Time Out says
Chicago's most well-known shopping district kicks off the holiday season by lighting up the trees that line Michigan Avenue. The fun begins on Friday, November 16, when Pioneer Court hosts family-friendly activities (including a visit from Santa Claus). On Saturday, November 17, stores on the Magnificent Mile will offer special experiences and offers throughout the day, before Michigan Avenue hosts a two-hour tree-lighting parade, which sets off from Oak Street. Head to the Chicago River by 6:55pm to catch the spectacular fireworks display that closes out the evening.