When it comes to Chicago weather, early fall is peak time since the crisp air makes everyone want to go out on the dance floor. Starting on September 15 at Douglass Park with the punk-fueled Riot Fest is the citywide World Music Festival, followed by the Hyde Park Jazz Festival and the Hyde Park Jazz Festival. Past headliners at the North Coast Music Festival have included The Chemical Brothers, Kid Cudi, and Fatboy Slim, so it's a good bet that you'll hear a wide range of musical styles there. https://driving-directions.co