Valentine's Day in Chicago is often a mixed bag when it comes to weather, and historical data confirms this. Since 1871, Chicago has experienced a wide range of conditions on February 14th, from balmy warmth to bitter cold and significant snowfall. According to data from the National Weather Service and reported by the Chicago Tribune, the warmest Valentine's Day in Chicago occurred in 1954, with a high temperature of 62°F (16°C). In stark contrast, the coldest Valentine's Day was recorded in 1905, plunging to a frigid low of -11°F (-24°C).