Windy City (also known as Windy City II, 1949–1964) was a British-bred Irish-trained Thoroughbred racehorse and sire. He was the leading European two-year-old of 1951 when he won four races including the Gimcrack Stakes and was awarded a Timeform rating of 142, which remains one of the highest in the organisation's history. In the following season he was sold and exported to the United States where he twice defeated the future Kentucky Derby winner Hill Gail before his racing career was ended by injury. He was retired to stud where he had some success as a breeding stallion.