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Cheap flights from Chicago O'Hare Intl Airport to Cayman Brac from $388

1 adult
1 adult, Economy, 0 bags

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
8:45 am - 5:50 pmORD  Chicago O'Hare Intl-CYB Cayman Brac Gerrard-Smith
32h 05m2 stops Toronto Pearson Intl George Town Owen Roberts Intl
Multiple Airlines Logo
6:20 pm - 7:58 pmCYB  Cayman Brac Gerrard-Smith-ORD Chicago O'Hare Intl
26h 38m2 stops George Town Owen Roberts Intl Toronto Pearson Intl
$786Multiple Airlines
Sat, Nov 7 - Mon, Nov 16
Multiple Airlines Logo
8:40 pm - 3:25 pmORD  Chicago O'Hare Intl-CYB Cayman Brac Gerrard-Smith
17h 45m2 stops Toronto Pearson Intl George Town Owen Roberts Intl
Multiple Airlines Logo
6:20 pm - 11:18 pmCYB  Cayman Brac Gerrard-Smith-ORD Chicago O'Hare Intl
29h 58m3 stops George Town Owen Roberts Intl Miami Atlanta Hartsfield-Jackson
$1,003Multiple Airlines
Tue, Nov 24 - Sun, Nov 29
Multiple Airlines Logo
8:45 am - 3:25 pmORD  Chicago O'Hare Intl-CYB Cayman Brac Gerrard-Smith
29h 40m2 stops Toronto Pearson Intl George Town Owen Roberts Intl
Multiple Airlines Logo
6:20 pm - 7:58 pmCYB  Cayman Brac Gerrard-Smith-ORD Chicago O'Hare Intl
26h 38m2 stops George Town Owen Roberts Intl Toronto Pearson Intl
$1,060Multiple Airlines
Tue, Jan 5 - Sun, Jan 31
Multiple Airlines Logo
8:50 pm - 3:10 pmORD  Chicago O'Hare Intl-CYB Cayman Brac Gerrard-Smith
17h 20m2 stops Toronto Pearson Intl George Town Owen Roberts Intl
Multiple Airlines Logo
3:55 pm - 7:58 pmCYB  Cayman Brac Gerrard-Smith-ORD Chicago O'Hare Intl
29h 03m2 stops George Town Owen Roberts Intl Toronto Pearson Intl
$1,063Multiple Airlines
Thu, Dec 31 - Mon, Jan 4
Multiple Airlines Logo
8:40 pm - 5:50 pmORD  Chicago O'Hare Intl-CYB Cayman Brac Gerrard-Smith
20h 10m2 stops Toronto Pearson Intl George Town Owen Roberts Intl
Multiple Airlines Logo
8:30 am - 12:43 amCYB  Cayman Brac Gerrard-Smith-ORD Chicago O'Hare Intl
17h 13m2 stops George Town Owen Roberts Intl Tampa
$1,106Multiple Airlines
Tue, Nov 24 - Sun, Nov 29
Multiple Airlines Logo
6:20 am - 5:50 pmORD  Chicago O'Hare Intl-CYB Cayman Brac Gerrard-Smith
34h 30m3 stops Tampa Toronto Pearson Intl George Town Owen Roberts Intl
Multiple Airlines Logo
6:20 pm - 11:18 pmCYB  Cayman Brac Gerrard-Smith-ORD Chicago O'Hare Intl
29h 58m3 stops George Town Owen Roberts Intl Miami Atlanta Hartsfield-Jackson
$1,159Multiple Airlines
Tue, Nov 24 - Sun, Nov 29
Multiple Airlines Logo
8:50 pm - 5:50 pmORD  Chicago O'Hare Intl-CYB Cayman Brac Gerrard-Smith
20h 00m2 stops Toronto Pearson Intl George Town Owen Roberts Intl
Multiple Airlines Logo
8:30 am - 9:08 amCYB  Cayman Brac Gerrard-Smith-ORD Chicago O'Hare Intl
25h 38m2 stops George Town Owen Roberts Intl Toronto Pearson Intl
$1,244Multiple Airlines
Wed, Dec 23 - Tue, Dec 29
Multiple Airlines Logo
8:50 pm - 3:25 pmORD  Chicago O'Hare Intl-CYB Cayman Brac Gerrard-Smith
18h 35m2 stops Toronto Pearson Intl George Town Owen Roberts Intl
Multiple Airlines Logo
8:30 am - 7:58 pmCYB  Cayman Brac Gerrard-Smith-ORD Chicago O'Hare Intl
11h 28m2 stops George Town Owen Roberts Intl Toronto Pearson Intl
$1,353Multiple Airlines
Sun, Mar 14 - Fri, Mar 19
Multiple Airlines Logo
8:50 pm - 3:10 pmORD  Chicago O'Hare Intl-CYB Cayman Brac Gerrard-Smith
17h 20m2 stops Toronto Pearson Intl George Town Owen Roberts Intl
Multiple Airlines Logo
8:30 am - 9:08 amCYB  Cayman Brac Gerrard-Smith-ORD Chicago O'Hare Intl
25h 38m2 stops George Town Owen Roberts Intl Toronto Pearson Intl
$1,492Multiple Airlines
Fri, Jan 1 - Tue, Jan 5
Multiple Airlines Logo
2:13 pm - 8:05 amORD  Chicago O'Hare Intl-CYB Cayman Brac Gerrard-Smith
40h 52m2 stops Panama City Tocumen Intl George Town Owen Roberts Intl
Multiple Airlines Logo
6:20 pm - 7:58 pmCYB  Cayman Brac Gerrard-Smith-ORD Chicago O'Hare Intl
26h 38m2 stops George Town Owen Roberts Intl Toronto Pearson Intl
$1,731Multiple Airlines
Sun, Nov 15 - Wed, Nov 18

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Use the filters below to find and compare flights from Chicago O'Hare Intl Airport to Cayman Brac that are best for you.

