O’hare international airport (ORD) is a major airport, so I think we Chicagoans are pretty lucky because we have access to most Caribbean islands. But not all those flight are non-stop. Here is a list of the nonstop flights from Chicago to the Caribbean islands.
These 6 locations offer nonstop flights year round! (order:shortest to longest)
1.Grand Cayman, Cayman Islands (4hrs)
2. Montego Bay, Jamaica (4hrs)
3. Nassau, Bahamas (4hrs)
4. San Juan, Puerto Rico (5hrs)
5. Punta Cana, Dominican Republic (5hrs)
6. Aruba (5hrs)
You are able to get non stop flights to St. Thomas, Sint Maarten, and Turks and Caicos but it is only during the winter season. Plan accordingly!