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Cheap flights from Chicago to Cayman Brac from $1,115

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 to Cayman Brac departing on 12/29. 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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Cheap round-trip flights

Enter your travel dates to find the best prices.
Multiple Airlines Logo
6:35 am - 5:50 pmORD-CYB
34h 15m3 stops
Multiple Airlines Logo
6:20 pm - 4:00 pmCYB-ORD
22h 40m3 stops
$1,115Multiple Airlines
Find Deal
Mon, Dec 29 - Sun, Jan 4
Multiple Airlines Logo
8:15 pm - 5:50 pmORD-CYB
20h 35m2 stops
Multiple Airlines Logo
3:55 pm - 4:00 pmCYB-ORD
25h 05m3 stops
$1,131Multiple Airlines
Find Deal
Mon, Dec 29 - Sun, Jan 4
Multiple Airlines Logo
8:15 pm - 5:50 pmORD-CYB
20h 35m2 stops
Multiple Airlines Logo
3:55 pm - 5:00 pmCYB-ORD
26h 05m2 stops
$1,198Multiple Airlines
Find Deal
Mon, Dec 29 - Sun, Jan 4
Multiple Airlines Logo
8:15 pm - 3:10 pmORD-CYB
17h 55m2 stops
Multiple Airlines Logo
10:55 am - 9:13 amCYB-ORD
23h 18m2 stops
$1,394Multiple Airlines
Find Deal
Thu, Dec 18 - Sun, Dec 21
Multiple Airlines Logo
5:10 pm - 8:05 amORD-CYB
37h 55m3 stops
Multiple Airlines Logo
6:20 pm - 3:25 pmCYB-ORD
46h 05m3 stops
$3,975Multiple Airlines
Find Deal
Tue, Dec 23 - Sun, Dec 28

momondo Fare Finder

 
Customize your flight search to find flights from Chicago 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 30, 2025.
Use the filters below to find and compare flights from Chicago 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

Mon 12/29

6:35 am-5:50 pm

3 stops34h 15m

Cayman Brac Gerrard-Smith

Sun 1/4

6:20 pm-4:00 pm

3 stops22h 40m

$1,115

ChicagoCayman Brac

ORD - CYB

ORDCYB

Chicago O'Hare Intl

Mon 12/29

8:15 pm-5:50 pm

2 stops20h 35m

Cayman Brac Gerrard-Smith

Sun 1/4

3:55 pm-4:00 pm

3 stops25h 05m

$1,131

ChicagoCayman Brac

ORD - CYB

ORDCYB

Chicago O'Hare Intl

Mon 12/29

8:15 pm-5:50 pm

2 stops20h 35m

Cayman Brac Gerrard-Smith

Sun 1/4

3:55 pm-5:00 pm

2 stops26h 05m

$1,198

ChicagoCayman Brac

ORD - CYB

ORDCYB

Chicago O'Hare Intl

Thu 12/18

8:15 pm-3:10 pm

2 stops17h 55m

Cayman Brac Gerrard-Smith

Sun 12/21

10:55 am-9:13 am

2 stops23h 18m

$1,394

ChicagoCayman Brac

ORD - CYB

ORDCYB

Chicago O'Hare Intl

Tue 12/23

5:10 pm-8:05 am

3 stops37h 55m

Cayman Brac Gerrard-Smith

Sun 12/28

6:20 pm-3:25 pm

3 stops46h 05m

$3,975

Flights are sorted by cheapest round-trip flights first.

Sorted by cheapest first

When to book flights from Chicago to Cayman Brac

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

Cheap Chicago to Cayman Brac (CHI to CYB) flight deals and tips

Find info about flight duration, direct flights, and airports for your flight from Chicago to Cayman Brac

Direct flights

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

    Chicago and Cayman Brac Gerrard-Smith are 1596.5 mi apart from one another. A reasonable flight in good conditions will take 17h 55m.

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

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

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

    The minimum age for a child to fly alone is five, but airlines offering an unaccompanied minor (UNMR) service may have their age restrictions, such as regulations concerning flight duration, timing, and layovers. It is recommended that you verify with the airline you are booking with for travel from Chicago to Cayman Brac Gerrard-Smith Airport.

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

    The necessary travel and health documents for your Cayman Brac Gerrard-Smith Airport trip may vary depending on your travel plans and individual circumstances. Generally, you should have various documents, such as a national ID card or driver's license and a passport that is valid for six months beyond your scheduled arrival date. We recommend seeking advice from your airline or a trusted third party, such as IATA.

  • How do I get Price Alerts for flights from Chicago to Cayman Brac?

    Confirm your travel details to search for the latest offers for flights from Chicago to Cayman Brac. While browsing offers there will be the option to toggle “Price Alerts”. You’ll then receive updates when prices for the flight route increase or decrease.

  • How can I save money on flights from Chicago to Cayman Brac with momondo?

    Plan your trips smart with the “Price Forecast” feature, which uses flight data to help you pick the best days to fly for the lowest fares. Our “Price Calendar” helps you get the most for your money by showing you when it’s most advantageous to fly. Curate your own travel experiences for less with “Explore”. Expert travel hacks to fuel your next adventure are a click away with “Discover” by momondo. Set up our “Price Alerts” to track fare changes and book when prices are at their lowest point.

  • How does momondo find its flight prices?

    We show prices from over 700+ competitors with a single click. With options from airlines and OTAs from across our 30 international markets, we are able to show you a diverse range of deals to create your adventure.

Why use momondo?

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

momondo compares prices from hundreds of airlines and agents so you can find and book the best deal on flights from Chicago to Cayman Brac. Millions of users trust and use momondo every year so you are in good hands.

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

momondo does allow users to show only those flights to Cayman Brac from Chicago which offer a flexible booking policy as well as other useful filters and features.

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

momondo helps you find the best flight between Chicago and Cayman Brac by providing filters to narrow your choice of flights to those matching your criteria. You can select flights based on numerous factors such as price, departure and landing times, airport and airline.

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

Yes. momondo can track prices for Chicago to Cayman Brac flights and alert you when they change. Perform a search to set up the price alert. All that is required is a valid email address.

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