$547+ Cheap flights from Illinois to Cayman Brac (CYB)
This is the cheapest round-trip flight price found by a Cheapflights user in the last 72 hours by searching for a flight departing on 1/16. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — CYB
ene. 30 — feb. 61
1 adult, Economy
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Best flights from Illinois to Cayman BracDiscover carefully curated flight deals from Illinois to Cayman Brac that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated diciembre 31, 2025.
Discover carefully curated flight deals from Illinois to Cayman Brac that have cost, travel time, and layovers in mind to ensure you get the best travel experience. Data last updated diciembre 31, 2025.
This Mytrip deal was found by Cheapflights users on 12/29. 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 Mytrip is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
vie. 1/168:43 pmORD - CYB
2 stops20h 07mMultiple Airlines
lun. 1/198:30 amCYB - ORD
2 stops34h 18mMultiple Airlines
Deal found 12/29![Multiple Airlines logo]()
$547
This FlightHub deal was found by Cheapflights users on 12/29. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
jue. 1/152:00 pmORD - CYB
2 stops24h 25mMultiple Airlines
jue. 1/228:30 amCYB - ORD
2 stops25h 43mMultiple Airlines
Deal found 12/29![Multiple Airlines logo]()
$596
This FlightHub deal was found by Cheapflights users on 12/30. Clicking the “Pick Dates” 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.
dom. 3/299:50 amORD - CYB
2 stops29h 35mMultiple Airlines
dom. 4/58:30 amCYB - ORD
2 stops26h 48mMultiple Airlines
Deal found 12/30![Multiple Airlines logo]()
$618
This FlightHub deal was found by Cheapflights users on 12/29. 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 FlightHub is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
sáb. 3/78:40 pmORD - CYB
2 stops34h 25mMultiple Airlines
vie. 3/278:30 amCYB - ORD
2 stops24h 43mMultiple Airlines
Deal found 12/29![Multiple Airlines logo]()
$619
This FlightHub deal was found by Cheapflights users on 12/30. Clicking the “Pick Dates” 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.
jue. 2/58:40 pmORD - CYB
2 stops17h 45mMultiple Airlines
dom. 2/810:55 amCYB - ORD
2 stops12h 10mMultiple Airlines
Deal found 12/30![Multiple Airlines logo]()
$807
This Mytrip deal was found by Cheapflights users on 12/30. Clicking the “Pick Dates” 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.
mar. 1/138:45 pmORD - CYB
3 stops20h 05mMultiple Airlines
vie. 1/168:30 amCYB - ORD
2 stops34h 46mMultiple Airlines
Deal found 12/30![Multiple Airlines logo]()
$930
Find flight deals from Illinois to Cayman Brac
Keep the following information in mind while searching for Illinois to Cayman Brac flight deals. Data was last updated diciembre 31, 2025.
Round-trip from | $547 (Mytrip) |
|---|
Cheapflights Fare Finder
Customize your flight search to find flights from Illinois to Cayman Brac 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 diciembre 31, 2025.
Use the filters below to find and compare flights from Illinois to Cayman Brac that are best for you.
Fly from
Illinois
Fly to
Cayman Brac
Route
Depart
Return
Price
ChicagoCayman Brac
ORD - CYB
ORDCYB
Chicago O'Hare Intl
vie. 1/16
8:43 pm-5:50 pm
2 stops20h 07m
Cayman Brac Gerrard-Smith
lun. 1/19
8:30 am-5:48 pm
2 stops34h 18m
$547
ChicagoCayman Brac
ORD - CYB
ORDCYB
Chicago O'Hare Intl
jue. 1/15
2:00 pm-3:25 pm
2 stops24h 25m
Cayman Brac Gerrard-Smith
jue. 1/22
8:30 am-9:13 am
2 stops25h 43m
$596
ChicagoCayman Brac
ORD - CYB
ORDCYB
Chicago O'Hare Intl
dom. 3/29
9:50 am-3:25 pm
2 stops29h 35m
Cayman Brac Gerrard-Smith
dom. 4/5
8:30 am-11:18 am
2 stops26h 48m
$618
ChicagoCayman Brac
ORD - CYB
ORDCYB
Chicago O'Hare Intl
sáb. 3/7
8:40 pm-8:05 am
2 stops34h 25m
Cayman Brac Gerrard-Smith
vie. 3/27
8:30 am-9:13 am
2 stops24h 43m
$619
ChicagoCayman Brac
ORD - CYB
ORDCYB
Chicago O'Hare Intl
jue. 2/5
8:40 pm-3:25 pm
2 stops17h 45m
Cayman Brac Gerrard-Smith
dom. 2/8
10:55 am-10:05 pm
2 stops12h 10m
$807
ChicagoCayman Brac
ORD - CYB
ORDCYB
Chicago O'Hare Intl
mar. 1/13
8:45 pm-5:50 pm
3 stops20h 05m
Cayman Brac Gerrard-Smith
vie. 1/16
8:30 am-6:16 pm
2 stops34h 46m
$930
Best time to book a flight from Illinois to Cayman Brac
Have a flexible travel schedule? Discover the best time to fly to Cayman Brac from Illinois with our price prediction graph.
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 Illinois to Cayman Brac
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