HomeSearch by dateVacation packagesHotelsFlight dealsCar rentalTravel tips & news
Cayman Brac

$913+ Cheap flights from O'Hare Intl (ORD) 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 4/9. Fares are subject to change and may not be available on all flights or dates of travel.
ORD — CYB
Feb 25 — Mar 41
Tue 2/25
Tue 3/4
1 adult, Economy
We work with more than 300 partners to bring you better travel deals

Find cheap flights from O'Hare Intl 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.

Cheap flight deals from O'Hare Intl to Cayman Brac

Discover tips and strategies to find the most affordable flight options for your journey from O'Hare Intl (ORD) to Cayman Brac (CYB). Learn about various techniques such as flexible date searches, comparing prices across and setting up price alerts. Use these methods to find the cheapest flights available for your travel needs. Data last updated February 20, 2025.

Most accurate provider

FlightHub
3 stars

Most trusted provider

FlightHub
3 stars

Round-trip from

$913
(Gotogate)
Provider with most accurate pricing for Chicago O'Hare Intl-Cayman Brac Gerrard-Smith flight deals.
Search Deals
Provider most trusted by Cheapflights users for Chicago O'Hare Intl-Cayman Brac Gerrard-Smith flights.
Search Deals
From Chicago O'Hare Intl to Cayman Brac Gerrard-Smith
Search Deals

Find flight deals from O'Hare Intl to Cayman Brac

Cheapest flights from O'Hare Intl to Cayman Brac
Explore the most affordable flight options available from O'Hare Intl to Cayman Brac. Find the lowest fares from popular airlines and budget airlines, with prices last updated on February 20, 2025.

This Gotogate deal was found by Cheapflights users on 2/19. 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 Gotogate is selected, and click “Compare selected” under the list of providers to see comparable flight deals.
Wed 4/98:25 pmORD - CYB
2 stops21h 25mMultiple Airlines
Sat 4/126:20 pmCYB - ORD
2 stops49h 10mMultiple Airlines
Deal found 2/19$913

Find flights from O'Hare Intl to Cayman Brac within your budget

Customize your flight search to find flights from O'Hare Intl 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 February 20, 2025.

Fly from

O'Hare Intl

Fly to

Cayman Brac

Route

Depart

Return

Price

ChicagoCayman Brac

ORD - CYB

ORDCYB

Chicago O'Hare Intl

Wed 4/9

8:25 pm-5:50 pm

2 stops21h 25m

Cayman Brac Gerrard-Smith

Sat 4/12

6:20 pm-7:30 pm

2 stops49h 10m

$913

Flights are sorted by cheapest round-trip flights first.

Deals found on 2/19

  • Most accurate provider: When it comes to deals on Chicago O'Hare Intl Airport-Cayman Brac flights, users find the pricing of FlightHub to be most consistent on Cheapflights vs. FlightHub Users can find the same prices on Chicago O'Hare Intl Airport-Cayman Brac flight deals on Cheapflights vs. FlightHub >95% of the time. Price accuracy is based on data collected from Chicago O'Hare Intl Airport-Cayman Brac flight searches over the past month and is updated monthly.
  • Most trusted provider: When it comes to deals on Chicago O'Hare Intl Airport-Cayman Brac flights, Cheapflights users trust FlightHub the most. FlightHub has received a user feedback score of 3 out of 3 stars (3 being the best), meaning they have been trusted the most by Cheapflights users looking for Chicago O'Hare Intl Airport-Cayman Brac flight deals. Provider user feedback score is based on Cheapflights searches over the past month and is updated monthly.

Best time to book a flight from O'Hare Intl to Cayman Brac

Have a flexible travel schedule? Discover the best time to fly to Cayman Brac from O'Hare Intl 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.

Related info for your journey

Find useful and relevant information for your journey from O'Hare Intl to Cayman Brac. Access travel guides, tips, and recommendations to enhance your travel experience. Get information about local attractions, weather, transportation options, and more.

  • What airport do you fly into for flights to Cayman Brac from Chicago O'Hare Intl?

    For a flight from Chicago O'Hare Intl to Cayman Brac, you will be flying into Gerrard-Smith. Cayman Brac Gerrard-Smith (CYB) is just 5.7 mi from the center of the city. Gerrard-Smith is the only Cayman Brac airport and it handles 0 inbound flights from Chicago O'Hare Intl per day. 0 airlines have flights to Cayman Brac Gerrard-Smith from Chicago O'Hare Intl on a regular basis.

  • Can I find deals for flights from O'Hare Intl to Cayman Brac that include hotel bookings?

    Yes. In addition to deals on O'Hare Intl to Cayman Brac flights, Cheapflights offers vacation packages that include both flights and hotel.

  • How can I find direct flights from O'Hare Intl to Cayman Brac?

    After entering your origin and destination, apply the non-stop filter on the search result page to find direct flights from O'Hare Intl to Cayman Brac.

  • Can I find deals for business class flights from O'Hare Intl to Cayman Brac?

    Yes. Cheapflights offers flight deals from O'Hare Intl to Cayman Brac by cabin class. In addition to browsing deals, you can also filter by cabin class on the search results page after making a search.

See more FAQs

Browse thousands of different options on Cheapflights for your next trip

Toggle through the tabs below to find thousands of options on Cheapflights for your next trip.

Alternative routes for O'Hare Intl to Cayman Brac

See prices for flight routes from nearby airports that may be better suited for you.
O'Hare Intl to George Town flights
Midway to George Town flights
100% Free
Cheapflights is completely free to use, so you can start saving the moment you arrive.
Book with Flexibility
Our users can plan ahead with confidence and find flights with no change fees
Travel Smart
Millions of people come to us for their flight needs every year. We help make travel planning easy by providing useful insights and data-driven graphs that can inform your decisions.