When searching for a good deal, it’s best to be prepared for potential fluctuations in price. We recommend booking at least 26 days in advance, which can save you up to 3% on flights from Chicago Midway Airport to Cayman Islands compared to booking the week you need them. Waiting 26 days out may not be for everyone, so we have options available for flights within the next two weeks, with the lowest price starting at $470. For sooner than that we have options available in the next 3 days from $485.
Flights from Chicago Midway Airport to Cayman Islands lean towards being more expensive in December. Prices are generally better when you fly from Chicago Midway Airport to Cayman Islands in September, with the cheapest ticket starting at $362.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Chicago Midway Airport to Cayman Islands as you normally would.