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The most popular time to visit Chicago is January. During this month, the city is alive with the festive spirit of winter, boasting a vibrant array of events and activities. With average temperatures ranging from -3 to 1°C, visitors can embrace the chill while enjoying the city's famous indoor attractions, such as the Art Institute of Chicago and the Field Museum, all conveniently located in the downtown area.From January to March, Chicago experiences its peak season, drawing many tourists eager to experience its unique winter charm. While the temperatures may be brisk, the city transforms into a winter wonderland, offering opportunities for ice skating in Millennium Park or indulging in hearty cuisine at its renowned restaurants. For those who appreciate a bustling atmosphere, this time of year is particularly delightful, as various festivals and events, including the Chicago Auto Show, take place.If you're seeking a quieter, more budget-friendly experience, consider planning your visit in May. This month ushers in milder temperatures, typically ranging from 12 to 20°C, allowing for enjoyable outdoor activities without the summer crowds. You can explore Chicago's beautiful lakefront parks or take a leisurely stroll along the Riverwalk, all while soaking in the city's stunning architecture.