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10Best's Chicago Events

If you’re lucky enough to visit during a special event, you’ll find Chicago that much more memorable. Whether it’s the North Side festivities surrounding Opening Day at Wrigley Field or a gourmet gala such as Taste of Chicago, there’s no question that the Windy City knows how to plan and throw a big party. Annual celebrations range from the artsy Chicago International Film Festival to true spectacles like mid-August’s Air and Water Show, one of the finest events of its kind in the country. Of course, Chicagoans are fond of live music, and recurring events like the Grant Park Music Festival (June to August, every Wednesday, Friday, and Saturday) are always packed – and not just because they show off Jay Pritzker Pavilion and Millennium Park. For admirers of the sweet science, live jazz takes center stage at Grant Park over Labor Day weekend, when the Chicago Jazz Festival and its slate of well-known performers kick into gear.