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Cheap flights from Chicago O'Hare Intl Airport to Cayman Brac from $536

This is the cheapest round-trip flight price found by a momondo user in the last 72 hours by searching for a flight from Chicago O'Hare Intl Airport to Cayman Brac departing on 11/14. Fares may change, and may not be available for all flights or travel dates. Click the price to refresh the search for this deal.
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Find the cheapest flights from Chicago O'Hare Intl Airport to Cayman Brac

Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
12:17 pm - 1:20 pmORD-CYB
24h 03m1 stop
Multiple Airlines Logo
10:55 am - 10:35 amCYB-ORD
24h 40m2 stops
$536Multiple Airlines
Find Deal
Fri, Nov 14 - Fri, Nov 21
Multiple Airlines Logo
8:15 pm - 3:25 pmORD-CYB
19h 10m2 stops
Multiple Airlines Logo
8:30 am - 9:09 amCYB-ORD
24h 39m2 stops
$906Multiple Airlines
Find Deal
Mon, Mar 23 - Tue, Mar 31
Multiple Airlines Logo
8:20 pm - 8:05 amORD-CYB
35h 45m2 stops
Multiple Airlines Logo
8:30 am - 1:00 pmCYB-ORD
28h 30m2 stops
$935Multiple Airlines
Find Deal
Sat, Apr 11 - Sun, Apr 19
Multiple Airlines Logo
8:15 pm - 5:50 pmORD-CYB
21h 35m2 stops
Multiple Airlines Logo
8:30 am - 9:59 pmCYB-ORD
13h 29m2 stops
$1,657Multiple Airlines
Find Deal
Sat, Mar 14 - Sun, Mar 22
Multiple Airlines Logo
6:10 pm - 3:25 pmORD-CYB
45h 15m3 stops
Multiple Airlines Logo
10:55 am - 5:00 pmCYB-ORD
30h 05m3 stops
$2,653Multiple Airlines
Find Deal
Mon, Mar 23 - Mon, Mar 30
Multiple Airlines Logo
6:10 pm - 3:25 pmORD-CYB
45h 15m3 stops
Multiple Airlines Logo
8:30 am - 5:00 pmCYB-ORD
32h 30m3 stops
$2,673Multiple Airlines
Find Deal
Tue, Mar 24 - Tue, Mar 31
Multiple Airlines Logo
8:40 pm - 8:05 amORD-CYB
58h 25m3 stops
Multiple Airlines Logo
8:30 am - 3:25 pmCYB-ORD
31h 55m3 stops
$3,115Multiple Airlines
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Mon, Nov 3 - Mon, Nov 10

momondo Fare Finder

 
Customize your flight search to find flights from Chicago O'Hare Intl Airport 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, momondo users made 832,500 searches. Data last updated October 16, 2025.
Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Cayman Brac that are best for you.

Fly from

Fly to

Route

Depart

Return

Price

ChicagoCayman Brac

ORD - CYB

ORDCYB

Chicago O'Hare Intl

Fri 11/14

12:17 pm-1:20 pm

1 stop24h 03m

Cayman Brac Gerrard-Smith

Fri 11/21

10:55 am-10:35 am

2 stops24h 40m

$536

ChicagoCayman Brac

ORD - CYB

ORDCYB

Chicago O'Hare Intl

Mon 3/23

8:15 pm-3:25 pm

2 stops19h 10m

Cayman Brac Gerrard-Smith

Tue 3/31

8:30 am-9:09 am

2 stops24h 39m

$906

ChicagoCayman Brac

ORD - CYB

ORDCYB

Chicago O'Hare Intl

Sat 4/11

8:20 pm-8:05 am

2 stops35h 45m

Cayman Brac Gerrard-Smith

Sun 4/19

8:30 am-1:00 pm

2 stops28h 30m

$935

ChicagoCayman Brac

ORD - CYB

ORDCYB

Chicago O'Hare Intl

Sat 3/14

8:15 pm-5:50 pm

2 stops21h 35m

Cayman Brac Gerrard-Smith

Sun 3/22

8:30 am-9:59 pm

2 stops13h 29m

$1,657

ChicagoCayman Brac

ORD - CYB

ORDCYB

Chicago O'Hare Intl

Mon 3/23

6:10 pm-3:25 pm

3 stops45h 15m

Cayman Brac Gerrard-Smith

Mon 3/30

10:55 am-5:00 pm

3 stops30h 05m

$2,653

ChicagoCayman Brac

ORD - CYB

ORDCYB

Chicago O'Hare Intl

Tue 3/24

6:10 pm-3:25 pm

3 stops45h 15m

Cayman Brac Gerrard-Smith

Tue 3/31

8:30 am-5:00 pm

3 stops32h 30m

$2,673

ChicagoCayman Brac

ORD - CYB

ORDCYB

Chicago O'Hare Intl

Mon 11/3

8:40 pm-8:05 am

3 stops58h 25m

Cayman Brac Gerrard-Smith

Mon 11/10

8:30 am-3:25 pm

3 stops31h 55m

$3,115

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

When to book flights from Chicago O'Hare Intl Airport to Cayman Brac

Are you open to changing your travel dates? Check out the ideal times to fly from Chicago O'Hare Intl Airport to Cayman Brac according to our flight data. Find out which month and days have the cheapest flights.
Estimated round-trip price

