While there are plenty of festivals going on this weekend, my recommendation is to make it to the Taste of Randolph festival.
Taste of Randolph, Friday through Sunday
The festival in the West Loop (Randolph & Peoria) features food from some of the top restaurants in the neighborhood, including Vevo, Veerasway, one sixtyblue, and Wishbone. On top of the great food choices, however, is an even better music line-up. Head over tonight to the Main Stage West to see local artist Rachele Eve (5:30), followed by Shilpa Ray and Her Happy Hookers (7:00) and The Heavy (8:30). Saturday’s West stage features sets acts including In Tall Buildings (3:30), JC Brooks and Uptown Sound (5:00), and Here We Go Magic (6:45). At the East stage on Saturday, you can see Chris Gelbuda (4:00), Hemmingbirds (5:30), and Occidental Brothers Dance Band International (8:30). The festival runs through Sunday night, with many more bands and DJs. Admission is $10.