Chicago Street Festivals in 2024 (Neighborhood Fests) Upcoming Street Festivals 16 May 16 May - 18 May Chicago Mayfest 2025 May 16, 2025 - May 18, 2025 Lincoln Park Celebration 30 May 30 May - 01 Jun Windy City Hot Dog Fest 2025 May 30, 2025 - June 1, 2025 Portage Park neighborhood Food Festival
