$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 12/12. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — CYB
dic. 6 — dic. 131
1 adult, Economy
We work with more than 300 partners to bring you better travel deals
Find cheap flights from Illinois to Cayman Brac 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.Find flight deals from Illinois to Cayman Brac
Cheapest flights from Illinois to Cayman BracExplore the most affordable flight options available from Illinois to Cayman Brac. Find the lowest fares from popular airlines and budget airlines, with prices last updated on noviembre 6, 2025.
Explore the most affordable flight options available from Illinois to Cayman Brac. Find the lowest fares from popular airlines and budget airlines, with prices last updated on noviembre 6, 2025.
This Kiwi.com deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” 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.
vie. 12/127:41 pmORD - CYB
1 stop16h 39mMultiple Airlines
mar. 12/166:20 pmCYB - ORD
2 stops25h 16mMultiple Airlines
Deal found 11/5![Multiple Airlines logo]()
$547
This FlightHub deal was found by Cheapflights users on 11/5. Clicking the “Pick Dates” 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. 11/232:07 pmORD - CYB
2 stops40h 58mMultiple Airlines
vie. 11/288:30 amCYB - ORD
2 stops25h 43mMultiple Airlines
Deal found 11/5![Multiple Airlines logo]()
$2,025
Cheap 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 noviembre 6, 2025.
Round-trip from | $547 (Kiwi.com) |
|---|
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 noviembre 6, 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. 12/12
7:41 pm-1:20 pm
1 stop16h 39m
Cayman Brac Gerrard-Smith
mar. 12/16
6:20 pm-6:36 pm
2 stops25h 16m
$547
ChicagoCayman Brac
ORD - CYB
ORDCYB
Chicago O'Hare Intl
dom. 11/23
2:07 pm-8:05 am
2 stops40h 58m
Cayman Brac Gerrard-Smith
vie. 11/28
8:30 am-9:13 am
2 stops25h 43m
$2,025
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
No data available for this route at this time. Please check back soon.