Upcoming Festivals and Special Events 02 May 02 May - 04 May Mexico Fest at Navy Pier 2025 May 2, 2025 - May 4, 2025 Navy Pier Cultural Festivals 16 May 16 May - 18 May Chicago Mayfest 2025 May 16, 2025 - May 18, 2025 Lincoln Park Neighborhood Festivals 23 May 23 May - 25 May Belmont Sheffield Music Festival 2025 May 23, 2025 - May 25, 2025 Belmont and Sheffield, Chicago Neighborhood Festivals 24 May 24 May - 25 May Randolph Street Market Festival 2025 May 24, 2025 at 10:00 AM - May 25, 2025 at 05:00 PM Chicago’s Plumbers Union Hall Vintage-Arts & Crafts 30 May 30 May - 01 Jun Windy City Hot Dog Fest 2025 May 30, 2025 - June 1, 2025 Portage Park Food Festivals 05 Jun 05 Jun - 08 Jun Chicago Blues Festival 2025 June 5, 2025 - June 8, 2025 Millennium Park Music Festivals 06 Jun 06 Jun - 08 Jun Lincoln Park Greek Fest 2025 June 6, 2025 - June 8, 2025 St. George Greek Orthodox Church Cultural Festivals 06 Jun 06 Jun - 08 Jun Ribfest Chicago 2025 June 6, 2025 - June 8, 2025 Lincoln Ave. between Irving Park Rd. and Berteau Ave. Food Festivals 07 Jun 07 Jun - 08 Jun 57th Street Art Fair 2025 June 7, 2025 - June 8, 2025 Hyde Park neighborhood Vintage-Arts & Crafts 31 Jul 31 Jul - 03 Aug Lollapalooza 2025 July 31, 2025 - August 3, 2025 Grant Park Music Festivals
