Cheap flights from Chicago to Grand Cayman from $109

The cheapest month to fly to Grand Cayman from Chicago is in February. Flight prices, which tend to average around $527, are often lower during this time because this is during the off-season. If you don’t want to visit Grand Cayman in February, then you should wait until October to fly from Chicago, when ticket prices are also cheap, with an average price of $539.

The cheapest day to depart from Chicago to Grand Cayman is on a Wednesday when prices can be found for as low as $526. On the other hand, Sunday is the most expensive day to depart from Chicago because it is more convenient for both business and leisure travelers. As a result, prices tend to be around $770.

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

You are more likely to see cheaper flights to Grand Cayman from Chicago when booking weeks ahead of your departure date. In general, you can expect to find flights to Grand Cayman for around $669 when searching weeks out. However, flight prices might be lower outside of this timeframe. For example, people recently found flights to Grand Cayman from Chicago for as low as $461 on momondo.

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

No. A direct flight is the cheapest option for a flight between Chicago to Grand Cayman.

As of March 2026, there are 1 flights per day flying from Chicago to Grand Cayman. The most common time of day flights depart is 9:00AM, with 100% of flights taking off at noon.

12 flights are operational weekly from Chicago to Grand Cayman as of March 2026. The most popular departure day for this route is Mon, with 17% of flights per week taking off on this day.