Are there any direct flights from Chicago to caribbean? There were direct flights available from Chicago to various Caribbean destinations. However, please note that flight schedules and routes can change, and new routes may have been added since then. To get the most accurate and up-to-date information, I recommend checking with airlines or using a flight booking platform. They will have the latest information on direct flights from Chicago to the Caribbean. Popular Caribbean destinations with direct flights from Chicago typically include places like Cancún, Puerto Rico, the Dominican Republic, Jamaica, and other island destinations.