THIS WEEKEND IN CHICAGO – Chicago Parties On, Post Labor Day!
I’m filling in for the incomparable Sue Moss this week. Labor Day may signal the end of summer, but the fun’s just getting started for a myriad of Chicago fall festivities!
Free and open to the public, the 45th Annual Taste of Chicago (301 S. Columbus Drive) returns to Grant Park Friday, Saturday and Sunday (11 a.m. to 9 p.m.) More than 50 food vendors and food trucks invite you to taste samples from Chicago’s diverse culinary delights, as well as enjoy world-class musical performances from headliners Lupe Fiasco, JoJo, and Elvis Crespo. Note: It’s a ‘cashless’ event.
In the South Loop, the 40th Annual Printers Row Lit Fest (Ida B. Wells Drive and Dearborn Street) celebrates the printed word and Chicago’s vibrant literary community on Saturday, September 6, and Sunday, September 7 (10 a.m. to 6 p.m.) The Midwest’s largest literary festival features keynote speaker Sandra Cisneros, author of ‘House on Mango Street,’ as well as more than 70 live programs, four Pulitzer Prize writers, over 100 independent booksellers, children’s storytelling, best selling authors, publishers, literary organizations, educational institutions, food vendors, and more. Admission is free!
At Lakeview’s Athenaeum Center for Thought & Culture, (2936 N. Southport Avenue) the 7th Annual Mandala Makers Festival is a three-day celebration (September 5-7) for emerging South Asian performing artists. (Starts Friday at 6 p.m., Saturday at 6 p.m., and Sunday at 2 p.m.) Performances feature vibrant South Asian Folk, Bollywood, Classical, EDM, and contemporary music and dance. The 2025 lineup includes Atish, Ochin Pakhi, Rini, Aikyam, Jamrok Tabla, Saqib Malik, Svanik Tandon, Jimmy Singh, Anindita Anaam x Shreevidya Vijayan, Desi x Street Project, and more. Most performances are free, but tickets/fees are required for the EDM and Bollywood Dance Parties.
Stroll down Roscoe Street and soak in the nostalgic vibes at the 30th Annual Retro on Roscoe, (2000 W. Roscoe Street, from Damen to Leavitt).Chicago ‘s beloved blast from the past (September 5-7) in Roscoe Village (Friday, 5 p.m.-10 p.m., Saturday, noon – 10 p.m. and Sunday, noon – 8 p.m.) is packed with live music, classic car shows, vintage shopping, and old-school fun for all ages. Musical acts include 16 Candles, the Buckinghams, Trippin’ Billies, and The Gingers. A $15 suggested donation supports local charities.
North of Roscoe Village, the Edgewater Music Fest (Broadway and Thorndale) returns for the first time since 2019. This revitalized, exuberant event features a stunning 35+ bands, 80+ vendors, as well as local food and local drinks over three days. (Friday from 5 p.m. to 10 p.m., and Saturday and Sunday from noon to 10 p.m.) Cloud Nothings, Ric Wilson, and Foxy Shazam headline the music acts. A $10 suggested donation supports the Edgewater Chamber of Commerce and local charities.
Finally, the NFL’s 2025-26 season opens on Sunday, but the Chicago Bears open their 106th season under new Head Coach Ben Johnson on Monday night, (September 8, 7 p.m.) at Soldier Field (1410 Special Olympics Drive.) Quarterback Caleb Williams and the team open up against J.J. McCarthy and the Minnesota Vikings. Incidentally, McCarthy grew up in La Grange Park and played for Nazareth Academy.
Alison Moran-Powers and Dean’s Team Chicago
