The cheapest times to fly from CYB to ORD are

  • May 7th to July 22nd
  • December 24th to March 25th (except the weeks of January 1st and January 29th)

based on data collected exclusively by Champion Traveler across tens of millions of flights. Among all the dates above, the very cheapest time to fly from CYB to ORD is early March. Prices can be as high as $2416 for Monday flights during early to mid October, or as low as $562 for Saturday flights around early March.


When to Fly to Chicago

Flying from Cayman Brac (CYB) to Chicago, IL (ORD) will usually cost between $640 to $2340 per person if booking more than four weeks in advance. On average the very cheapest time to fly is early March with an average ticket price of $970. Due to high demand the most expensive time to fly is early to mid October, with an average price of $2242. Planning your trip to low-cost times can easily save you $1272 on economy flights and even more on first-class flights. Generally, any price below $1202 can be considered a good price for a round-trip CYB to ORD flight.

See below for a graph of average weekly prices for the CYB to ORD route. All prices are for round-trip tickets in USD.

CYB to ORD Flight Prices

Compared to other flights, the CYB to ORD flight is slightly more expensive than the average and costs slightly more than the average flight leaving from Cayman Brac. The average price per mile (for a direct flight) is $0.46, which is a bit above average.


Flight Prices by Day of the Week

Saturday is usually the cheapest day to depart and return on this flight. Mondays are the most expensive days to fly out or take a return trip. Selecting flights on the least expensive days could save you up to $947 (45%) on this flight.

Departing prices are for round-trip flights returning on the day of departure. For example, a flight departing on Saturday and returning a week later will cost an average of $932. Return trip prices are from the ORD to CYB flight, and often highlight the quality of our data in showing the same trend.

Departing Prices by Day

Departure Day Prices

Return Trip Prices by Day

Return Day Prices


Nonstop Flights and Layovers

Travelers looking to fly from CYB to ORD can generally find a 2-layover flight. Because there is not usually a direct flight option the real-world direct flight time of 3 hour 53 minutes may not be realistic.


Flight Hacking CYB to ORD

Flight hacking is when you book two tickets instead of a layover, sometimes with different airlines. You will need to either bring only a carry-on bag (highly recommended) or leave yourself plenty of time to go through security again. Flight hacking is completely allowed, but airlines don’t always tell you the cheapest way to get from CYB to ORD — but Champion Traveler does!

Hack #1: Miami, FL (CYB > MIA > ORD)

  • Price for both tickets: $514
  • Average savings: $688 (57.24%)

See CYB to GCM flights

Hack #2: Grand Cayman (CYB > GCM > ORD)

  • Price for both tickets: $570
  • Average savings: $632 (52.58%)

See CYB to MIA flights

Hack #3: Fort Lauderdale, FL (CYB > FLL > ORD)

  • Price for both tickets: $910
  • Average savings: $293 (24.33%)

See CYB to FLL flights


Flight Questions Answered

Still have questions about flying from CYB to ORD? We’ve got answers.

Which airlines fly this route?

You can find 4 major airlines flying this route most often: American, Cayman Airways, Delta, United, and potentially more during busy seasons.

How far away is it from Chicago O’Hare International Airport to Charles Kirkconnell International Airport?

The distance between the two airports is roughly 1610 miles or 2591 kilometers.

How long does it take to fly from CYB to ORD?

The real-world flight time for a nonstop CYB to ORD flight is about 3 hour 53 minutes.

How many flights go between Cayman Brac and Chicago, IL?

It depends on the day of the week and the date, but a typical day might have around 5 available flights from CYB to ORD.


Airport Location Info


Departing Airport

Origination code CYB
Origination airport name Charles Kirkconnell International Airport
City Cayman Brac
Country the Cayman Islands
Latitude 19.7
Longitude -79.9

Return Airport

Destination code ORD
Destination airport name Chicago O’Hare International Airport
City Chicago, IL
Country the United States
Latitude 42
Longitude -87.9


Other Resources

Please note that while we’ve worked hard to analyzed tens of millions of flights to get you this data, we do not calculate current live prices or guarantee pricing. Please see our partners using the links above for current offers.