$131 | Average$201 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$137 | Average$351 | FlexibilityNo cancel fee | On-time62% | |
| Cheapest$256 | Average$525 | FlexibilityNo cancel fee | On-time69% | |
| Cheapest$258 | Average$557 | FlexibilityNo cancel fee | On-time71% | |
| Cheapest$392 | Average$548 | FlexibilityNo cancel fee | On-time63% |