Chicago Street Festivals in 2024 (Neighborhood Fests) Upcoming Street Festivals 24 May 24 May - 26 May Belmont-Sheffield Music Fest 2024 May 24, 2024 - May 26, 2024 Belmont-Sheffield (Chicago) Music Festival 25 May 25 May - 26 May Randolph Street Market Festival – May 2024 May 25, 2024 at 10:00 AM - May 26, 2024 at 05:00 PM 1341 W Randolph St Vintage-Arts & Crafts 31 May 31 May - 02 Jun Lincoln Park Greek Fest 2024 May 31, 2024 - June 2, 2024 St. George Greek Orthodox Church Cultural Festival 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