Chicago Food Festivals in 2024 Upcoming Wine Festivals 20 Jul 20 Jul - 21 Jul Chicago Food Truck Festival – Summer 2024 July 20, 2024 at 11:00 AM - July 21, 2024 at 07:00 PM 2300 S. Indiana Ave. (South Loop) Food Festival 06 Sep 06 Sep - 08 Sep Taste of Chicago 2024 September 6, 2024 - September 8, 2024 - Food Festival