Due to multiple factors, expect to potentially pay more when booking in June. For low rates, October can be a great choice for travel to Trinidad and Tobago. Flights to Trinidad and Tobago from Cleveland in October are about $518 on average during October, but can be found for as low as $343.
Regardless of the time of day you decide to fly, the ticket price will remain around the same. Book flights from Cleveland to Trinidad and Tobago as you normally would.