Cheap Chicago O'Hare Intl Airport to Cayman Brac (ORD to CYB) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago O'Hare Intl Airport to Cayman Brac

Direct flights

None
There are no direct flights from Chicago O'Hare Intl Airport to Cayman Brac. There are no popular flight routes from Chicago O'Hare Intl Airport to Cayman Brac.
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  • How far is Chicago O'Hare Intl to Cayman Brac Gerrard-Smith by plane?

    Cayman Brac Gerrard-Smith is 1608.0 mi away from Chicago O'Hare Intl. Flights usually cover this in 19h 10m, depending on flying conditions and air traffic around both airports.

  • When did momondo last update prices for flights from Chicago O'Hare Intl Airport to Cayman Brac Gerrard-Smith Airport?

    Prices for flights from Chicago O'Hare Intl Airport to Cayman Brac Gerrard-Smith Airport are updated daily.

  • How old do you have to be to fly from Chicago O'Hare Intl Airport to Cayman Brac Gerrard-Smith Airport?

    The minimum age a child must be to fly alone is five but airlines that offer an unaccompanied minor (UNMR) service will have their own age restrictions, including rules around flight length, timings, and stopovers. We always recommend checking with the individual airline you are booking with to travel from Chicago O'Hare Intl Airport to Cayman Brac Gerrard-Smith Airport.

  • What documentation or ID do you need to fly to Cayman Brac Gerrard-Smith Airport?

    The travel and health documents you'll need for your trip to Cayman Brac Gerrard-Smith Airport may differ based on your itinerary and personal situation. Typically, you should have several documents on hand, such as a national ID card or driver's license and a passport that is valid for six months after your intended arrival at Cayman Brac Gerrard-Smith Airport. It is always advisable to seek advice from your airline or a trusted third party, such as IATA.

  • How do I get Price Alerts for flights from Chicago O'Hare Intl Airport to Cayman Brac?

    You can take advantage of momondo’s Price Alerts by first searching for your flights to Chicago O'Hare Intl Airport from Cayman Brac. Flight offers will be shown to you in real-time. From there you can create a Price Alert by using our on-site widget.

  • How can I save money on flights from Chicago O'Hare Intl Airport to Cayman Brac with momondo?

    With “Price Forecast”, learn how soon you should book your flight in advance. Down to the day of week and time of day, our information can inform you on the ideal time to book to save on your travel. Our “Price Calendar” shows you at a quick glance when to book your travel for lower rates. By setting “Price Alerts” you can monitor changes in price and target the ideal time to book. Search for your trip destination by budget amount via our “Explore” feature. Whether you’re looking for ideas for your next travel adventure or cost-cutting tips, our “Discover” content is a great place to start.

  • How does momondo find its flight prices?

    We compare prices from 700+ competitors to help you find the price that works best for you. momondo operates in over 30 international markets, bringing you access to a wide range of fares and deals. Search for your travel using momondo for a diverse range of options from airlines and OTAs.

Why use momondo?

Why should I use momondo to find a flight deal from Chicago to Cayman Brac?

It is quick and easy to find Chicago to Cayman Brac flights on momondo. We search and return numerous flight options from various airlines and agents. You can then use our filters to narrow your search until you have found the most convenient flight to Cayman Brac that suits you.

Can I find flights from Chicago to Cayman Brac with flexible booking policies on momondo?

Yes. momondo allows you to filter the results for Chicago to Cayman Brac flights to just show those with flexible booking policies.

How can momondo help me find flights from Chicago to Cayman Brac?

Once you have performed a search in the form on the page, momondo provides useful filters and insights. We can show you the cheapest days and times to fly as well as help filter your options to help you make an informed choice when booking flights to Cayman Brac from Chicago.

I’m not ready to book a flight from Chicago to Cayman Brac right now. Can momondo alert me if prices change?

Of course. momondo tracks the price of Chicago to Cayman Brac flights. All you need is a valid email address and we will do the rest; it is that quick and easy.

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Sat 11/15
Sat 11/22
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