Maggianos Little Italy opened the doors of its first location on the corners of Clark Street and Grand Avenue in Chicago Illinois November 11 1991.With a successful opening at the Clark and Grand location a second restaurant was opened in Oak Brook Illinois and two years later in Skokie Illinois. Maggianos Little Italy opened the doors of its first location on the corners of Clark Street and Grand Avenue in Chicago Illinois November 11 1991.With a successful opening at the Clark and Grand location a second restaurant was opened in Oak Brook Illinois and two years later in Skokie Illinois.