Cheap flights from the Cayman Islands to Chicago from $232

The month of February is another great option to travel to Chicago O'Hare Intl Airport, with average flight prices from Cayman Islands averaging around $483.

The cheapest day to depart on your flight to Chicago O'Hare Intl Airport is on a Sunday when prices can be found for as low as $381. This is often the case because there is less demand to fly during this day of the week. On the other hand, Friday is the most expensive day to depart from Cayman Islands because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $2,559.

Flying to Chicago O'Hare Intl Airport from Cayman Islands at noon is the least expensive time of day to depart. momondo users have found prices as low as $597 when looking at flights departing at noon. Try not to purchase tickets in the afternoon because they tend to be around $707. Of course, these prices can vary depending on the time of year and what airport you fly to.

Fly from George Town Owen Roberts Intl to Chicago O'Hare Intl for the best Cayman Islands - Chicago O'Hare Intl flight prices

There are 2 cabin classes available to choose from on Cayman Islands to Chicago O'Hare Intl flights. Cabin price and availability will vary by airline so perform a search above to find the right deals for you.

You could potentially save up to 45% on your flight if you consider stops on a Cayman Islands to Chicago O'Hare Intl Airport flight.

As of April 2026, there are 1 flights per day flying from Cayman Islands to Chicago O'Hare Intl Airport. The most common time of day flights depart is 1:00PM, with 100% of flights taking off in the afternoon.

The number of flights available between Cayman Islands and Chicago O'Hare Intl Airport is 7 per week as of April 2026. The most frequent departure day is Mon, with 14% of weekly flights leaving on this day.