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Cheapest round-trip

ChicagoCayman Brac

ORD Chicago O'Hare Intl - CYB Cayman Brac Gerrard-Smith

ORDCYB

Chicago O'Hare Intl

Sat 11/7

8:45 am-5:50 pm

2 stops32h 05m

Cayman Brac Gerrard-Smith

Mon 11/16

6:20 pm-7:58 pm

2 stops26h 38m

$786

ChicagoCayman Brac

ORD Chicago O'Hare Intl - CYB Cayman Brac Gerrard-Smith

ORDCYB

Chicago O'Hare Intl

Tue 11/24

8:40 pm-3:25 pm

2 stops17h 45m

Cayman Brac Gerrard-Smith

Sun 11/29

6:20 pm-11:18 pm

3 stops29h 58m

$1,003

ChicagoCayman Brac

ORD Chicago O'Hare Intl - CYB Cayman Brac Gerrard-Smith

ORDCYB

Chicago O'Hare Intl

Tue 1/5

8:45 am-3:25 pm

2 stops29h 40m

Cayman Brac Gerrard-Smith

Sun 1/31

6:20 pm-7:58 pm

2 stops26h 38m

$1,060

ChicagoCayman Brac

ORD Chicago O'Hare Intl - CYB Cayman Brac Gerrard-Smith

ORDCYB

Chicago O'Hare Intl

Thu 12/31

8:50 pm-3:10 pm

2 stops17h 20m

Cayman Brac Gerrard-Smith

Mon 1/4

3:55 pm-7:58 pm

2 stops29h 03m

$1,063

ChicagoCayman Brac

ORD Chicago O'Hare Intl - CYB Cayman Brac Gerrard-Smith

ORDCYB

Chicago O'Hare Intl

Tue 11/24

8:40 pm-5:50 pm

2 stops20h 10m

Cayman Brac Gerrard-Smith

Sun 11/29

8:30 am-12:43 am

2 stops17h 13m

$1,106

ChicagoCayman Brac

ORD Chicago O'Hare Intl - CYB Cayman Brac Gerrard-Smith

ORDCYB

Chicago O'Hare Intl

Tue 11/24

6:20 am-5:50 pm

3 stops34h 30m

Cayman Brac Gerrard-Smith

Sun 11/29

6:20 pm-11:18 pm

3 stops29h 58m

$1,159

ChicagoCayman Brac

ORD Chicago O'Hare Intl - CYB Cayman Brac Gerrard-Smith

ORDCYB

Chicago O'Hare Intl

Wed 12/23

8:50 pm-5:50 pm

2 stops20h 00m

Cayman Brac Gerrard-Smith

Tue 12/29

8:30 am-9:08 am

2 stops25h 38m

$1,244
Quickest round-trip

ChicagoCayman Brac

ORD Chicago O'Hare Intl - CYB Cayman Brac Gerrard-Smith

ORDCYB

Chicago O'Hare Intl

Sun 3/14

8:50 pm-3:25 pm

2 stops18h 35m

Cayman Brac Gerrard-Smith

Fri 3/19

8:30 am-7:58 pm

2 stops11h 28m

$1,353

ChicagoCayman Brac

ORD Chicago O'Hare Intl - CYB Cayman Brac Gerrard-Smith

ORDCYB

Chicago O'Hare Intl

Fri 1/1

8:50 pm-3:10 pm

2 stops17h 20m

Cayman Brac Gerrard-Smith

Tue 1/5

8:30 am-9:08 am

2 stops25h 38m

$1,492

ChicagoCayman Brac

ORD Chicago O'Hare Intl - CYB Cayman Brac Gerrard-Smith

ORDCYB

Chicago O'Hare Intl

Sun 11/15

2:13 pm-8:05 am

2 stops40h 52m

Cayman Brac Gerrard-Smith

Wed 11/18

6:20 pm-7:58 pm

2 stops26h 38m

$1,731

Flights are sorted by cheapest round-trip flights first.

Showing 1-10 of 12 resultsSorted by cheapest first
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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

Best Price Found

$388

Fastest flight time

17h 20m

Direct flights

None
The best one-way flight to Cayman Brac from Chicago O'Hare Intl Airport in the past 72 hours is $388. The best round-trip flight deal from Chicago O'Hare Intl Airport to Cayman Brac found on momondo in the last 72 hours is $786.
The fastest flight from Chicago O'Hare Intl Airport to Cayman Brac takes 17h 20m
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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Frequently asked questions about flying from Chicago O'Hare Intl Airport to Cayman Brac

  • 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 17h 20m, 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.

Frequently asked questions about flying from Chicago O'Hare Intl Airport to Cayman Brac

  • 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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