To travel from Chicago to Jamaica, one would typically fly, as there is no direct land route. The flight distance between Chicago O'Hare International Airport (ORD) and Kingston Norman Manley International Airport (KIN), the largest international airport in Jamaica, is approximately 1,950 miles (3,150 kilometers). Flight time can vary depending on factors like winds and layovers but generally takes around 5 to 6 hours non-stop.