Chicago's biggest music festival welcomes 400,000 attendees to Grant Park for a four-day music festival that's packed with some of the biggest names in pop, rock and hip-hop.
Each week, our team at Time Out Chicago curates the ultimate weekly event guide, featuring the big events, IYKYK pop-ups and everything in between. Here, you'll find the happenings that are worth your time and money, from family-friendly activities and daytime events to late-night shenanigans and the low-key functions that you won't hear about on TikTok.
Updated July 27, 2026: Get ready, Chicago: It's Lollapalooza week! The four-day festival kicks off on Thursday, so if you're going, check out our ultimate guide to Lollapalooza. If you're planning to stay away from the chaos around Grant Park, there are a lot of other events this weekend, like Chicago's first Italian Beef Festival and concerts at Ravinia Festival. And if you're thinking of fleeing the city altogether, check out the best day trips from Chicago. Keep scrolling for more of the best happenings across Chicago this week.
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