Trip.com
>
Flights
>
Flights to Cayman Islands
>
Flights to Sister Islands
>
Flights to Cayman Brac
>
Flights from Chicago to Cayman Brac

Cheap flight deals from Chicago to Cayman Brac

Find the cheapest flights from Chicago to Cayman Brac within the next three months. Book one-way flights from AED 1,128 or round-trip tickets from AED 2,054.

  • Round-trip
  • One way

Crossed out prices are calculated based on the average price of the corresponding route on Trip.com.

Flight Info | Chicago to Cayman Brac

The distance between Chicago and Cayman Brac is about 2,573.2 km. The most popular month to Cayman Brac is March. The off-season for travel is March.

Cheapest one-way flight price AED 1,128
Cheapest return ticket price AED 2,055
Off-season for travel March
Peak season for travel March
Flight distance 2,573.2 km

When is the cheapest time to fly from Chicago to Cayman Brac?

The best time to book the cheapest flights from Chicago to Cayman Brac is between Jul 6 and Jul 13. One-way ticket prices start at AED 851 according to our flight calendar.

Cheapest flights
From price
Search

  • Jul

    29 6
  • 6 13
  • 13 20
  • 20 27

  • Aug

    27 3
  • 3 10
  • 10 17
  • 17 24
  • 24 31

  • Sep

    31 7
  • 7 14
  • 14 21
Displayed prices are calculated based on the cheapest average weekly prices of the corresponding route on Trip.com.

Frequently Asked Questions

  • When are flight tickets from Chicago (CHI) to Cayman Brac (CYB) the cheapest?

    Airlines adjust prices for flights from Chicago to Cayman Brac based on the date and time of your booking. By analyzing data from all airlines, on Trip.com, you can find the lowest flight prices on Tuesdays, Wednesdays, and Saturdays.

  • How much do flights from Chicago (CHI) to Cayman Brac (CYB) cost?

    According to Trip.com's data, the lowest price is around AED 3,550.

  • How many airports are there in Cayman Brac (CYB)?

    There are 1 airport(s) near Cayman Brac (CYB): Charles Kirkconnell International Airport.

How to find a cheap flight from Chicago to Cayman Brac

Wait until the last minute and flight costs are often sky-high. Plan ahead, book the right way, and your savings can soar. We have loads of saving tips to help you find a cheap flight from Chicago to Cayman Brac. Book your flights at the right time and save more.
1
Being flexible with your dates to get the cheapest Chicago to Cayman Brac ticket.
Tap "Date" on flight search bar to scan through the calender for Chicago to Cayman Brac airfare over next 6 months in 2025. If you would like to fly in next 3 months, it seems the cheapest date is on Fri, Jul 11 at AED 1128 for one-way flights.
2
Compare cheap Chicago to Cayman Brac flight deals from over hundreds of airlines.
Our extensive search allows you to compare prices from over 500 airlines to choose the cheapest flight tickets from Chicago to Cayman Brac. The cheapest airline operating is United Airlines.
3
Set up a Price Alert
By setting up a Price Alert for your Chicago to Cayman Brac route, you can easily track the price of your airline tickets from without manually checking every day.
4
Don't miss cheap Chicago to Cayman Brac flight deals and promo codes.
You can always get the latest deals through Trip.com Deals and Promo Codes for cheap flights. If registering a free membership, you can receive more deals for your flights.
5
Book early or wait unitl the last minute.
It's always better to book early. Flight tickets tend to be the cheapest when they are first released, normally about a year before the departure date. So, check online as soon as the flights you want become available. If you miss the cheapest time, you can still find lower-priced tickets as the flight date approaches.
6
Search for flights on the go.
To get the best flight booking experience on the go, download Trip.com and search for cheap flight tickets from Chicago to Cayman Brac to get exclusive deals for you.

More Travel Options

  • Top Routes from Chicago
  • Top Routes to Cayman Brac
  • Trending Airlines