$191 Find Cheap Flights from Chicago to the Cayman Islands - Compare and Save

The cheapest ticket to the Cayman Islands from Chicago found in the last 5 days was to George Town, at $631 round-trip. The most popular route is from Chicago O'Hare Intl Airport (ORD) to George Town (GCM), and the cheapest round-trip airline ticket found on this route in the last 5 days was $631.

The cheapest time of day to fly to the Cayman Islands is generally in the morning, when round-trip flights cost $628 on average. The most expensive time of day to fly to the Cayman Islands is generally in the morning, which is peak travel time and where the average cost of a ticket is $628.

Yes, flying with a layover may cost you more time, but you can also save money on the route, with a 2 stops layover the cheapest option at $681 on average.

The cheapest month for flights from Chicago to the Cayman Islands is December, when tickets cost $172 (return) on average. On the other hand, the most expensive months are September and July, when the average cost of round-trip tickets is $621 and $563 respectively.

For Chicago to Cayman Islands, Thursday is the cheapest day to fly on average and Sunday is the most expensive. Flying from Cayman Islands back to Chicago, the best deals are generally found on Saturday, with Friday being the most expensive.

To get a below average price on the flight from Chicago to the Cayman Islands, you should book around 2 weeks before departure, which saves you about 16% compared to booking last minute. For the absolute cheapest price, our data suggests you should book 15 weeks before departure.

There are 2 airlines that fly nonstop from Chicago to the Cayman Islands. They are American Airlines and United Airlines. The cheapest airline for this route is United Airlines, with the best round-trip deal found costing $341 and arriving in George Town (GCM). On average, United Airlines offers the best prices for nonstop flights between Chicago and Cayman Islands.

In the past 5 days, the cheapest round-trip tickets from Chicago to the Cayman Islands were found on Southwest ($426) and Air Canada ($481).

The duration of a flight to the Cayman Islands depends on your arrival airport. The shortest routes to the Cayman Islands from Chicago are to George Town, which takes 4h 47m, and Cayman Brac, which takes 18h 45m.

There are 3 cabin class options for the route. These are Business, Economy and Prem Economy. Perform a search on KAYAK to find the latest prices and availability for all cabin fares, which differ across airlines.

The earliest flight from Chicago to the Cayman Islands departs at 9:29 am, landing in George Town at 1:30 pm.

If you prefer to fly at night, the latest flight from Chicago to the Cayman Islands jets off at 9:29 am and lands in George Town at 1:30 pm.